Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds

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Often driven by the knowledge derived from the ethnobotanical use of plants, bioprospection explores the existing biodiversity through integration of modern omics techniques with targeted bioactivity assays. In this work we set up a bioprospection plan to investigate the phytochemical diversity and the potential bioactivity of five Artemisia species with recognized ethnobotanical tradition ( A. absinthium , A. alba , A. annua , A. verlotiorum and A. vulgaris ), growing wild in the natural areas of the Verona province. We characterized the specialized metabolomes of the species (including sesquiterpenoids from the artemisinin biosynthesis pathway) through an LC-MS based untargeted approach and, in order to identify potential bioactive metabolites, we correlated their composition with the in vitro antioxidant activity. We propose as potential bioactive compounds several isomers of caffeoyl and feruloyl quinic acid esters (e.g. dicaffeoylquinic acids, feruloylquinic acids and caffeoylferuloylquinic acids), which strongly characterize the most antioxidant species A. verlotiorum and A. annua . Morevoer, in this study we report for the first time the occurrence of sesquiterpenoids from the artemisinin biosynthesis pathway in the species A. alba . Biological sciences/Chemical biology/Metabolomics Biological sciences/Plant sciences Artemisia spp. bioprospection antioxidants dicaffeoylquinic acids sesquiterpenes artemisinin Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Introduction Bioprospection is defined as the systematic and organized exploration of natural resources and products derived from microorganisms, plants, fungi and animals, whose exploitation has the potential to generate significant economic and social benefits [ 1 ]. This approach has been applied for centuries by humans, who have always looked at plants as a crucial source of botanical drugs and other compounds for their well-being. Nowadays, about 25% of the drugs prescribed in modern medicine come from plants or are synthetic derivatives obtained from molecular plant precursors [ 2 ], while, on the other side, a great part of the population living in developing countries still relies on traditional herbal remedies for their primary healthcare (WHO reports). However, recent literature estimates that only 15% of the species that are used for the treatment of diseases (about 70,000) have been studied for their medical use [ 2 ], emphasizing the imperative for additional exploration. The discovery of new plant-derived drugs has classically relied on ethnobotanical information [ 3 ], as in the case of artemisinin discovery from the herbaceous plant Artemisia annua [ 4 , 5 ]. Nonetheless, with the rise of omics sciences, new perspectives have emerged about the combination of ethnobotanical, phytochemical, and molecular phylogenetic data, and promising predictions of medicinal plant uses have been developed [ 3 , 6 ]. For instance, the improvement of DNA sequencing techniques enabled the phylogenetic reconstruction of plant clusters that include species with a prominent medicinal use and demonstrated bioactivities, allowing the acceleration for the discovery of new potential bioactive compounds in related taxa [ 3 ]. The Artemisia genus (family Asteraceae) comprises about 500 species of herbs and shrubs that are either biannual, annual or perennial [ 7 ] and that are widely distributed in temperate regions of Europe, Asia, North Africa and North America. In many cultures, several species from this genus are characterized by a long-standing ethnobotanical use including preparation of herbal remedies for treatment of major and minor ailments (e.g. fever, hypertension, diabetes and malaria), preparation of herbal teas, alcoholic beverages, tonics and cosmetics or cultivation as crops [ 8 , 9 ]. Many recent studies have unveiled the pleiotropic pharmacological profile of the genus reporting a broad spectrum of bioactivities reflecting the huge number and variety of phytochemicals found in each species. These include anthelmintic, antimalarial, antitubercular, antiviral, antihyperlipidemic, antiemetic, antidepressant, anticancer, anti-asthmatic, antihypertensive, antidiabetic, anxiolytic, hepatoprotective, gastroprotective, and insecticidal action [ 7 , 10 – 12 ]. In this work we set up a bioprospection plan based on literature of local flora to investigate the phytochemical diversity and the potential bioactivity of five Artemisia species with recognized ethnobotanical tradition: A. absinthium L., A. alba Turra, A. annua L., A. verlotiorum Lamotte, A. vulgaris L. (Table 1 ). These species grow spontaneously in the natural areas within the province of Verona and within the Lessinia regional park, an area featured by hilly and mountainous environments, where the climate is classified as cold with no dry season and warm summer [ 13 ]. In this bioprospection work, we combined a sampling plan covering different growing seasons with an untargeted metabolomics approach to profile the specialized metabolomes of the five Artemisia species (including sesquiterpenoids from the artemisinin biosynthesis pathway) and correlate them with the in vitro antioxidant activity measured by FRAP and DPPH assays. Table 1 Five selected Artemisia spp. used in this work with their ascribed medicinal properties Species Geographic distribution Growing season Medicinal use/bioactivities References A. absinthium (wormwood) Europe, Middle East, North Africa, Asia; Italy: indigenous entity perennial shrub treatment of gastrointestinal problems, anorexia, and indigestion; antiparasitic effects, pain; antispasmodic, febrifuge, stomachic, cardiac stimulant and anthelmintic effects [ 23 , 57 , 69 , 70 ] A. alba (white wormwood) Europe south-east; Italy: indigenous entity perennial shrub Burns, contusion, digestive antimicrobial activity [ 45 , 64 , 71 ] A. annua (sweet wormwood) Asia, Europe, North Africa and North America Italy: neophyte allochthonous invasive species (Galasso et al., 2018). annual herb antimalarial, anthelmintic, antipyretic, antiseptic, antispasmodics activities [ 23 , 56 , 72 , 73 ] A. verlotiorum (Chinese mugwort) Eastern Asia, South central Europe; Italy: neophyte allochthonous invasive species (Galasso et al., 2018). perennial herb treatment of hypertension; fever; psoriasis; circulatory, digestive, genito-urinary and respiratory disorders; [ 74 , 75 ] A. vulgaris (common mugwort) Asia, Europe, North America; Italy: indigenous entity perennial herb antioxidant, hypolipidemic, hepatoprotective, antispasmolytic, analgesic, estrogenic, cytotoxic, antibacterial, antifungal, hypotensive, and broncholytic effects [ 70 , 76 – 78 ] Results and Discussion 6.1 Metabolic profiles of Artemisia spp. methanolic extracts In this work, the high sensitivity and wide analytical range of an LC-MS-based untargeted approach was used to profile nonvolatile medium-polar metabolites extracted from the aerial organs of five Artemisia species ( A. absinthium , Aab; A. alba , Aal; A. annua , Aan; A. verlotiorum , Ave; A. vulgaris , Avu) collected throughout three sampling seasons (2019–2021) in the natural areas around Verona (Fig. 1 ). Methanolic extracts of Artemisia spp. leaves and stems were produced and analyzed by untargeted UPLC-ESI-MS leading to the detection of 226 m/z features in negative ionization mode (Supplementary File 1) and to the identification of 80 secondary metabolites. The latter are listed in Table 2 together with their chromatographic and spectral features. Representative chromatographic profiles of leaf and stem methanolic extracts are shown in Fig. 2 , together with pie charts depicting the metabolome composition according to the percentage of each metabolite class with respect to the total LC-MS signal detected. Moreover, to describe single compounds characterizing the various Artemisia species, a relative comparison of the percentages of all identified metabolites, grouped according to the respective metabolite class, is reported in the heatmap of Fig. 3 . Table 2 Secondary metabolites identified in Artemisia spp. samples by UPLC-ESI-MS − analysis. Peak IDs refer to peak numbers represented in Fig. 2 . Rt, retention time. MS/MS diagnostic fragments detected; na, not available. Identification level was established according to metabolomics standards initiative (MSI) [ 79 ]: unambiguous identifications (level 1), comparison with reference standards analyzed under equal experimental conditions; putative assignments (level 2), MS data similarity with literature data or public databases; level 3 was established by spectral similarity to chemical class of compounds and chemotaxonomic data when no literature/database data are available for proposed structures, level 4 unidentified Rt (min) m/z (-) detected Putative identification formula ESI − detected ion m/z (-) expected mass error (ppm) MS/MS λ max (nm) UV-vis MSI Ref. 1 3.54 315.0716 Dihydroxybenzoic acid hexoside isomer C 13 H 16 O 9 [M-H] − 315.0710 1.766 108.022; 153.018 na 2 2 3.92 315.0717 Dihydroxybenzoic acid hexoside isomer C 13 H 16 O 9 [M-H] − 315.0710 2.110 108.022; 153.018 na 2 3 4.09 353.0872 Neochlorogenic acid (5-caffeoylquinic acid) C 16 H 18 O 9 [M-H] − 353.0873 -0.072 135.044; 179.035; 191.057 245, 326 1 4 4.27 315.0719 Dihydroxybenzoic acid hexoside isomer C 13 H 16 O 9 [M-H] − 315.0710 2.935 108.022; 153.018 na 2 5 4.31 285.0619 Dihydroxybenzoic acid pentoside C 12 H 14 O 8 [M-H] − 285.0610 -0.308 108.022; 153.018 na 2 6 4.33 339.0715 Esculetin hexoside C 15 H 16 O 9 [M-H] − 339.0716 -0.290 177.0194 na 2 [ 15 ] 7 4.41 515.1400 Caffeoylquinic acid hexoside isomer C 22 H 28 O 14 [M-H] − 515.1401 -0.082 na na 2 8 4.50 369.0820 Coumarin-O-hexoside C 15 H 16 O 8 [M + FA-H] − 369.0822 -0.412 133.024; 162.025 246, 317 2 [ 80 ] 9 4.76 353.0875 Chlorogenic acid (3-caffeoilquinic acid) C 16 H 18 O 9 [M-H] − 353.0872 -0.073 135.044; 179.035; 191.057 242, 325 1 10 4.86 399.0926 Methoxycoumarin-O-hexoside C 16 H 18 O 9 [M + FA-H] − 399.0927 -0.268 191.034; 176.010 247, 290, 336 2 11 4.88 189.0767 Unidentified C 8 H 14 O 5 [M-H] − 189.0763 - 115.040; 99.081 na 12 4.89 325.0923 trans -Melilotoside C 15 H 18 O 8 [M-H] − 325.0923 -0.126 163.039 275, 310 2 [ 19 ] 13 5.12 429.1033 Dimethoxycoumarin-O-hexoside C 17 H 20 O 10 [M + FA-H] − 429.1033 -0.061 221.046; 206.021 246, 293, 330 2 [ 81 ] 14 5.16 581.1511 Unidentified C 26 H 30 O 15 [M-H] − 581.1506 0.772 239.056; 209.046; 167.035; 269.067 na 4 15 5.39 353.0876 Caffeoylquinic acid isomer C 16 H 18 O 9 [M-H] − 353.0872 -0.115 135.044; 179.035; 191.057 243, 319 2 16 5.40 387.1656 Tuberonic acid hexoside C 18 H 28 O 9 [M-H] − 387.1655 0.258 207.102; 163.112 na 2 [ 18 ] 17 5.52 311.0771 Caffeoylpentoside C 14 H 16 O 8 [M-H] − 311.0766 -0.159 179.035 246, 323 2 18 5.57 515.1184 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.095 135.044; 179.035; 191.057; 353.085 2 19 5.81 367.1026 Feruloylquinic acid isomer C 17 H 20 O 9 [M-H] − 367.1029 -0.932 191.057; 193.051 246, 325 2 20 5.91 325.0923 cis -Melilotoside C 15 H 18 O 8 [M-H] − 325.0923 -0.190 163.039 261 2 [ 19 ] 21 6.26 367.1028 Feruloylquinic acid isomer C 17 H 20 O 9 [M-H] − 367.1029 -0.159 191.057; 193.051 246, 325 2 22 6.34 609.1455 Quercetin-3-O-rutinoside C 27 H 30 O 16 [M-H] − 609.1450 0.790 300.029; 301.033 254, 348 1 23 6.44 593.1512 Kaempherol-O-hexoside-deoxyhexoside C 27 H 30 O 15 [M-H] − 593.1506 0.974 na na 2 24 6.57 463.0874 Quercetin-3-O-glucoside C 21 H 20 O 12 [M-H] − 463.0876 -0.452 300.027; 271.024; 255.029; 301.035 254, 353 1 25 6.61 677.1730 Dicaffeoylquinic acid hexoside C 31 H 34 O 17 [M-H] − 677.1718 1.748 na na 2 26 6.64 493.0978 Mearnsetin-O-hexoside C 22 H 22 O 13 [M-H] − 493.0982 -0.893 315.015; 316.022; 330.039; 331.043 253, 339 2 [ 82 ] 27 6.78 389.1082 Unidentified (hexoside) C 15 H 20 O 9 [M + FA-H] − 389.1084 -0.637 343.104; 181.052 282, 340 4 28 6.83 515.1187 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.044 135.044; 179.035; 191.057; 353.085 246, 326 2 29 6.83 593.1512 Kaempherol-3-O-rutinoside C 27 H 30 O 15 [M-H] − 593.1506 0.915 285.041; 284.032; 255.027; 227.034 364, 346 1 30 6.93 623.1610 Isorhamnetin-O-hexoside-deoxyhexoside C 28 H 32 O 16 [M-H] − 623.1612 -0.298 315.051 357 2 31 7.00 577.1565 Apigenin-O-hexoside-deoxyhexoside C 27 H 30 O 14 [M-H] − 577.1557 1.263 269.046 na 2 32 7.00 653.1719 Eupatolitin-O-hexoside-O-deoxyhexoside C 29 H 34 O 17 [M-H] − 653.1718 0.181 345.083 na 2 [ 15 ] 33 7.05 515.1180 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.175 135.044; 179.035; 191.057; 353.085 244, 325 2 34 7.11 515.1188 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.029 135.044; 179.035; 191.057; 353.085 244, 325 2 35 7.14 695.1242 Tricaffeoylhexaric acid isomer C 33 H 28 O 17 [M-H] − 695.1248 0.092 533.083; 371.061 247, 325 2 36 7.18 477.1028 Isorhamnetin-3-O-glucoside C 22 H 22 O 12 [M-H] − 477.1033 -0.998 271.023; 243.029; 314.037; 299.018; 285.037; 215.031 na 1 37 7.25 515.1180 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.175 135.044; 179.035; 191.057; 353.085 246, 326 2 38 7.27 515.1190 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 -0.021 135.044; 179.035; 191.057; 353.085 243, 326 2 39 7.29 431.0976 Apigenin-7-O-glucoside C 21 H 20 O 10 [M-H] − 431.0970 -0.142 268.035; 269.045 266, 332 1 40 7.41 515.1188 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.013 135.044; 179.035; 191.057; 353.085 246, 326 2 41 7.45 515.1187 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.048 135.044; 179.035; 191.057; 353.085 2 42 7.47 693.2023 Ferulic acid derivative - [M-H] − - - 193.052; 175.038; 160.016 246, 328 2 [ 83 ] 43 7.53 625.1197 Quercetin-O-caffeoylhexoside C 30 H 26 O 15 [M-H] − 625.1193 0.568 300.029; 301.033; 463.086 2 44 7.53 695.1261 Tricaffeoylhexaric acid isomer C 33 H 28 O 17 [M-H] − 695.1248 -0.178 371.061; 209.031; 191.057; 191.020; 179.035; 161.022; 135.044 247, 325 2 45 7.66 529.1340 Caffeoylferuloylquinic acid isomer C 26 H 26 O 12 [M-H] − 529.1340 0.076 191.057 246, 326 2 46 7.66 549.1975 Tracheloside isomer C 27 H 34 O 12 [M-H] − 549.1972 0.538 387.1650; 161.025 247, 323 2 [ 15 ] 47 7.68 499.1235 Coumaroylcaffeoylquinic acid isomer C 25 H 24 O 11 [M-H] − 499.1240 0.099 191.057; 179.034; 163.042 247, 323 2 48 7.71 695.1271 Tricaffeoylhexaric acid isomer C 33 H 28 O 17 [M-H] − 695.1248 -0.328 371.061; 209.031; 191.057; 191.020; 179.035; 161.023; 135.044 247, 325 2 49 7.73 461.1084 Dihydroxy-methoxy-flavone-O-hexoside isomer C 22 H 22 O 11 [M-H] − 461.1080 -0.094 na na 2 50 7.92 529.1343 Caffeoylferuloylquinic acid isomer C 26 H 26 O 12 [M-H] − 529.1346 -0.551 191.057 246, 326 2 51 8.02 529.1343 Caffeoylferuloylquinic acid isomer C 26 H 26 O 12 [M-H] − 529.1346 -0.551 191.057 246, 326 2 52 8.05 499.1238 Coumaroylcaffeoylquinic acid isomer C 25 H 24 O 11 [M-H] − 499.1240 0.038 191.057; 179.035; 163.042 247, 323 2 53 8.05 549.1972 Tracheloside isomer C 27 H 34 O 12 [M-H] − 549.1972 -0.053 na na 2 54 8.09 529.1350 Caffeoylferuloylquinic acid isomer C 26 H 26 O 12 [M-H] − 529.1340 1.951 191.057 246, 326 2 55 8.09 515.1186 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 0.053 135.044; 179.035; 191.057; 353.085 246, 326 2 56 8.23 461.1083 Dihydroxy-methoxy-flavone-O-hexoside isomer C 22 H 22 O 11 [M-H] − 461.1080 -0.065 na na 2 57 8.37 695.1267 Tricaffeoylhexaric acid isomer C 33 H 28 O 17 [M-H] − 695.1248 -0.270 371.061; 209.031; 191.057; 191.020; 179.035; 161.022; 135.044 247, 325 2 58 8.58 735.2127 Ferulic acid derivative isomer - [M-H] − - - 175.040; 193.051; 160.016; 539.137 247, 329 2 59 8.77 529.1344 Caffeoylferuloylquinic acid isomer C 26 H 26 O 12 [M-H] − 529.1340 0.795 191.057 246, 326 2 60 8.78 677.1507 Tricaffeoylquinic acid isomer C 34 H 30 O 15 [M-H] − 677.1500 -0.103 191.057; 515.118 248, 329 2 61 8.82 515.1186 Dicaffeoylquinic acid isomer C 25 H 24 O 12 [M-H] − 515.1189 -0.671 135.044; 179.035; 191.057; 353.085 246, 326 2 62 8.82 735.2133 Ferulic acid derivative isomer - [M-H] − - - 175.040; 193.051; 160.016; 539.137 247, 329 3 63 8.88 543.1500 Diferuloylquinic acid isomer C 27 H 28 O 12 [M-H] − 543.1502 -0.477 191.057; 193.051 249, 327 2 64 8.97 735.2124 Ferulic acid derivative isomer - [M-H] − - - 175.040; 193.051; 160.016; 539.137 247, 329 3 65 9.04 677.1509 Tricaffeoylquinic acid isomer C 34 H 30 O 15 [M-H] − 677.1500 1.382 191.057; 515.118 na 2 66 9.26 345.0612 Tetrahydroxydimethoxyflavone isomer C 17 H 14 O 8 [M-H] − 345.0610 0.518 327.012; 315.015 250, 340 2 [ 15 ] 67 9.34 487.2530 Farnesane sesquiterpene acetylhexose isomer C 23 H 38 O 8 [M + FA-H] − 487.2543 -2.66 441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026 na 4 68 9.36 677.1530 Tricaffeoylquinic acid isomer C 34 H 30 O 15 [M-H] − 677.1500 4.427 191.057; 515.118 na 2 69 9.45 765.1673 Isobutyril-tricaffeoylhexaric acid isomer C 37 H 34 O 18 [M-H] − 765.1660 -0.17 279.071; 441.104; 603.137; 191.023 2 70 9.70 765.1702 Isobutyril-tricaffeoylhexaric acid isomer C 37 H 34 O 18 [M-H] − 765.1660 -0.55 279.071; 441.104; 603.137; 191.023 2 [ 20 ] 71 9.76 487.2532 Farnesane sesquiterpene acetylhexose isomer C 23 H 38 O 8 [M + FA-H] − 487.2543 -2.29 441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026 248, 341 4 72 9.92 765.1683 Isobutyril-tricaffeoylhexaric acid isomer C 37 H 34 O 18 [M-H] − 765.1660 -0.31 279.071; 441.104; 603.137; 191.023 2 [ 20 ] 73 10.05 779.1798 Acylated tricaffeoylhexaric acid isomer C 38 H 36 O 18 [M-H] − 779.1820 0.28 293.087; 455.118; 617.148 3 [ 20 ] 74 10.10 345.0606 Tetrahydroxydimethoxyflavone isomer C 17 H 14 O 8 [M-H] − 345.0610 -1.266 na na 2 [ 15 ] 75 10.48 955.4918 Ginsenoside-like saponin C 48 H 76 O 19 [M-H] − 955.4902 1.605 793.441; 731.434; 613.374; 569.381; 523.377 na 3 [ 84 ] 76 10.51 779.1781 Acylated tricaffeoylhexaric acid isomer C 38 H 36 O 18 [M-H] − 779.1820 0.50 293.087; 455.118; 617.148 3 [ 20 ] 77 10.54 359.0765 Trihydroxytrimethoxyflavone isomer C 18 H 15 O 8 [M-H] − 359.0767 -0.518 286.013; 344.053; 329.030; 314.007; 258.017; 230.022; 202.027 250, 350 2 [ 85 ] 78 11.10 793.4369 Calenduloside-like saponin C 42 H 66 O 14 [M-H] − 793.4374 -0.702 631.381; 613.374; 569.386; 455.354 na 3 [ 86 ] 79 11.35 487.2536 Farnesane sesquiterpene acetylhexose isomer C 23 H 38 O 8 [M + FA-H] − 487.2543 -1.458 441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026 na 4 80 11.83 373.0923 Casticin C 19 H 18 O 8 [M-H] − 373.0923 -0.202 358.071; 343.043; 285.003; 257.009; 229.015 254, 350 2 [ 15 ] 81 11.85 541.2799 Absinthin C 30 H 40 O 6 [M + FA-H] − 541.2801 -0.404 495.272; 451.284; 433.274; 337.804; 293.820 251, 353 1 82 12.66 265.1443 Unidentified C 15 H 22 O 4 [M-H] − 265.1440 1.146 233.115; 189.126; 177.093 na 4 83 12.92 571.2543 Unidentified - - - - na na 84 13.76 539.2639 Putative guaiane-type sesquiterpenoid dimer C 30 H 38 O 6 [M + FA-H] − 539.2645 -1.113 493.269; 471.232; 293.105; 251, 353 4 [ 17 ] 85 14.86 507.2379 Putative guaiane-type sesquiterpenoid dimer C 30 H 36 O 7 [M-H] − 507.2383 -0.79 463.246; 445.243; 259.099; 215.108 na 4 [ 16 ] The main specialized metabolites composing the metabolomes of Artemisia spp. comprise derivatives of hydroxycinnamic acid (HCA), mainly caffeic and ferulic acid differentially esterified with one or multiple organic acid moieties, O-glycosylated flavonoids (mainly flavonols and flavones together with their O-methylated derivatives), glycosylated coumarins and a few other metabolites identified as glycosides of hydroxybenzoic acids, lignans, saponins and sesquiterpenes. In general, a high level of metabolome characterization was achieved, resulting in a metabolite annotation range of 85–97% of total LC-MS signal, with A. annua and A. abisnthium being the species with the higher proportion of unidentified metabolites left. The HCA derivatives represented the most abundant metabolite class, ranging from 62 to 94% of total LC-MS signal in A. absinthium and A. verlotiorum , respectively. As can be observed in the chromatograms of Fig. 2 , in all five species this class was dominated by the caffeic acid esters of quinic acid, in particular two caffeoylquinic acid isomers (compounds 9 , 15 ) and many isomers of dicaffeoylquinic acid ( 28 , 33 , 34 , 37 , 38 , 40 , 41 ). The prevalence of caffeic acid derivatives in the Artemisia metabolome is well pronounced in A. absinthium, A. verlotiorum and A. vulgaris , in which they represent the main peaks, whereas a more diversified profile is observed in favor of other compound classes in A.alba and A,annua (e.g., other HCA derivatives, coumarins and flavonoids). A detailed description of the metabolic profiles of leaves and stems of the five Artemisia species is reported below according to data presented in Figs. 2 and 3 . A. absinthium (Fig. 2 A) leaves are mainly characterized by the presence of two isomers ( 9 , 15 ) of caffeoylquinic acid, one of them identified as 3-O-caffeoylquini acid (chlorogenic acid; 15 ) and of two abundant isomers of dicaffeoylquinic acid ( 34 , 38) ; also caffeoylquinic acid hexoside was best represented in this species ( 7 ). The leaves of A. absinthium , compared to the other species, present higher proportion of the flavonols kaempferol-O-hexoside-deoxyhexoside ( 23 ), isorhamnetin-O-hexoside-deoxyhexoside ( 30 ), eupatolitin-O-deoxyhexoside-O-hexoside ( 32 ) and isorhamnetin-3-O-glucoside ( 36 ). Moreover, in leaves and, at a lower level, in stems of this species only, we detected high amounts of the dimeric guaianolide absinthin ( 81 ), which is described as a specific marker of A. absinthium and is responsible for the bitterness of absinth [ 7 , 14 , 15 ]. In addition, two other compounds annotated as guaiane-type sesquiterpene dimers ( 84 , 85 ) were putatively identified according to recent literature data and in silico fragmentation analysis [ 16 , 17 ]. The stems of A. absinthium showed a much more simplified profile, including the same caffeoylquinic acid isomers found in the leaves together with two less represented dicaffeoylquinic acid isomers ( 40 , 55 ). Furthermore, in both leaves and stems we observed two unidentified metabolites with a molecular ion of 189.07 m/z ( 11) and 571.25 m/z ( 83 ) characterized, respectively, by higher and lower polarity. Leaves and stems of A. alba (Fig. 2 B) were strongly characterized by the glycosides of different coumarins including esculetin hexoside ( 6 ), coumarin-O-hexoside ( 8 ), methoxycoumarin-O-hexoside ( 10 ) and dimethoxycoumarin-O-hexoside ( 13 ). These organs present major peaks attributed to caffeoylquinic acids ( 9 , 15 ) and various isomers of dicaffeoylquinic acid ( 28 , 34 , 37 , 38 , 40 ). Less represented hydroxycinnamic acid derivatives include dicaffeoylquinic acid hexoside ( 25 ), caffeoylpentoside ( 17 ) and three isomers of tricaffeoylquinic acid ( 60 , 65 , 68 ), which were mostly abundant in the leaves. Moreover, this species is strongly characterized by the presence of four ferulic acid derivatives, one with a molecular ion of 693.20 m/z ( 42) and three isomers showing a molecular ion of 735.21 m/z ( 58 , 62 , 64 ,); the resulting neutral loss of 42.01 Da and the higher retention time strongly suggest that the latter could be the acetylated forms of compound 42 . With respect to stems, A. alba leaves presented higher levels of one isomer of a dihydroxybenzoic acid hexoside ( 4 ) and various flavonoids glycosides including quercetin-3-O-rutinoside ( 22 ), kaempferol-O-hexoside-deoxyhexoside ( 23 ), kaempferol-3-O-rutinoside ( 29 ), isorhamnetin-O-hexoside-deoxyhexoside ( 30 ) and apigenin-O-hexoside-deoxyhexoside ( 31 ). Interestingly, according to literature [ 18 ], we detected high levels in the leaves of A. alba of tuberonic acid hexoside ( 16 ), which belong to the class of jasmonate glycosylated derivatives, i.e. phospholipid-derived hormones that regulate plant development and responses to environmental stress. A. annua (Fig. 2 C) was the species presenting the most diversified profile of its secondary metabolome, being characterized by many major compounds belonging to different metabolite classes. In general, the highest diversification was observed within the class of hydroxycinnamic acid derivatives and their esters. In particular, two isomers ( 12 , 20 ) of o -coumaric acid glucoside ( trans - and cis -melilotoside), previously reported in A. annua tea infusions [ 19 ], were detected at high levels in the leaves together with other hydroxycinnamate esters that include feruloyl moieties, such as two feruloylquinic acid isomers ( 19 , 21 ), one diferuloylquinic acid isomer ( 63 ) and five caffeoylferuloylquinic acid isomers, one characterizing mostly the leaves ( 50 ) and the other ones the stems ( 45 , 51 , 54 , 59 ). Also, caffeoyl- ( 9 , 15 ), dicaffeoyl- ( 33 , 34 , 37 , 38 , 40, 61 ) and tricaffeoyl- ( 60 , 65 , 68 ) quinic acids were well represented in both leaves and stems within this species. Among the coumarins, the stems reported the highest levels of methoxycoumarin-O-hexoside ( 10 ). Leaves, on the other hand, were characterized by high amounts of flavonoids, especially methoxylated and often in aglycone form, such as casticin ( 80 ), which is described as a marker of A. annua [ 15 ] and a trihydroxytrimethoxyflavone isomer ( 77 ). The latter, together with the methoxylated flavonol mearnsetin-O-hexoside ( 26 ), represented the major flavonoid peaks of the A. annua leaf chromatograms. Other characteristic flavonoids included two isomers of a tetrahydroxydimethoxyflavone ( 66 , 74 ), quercetin-3-O-glucoside ( 24 ) and apigenin-7-O-glucoside ( 39 ). Finally, three unidentified metabolites ( 14 , 27 , 82 ) were detected at high levels in A. annua . In particular, compound 27 forms a molecular adduct with formic acid at 389.11 m/z under negative ionization conditions; its fragmentation results in the molecular ion at 343.10 m/z and in the fragment 181.05 m/z , which is indicative of the neutral loss of a hexose (-162.05 Da). Moreover, the UV-vis absorbance at 282 and 340 nm together with the fact that it is detected as formic acid adduct, supports the hypothesis that this metabolite could belong to the class of coumarins. A. verlotiorum (Fig. 2 D) and A. vulgaris (Fig. 2 E) presented much simpler profiles respect to the other species. A. verlotiorum was distinct from all the other species for the higher content of two lignans (tracheloside isomers; 46 , 53 ) and three compounds that were putatively annotated as farnesane sesquiterpene acetyl-hexose isomers according to their fragmentation pattern ( 67 , 71 , 79 ). Another peculiarity of this species was the high relative levels of various tricaffeoylhexaric acid isomers ( 35 , 44 , 48 , 57 ), including those acylated to isobutyric acid moieties commonly found in other Asteraceae species ( 69 , 70 , 72) ; [ 20 ] and other tricaffeoyl acid esters ( 73 , 76 ) that were particularly high in the stems. The leaves and stems were also characterized by many different isomers of dicaffeoyl ( 18 , 28 , 33 , 34 , 37 , 38 , 40 , 41 , 55 ) and tricaffeoyl ( 60 , 65 , 68 ) quinic acid, by dicaffeoylquinic acid hexoside ( 25 ) and coumaroylcaffeoylquinic acid isomers ( 47 , 52 ), while neochlorogenic acid ( 3 ) levels were higher in the leaves of this species. Other characteristic metabolites of A. verlotiorum leaves were represented by hexose ( 1 ) and pentose ( 5 ) esters of a dihydroxybenzoic acid, by quercetin-O-caffeoylhexoside ( 43 ) and by four flavone glycosides, which included apigenin-O-hexoside-deoxyhexoside ( 31 ), apigenin-7-O-glucoside ( 39 ) and two dihydroxymethoxyflavone-O-hexoside isomers ( 49 , 56 ), the latter best represented in the stems. A. vulgaris , within the five species, contained lower levels of flavonoids but its stems were characterized by the presence of ginsenoside-like ( 75 ) and calenduloside-like ( 78 ) saponins. Moreover, leaves were characterized by three dicaffeoylquinic acid isomers ( 34 , 37 , 38 ), which were much more represented in this species respect to other ones, yet at lower amounts. In proportion, also neochlorogenic acid ( 3 ), caffeoyl pentoside ( 17 ), two dihydroxybenzoic acid hexosides ( 2 , 4 ) and one sesquiterpene diol monohexoside derivative ( 79 ) characterize A. vulgaris aerial organs. The HCA derivatives, in particular the esters of caffeic acid, were the most characterizing compounds in all the five Artemisia species considered in this work. All these metabolites showed accumulation patterns similar to those already reported in literature for several Artemisia species by using similar extraction methods and identified with different techniques from LC-MS such as NMR and HPLC-DAD [ 21 – 23 ]. The degree and the nature of esterification determines the type of the specific ester isomer that is produced and, for several HCA derivatives, we observed species-specific esterification patterns. This indicates a diversification in the late enzyme of the pathway, among Artemisia spp., such those involving the esterases [ 24 ]. It is interesting to notice how distribution of isomers of different esters of caffeic acid changes also between different organs (stems or leaves) of each species. For instance, various tricaffeoylhexaric acid isomers, a molecule that has been already detected in various Asteraceae [ 25 , 26 ], were found at high levels in A. verlotiorum stems, while tricaffeoylquinic acids were located mostly in the leaves. This is probably due to a different spatial distribution in the enzyme involved in the esterification of HCA biosynthesis between the different organs in each species. As already reported by the literature, flavonoids are another widely represented class of metabolites in the Artemisia genus [ 10 , 22 , 27 ]. Ubiquitous presence of different glycosylated and methoxy-glycosylated flavonoids among all the five species investigated has been observed. Interestingly, in A. annua , and to a lesser extent also in A. absinthium and A. alba , aglycone form of different flavonoids, including the methoxylated flavonol casticin, were observed. Within plant cells, most flavonoids are present as O- or C-glycosides [ 28 , 29 ], while the aglycones are more typical of extracellular exudates [ 30 ]. The presence of different flavonoid aglycones has been reported in plant exudates of different Artemisia species [ 31 , 32 ]. For instance, in A. absinthium, A. alba and A. vulgaris , different polymethoxylated flavonoid aglycones were found on the surface of aerial parts, in the extracellular environment, predominantly in leaves and floral buddings, where they probably have protective roles and/or allelopathic functions [ 12 , 33 ]. The occurrence of these compounds is probably related to the presence on the leaf surface of epidermal trichomes, which can synthetize and store large quantities of specialized metabolites [ 34 ]. Trichomes are epidermis appendages and can be divided into glandular trichomes (GTs) and non-glandular (NGTs) according to their morphology [ 35 ]. In particular, glandular trichomes can synthesize, store, and secrete large amounts of exudates, including alkaloids, polysaccharides, terpenoids, polyphenols, organic acids, and defensive proteins. In turn, these exudates can entrap or poison herbivores and prevent pathogen infection [ 36 , 37 ]. Usually Asteraceae, harbors mainly GTs, where high-value secondary metabolites, including artemisinin in A. annua , are produced and then stored, ready to be used in plant defensive mechanism against both biotic and abiotic stress [ 35 , 38 ]. Presence of glandular trichomes, has been reported for all the species investigated in this work, and can explain the observation of the above mentioned flavonoid aglycones in our samples [ 39 , 40 ]. Considering the three different growing seasons, the strongest differences were observed for A. annua and A. verlotiorum . In A. annua , the relative levels of many flavonoids and hydroxycinnamic acid derivatives during 2019 was lower than 2020 and 2021. In A. verlotiorum , some flavonoids and various hydroxycinnamic acid derivatives showed higher relative level in 2021 compared with 2019 and 2020. This variation could be expected for herbaceous annual species [ 23 ], such as A. annua , if we consider that the sampling of potentially distinct individuals over three years could have increased the genotypic variability of the samples. It is not excluded that some Artemisia species are more sensitive to environmental conditions than others and modulate the levels of single or groups of metabolites in response to different stimuli. However, the type of experimental design that we adopted in this work does not allow us to precisely dissect the effects of specific climate or geographic conditions and, thus, is not suitable to investigate such complex environment-metabolome interactions. 6.2 Antioxidant assays of Artemisia spp. methanolic extracts In this work we performed in vitro antioxidant assays as low cost and easy to use high-throughput screening systems for the identification of potential sources of antioxidants [ 41 , 42 ]. These should then be followed by confirmatory in vivo biological tests with simulated digestion samples [ 43 ] to assess the antioxidant activity in a more physiological context. It is commonly accepted that antioxidant activity must not be tested on the basis of a single method [ 44 ] given the involvement of different antioxidant mechanisms by the molecules present in a phytocomplex. Thus, we used FRAP and DPPH to assess the reducing capacity and radical scavenging activity, respectively, of leaf and stem methanolic extracts of the five Artemisia species. In general, extracts from leaves showed higher antioxidant capacity compared with extracts from stems in both assays (Fig. 4 ). Within the five species, A. absinthium showed the lowest antioxidant activity (up to 30.0 and 24.8 mmolTE/Kg fr. wt in FRAP and DPPH), while A. verlotiorum showed the highest antioxidant power for both FRAP (121.2 mmolTE/Kg fr. wt) and DPPH (up 88.7 mmolTE/Kg fr.wt), about four times higher than A. absinthium . In between these two species, A. annua , A. alba and A. vulgaris displayed a medium to high antioxidant activity (see Supplementary Table 1). Many studies report the antioxidant activity of different Artemisia spp. extracts assayed with a broad panel of methods but a comparison with the results presented in this work is challenged by non-homogeneous expression of data (e.g. TEAC, IC 50 , percentage of radical scavenging, etc.) or the use of reference compounds other than Trolox. A few recent studies report the antioxidant activity of methanolic extracts of various Artemisia species in comparison to Trolox[ 15 , 45 , 46 ] (Supplementary Table 2). Our results are in line with the trend observed by Trifan and colleagues for FRAP assay, in which A. absinthium displayed the lowest antioxidant activity. On the other hand, we did not observe higher antioxidant activity for A. vulgaris , as reported by the authors. In general, the TEAC values reported in all these studies for the five Artemisia species are five to ten times higher than our results, but this is justified by the fact that dried instead of fresh plant material was used to produce the extracts, thus resulting in higher concentrations of antioxidant compounds. In Fig. 5 the antioxidant activity in each of the three years of sampling is shown (see also Supplementary Table 1). In some cases, a clear impact of the specific growing season on antioxidant activity was observed. For example, A. verlotiorum extracts showed higher antioxidant activities in 2021 than 2019 and 2020 in both FRAP (Fig. 5 G) and DPPH (Fig. 5 H), while A. annua and A. vulgaris showed lower antioxidant activities in 2019 compared with 2020 and 2021 (Fig. 5 E, F, I, L). On the other hand, the antioxidant activity of the leaves of A. absinthium (Fig. 5 A, B) and A. alba (Fig. 5 C, D), did not vary significantly throughout the three years. According to these data, the antioxidant activity of species like A. absinthium and A. alba seems to be less influenced by the growing season as it occurs in the case of A. annua , A. vulgaris and A. verlotiorum . 6.3 Correlation analysis of antioxidant data and metabolic profiles of Artemisia spp. In order to obtain information on which metabolites may be responsible for antioxidant activity of Artemisia spp. methanolic extracts, a statistical tool of multivariate analysis (OPLS) was used to find linear relations between the metabolite levels (whose m/z features were assigned as X variables) and the antioxidant capacity (whose mmolTE/Kg were assigned as Y variables). The score scatter plots of Fig. 6 show a good, yet not too strong, linear correlation between the metabolite levels (t, x axis) and the antioxidant activity (u, y axis), for both FRAP and DPPH (0.86 < R 2 < 0.90), thus recalling the need for an independent OPLS analysis in each different species; this is expected, since different set of metabolites could be responsible for the overall antioxidant activity of each species. In this analysis, samples that displayed the highest mmol TE/Kg of fresh plant material clustered on the top right corner of the graph and those with the lower values in the left-down corner. The same analysis was applied to each of the individual species. The OPLS individual models for leaves and stem extracts of each of the species are shown in Fig. 7 . The loadings of these OPLS analyses can be used to evaluate the contribution of each m/z feature, i.e. of each detected metabolite, to the observed antioxidant activity (Tables 3 , 4 ). Table 3 Lists of metabolites that correlate with FRAP activity in Artemisia spp. samples. Only metabolites with pq(corr) > 0.85 are reported. species ID FRAP- correlating metabolites pq(corr) Aab 15 Caffeoylquinic acid isomer 0.96 9 Chlorogenic acid 0.95 81 Absinthin 0.94 29 Kaempherol-3-O-rutinoside 0.93 80 Casticin 0.91 77 Trihydroxytrimethoxyflavone 0.89 23 Kaempherol-O-hexoside-deoxyhexoside 0.89 85 Putative guaiane-type sesquiterpenoid dimer 0.88 30 Isorhamnetin-O-hexoside-deoxyhexoside 0.87 84 Putative guaiane-type sesquiterpenoid dimer 0.87 Aal 22 Quercetin-3-O-rutinoside 0.91 23 Kaempherol-O-hexoside-deoxyhexoside 0.88 29 Kaempherol-3-O-rutinoside 0.87 Aan 37 Dicaffeoylquinic acid isomer 0.99 51 Caffeoylferuloylquinic acid isomer 0.98 34 Dicaffeoylquinic acid isomer 0.98 21 Feruloylquinic acid isomer 0.96 15 Caffeoylquinic acid isomer 0.95 19 Feruloylquinic acid isomer 0.95 40 Dicaffeoylquinic acid isomer 0.94 9 Chlorogenic acid 0.94 65 Tricaffeoylquinic acid isomer 0.91 38 Dicaffeoylquinic acid isomer 0.91 50 Caffeoylferuloylquinic acid isomer 0.91 60 Tricaffeoylquinic acid isomer 0.89 63 Diferuloylquinic acid isomer 0.88 Ave 34 Dicaffeoylquinic acid isomer 1.00 37 Dicaffeoylquinic acid isomer 0.99 40 Dicaffeoylquinic acid isomer 0.97 55 Dicaffeoylquinic acid isomer 0.94 3 Neochlorogenic acid 0.91 33 Dicaffeoylquinic acid isomer 0.91 5 Dihydroxybenzoic acid pentoside 0.88 39 Apigenin-7-O-glucoside 0.88 38 Dicaffeoylquinic acid isomer 0.88 26 Mearnsetin-O-hexoside 0.86 21 Feruloylquinic acid isomer 0.86 23 Kaempherol-O-hexoside-deoxyhexoside 0.86 43 Quercetin-O-caffeoylhexoside 0.86 Avu 38 Dicaffeoylquinic acid isomer 1.00 37 Dicaffeoylquinic acid isomer 1.00 34 Dicaffeoylquinic acid isomer 0.99 33 Dicaffeoylquinic acid isomer 0.96 Table 4 Lists of metabolites that correlate with DPPH activity in Artemisia spp. samples. Only metabolites with pq(corr) > 0.85 are reported. species ID DPPH – correlating metabolites pq(corr) Aab 15 Caffeoylquinic acid isomer 0.85 9 Chlorogenic acid 0.85 Aal 38 Dicaffeoylquinic acid isomer 0.90 37 Dicaffeoylquinic acid isomer 0.90 34 Dicaffeoylquinic acid isomer 0.89 9 Chlorogenic acid 0.86 Aan 34 Dicaffeoylquinic acid isomer 0.98 40 Dicaffeoylquinic acid isomer 0.98 21 Feruloylquinic acid isomer 0.97 19 Feruloylquinic acid isomer 0.97 50 Caffeoylferuloylquinic acid isomer 0.96 37 Dicaffeoylquinic acid isomer 0.96 9 Chlorogenic acid 0.96 51 Caffeoylferuloylquinic acid isomer 0.96 15 Caffeoylquinic acid isomer 0.96 33 Dicaffeoylquinic acid isomer 0.94 65 Tricaffeoylquinic acid isomer 0.94 63 Diferuloylquinic acid isomer 0.93 26 Mearnsetin-O-hexoside 0.92 24 Quercetin-3-O-glucoside 0.90 36 Isorhamnetin-3-O-Glucoside 0.88 61 Dicaffeoylquinic acid isomer 0.87 59 Caffeoylferuloylquinic acid isomer 0.86 Ave 34 Dicaffeoylquinic acid isomer 0.99 37 Dicaffeoylquinic acid isomer 0.98 40 Dicaffeoylquinic acid isomer 0.97 33 Dicaffeoylquinic acid isomer 0.92 55 Dicaffeoylquinic acid isomer 0.92 31 Apigenin-O-hexoside-deoxyhexoside 0.90 3 Neochlorogenic acid 0.89 19 Feruloylquinic acid isomer 0.88 26 Mearnsetin-O-hexoside 0.86 38 Dicaffeoylquinic acid isomer 0.86 Avu 38 Dicaffeoylquinic acid isomer 0.86 37 Dicaffeoylquinic acid isomer 0.86 Consistently to what observed in the previous paragraphs, the antioxidant activity of leaf extracts is in general higher than those of stem extracts (Fig. 7 ). This comparative analysis between the species, showed that the higher antioxidant activity of A. verlotiorum , described in the previous paragraph, may be mainly due to caffeic and ferulic acid derivatives and flavonoids; also, various unidentified metabolite showed high correlation with antioxidant activity (data not shown). In A. vulgaris the antioxidant activity correlated with caffeic acid derivatives, in A. annua , with coumaric, caffeic and ferulic acid derivatives. In A. alba , which showed the lowest linear correlation between metabolome composition and antioxidant activity (Fig. 7 ), also flavonoids were found to strongly correlate with antioxidant activity in FRAP assay, while the scavenging activity measured by DPPH was mostly correlated with dicaffeoylquinic acid isomers. Interestingly, coumarins accumulated at high levels in A. alba but did not strongly correlate with the antioxidant activity. Finally, in A. absinthium the antioxidant activity strongly correlated with caffeoylquinic acids, absinthin and flavonoids. The hydroxycinnamates esterified with quinic acid, in particular some isomers of dicaffeoylquinic acid, were found to be metabolites with the strongest correlation with antioxidant activity in all species. This class of molecules has been extensively studied in the past years for their potential use in medicine. Caffeoylquinic acid derivatives are natural compounds isolated from a variety of traditional medicinal plants and possess a wide range of pharmacological properties, including antioxidant, hepatoprotective, antibacterial, antihistaminic and other biological effects [ 47 ]. Currently, in literature, caffeoyl and dicaffeoylquinic acids have been widely tested through in vitro and in vivo assays to evaluate their bioactive properties. Two caffeoylquinic acids extracted from Aronia melanocarpa berries, i.e. 3-caffeoylquinic acid and 4-caffeoylquinic acid, were identified as inhibitor of the dipeptidyl peptidase IV, an enzyme involved in the development of type 2 diabetes mellitus [ 48 ]. The protective effect of chlorogenic acid against neurotoxic effect of arsenic poisoning was demonstrated in mice model [ 49 ]. Potential benefits with therapeutic applications were reported also for dicaffeoylquinic acids. For example, Kim and collaborators demonstrated the neuroprotective effect of 3,5-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid from Dipsacus asper on hydrogen peroxide-induced cell death in SH-SY5Y human cells [ 50 ]. In another study it is reported that 1,5-dicaffeoylquinic acid (cynarin) downregulates the expression of inducible nitric oxide synthase, expressed under conditions of inflammation, sepsis, or oxidative stress, in human coronary smooth muscle cells [ 51 ]. In addition, the dicaffeoyl quinic acid cynarin affects the survival, growth, and stress response of normal, immortalized, and cancerous human cells [ 52 ]. Protective effects of cynarin against hepatoxicity effects of cyclophosphamide, an important anticancer drug which belongs to the class of alkylating agents, as well as its antihypertensive and vasodilator effects have been observed in in vivo studies [ 53 , 54 ]. Artemisia spp., which were able to accumulate various isomers of caffeoyl- and dicaffeoylquinic acid, could thus represent a valuable source of these potentially bioactive compounds. A further characterization to reveal the precise identity of the various isomers accumulated by the five species is thus required. 6.4 Looking for a new artemisinin source The sesquiterpene lactone artemisinin and its semi-synthetic derivatives are very important from a pharmaceutical perspective for their anti-malarial properties. Isolated from A. annua plants, artemisinin earned in short time the status of most potent antimalarial drug and recently new evidence of many other bioactivities (e,g, anticancer, anti-inflammatory and antiviral) have emerged [ 55 ]. For this reason, a great interest arose in the search for artemisinin-rich A. annua ecotypes and towards the manipulation of its biosynthetic pathway through different biotechnological tools [ 56 ]. Moreover, since antimalarial activity was reported for different Artemisia species [ 57 ], many studies have been conducted to find alternative natural sources for artemisinin within the Artemisia genus. Despite artemisinin was demonstrated to occur in different amounts in A. dubia [ 58 ], A. scoparia [ 59 ], A. cina [ 60 ], A. vachanica and A. dracunculus [ 61 ], A. verlotiorum and A. vulgaris [ 62 ], the major source of this metabolite still remains A. annua [ 63 ]. In this work we explored the capacity of the Artemisia plants collected in the province of Verona to produce the antimalaria lead drug artemisinin and related compounds from its biosynthesis pathway. We therefore performed an LC-MS analysis in positive ionization mode, which is more suitable for the ionization of sesquiterpenoid molecules, and we searched for the final products of the pathway (artemisinin and arteannuin B) and their immediate precursors (dihydroartemisinic acid and artemisinic acid, respectively). Their identification was made through the comparison of m/z values, fragmentation patterns and retention times with those of the respective reference standards (Table 5 ). The relative comparison of their levels within the leaves of the five Artemisia species is reported in Fig. 8 . Table 5 Metabolites from the artemisinin pathway with their MS features searched in LC-MS ESI + analysis. Metabolite Formula Rt (min) Neutral mass (Da) [M + H] + [M + Na] + MS/MS Arteannuin B C 15 H 20 O 3 12.14 248.141 249.14 271.131 231.138 [M + H-H 2 O]; 185.134 [M + H-H 2 O-2CH 3 -O] Artemisinin C 15 H 22 O 5 12.98 282.147 283.154 305.136 247.133 [M + H-2H 2 O]; 265.144 [M + H-H 2 O] Artemisinic acid C 15 H 22 O 2 14.93 234.162 235.169 217.159 [M + H-H 2 O]; 199.149 [M + H-2H 2 O] Dihydroartemisinic acid C 15 H 24 O 2 14.75 236.178 237.185 219.175 [M + H-H 2 O] A. annua is the only species reporting detectable levels of artemisinin. Interestingly, the precursor of artemisinin, dihydroartemisinic acid, is present not only in A. annua but also in A. alba and A. verlotiorum . Arteannuin B, the final metabolite of a parallel pathway that originates from artemisinic aldehyde, was detected at high levels in A. annua and at considerably lower levels in A. absinthium and A. alba but was absent in A. verlotiorum . The precursor of both arteannuin B and artemisinin, artemisinic acid, is present in A. annua , as expected, but we did not detect it in A. absinthium nor A. alba , despite the fact that arteannuin B has been detected in both species. A. vulgaris does not produce any of the metabolites from the selected pathway. According to the literature, the presence of artemisinin has been recently reported in A. verlotiorum [ 62 ], A. absinthium [ 57 ] and A. vulgaris [ 62 ]. On the other hand, we reported for the first time the presence of artemisinin intermediates in A. alba , thus furtherly increasing the number of sesquiterpene compounds (e.g. germacrane and eudesmane) that were previously reported in this species [ 64 ]. Although we did not detect traces of artemisinin, the presence of the precursor, dihydroartemisinic acid, and side product of the pathway, arteannuin B, indicates that genes of artemisinin biosynthetic pathway are all expressed in these plants, since the last step of artemisinin biosynthesis is a non-enzymatic photooxidative process [ 65 ]. One possible explanation for the absence of artemisinin could be the sampling time. It has been reported that peak in artemisinin content in A. annua and A. vulgaris corresponds to the budding stage, while for A. absinthium maximum accumulation is reached during the flowering stage [ 66 – 68 ]. All the plants used in this work were sampled during their vegetative stage. This could have prevented the artemisinin detection in species with lower levels of this metabolite. However, results obtained in this work strengthen the hypothesis that the artemisinin biosynthetic pathway may be an ancestral characteristic shared within plants belonging to Artemisia [ 57 ]. Experimental section 7.1 Plant material The five selected Artemisia species were sampled independently throughout three growing seasons in June of the years 2019, 2020, 2021 from three hills and mountain areas in the province of Verona. The formal identification of plant material was performed by Sebastiano Andreatta (from the “Museo di Storia Naturale” of Verona), the plants were given the barcode number and a voucher specimen of each species is available at the publicly available herbarium present in the “Museo di Storia Naturale” of Verona (Supplementary Table 3). Sampling complied with relevant institutional, national and international guidelines and legislations. In each sampling site, plants were collected from three distinct spots ( i.e. three different plant populations representing three biological replicates), far enough to avoid the sampling of plant populations deriving from the same genetic source. For each replicate, leaves and stems were collected from at least 5 individuals and pooled together according to the organ. The samples were immediately frozen in dry ice and then stored at -80°C. The frozen plant material was homogenized in liquid nitrogen using an IKA A11 basic mill (IKA, Germany). 7.2 Chemicals and reagents Reference standard of artemisinin was purchased from Sigma-Aldrich (St. Louis, USA). Reference standards of arteannuin B and artemisinic acid were purchased from Biosynth® Carbosynth (Bratislava, Slovakia). Reference standard of dihydroartemisinic acid was purchased from Toronto Reasearch Chemical (Toronto, Canada). Methanol, acetonitrile and water (all LC-MS grade) were purchased from Honeywell (Charlotte, USA). Formic acid (LC-MS grade) was purchased from Biosolve Chimie (Dieuze, France). Trolox and DPPH were purchased, respectively, from Sigma-Aldrich and Thermo Fisher Scientific. 7.3 Metabolites extraction 100 mg of frozen powder were extracted in 1.5 ml methanol, mixed vigorously for 30 sec, sonicated at 40 KHz in an ultrasonic bath Sonica® Ultrasonic Cleaner (SOLTEC, Milan, Italy) at 4°C for 15 min and centrifuged (16000 g , 15 min, 4°C). The supernatants were opportunely diluted in 100% methanol. Just before the analysis, the samples were diluted 1:2 (V:V) with ultrapure water (Honeywell, USA). The final mixtures were passed through Minisart RC4 filters (0.2 µm pores) (Sartorious, Göttingen, Germany) and 1 µl was injected into the UPLC device. 7.4 UPLC-ESI-MS analysis An Acquity I Class UPLC system (Waters, Milford, USA) with a BEH C18 column (Waters), coupled online with a PDA (photo-diode array) and to a Xevo G2-XS qTOF mass spectrometer (Waters), equipped with an electrospray ionization (ESI) source were used. The extracts were injected through a cooled autosampler (8°C) and a flow rate of 0.350 ml/min was used. The mobile phases were 0.1% formic acid in water (solvent A) and acetonitrile (solvent B), and the elution gradient was as follows: 0-1min, 1% B; 1–10 min, 1 to 40% B ; 10-13.50 min, 40 to 70% B; 13.50–15.00 min, 70 to 90% B; 15.00-16.50 min, 90 to 100% B; 16.50–20 min 100% B; 20-20.1, 100 to 1% B; 20.1–25 min, 1% B (initial conditions). The sample analysis sequence was randomized. A quality control (QC) prepared by mixing equal part of all the extracts was analyzed along the whole experiment every ten sample analysis. The ion source parameters were the following: capillary voltage 0.8 Kv, sampling cone voltage 40 V, source offset voltage 80 V, source temperature 120°C, desolvation temperature 500°C, cone gas flow rate 50 l/h and desolvation gas flow rate 1000 l/h. Nitrogen gas was used for the nebulizer and in desolvation whereas argon was used to generate collision-induced dissociation. MS data were acquired in continuum in both negative and positive ionization mode within the range 50-2000 m/z using a fixed collision energy of 35 V. Data were acquired through the Mass Lynx v4.2 software (Waters). 7.5 Processing of LC-MS data and metabolites identification The chromatograms were manually inspected through Mass Lynx software. Metabolites were identified by relying on m/z value of the monoisotopic molecular ion, retention time and MS/MS fragmentation pattern by comparison with an in-house library of authentic standard. When no standard compounds were available, the identification was tentatively assigned comparing m/z , isotopic ratio, fragmentation pattern and UV/vis absorbance spectra with those reported in scientific literature and public databases (Chemspider, Human Metabolome Database, Lotus Natural Products, MassBank, MoNA, Pubchem, etc.). In particular, for the characterization of caffeoyl ester derivatives and various glycosides the following neutral losses (Da) were considered: 132.042 (pentose), 146.058 (deoxyhexose), 162.032 (caffeic acid moiety), 162.053 (hexose), The chromatograms acquired in negative ionization mode were processed with Progenesis QI software (Waters) to obtain the Feature Quantification Matrix (FQM; Supplementary File 1). 7.6 Antioxidant assays The same methanolic extracts used for UPLC-ESI-MS analysis were used for determination of antioxidant activity in vitro by FRAP and DPPH assays in transparent 96-well microplates. A FRAP solution was prepared mixing in a ratio of 10:1:1 (V:V:V) the following reagents: FRAP buffer (3.1 g/l sodium acetate trihydrate, 16 ml/l acetic acid pH 3.6), 10 mM TPTZ (2,4,6-tri(2-pyridyl)-1,2,5-triazine) in HCl 40 Mm, FeCl 3 *6H 2 O 20Mm, The test was carried out mixing 200 µl of the FRAP solution to 20 µl of the sample, or solutions of Trolox at different concentrations or methanol (blank). Methanolic extracts of samples were diluted 1:20 for leaves and in a range from 1:3 to 1:10 for stems. Each sample was tested in three technical replicates. The microplate was incubated at 37°C in the dark for 15 min and then kept cooling at room temperature for 4 min. The absorbance was measured at 593 nm using the Infinite 200 PRO plate reader (Tecan, Männedorf, Switzerland). 1 mM DPPH stock solution was freshly prepared in methanol at least 2 hours before the assay. 100 µM of working solution was prepared diluting 1:10 (V:V) in 70% methanol the DPPH solution. 200 µl of the DPPH solution were added to 20 µl of the sample, i.e. diluted plant extracts or solutions of Trolox at different concentrations or methanol (blank). Methanolic extracts were diluted in a range from 1:10 to 1:20 and from 1:3 to 1:10 for leaves and stems, respectively. Each sample was tested in three technical replicates. The microplate was incubated at 25°C in the dark for 30 min and then the absorbance was measured at 517 nm using the Infinite 200 PRO plate reader (Tecan). The compound Trolox, a water-soluble Vitamin E analogue, was used as reference antioxidant in order to express the antioxidant power of the plant extracts, expressed as Trolox Equivalent Antioxidant Capacity (TEAC), whose unit is mmol of Trolox Equivalent for Kg (mmol/kg). 20 µl of Trolox solutions with concentrations spanning from 500 µM to 5 µM was added to 200 µl of FRAP or DPPH solution to generate a Trolox calibration curve in each assay. 7.7 Statistical analysis The FQM and antioxidant (TEAC values) data were analyzed with SIMCA-P software (Umetrics, Sweden) for multivariate statistical analysis in order to look for relationships among the in-vitro antioxidant activity of the plant extracts and their metabolite composition. The m/z features (i.e. the metabolites) of the dataset were assigned as X variables (Pareto scaling) and the antioxidant activity as Y variables (UV scaling). Orthogonal Partial Least Square (OPLS) analysis was used. 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Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Fabio","middleName":"","lastName":"Pietrolucci","suffix":""},{"id":249634644,"identity":"a6395d4b-4a54-4762-aa34-6db8b8a0c55f","order_by":2,"name":"Sebastiano Andreatta","email":"","orcid":"","institution":"Natural History Museum, verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Sebastiano","middleName":"","lastName":"Andreatta","suffix":""},{"id":249634645,"identity":"8fac7181-259d-49ca-bc4c-28107d30726b","order_by":3,"name":"Ruth Njoku","email":"","orcid":"","institution":"University of Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Ruth","middleName":"","lastName":"Njoku","suffix":""},{"id":249634646,"identity":"189846a1-ce06-4ea0-b870-fd5bdb364a89","order_by":4,"name":"Carolina Antunes Silva Nogueira Ramos","email":"","orcid":"","institution":"University of Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Carolina","middleName":"Antunes Silva Nogueira","lastName":"Ramos","suffix":""},{"id":249634647,"identity":"e73ddfbd-1b87-4c5b-a527-2024858070ff","order_by":5,"name":"Massimo Crimi","email":"","orcid":"","institution":"University of Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Massimo","middleName":"","lastName":"Crimi","suffix":""},{"id":249634648,"identity":"227f3f9f-00b1-4e30-9a47-98942e1e0e81","order_by":6,"name":"Mauro Commisso","email":"","orcid":"","institution":"University of Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Mauro","middleName":"","lastName":"Commisso","suffix":""},{"id":249634649,"identity":"25d0d224-b010-41ca-b1fd-0c7e5aefb562","order_by":7,"name":"Flavia Guzzo","email":"","orcid":"","institution":"University of Verona","correspondingAuthor":false,"submittingAuthor":false,"prefix":"","firstName":"Flavia","middleName":"","lastName":"Guzzo","suffix":""},{"id":249634650,"identity":"7cb8aff8-a64e-44bc-80de-9f37453886cb","order_by":8,"name":"Linda Avesani","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA4UlEQVRIiWNgGAWjYBACPmYGBgk4L6GCgYENzMCjhQ1VyxmYFjx6QAoQWhjb4JrxaGHnPXjjB4NdYj//4WcPHs47nMcnkfuA4eEPfA7jS7bsYUhOnDkjzdwgcdvhYjaJdAP8DmPmMZPgYWA2NrjBYCYB1JLYxnOMgF+AWiT/MNQb258//k0icQ6RWqR5GA7LGTDkAG1pAGphbyOoxdhaxuC4nMSNnDKJhGPpYC0HEtJwa+HnP2N4801FNQ9///Ftkj9qrBPnN7MxPvxhg1sLBBig8Q8Q0jAKRsEoGAWjAD8AAFuqQrcHalkYAAAAAElFTkSuQmCC","orcid":"","institution":"University of Verona","correspondingAuthor":true,"submittingAuthor":false,"prefix":"","firstName":"Linda","middleName":"","lastName":"Avesani","suffix":""}],"badges":[],"createdAt":"2023-11-13 09:59:19","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-3604409/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-3604409/v1","draftVersion":[],"editorialEvents":[{"content":"https://doi.org/10.1038/s41598-024-55128-z","type":"published","date":"2024-02-27T15:01:55+00:00"}],"editorialNote":"","failedWorkflow":false,"files":[{"id":46673138,"identity":"cb7a764d-6126-4a20-bc76-58f301ae2024","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":2462733,"visible":true,"origin":"","legend":"\u003cp\u003eGeolocation of the sampling spots in the northern area of the Verona province (A) and pictures of the five \u003cem\u003eArtemisia \u003c/em\u003espp. plants collected (B).\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/1762c6cc918254d59749949a.png"},{"id":46673143,"identity":"1f401b82-bcf5-4b30-b1b5-382b80f7dcc5","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":823236,"visible":true,"origin":"","legend":"\u003cp\u003eSecondary metabolomes of \u003cem\u003eArtemisia \u003c/em\u003espp. Exemplificative base peak chromatograms recorded in LC-MS-ESI\u003csup\u003e-\u003c/sup\u003e (intensity scaled to 2.5 x 10\u003csup\u003e5\u003c/sup\u003e) of leaves (left) and stems (right) are shown together with pie charts representing the metabolite classes according to the total LC-MS signal detected. Peak annotation numbers refer to Table 2. HBA, hydroxybenzoic acid, HCA, hydroxycinnamic acid derivatives.\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/0affd0196bcc4814c86557ad.png"},{"id":46673140,"identity":"0b319497-597a-4d27-a51b-dee60ff5b3d8","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":178782,"visible":true,"origin":"","legend":"\u003cp\u003eHeat map showing the average relative percentage abundance (respect to the total LC-MS signal of each metabolome) of all metabolites tentatively identified in \u003cem\u003eArtemisia \u003c/em\u003espp. Leaves (L) and stems (S) over a three-year sampling period (2019, 2020, 2021). The metabolite identification numbers match those in the dataset. Aab, \u003cem\u003eA.\u003c/em\u003e \u003cem\u003eabsinthium; \u003c/em\u003eAal, \u003cem\u003eA.\u003c/em\u003e \u003cem\u003ealba; \u003c/em\u003eAan,\u003cem\u003e A.\u003c/em\u003e \u003cem\u003eannua; \u003c/em\u003eAve, \u003cem\u003eA.\u003c/em\u003e \u003cem\u003everlotiorum; \u003c/em\u003eAvu, \u003cem\u003eA. vulgaris. \u003c/em\u003eCf, caffeoyl; CfQa, caffeoylquinic acids; CfHa, caffeoylhexaric acids; HBA, hydroxybenzoic acid; HCA, hydroxycinnamic acid; der, derivatives.\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/f6366e3419dd66476895e4e9.png"},{"id":46673615,"identity":"159cc7d5-2970-4a49-8744-1e1f2b8a54a4","added_by":"auto","created_at":"2023-11-17 18:51:10","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":271102,"visible":true,"origin":"","legend":"\u003cp\u003eAntioxidant activity\u003cem\u003e\u003cstrong\u003e \u003c/strong\u003e\u003c/em\u003eof extracts from \u003cem\u003eArtemisia\u003c/em\u003e spp. leaves and stems, sampled in three independent growing seasons, and determined by FRAP (A,B) and\u003cem\u003e\u003cstrong\u003e \u003c/strong\u003e\u003c/em\u003eDPPH (C,D) assays, and expressed as Trolox Equivalent Antioxidant Capacity (TEAC), in millimoles of Trolox Equivalents/kg of tissue (leaves or stem), fr. wt. Values are expressed as mean +/- standard deviation (n=9)\u003cem\u003e. \u003c/em\u003eSignificant differences were calculated with\u003cem\u003e \u003c/em\u003eone-way ANOVA.\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/bc29ea320feb959bf13bd5a0.png"},{"id":46673613,"identity":"6e475ca3-73c8-4c31-acad-b239ddf85f57","added_by":"auto","created_at":"2023-11-17 18:51:10","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":868461,"visible":true,"origin":"","legend":"\u003cp\u003eAntioxidant activity\u003cem\u003e\u003cstrong\u003e \u003c/strong\u003e\u003c/em\u003eof extracts from \u003cem\u003eArtemisia\u003c/em\u003e spp. leaves and stems, sampled in three independent growing seasons, and determined by FRAP (A, C, G, I) and\u003cem\u003e\u003cstrong\u003e \u003c/strong\u003e\u003c/em\u003eDPPH (B, D, F, H, L) assays, and expressed as Trolox Equivalent Antioxidant Capacity (TEAC), in millimoles of Trolox Equivalents/kg of tissue (leaves or stem), fresh weight. Values are expressed as mean +/- standard deviation (n=9)\u003cem\u003e. \u003c/em\u003eAab, \u003cem\u003eabsinthium; \u003c/em\u003eAal, \u003cem\u003ealba; \u003c/em\u003eAan, \u003cem\u003eannua; \u003c/em\u003eAve, \u003cem\u003everlotiorum; \u003c/em\u003eAvu, \u003cem\u003evulgaris. \u003c/em\u003eSignificant differences calculated with two-way ANOVA.\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/a0a416f537e754da3448f35f.png"},{"id":46673148,"identity":"49caf5df-afd1-4aa4-a57a-f3e77779936f","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":154821,"visible":true,"origin":"","legend":"\u003cp\u003eScatter plot of OPLS analysis that correlates antioxidant activity (u) (FRAP on the left and DPPH on the right) with metabolic composition (t). Samples are colored according to the species.\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/ea1e94710c240395c29fcb16.png"},{"id":46673149,"identity":"212aaf30-52f8-40f2-bfb4-094655c05056","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":427754,"visible":true,"origin":"","legend":"\u003cp\u003eScatter plot of OPLS analysis that correlates antioxidant activity (u) (FRAP on the left and DPPH on the right) with metabolic composition (t)\u003cstrong\u003e. \u003c/strong\u003eSamples are colored according to the organs.\u003cstrong\u003e A) \u003c/strong\u003e\u003cem\u003eA. absinthium \u003c/em\u003e(Aab); \u003cstrong\u003eB) \u003c/strong\u003e\u003cem\u003eA. alba \u003c/em\u003e(Aal); \u003cstrong\u003eC) \u003c/strong\u003e\u003cem\u003eA. annua\u003c/em\u003e (Aan); \u003cstrong\u003eD) \u003c/strong\u003e\u003cem\u003eA. verlotiorum \u003c/em\u003e(Ave); \u003cstrong\u003eE) \u003c/strong\u003e\u003cem\u003eA. vulgaris \u003c/em\u003e(Avu).\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/66e322df97ddfcad56f05575.png"},{"id":46673147,"identity":"c4e42147-2324-4be9-a8ea-ccaf0d89b242","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":309544,"visible":true,"origin":"","legend":"\u003cp\u003eRelative comparison of the final sesquiterpenoid products from the artemisinin biosynthesis pathway in the five \u003cem\u003eArtemisia \u003c/em\u003especies. Y axis: peak area arbitrary units. Bars represent SD (n=3)\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/c7ea82955c63a303b3d3280f.png"},{"id":51958820,"identity":"5c0e6b44-4e28-4bc7-b434-2cdfc04d08cd","added_by":"auto","created_at":"2024-03-04 15:18:18","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":4509720,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/0d3ecbe3-0874-4c74-a02e-eb66cfc70912.pdf"},{"id":46673137,"identity":"3d364bf3-9099-4db3-849f-1a320019e9a9","added_by":"auto","created_at":"2023-11-17 18:43:09","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":19157,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryTable1.docx","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/bb522af74ed8d8cf0f413c48.docx"},{"id":46673136,"identity":"b290c6e8-695f-49c3-8779-151c164f0972","added_by":"auto","created_at":"2023-11-17 18:43:09","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":16442,"visible":true,"origin":"","legend":"","description":"","filename":"supplementaryTable2.docx","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/126095be37c19c7fbe743ae8.docx"},{"id":46673828,"identity":"403a0bc2-b5fd-452c-bcf8-1a138f6cd98b","added_by":"auto","created_at":"2023-11-17 18:59:10","extension":"docx","order_by":3,"title":"","display":"","copyAsset":false,"role":"supplement","size":14064,"visible":true,"origin":"","legend":"","description":"","filename":"SupplementaryTable3.docx","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/94bfd4aa2b05f41fd831995f.docx"},{"id":46673146,"identity":"815a4115-a378-47eb-86dd-0369b72e8b51","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"xlsx","order_by":4,"title":"","display":"","copyAsset":false,"role":"supplement","size":36669,"visible":true,"origin":"","legend":"","description":"","filename":"Supplementaryfile1.xlsx","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/8317f40d0053a72ec4dc5dd6.xlsx"},{"id":46673827,"identity":"a1367eb1-b899-42f8-a4ff-584b982e17a3","added_by":"auto","created_at":"2023-11-17 18:59:10","extension":"docx","order_by":5,"title":"","display":"","copyAsset":false,"role":"supplement","size":16434,"visible":true,"origin":"","legend":"","description":"","filename":"supplementaryfile2.docx","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/cfac647e40eedbeb604fc851.docx"},{"id":46673145,"identity":"cbae8b0f-8880-4ca7-9ffd-488a8648cdf1","added_by":"auto","created_at":"2023-11-17 18:43:10","extension":"png","order_by":6,"title":"","display":"","copyAsset":false,"role":"supplement","size":335929,"visible":true,"origin":"","legend":"\u003cp\u003eGraphical abstract\u003c/p\u003e","description":"","filename":"Graphicalabstract.png","url":"https://assets-eu.researchsquare.com/files/rs-3604409/v1/fdb7cf0b4e48562fae50f634.png"}],"financialInterests":"No competing interests reported.","formattedTitle":"Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds","fulltext":[{"header":"Introduction","content":"\u003cp\u003eBioprospection is defined as the systematic and organized exploration of natural resources and products derived from microorganisms, plants, fungi and animals, whose exploitation has the potential to generate significant economic and social benefits [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e]. This approach has been applied for centuries by humans, who have always looked at plants as a crucial source of botanical drugs and other compounds for their well-being. Nowadays, about 25% of the drugs prescribed in modern medicine come from plants or are synthetic derivatives obtained from molecular plant precursors [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e], while, on the other side, a great part of the population living in developing countries still relies on traditional herbal remedies for their primary healthcare (WHO reports). However, recent literature estimates that only 15% of the species that are used for the treatment of diseases (about 70,000) have been studied for their medical use [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e], emphasizing the imperative for additional exploration. The discovery of new plant-derived drugs has classically relied on ethnobotanical information [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e], as in the case of artemisinin discovery from the herbaceous plant \u003cem\u003eArtemisia annua\u003c/em\u003e [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e, \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e]. Nonetheless, with the rise of \u003cem\u003eomics\u003c/em\u003e sciences, new perspectives have emerged about the combination of ethnobotanical, phytochemical, and molecular phylogenetic data, and promising predictions of medicinal plant uses have been developed [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e, \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e]. For instance, the improvement of DNA sequencing techniques enabled the phylogenetic reconstruction of plant clusters that include species with a prominent medicinal use and demonstrated bioactivities, allowing the acceleration for the discovery of new potential bioactive compounds in related taxa [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eThe \u003cem\u003eArtemisia\u003c/em\u003e genus (family Asteraceae) comprises about 500 species of herbs and shrubs that are either biannual, annual or perennial [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e] and that are widely distributed in temperate regions of Europe, Asia, North Africa and North America. In many cultures, several species from this genus are characterized by a long-standing ethnobotanical use including preparation of herbal remedies for treatment of major and minor ailments (e.g. fever, hypertension, diabetes and malaria), preparation of herbal teas, alcoholic beverages, tonics and cosmetics or cultivation as crops [\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e, \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e]. Many recent studies have unveiled the pleiotropic pharmacological profile of the genus reporting a broad spectrum of bioactivities reflecting the huge number and variety of phytochemicals found in each species. These include anthelmintic, antimalarial, antitubercular, antiviral, antihyperlipidemic, antiemetic, antidepressant, anticancer, anti-asthmatic, antihypertensive, antidiabetic, anxiolytic, hepatoprotective, gastroprotective, and insecticidal action [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e, \u003cspan additionalcitationids=\"CR11\" citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eIn this work we set up a bioprospection plan based on literature of local flora to investigate the phytochemical diversity and the potential bioactivity of five \u003cem\u003eArtemisia\u003c/em\u003e species with recognized ethnobotanical tradition: \u003cem\u003eA. absinthium\u003c/em\u003e L., \u003cem\u003eA. alba\u003c/em\u003e Turra, \u003cem\u003eA. annua\u003c/em\u003e L., \u003cem\u003eA. verlotiorum\u003c/em\u003e Lamotte, \u003cem\u003eA. vulgaris\u003c/em\u003e L. (Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e). These species grow spontaneously in the natural areas within the province of Verona and within the Lessinia regional park, an area featured by hilly and mountainous environments, where the climate is classified as cold with no dry season and warm summer [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. In this bioprospection work, we combined a sampling plan covering different growing seasons with an untargeted metabolomics approach to profile the specialized metabolomes of the five \u003cem\u003eArtemisia\u003c/em\u003e species (including sesquiterpenoids from the artemisinin biosynthesis pathway) and correlate them with the \u003cem\u003ein vitro\u003c/em\u003e antioxidant activity measured by FRAP and DPPH assays.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eFive selected \u003cem\u003eArtemisia\u003c/em\u003e spp. used in this work with their ascribed medicinal properties\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"5\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eSpecies\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eGeographic distribution\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eGrowing season\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eMedicinal use/bioactivities\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eReferences\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eA. absinthium\u003c/em\u003e\u003c/p\u003e \u003cp\u003e(wormwood)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eEurope, Middle East, North Africa,\u003c/p\u003e \u003cp\u003eAsia;\u003c/p\u003e \u003cp\u003eItaly: indigenous entity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eperennial shrub\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003etreatment of gastrointestinal problems, anorexia, and indigestion; antiparasitic effects, pain; antispasmodic, febrifuge, stomachic, cardiac stimulant and anthelmintic effects\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e, \u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e, \u003cspan citationid=\"CR69\" class=\"CitationRef\"\u003e69\u003c/span\u003e, \u003cspan citationid=\"CR70\" class=\"CitationRef\"\u003e70\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eA. alba\u003c/em\u003e\u003c/p\u003e \u003cp\u003e(white wormwood)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eEurope south-east;\u003c/p\u003e \u003cp\u003eItaly: indigenous entity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eperennial shrub\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eBurns, contusion, digestive\u003c/p\u003e \u003cp\u003eantimicrobial activity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e, \u003cspan citationid=\"CR64\" class=\"CitationRef\"\u003e64\u003c/span\u003e, \u003cspan citationid=\"CR71\" class=\"CitationRef\"\u003e71\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eA. annua\u003c/em\u003e\u003c/p\u003e \u003cp\u003e(sweet wormwood)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eAsia, Europe, North Africa and North America\u003c/p\u003e \u003cp\u003eItaly: neophyte allochthonous invasive species (Galasso et al., 2018).\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eannual herb\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eantimalarial, anthelmintic, antipyretic, antiseptic, antispasmodics activities\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e, \u003cspan citationid=\"CR56\" class=\"CitationRef\"\u003e56\u003c/span\u003e, \u003cspan citationid=\"CR72\" class=\"CitationRef\"\u003e72\u003c/span\u003e, \u003cspan citationid=\"CR73\" class=\"CitationRef\"\u003e73\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eA. verlotiorum\u003c/em\u003e (Chinese mugwort)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eEastern Asia, South central Europe;\u003c/p\u003e \u003cp\u003eItaly: neophyte allochthonous invasive species (Galasso et al., 2018).\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eperennial\u003c/p\u003e \u003cp\u003eherb\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003etreatment of hypertension; fever; psoriasis; circulatory, digestive, genito-urinary and respiratory disorders;\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR74\" class=\"CitationRef\"\u003e74\u003c/span\u003e, \u003cspan citationid=\"CR75\" class=\"CitationRef\"\u003e75\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cem\u003eA. vulgaris\u003c/em\u003e\u003c/p\u003e \u003cp\u003e(common mugwort)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eAsia, Europe, North America;\u003c/p\u003e \u003cp\u003eItaly: indigenous entity\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eperennial\u003c/p\u003e \u003cp\u003eherb\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eantioxidant, hypolipidemic, hepatoprotective, antispasmolytic, analgesic, estrogenic, cytotoxic, antibacterial, antifungal, hypotensive, and broncholytic effects\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR70\" class=\"CitationRef\"\u003e70\u003c/span\u003e, \u003cspan additionalcitationids=\"CR77\" citationid=\"CR76\" class=\"CitationRef\"\u003e76\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR78\" class=\"CitationRef\"\u003e78\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e"},{"header":"Results and Discussion","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e6.1 Metabolic profiles of \u003cem\u003eArtemisia\u003c/em\u003e spp. methanolic extracts\u003c/h2\u003e \u003cp\u003eIn this work, the high sensitivity and wide analytical range of an LC-MS-based untargeted approach was used to profile nonvolatile medium-polar metabolites extracted from the aerial organs of five \u003cem\u003eArtemisia\u003c/em\u003e species (\u003cem\u003eA. absinthium\u003c/em\u003e, Aab; \u003cem\u003eA. alba\u003c/em\u003e, Aal; \u003cem\u003eA. annua\u003c/em\u003e, Aan; \u003cem\u003eA. verlotiorum\u003c/em\u003e, Ave; \u003cem\u003eA. vulgaris\u003c/em\u003e, Avu) collected throughout three sampling seasons (2019\u0026ndash;2021) in the natural areas around Verona (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eMethanolic extracts of \u003cem\u003eArtemisia\u003c/em\u003e spp. leaves and stems were produced and analyzed by untargeted UPLC-ESI-MS leading to the detection of 226 \u003cem\u003em/z\u003c/em\u003e features in negative ionization mode (Supplementary File 1) and to the identification of 80 secondary metabolites. The latter are listed in Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e together with their chromatographic and spectral features. Representative chromatographic profiles of leaf and stem methanolic extracts are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, together with pie charts depicting the metabolome composition according to the percentage of each metabolite class with respect to the total LC-MS signal detected. Moreover, to describe single compounds characterizing the various \u003cem\u003eArtemisia\u003c/em\u003e species, a relative comparison of the percentages of all identified metabolites, grouped according to the respective metabolite class, is reported in the heatmap of Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eSecondary metabolites identified in \u003cem\u003eArtemisia\u003c/em\u003e spp. samples by UPLC-ESI-MS\u003csup\u003e\u0026minus;\u003c/sup\u003e analysis. Peak IDs refer to peak numbers represented in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e. Rt, retention time. MS/MS diagnostic fragments detected; na, not available. Identification level was established according to metabolomics standards initiative (MSI) [\u003cspan citationid=\"CR79\" class=\"CitationRef\"\u003e79\u003c/span\u003e]: unambiguous identifications (level 1), comparison with reference standards analyzed under equal experimental conditions; putative assignments (level 2), MS data similarity with literature data or public databases; level 3 was established by spectral similarity to chemical class of compounds and chemotaxonomic data when no literature/database data are available for proposed structures, level 4 unidentified\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"12\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c11\" colnum=\"11\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c12\" colnum=\"12\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eRt (min)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003em/z (-)\u003c/p\u003e \u003cp\u003edetected\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePutative identification\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eformula\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eESI\u003csup\u003e\u0026minus;\u003c/sup\u003e detected ion\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003em/z (-)\u003c/p\u003e \u003cp\u003eexpected\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c8\"\u003e \u003cp\u003emass error\u003c/p\u003e \u003cp\u003e(ppm)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c9\"\u003e \u003cp\u003eMS/MS\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c10\"\u003e \u003cp\u003eλ max (nm)\u003c/p\u003e \u003cp\u003eUV-vis\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c11\"\u003e \u003cp\u003eMSI\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c12\"\u003e \u003cp\u003eRef.\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e3.54\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e315.0716\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxybenzoic acid hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e315.0710\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.766\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e108.022; 153.018\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e3.92\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e315.0717\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxybenzoic acid hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e315.0710\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e2.110\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e108.022; 153.018\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e3\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.09\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e353.0872\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eNeochlorogenic acid (5-caffeoylquinic acid)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e353.0873\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.072\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e245, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e4\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.27\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e315.0719\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxybenzoic acid hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e315.0710\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e2.935\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e108.022; 153.018\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e5\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.31\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e285.0619\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxybenzoic acid pentoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e285.0610\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.308\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e108.022; 153.018\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e6\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e339.0715\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eEsculetin hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e339.0716\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.290\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e177.0194\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.41\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1400\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylquinic acid hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e14\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1401\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.082\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e8\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.50\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e369.0820\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCoumarin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e369.0822\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.412\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e133.024; 162.025\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 317\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR80\" class=\"CitationRef\"\u003e80\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e9\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.76\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e353.0875\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eChlorogenic acid (3-caffeoilquinic acid)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e353.0872\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.073\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e242, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e10\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.86\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e399.0926\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eMethoxycoumarin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e399.0927\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.268\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.034; 176.010\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 290, 336\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e11\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.88\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e189.0767\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eUnidentified\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e189.0763\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e115.040; 99.081\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c11\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e12\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e4.89\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e325.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e\u003cem\u003etrans\u003c/em\u003e-Melilotoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e325.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.126\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e163.039\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e275, 310\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e13\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e429.1033\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDimethoxycoumarin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e10\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e429.1033\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.061\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e221.046; 206.021\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 293, 330\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR81\" class=\"CitationRef\"\u003e81\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e14\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.16\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e581.1511\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eUnidentified\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e581.1506\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.772\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e239.056; 209.046; 167.035; 269.067\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e15\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.39\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e353.0876\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e353.0872\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.115\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e243, 319\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e16\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.40\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e387.1656\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTuberonic acid hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e387.1655\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.258\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e207.102; 163.112\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e17\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.52\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e311.0771\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylpentoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e311.0766\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.159\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e179.035\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 323\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.57\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1184\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.095\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e19\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e367.1026\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e367.1029\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.932\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 193.051\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e20\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5.91\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e325.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e\u003cem\u003ecis\u003c/em\u003e-Melilotoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e325.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.190\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e163.039\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e261\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e21\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.26\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e367.1028\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e367.1029\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.159\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 193.051\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e22\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e609.1455\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eQuercetin-3-O-rutinoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e16\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e609.1450\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.790\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e300.029; 301.033\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e254, 348\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e23\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.44\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e593.1512\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eKaempherol-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e593.1506\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.974\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e24\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.57\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e463.0874\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eQuercetin-3-O-glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e463.0876\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.452\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e300.027; 271.024; 255.029; 301.035\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e254, 353\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e25\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.61\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e677.1730\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e31\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e677.1718\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.748\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e26\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.64\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e493.0978\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eMearnsetin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e13\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e493.0982\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.893\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e315.015; 316.022; 330.039; 331.043\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e253, 339\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR82\" class=\"CitationRef\"\u003e82\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e27\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.78\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e389.1082\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eUnidentified (hexoside)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e9\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e389.1084\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.637\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e343.104; 181.052\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e282, 340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e28\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.83\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1187\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.044\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e29\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.83\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e593.1512\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eKaempherol-3-O-rutinoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e593.1506\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.915\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e285.041; 284.032; 255.027; 227.034\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e364, 346\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e30\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e6.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e623.1610\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eIsorhamnetin-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e28\u003c/sub\u003eH\u003csub\u003e32\u003c/sub\u003eO\u003csub\u003e16\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e623.1612\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.298\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e315.051\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e357\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e31\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.00\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e577.1565\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eApigenin-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e14\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e577.1557\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.263\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e269.046\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e32\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.00\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e653.1719\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eEupatolitin-O-hexoside-O-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e653.1718\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.181\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e345.083\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e33\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.05\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1180\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.175\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e244, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e34\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1188\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.029\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e244, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e35\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e695.1242\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e695.1248\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.092\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e533.083; 371.061\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e36\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.18\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e477.1028\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eIsorhamnetin-3-O-glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e477.1033\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.998\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e271.023; 243.029; 314.037; 299.018; 285.037; 215.031\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e37\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1180\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.175\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e38\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.27\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1190\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.021\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e243, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e39\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.29\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e431.0976\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eApigenin-7-O-glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e10\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e431.0970\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.142\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e268.035; 269.045\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e266, 332\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e40\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.41\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1188\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.013\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e41\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1187\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.048\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e42\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.47\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e693.2023\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFerulic acid derivative\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e193.052; 175.038; 160.016\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 328\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR83\" class=\"CitationRef\"\u003e83\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e43\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.53\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e625.1197\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eQuercetin-O-caffeoylhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e625.1193\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.568\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e300.029; 301.033; 463.086\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e44\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.53\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e695.1261\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e695.1248\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.178\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e371.061; 209.031; 191.057; 191.020; 179.035; 161.022; 135.044\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e45\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e529.1340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e529.1340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.076\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e46\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e549.1975\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTracheloside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e549.1972\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.538\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e387.1650; 161.025\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 323\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e47\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.68\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e499.1235\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCoumaroylcaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e11\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e499.1240\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.099\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 179.034; 163.042\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 323\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e48\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.71\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e695.1271\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e695.1248\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.328\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e371.061; 209.031; 191.057; 191.020; 179.035; 161.023; 135.044\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e49\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.73\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e461.1084\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxy-methoxy-flavone-O-hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e11\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e461.1080\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.094\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e50\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e7.92\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e529.1343\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e529.1346\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.551\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e51\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.02\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e529.1343\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e529.1346\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.551\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e52\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.05\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e499.1238\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCoumaroylcaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e11\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e499.1240\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.038\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 179.035; 163.042\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 323\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e53\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.05\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e549.1972\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTracheloside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e549.1972\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.053\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e54\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.09\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e529.1350\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e529.1340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.951\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e55\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.09\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1186\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.053\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e56\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.23\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e461.1083\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDihydroxy-methoxy-flavone-O-hexoside isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e11\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e461.1080\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.065\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e57\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e695.1267\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e17\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e695.1248\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.270\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e371.061; 209.031; 191.057; 191.020; 179.035; 161.022; 135.044\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 325\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e58\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.58\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e735.2127\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFerulic acid derivative isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e175.040; 193.051; 160.016; 539.137\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 329\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e59\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e529.1344\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e26\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e529.1340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.795\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e60\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.78\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e677.1507\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e34\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e677.1500\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.103\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 515.118\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e248, 329\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e61\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.82\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e515.1186\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e515.1189\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.671\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e135.044; 179.035; 191.057; 353.085\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e246, 326\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e62\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.82\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e735.2133\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFerulic acid derivative isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e175.040; 193.051; 160.016; 539.137\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 329\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e63\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.88\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e543.1500\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDiferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e27\u003c/sub\u003eH\u003csub\u003e28\u003c/sub\u003eO\u003csub\u003e12\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e543.1502\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.477\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 193.051\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e249, 327\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e64\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e8.97\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e735.2124\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFerulic acid derivative isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e175.040; 193.051; 160.016; 539.137\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e247, 329\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e65\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.04\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e677.1509\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e34\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e677.1500\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.382\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 515.118\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e66\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.26\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e345.0612\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTetrahydroxydimethoxyflavone isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e345.0610\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.518\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e327.012; 315.015\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e250, 340\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e67\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e487.2530\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFarnesane sesquiterpene acetylhexose isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e487.2543\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-2.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e68\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.36\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e677.1530\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e34\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eO\u003csub\u003e15\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e677.1500\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e4.427\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e191.057; 515.118\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e69\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e765.1673\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eIsobutyril-tricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e18\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e765.1660\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e279.071; 441.104; 603.137; 191.023\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e70\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.70\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e765.1702\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eIsobutyril-tricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e18\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e765.1660\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.55\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e279.071; 441.104; 603.137; 191.023\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e71\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.76\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e487.2532\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFarnesane sesquiterpene acetylhexose isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e487.2543\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-2.29\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e248, 341\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e72\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.92\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e765.1683\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eIsobutyril-tricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e34\u003c/sub\u003eO\u003csub\u003e18\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e765.1660\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.31\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e279.071; 441.104; 603.137; 191.023\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e73\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e10.05\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e779.1798\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eAcylated tricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e38\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e18\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e779.1820\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.28\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e293.087; 455.118; 617.148\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e74\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e10.10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e345.0606\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTetrahydroxydimethoxyflavone isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e17\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e345.0610\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-1.266\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e75\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e10.48\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e955.4918\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eGinsenoside-like saponin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e48\u003c/sub\u003eH\u003csub\u003e76\u003c/sub\u003eO\u003csub\u003e19\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e955.4902\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.605\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e793.441; 731.434; 613.374; 569.381; 523.377\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR84\" class=\"CitationRef\"\u003e84\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e76\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e10.51\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e779.1781\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eAcylated tricaffeoylhexaric acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e38\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e18\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e779.1820\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e0.50\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e293.087; 455.118; 617.148\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e77\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e10.54\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e359.0765\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTrihydroxytrimethoxyflavone isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e359.0767\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.518\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e286.013; 344.053; 329.030; 314.007; 258.017; 230.022; 202.027\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e250, 350\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR85\" class=\"CitationRef\"\u003e85\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e78\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e11.10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e793.4369\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCalenduloside-like saponin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e42\u003c/sub\u003eH\u003csub\u003e66\u003c/sub\u003eO\u003csub\u003e14\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e793.4374\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.702\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e631.381; 613.374; 569.386; 455.354\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR86\" class=\"CitationRef\"\u003e86\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e79\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e11.35\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e487.2536\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eFarnesane sesquiterpene acetylhexose isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e23\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e487.2543\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-1.458\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e441.248; 221.066; 161.045; 149.047; 131.032; 113.028; 101.026\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e80\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e11.83\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e373.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCasticin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e19\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e373.0923\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.202\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e358.071; 343.043; 285.003; 257.009; 229.015\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e254, 350\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e81\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e11.85\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e541.2799\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eAbsinthin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e40\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e541.2801\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.404\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e495.272; 451.284; 433.274; 337.804; 293.820\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e251, 353\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e82\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e12.66\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e265.1443\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eUnidentified\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e265.1440\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e1.146\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e233.115; 189.126; 177.093\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e83\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e12.92\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e571.2543\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eUnidentified\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c11\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e84\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e13.76\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e539.2639\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePutative guaiane-type sesquiterpenoid dimer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e38\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;FA-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e539.2645\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-1.113\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e493.269; 471.232; 293.105;\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e251, 353\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003e85\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e14.86\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e507.2379\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003ePutative guaiane-type sesquiterpenoid dimer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eC\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e36\u003c/sub\u003eO\u003csub\u003e7\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M-H]\u003csup\u003e\u0026minus;\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e507.2383\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-0.79\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e463.246; 445.243; 259.099; 215.108\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003ena\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c11\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c12\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eThe main specialized metabolites composing the metabolomes of \u003cem\u003eArtemisia\u003c/em\u003e spp. comprise derivatives of hydroxycinnamic acid (HCA), mainly caffeic and ferulic acid differentially esterified with one or multiple organic acid moieties, O-glycosylated flavonoids (mainly flavonols and flavones together with their O-methylated derivatives), glycosylated coumarins and a few other metabolites identified as glycosides of hydroxybenzoic acids, lignans, saponins and sesquiterpenes. In general, a high level of metabolome characterization was achieved, resulting in a metabolite annotation range of 85\u0026ndash;97% of total LC-MS signal, with \u003cem\u003eA. annua\u003c/em\u003e and \u003cem\u003eA. abisnthium\u003c/em\u003e being the species with the higher proportion of unidentified metabolites left. The HCA derivatives represented the most abundant metabolite class, ranging from 62 to 94% of total LC-MS signal in \u003cem\u003eA. absinthium\u003c/em\u003e and \u003cem\u003eA. verlotiorum\u003c/em\u003e, respectively. As can be observed in the chromatograms of Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, in all five species this class was dominated by the caffeic acid esters of quinic acid, in particular two caffeoylquinic acid isomers (compounds \u003cb\u003e9\u003c/b\u003e, \u003cb\u003e15\u003c/b\u003e) and many isomers of dicaffeoylquinic acid (\u003cb\u003e28\u003c/b\u003e, \u003cb\u003e33\u003c/b\u003e, \u003cb\u003e34\u003c/b\u003e, \u003cb\u003e37\u003c/b\u003e, \u003cb\u003e38\u003c/b\u003e, \u003cb\u003e40\u003c/b\u003e, \u003cb\u003e41\u003c/b\u003e). The prevalence of caffeic acid derivatives in the \u003cem\u003eArtemisia\u003c/em\u003e metabolome is well pronounced in \u003cem\u003eA. absinthium, A. verlotiorum\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e, in which they represent the main peaks, whereas a more diversified profile is observed in favor of other compound classes in \u003cem\u003eA.alba\u003c/em\u003e and \u003cem\u003eA,annua\u003c/em\u003e (e.g., other HCA derivatives, coumarins and flavonoids).\u003c/p\u003e \u003cp\u003eA detailed description of the metabolic profiles of leaves and stems of the five \u003cem\u003eArtemisia\u003c/em\u003e species is reported below according to data presented in Figs.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e and \u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003cem\u003eA. absinthium\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eA) leaves are mainly characterized by the presence of two isomers (\u003cb\u003e9\u003c/b\u003e, \u003cb\u003e15\u003c/b\u003e) of caffeoylquinic acid, one of them identified as 3-O-caffeoylquini acid (chlorogenic acid; \u003cb\u003e15\u003c/b\u003e) and of two abundant isomers of dicaffeoylquinic acid (\u003cb\u003e34\u003c/b\u003e, \u003cb\u003e38)\u003c/b\u003e; also caffeoylquinic acid hexoside was best represented in this species (\u003cb\u003e7\u003c/b\u003e). The leaves of \u003cem\u003eA. absinthium\u003c/em\u003e, compared to the other species, present higher proportion of the flavonols kaempferol-O-hexoside-deoxyhexoside (\u003cb\u003e23\u003c/b\u003e), isorhamnetin-O-hexoside-deoxyhexoside (\u003cb\u003e30\u003c/b\u003e), eupatolitin-O-deoxyhexoside-O-hexoside (\u003cb\u003e32\u003c/b\u003e) and isorhamnetin-3-O-glucoside (\u003cb\u003e36\u003c/b\u003e). Moreover, in leaves and, at a lower level, in stems of this species only, we detected high amounts of the dimeric guaianolide absinthin (\u003cb\u003e81\u003c/b\u003e), which is described as a specific marker of \u003cem\u003eA. absinthium\u003c/em\u003e and is responsible for the bitterness of absinth [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e, \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e, \u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]. In addition, two other compounds annotated as guaiane-type sesquiterpene dimers (\u003cb\u003e84\u003c/b\u003e, \u003cb\u003e85\u003c/b\u003e) were putatively identified according to recent literature data and \u003cem\u003ein silico\u003c/em\u003e fragmentation analysis [\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e, \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e]. The stems of \u003cem\u003eA. absinthium\u003c/em\u003e showed a much more simplified profile, including the same caffeoylquinic acid isomers found in the leaves together with two less represented dicaffeoylquinic acid isomers (\u003cb\u003e40\u003c/b\u003e, \u003cb\u003e55\u003c/b\u003e). Furthermore, in both leaves and stems we observed two unidentified metabolites with a molecular ion of 189.07 \u003cem\u003em/z\u003c/em\u003e (\u003cb\u003e11)\u003c/b\u003e and 571.25 \u003cem\u003em/z\u003c/em\u003e (\u003cb\u003e83\u003c/b\u003e) characterized, respectively, by higher and lower polarity.\u003c/p\u003e \u003cp\u003eLeaves and stems of \u003cem\u003eA. alba\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eB) were strongly characterized by the glycosides of different coumarins including esculetin hexoside (\u003cb\u003e6\u003c/b\u003e), coumarin-O-hexoside (\u003cb\u003e8\u003c/b\u003e), methoxycoumarin-O-hexoside (\u003cb\u003e10\u003c/b\u003e) and dimethoxycoumarin-O-hexoside (\u003cb\u003e13\u003c/b\u003e). These organs present major peaks attributed to caffeoylquinic acids (\u003cb\u003e9\u003c/b\u003e, \u003cb\u003e15\u003c/b\u003e) and various isomers of dicaffeoylquinic acid (\u003cb\u003e28\u003c/b\u003e, \u003cb\u003e34\u003c/b\u003e, \u003cb\u003e37\u003c/b\u003e, \u003cb\u003e38\u003c/b\u003e, \u003cb\u003e40\u003c/b\u003e). Less represented hydroxycinnamic acid derivatives include dicaffeoylquinic acid hexoside (\u003cb\u003e25\u003c/b\u003e), caffeoylpentoside (\u003cb\u003e17\u003c/b\u003e) and three isomers of tricaffeoylquinic acid (\u003cb\u003e60\u003c/b\u003e, \u003cb\u003e65\u003c/b\u003e, \u003cb\u003e68\u003c/b\u003e), which were mostly abundant in the leaves. Moreover, this species is strongly characterized by the presence of four ferulic acid derivatives, one with a molecular ion of 693.20 \u003cem\u003em/z\u003c/em\u003e (\u003cb\u003e42)\u003c/b\u003e and three isomers showing a molecular ion of 735.21 \u003cem\u003em/z\u003c/em\u003e (\u003cb\u003e58\u003c/b\u003e, \u003cb\u003e62\u003c/b\u003e, \u003cb\u003e64\u003c/b\u003e,); the resulting neutral loss of 42.01 Da and the higher retention time strongly suggest that the latter could be the acetylated forms of compound \u003cb\u003e42\u003c/b\u003e. With respect to stems, \u003cem\u003eA. alba\u003c/em\u003e leaves presented higher levels of one isomer of a dihydroxybenzoic acid hexoside (\u003cb\u003e4\u003c/b\u003e) and various flavonoids glycosides including quercetin-3-O-rutinoside (\u003cb\u003e22\u003c/b\u003e), kaempferol-O-hexoside-deoxyhexoside (\u003cb\u003e23\u003c/b\u003e), kaempferol-3-O-rutinoside (\u003cb\u003e29\u003c/b\u003e), isorhamnetin-O-hexoside-deoxyhexoside (\u003cb\u003e30\u003c/b\u003e) and apigenin-O-hexoside-deoxyhexoside (\u003cb\u003e31\u003c/b\u003e). Interestingly, according to literature [\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e], we detected high levels in the leaves of \u003cem\u003eA. alba\u003c/em\u003e of tuberonic acid hexoside (\u003cb\u003e16\u003c/b\u003e), which belong to the class of jasmonate glycosylated derivatives, i.e. phospholipid-derived hormones that regulate plant development and responses to environmental stress.\u003c/p\u003e \u003cp\u003e \u003cem\u003eA. annua\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eC) was the species presenting the most diversified profile of its secondary metabolome, being characterized by many major compounds belonging to different metabolite classes. In general, the highest diversification was observed within the class of hydroxycinnamic acid derivatives and their esters. In particular, two isomers (\u003cb\u003e12\u003c/b\u003e, \u003cb\u003e20\u003c/b\u003e) of \u003cem\u003eo\u003c/em\u003e-coumaric acid glucoside (\u003cem\u003etrans\u003c/em\u003e- and \u003cem\u003ecis\u003c/em\u003e-melilotoside), previously reported in \u003cem\u003eA. annua\u003c/em\u003e tea infusions [\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e], were detected at high levels in the leaves together with other hydroxycinnamate esters that include feruloyl moieties, such as two feruloylquinic acid isomers (\u003cb\u003e19\u003c/b\u003e, \u003cb\u003e21\u003c/b\u003e), one diferuloylquinic acid isomer (\u003cb\u003e63\u003c/b\u003e) and five caffeoylferuloylquinic acid isomers, one characterizing mostly the leaves (\u003cb\u003e50\u003c/b\u003e) and the other ones the stems (\u003cb\u003e45\u003c/b\u003e, \u003cb\u003e51\u003c/b\u003e, \u003cb\u003e54\u003c/b\u003e, \u003cb\u003e59\u003c/b\u003e). Also, caffeoyl- (\u003cb\u003e9\u003c/b\u003e, \u003cb\u003e15\u003c/b\u003e), dicaffeoyl- (\u003cb\u003e33\u003c/b\u003e, \u003cb\u003e34\u003c/b\u003e, \u003cb\u003e37\u003c/b\u003e, \u003cb\u003e38\u003c/b\u003e, \u003cb\u003e40, 61\u003c/b\u003e) and tricaffeoyl- (\u003cb\u003e60\u003c/b\u003e, \u003cb\u003e65\u003c/b\u003e, \u003cb\u003e68\u003c/b\u003e) quinic acids were well represented in both leaves and stems within this species. Among the coumarins, the stems reported the highest levels of methoxycoumarin-O-hexoside (\u003cb\u003e10\u003c/b\u003e). Leaves, on the other hand, were characterized by high amounts of flavonoids, especially methoxylated and often in aglycone form, such as casticin (\u003cb\u003e80\u003c/b\u003e), which is described as a marker of \u003cem\u003eA. annua\u003c/em\u003e [\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e] and a trihydroxytrimethoxyflavone isomer (\u003cb\u003e77\u003c/b\u003e). The latter, together with the methoxylated flavonol mearnsetin-O-hexoside (\u003cb\u003e26\u003c/b\u003e), represented the major flavonoid peaks of the \u003cem\u003eA. annua\u003c/em\u003e leaf chromatograms. Other characteristic flavonoids included two isomers of a tetrahydroxydimethoxyflavone (\u003cb\u003e66\u003c/b\u003e, \u003cb\u003e74\u003c/b\u003e), quercetin-3-O-glucoside (\u003cb\u003e24\u003c/b\u003e) and apigenin-7-O-glucoside (\u003cb\u003e39\u003c/b\u003e).\u003c/p\u003e \u003cp\u003eFinally, three unidentified metabolites (\u003cb\u003e14\u003c/b\u003e, \u003cb\u003e27\u003c/b\u003e, \u003cb\u003e82\u003c/b\u003e) were detected at high levels in \u003cem\u003eA. annua\u003c/em\u003e. In particular, compound \u003cb\u003e27\u003c/b\u003e forms a molecular adduct with formic acid at 389.11 \u003cem\u003em/z\u003c/em\u003e under negative ionization conditions; its fragmentation results in the molecular ion at 343.10 \u003cem\u003em/z\u003c/em\u003e and in the fragment 181.05 \u003cem\u003em/z\u003c/em\u003e, which is indicative of the neutral loss of a hexose (-162.05 Da). Moreover, the UV-vis absorbance at 282 and 340 nm together with the fact that it is detected as formic acid adduct, supports the hypothesis that this metabolite could belong to the class of coumarins.\u003c/p\u003e \u003cp\u003e \u003cem\u003eA. verlotiorum\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eD) and \u003cem\u003eA. vulgaris\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eE) presented much simpler profiles respect to the other species.\u003c/p\u003e \u003cp\u003e \u003cem\u003eA. verlotiorum\u003c/em\u003e was distinct from all the other species for the higher content of two lignans (tracheloside isomers; \u003cb\u003e46\u003c/b\u003e, \u003cb\u003e53\u003c/b\u003e) and three compounds that were putatively annotated as farnesane sesquiterpene acetyl-hexose isomers according to their fragmentation pattern (\u003cb\u003e67\u003c/b\u003e, \u003cb\u003e71\u003c/b\u003e, \u003cb\u003e79\u003c/b\u003e). Another peculiarity of this species was the high relative levels of various tricaffeoylhexaric acid isomers (\u003cb\u003e35\u003c/b\u003e, \u003cb\u003e44\u003c/b\u003e, \u003cb\u003e48\u003c/b\u003e, \u003cb\u003e57\u003c/b\u003e), including those acylated to isobutyric acid moieties commonly found in other Asteraceae species (\u003cb\u003e69\u003c/b\u003e, \u003cb\u003e70\u003c/b\u003e, \u003cb\u003e72)\u003c/b\u003e; [\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e] and other tricaffeoyl acid esters (\u003cb\u003e73\u003c/b\u003e, \u003cb\u003e76\u003c/b\u003e) that were particularly high in the stems. The leaves and stems were also characterized by many different isomers of dicaffeoyl (\u003cb\u003e18\u003c/b\u003e, \u003cb\u003e28\u003c/b\u003e, \u003cb\u003e33\u003c/b\u003e, \u003cb\u003e34\u003c/b\u003e, \u003cb\u003e37\u003c/b\u003e, \u003cb\u003e38\u003c/b\u003e, \u003cb\u003e40\u003c/b\u003e, \u003cb\u003e41\u003c/b\u003e, \u003cb\u003e55\u003c/b\u003e) and tricaffeoyl (\u003cb\u003e60\u003c/b\u003e, \u003cb\u003e65\u003c/b\u003e, \u003cb\u003e68\u003c/b\u003e) quinic acid, by dicaffeoylquinic acid hexoside (\u003cb\u003e25\u003c/b\u003e) and coumaroylcaffeoylquinic acid isomers (\u003cb\u003e47\u003c/b\u003e, \u003cb\u003e52\u003c/b\u003e), while neochlorogenic acid (\u003cb\u003e3\u003c/b\u003e) levels were higher in the leaves of this species. Other characteristic metabolites of \u003cem\u003eA. verlotiorum\u003c/em\u003e leaves were represented by hexose (\u003cb\u003e1\u003c/b\u003e) and pentose (\u003cb\u003e5\u003c/b\u003e) esters of a dihydroxybenzoic acid, by quercetin-O-caffeoylhexoside (\u003cb\u003e43\u003c/b\u003e) and by four flavone glycosides, which included apigenin-O-hexoside-deoxyhexoside (\u003cb\u003e31\u003c/b\u003e), apigenin-7-O-glucoside (\u003cb\u003e39\u003c/b\u003e) and two dihydroxymethoxyflavone-O-hexoside isomers (\u003cb\u003e49\u003c/b\u003e, \u003cb\u003e56\u003c/b\u003e), the latter best represented in the stems.\u003c/p\u003e \u003cp\u003e \u003cem\u003eA. vulgaris\u003c/em\u003e, within the five species, contained lower levels of flavonoids but its stems were characterized by the presence of ginsenoside-like (\u003cb\u003e75\u003c/b\u003e) and calenduloside-like (\u003cb\u003e78\u003c/b\u003e) saponins. Moreover, leaves were characterized by three dicaffeoylquinic acid isomers (\u003cb\u003e34\u003c/b\u003e, \u003cb\u003e37\u003c/b\u003e, \u003cb\u003e38\u003c/b\u003e), which were much more represented in this species respect to other ones, yet at lower amounts. In proportion, also neochlorogenic acid (\u003cb\u003e3\u003c/b\u003e), caffeoyl pentoside (\u003cb\u003e17\u003c/b\u003e), two dihydroxybenzoic acid hexosides (\u003cb\u003e2\u003c/b\u003e, \u003cb\u003e4\u003c/b\u003e) and one sesquiterpene diol monohexoside derivative (\u003cb\u003e79\u003c/b\u003e) characterize \u003cem\u003eA. vulgaris\u003c/em\u003e aerial organs.\u003c/p\u003e \u003cp\u003eThe HCA derivatives, in particular the esters of caffeic acid, were the most characterizing compounds in all the five \u003cem\u003eArtemisia\u003c/em\u003e species considered in this work. All these metabolites showed accumulation patterns similar to those already reported in literature for several \u003cem\u003eArtemisia\u003c/em\u003e species by using similar extraction methods and identified with different techniques from LC-MS such as NMR and HPLC-DAD [\u003cspan additionalcitationids=\"CR22\" citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e]. The degree and the nature of esterification determines the type of the specific ester isomer that is produced and, for several HCA derivatives, we observed species-specific esterification patterns. This indicates a diversification in the late enzyme of the pathway, among \u003cem\u003eArtemisia\u003c/em\u003e spp., such those involving the esterases [\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e]. It is interesting to notice how distribution of isomers of different esters of caffeic acid changes also between different organs (stems or leaves) of each species. For instance, various tricaffeoylhexaric acid isomers, a molecule that has been already detected in various Asteraceae [\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e, \u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e], were found at high levels in \u003cem\u003eA. verlotiorum\u003c/em\u003e stems, while tricaffeoylquinic acids were located mostly in the leaves. This is probably due to a different spatial distribution in the enzyme involved in the esterification of HCA biosynthesis between the different organs in each species.\u003c/p\u003e \u003cp\u003eAs already reported by the literature, flavonoids are another widely represented class of metabolites in the \u003cem\u003eArtemisia\u003c/em\u003e genus [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e, \u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e, \u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e]. Ubiquitous presence of different glycosylated and methoxy-glycosylated flavonoids among all the five species investigated has been observed. Interestingly, in \u003cem\u003eA. annua\u003c/em\u003e, and to a lesser extent also in \u003cem\u003eA. absinthium\u003c/em\u003e and \u003cem\u003eA. alba\u003c/em\u003e, aglycone form of different flavonoids, including the methoxylated flavonol casticin, were observed. Within plant cells, most flavonoids are present as O- or C-glycosides [\u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e28\u003c/span\u003e, \u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e29\u003c/span\u003e], while the aglycones are more typical of extracellular exudates [\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e]. The presence of different flavonoid aglycones has been reported in plant exudates of different \u003cem\u003eArtemisia\u003c/em\u003e species [\u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e, \u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e]. For instance, in \u003cem\u003eA. absinthium, A. alba\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e, different polymethoxylated flavonoid aglycones were found on the surface of aerial parts, in the extracellular environment, predominantly in leaves and floral buddings, where they probably have protective roles and/or allelopathic functions [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e, \u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e]. The occurrence of these compounds is probably related to the presence on the leaf surface of epidermal trichomes, which can synthetize and store large quantities of specialized metabolites [\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e]. Trichomes are epidermis appendages and can be divided into glandular trichomes (GTs) and non-glandular (NGTs) according to their morphology [\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e]. In particular, glandular trichomes can synthesize, store, and secrete large amounts of exudates, including alkaloids, polysaccharides, terpenoids, polyphenols, organic acids, and defensive proteins. In turn, these exudates can entrap or poison herbivores and prevent pathogen infection [\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e, \u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e]. Usually Asteraceae, harbors mainly GTs, where high-value secondary metabolites, including artemisinin in \u003cem\u003eA. annua\u003c/em\u003e, are produced and then stored, ready to be used in plant defensive mechanism against both biotic and abiotic stress [\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e, \u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e38\u003c/span\u003e]. Presence of glandular trichomes, has been reported for all the species investigated in this work, and can explain the observation of the above mentioned flavonoid aglycones in our samples [\u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e, \u003cspan citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eConsidering the three different growing seasons, the strongest differences were observed for \u003cem\u003eA. annua\u003c/em\u003e and \u003cem\u003eA. verlotiorum\u003c/em\u003e. In \u003cem\u003eA. annua\u003c/em\u003e, the relative levels of many flavonoids and hydroxycinnamic acid derivatives during 2019 was lower than 2020 and 2021. In \u003cem\u003eA. verlotiorum\u003c/em\u003e, some flavonoids and various hydroxycinnamic acid derivatives showed higher relative level in 2021 compared with 2019 and 2020. This variation could be expected for herbaceous annual species [\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e], such as \u003cem\u003eA. annua\u003c/em\u003e, if we consider that the sampling of potentially distinct individuals over three years could have increased the genotypic variability of the samples. It is not excluded that some \u003cem\u003eArtemisia\u003c/em\u003e species are more sensitive to environmental conditions than others and modulate the levels of single or groups of metabolites in response to different stimuli. However, the type of experimental design that we adopted in this work does not allow us to precisely dissect the effects of specific climate or geographic conditions and, thus, is not suitable to investigate such complex environment-metabolome interactions.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e6.2 Antioxidant assays of \u003cem\u003eArtemisia\u003c/em\u003e spp. methanolic extracts\u003c/h2\u003e \u003cp\u003e \u003cdiv class=\"BlockQuote\"\u003e \u003cp\u003eIn this work we performed \u003cem\u003ein vitro\u003c/em\u003e antioxidant assays as low cost and easy to use high-throughput screening systems for the identification of potential sources of antioxidants [\u003cspan citationid=\"CR41\" class=\"CitationRef\"\u003e41\u003c/span\u003e, \u003cspan citationid=\"CR42\" class=\"CitationRef\"\u003e42\u003c/span\u003e]. These should then be followed by confirmatory \u003cem\u003ein vivo\u003c/em\u003e biological tests with simulated digestion samples [\u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e] to assess the antioxidant activity in a more physiological context. It is commonly accepted that antioxidant activity must not be tested on the basis of a single method [\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e] given the involvement of different antioxidant mechanisms by the molecules present in a phytocomplex. Thus, we used FRAP and DPPH to assess the reducing capacity and radical scavenging activity, respectively, of leaf and stem methanolic extracts of the five \u003cem\u003eArtemisia\u003c/em\u003e species.\u003c/p\u003e \u003c/div\u003e \u003c/p\u003e \u003cp\u003eIn general, extracts from leaves showed higher antioxidant capacity compared with extracts from stems in both assays (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eWithin the five species, \u003cem\u003eA. absinthium\u003c/em\u003e showed the lowest antioxidant activity (up to 30.0 and 24.8 mmolTE/Kg fr. wt in FRAP and DPPH), while \u003cem\u003eA. verlotiorum\u003c/em\u003e showed the highest antioxidant power for both FRAP (121.2 mmolTE/Kg fr. wt) and DPPH (up 88.7 mmolTE/Kg fr.wt), about four times higher than \u003cem\u003eA. absinthium\u003c/em\u003e. In between these two species, \u003cem\u003eA. annua\u003c/em\u003e, \u003cem\u003eA. alba\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e displayed a medium to high antioxidant activity (see Supplementary Table\u0026nbsp;1).\u003c/p\u003e \u003cp\u003eMany studies report the antioxidant activity of different \u003cem\u003eArtemisia\u003c/em\u003e spp. extracts assayed with a broad panel of methods but a comparison with the results presented in this work is challenged by non-homogeneous expression of data (e.g. TEAC, IC\u003csub\u003e50\u003c/sub\u003e, percentage of radical scavenging, etc.) or the use of reference compounds other than Trolox. A few recent studies report the antioxidant activity of methanolic extracts of various \u003cem\u003eArtemisia\u003c/em\u003e species in comparison to Trolox[\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e, \u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e, \u003cspan citationid=\"CR46\" class=\"CitationRef\"\u003e46\u003c/span\u003e] (Supplementary Table\u0026nbsp;2). Our results are in line with the trend observed by Trifan and colleagues for FRAP assay, in which \u003cem\u003eA. absinthium\u003c/em\u003e displayed the lowest antioxidant activity. On the other hand, we did not observe higher antioxidant activity for \u003cem\u003eA. vulgaris\u003c/em\u003e, as reported by the authors. In general, the TEAC values reported in all these studies for the five \u003cem\u003eArtemisia\u003c/em\u003e species are five to ten times higher than our results, but this is justified by the fact that dried instead of fresh plant material was used to produce the extracts, thus resulting in higher concentrations of antioxidant compounds.\u003cdiv class=\"BlockQuote\"\u003e\u003cp\u003eIn Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e the antioxidant activity in each of the three years of sampling is shown (see also Supplementary Table\u0026nbsp;1). In some cases, a clear impact of the specific growing season on antioxidant activity was observed. For example, \u003cem\u003eA. verlotiorum\u003c/em\u003e extracts showed higher antioxidant activities in 2021 than 2019 and 2020 in both FRAP (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003eG) and DPPH (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003eH), while \u003cem\u003eA. annua\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e showed lower antioxidant activities in 2019 compared with 2020 and 2021 (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003eE, F, I, L). On the other hand, the antioxidant activity of the leaves of \u003cem\u003eA. absinthium\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003eA, B) and \u003cem\u003eA. alba\u003c/em\u003e (Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003eC, D), did not vary significantly throughout the three years. According to these data, the antioxidant activity of species like \u003cem\u003eA. absinthium\u003c/em\u003e and \u003cem\u003eA. alba\u003c/em\u003e seems to be less influenced by the growing season as it occurs in the case of \u003cem\u003eA. annua\u003c/em\u003e, \u003cem\u003eA. vulgaris\u003c/em\u003e and \u003cem\u003eA. verlotiorum\u003c/em\u003e.\u003c/p\u003e\u003c/div\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e6.3 Correlation analysis of antioxidant data and metabolic profiles of \u003cem\u003eArtemisia\u003c/em\u003e spp.\u003c/h2\u003e \u003cp\u003eIn order to obtain information on which metabolites may be responsible for antioxidant activity of \u003cem\u003eArtemisia\u003c/em\u003e spp. methanolic extracts, a statistical tool of multivariate analysis (OPLS) was used to find linear relations between the metabolite levels (whose \u003cem\u003em/z\u003c/em\u003e features were assigned as X variables) and the antioxidant capacity (whose mmolTE/Kg were assigned as Y variables). The score scatter plots of Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e show a good, yet not too strong, linear correlation between the metabolite levels (t, x axis) and the antioxidant activity (u, y axis), for both FRAP and DPPH (0.86\u0026thinsp;\u0026lt;\u0026thinsp;R\u003csup\u003e2\u003c/sup\u003e\u0026thinsp;\u0026lt;\u0026thinsp;0.90), thus recalling the need for an independent OPLS analysis in each different species; this is expected, since different set of metabolites could be responsible for the overall antioxidant activity of each species. In this analysis, samples that displayed the highest mmol TE/Kg of fresh plant material clustered on the top right corner of the graph and those with the lower values in the left-down corner.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe same analysis was applied to each of the individual species. The OPLS individual models for leaves and stem extracts of each of the species are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e. The \u003cem\u003eloadings\u003c/em\u003e of these OPLS analyses can be used to evaluate the contribution of each \u003cem\u003em/z\u003c/em\u003e feature, \u003cem\u003ei.e.\u003c/em\u003e of each detected metabolite, to the observed antioxidant activity (Tables\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, \u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab3\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eLists of metabolites that correlate with FRAP activity in \u003cem\u003eArtemisia\u003c/em\u003e spp. samples. Only metabolites with pq(corr)\u0026thinsp;\u0026gt;\u0026thinsp;0.85 are reported.\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"4\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003especies\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eID\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFRAP- correlating metabolites\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003epq(corr)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAab\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eChlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.95\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eAbsinthin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e29\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKaempherol-3-O-rutinoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.93\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCasticin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eTrihydroxytrimethoxyflavone\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e23\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKaempherol-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e85\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ePutative guaiane-type sesquiterpenoid dimer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e30\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eIsorhamnetin-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.87\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e84\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ePutative guaiane-type sesquiterpenoid dimer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.87\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAal\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e22\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eQuercetin-3-O-rutinoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e23\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKaempherol-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e29\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKaempherol-3-O-rutinoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.87\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAan\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.99\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e51\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.98\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.98\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.95\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e19\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.95\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e40\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eChlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e50\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e60\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e63\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDiferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAve\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e1.00\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.99\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e40\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e55\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNeochlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDihydroxybenzoic acid pentoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e39\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eApigenin-7-O-glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e26\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eMearnsetin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e23\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKaempherol-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e43\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eQuercetin-O-caffeoylhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAvu\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e1.00\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e1.00\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.99\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab4\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eLists of metabolites that correlate with DPPH activity in \u003cem\u003eArtemisia\u003c/em\u003e spp. samples. Only metabolites with pq(corr)\u0026thinsp;\u0026gt;\u0026thinsp;0.85 are reported.\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"4\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003especies\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eID\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDPPH \u0026ndash; correlating metabolites\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003epq(corr)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAab\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.85\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eChlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.85\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAal\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.90\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.90\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eChlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAan\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.98\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e40\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.98\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e21\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e19\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e50\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eChlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e51\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eTricaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.94\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e63\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDiferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.93\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e26\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eMearnsetin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.92\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e24\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eQuercetin-3-O-glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.90\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e36\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eIsorhamnetin-3-O-Glucoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e61\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.87\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e59\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCaffeoylferuloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAve\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e34\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.99\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.98\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e40\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.92\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e55\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.92\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e31\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eApigenin-O-hexoside-deoxyhexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.90\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNeochlorogenic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.89\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e19\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eFeruloylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.88\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e26\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eMearnsetin-O-hexoside\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eAvu\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e37\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDicaffeoylquinic acid isomer\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e0.86\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eConsistently to what observed in the previous paragraphs, the antioxidant activity of leaf extracts is in general higher than those of stem extracts (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e). This comparative analysis between the species, showed that the higher antioxidant activity of \u003cem\u003eA. verlotiorum\u003c/em\u003e, described in the previous paragraph, may be mainly due to caffeic and ferulic acid derivatives and flavonoids; also, various unidentified metabolite showed high correlation with antioxidant activity (data not shown). In \u003cem\u003eA. vulgaris\u003c/em\u003e the antioxidant activity correlated with caffeic acid derivatives, in A. \u003cem\u003eannua\u003c/em\u003e, with coumaric, caffeic and ferulic acid derivatives. In \u003cem\u003eA. alba\u003c/em\u003e, which showed the lowest linear correlation between metabolome composition and antioxidant activity (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e), also flavonoids were found to strongly correlate with antioxidant activity in FRAP assay, while the scavenging activity measured by DPPH was mostly correlated with dicaffeoylquinic acid isomers. Interestingly, coumarins accumulated at high levels in \u003cem\u003eA. alba\u003c/em\u003e but did not strongly correlate with the antioxidant activity. Finally, in \u003cem\u003eA. absinthium\u003c/em\u003e the antioxidant activity strongly correlated with caffeoylquinic acids, absinthin and flavonoids.\u003cdiv class=\"BlockQuote\"\u003e\u003cp\u003eThe hydroxycinnamates esterified with quinic acid, in particular some isomers of dicaffeoylquinic acid, were found to be metabolites with the strongest correlation with antioxidant activity in all species. This class of molecules has been extensively studied in the past years for their potential use in medicine. Caffeoylquinic acid derivatives are natural compounds isolated from a variety of traditional medicinal plants and possess a wide range of pharmacological properties, including antioxidant, hepatoprotective, antibacterial, antihistaminic and other biological effects [\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e]. Currently, in literature, caffeoyl and dicaffeoylquinic acids have been widely tested through \u003cem\u003ein vitro\u003c/em\u003e and \u003cem\u003ein vivo\u003c/em\u003e assays to evaluate their bioactive properties. Two caffeoylquinic acids extracted from \u003cem\u003eAronia melanocarpa\u003c/em\u003e berries, \u003cem\u003ei.e.\u003c/em\u003e 3-caffeoylquinic acid and 4-caffeoylquinic acid, were identified as inhibitor of the dipeptidyl peptidase IV, an enzyme involved in the development of type 2 diabetes mellitus [\u003cspan citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e]. The protective effect of chlorogenic acid against neurotoxic effect of arsenic poisoning was demonstrated in mice model [\u003cspan citationid=\"CR49\" class=\"CitationRef\"\u003e49\u003c/span\u003e]. Potential benefits with therapeutic applications were reported also for dicaffeoylquinic acids. For example, Kim and collaborators demonstrated the neuroprotective effect of 3,5-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid from \u003cem\u003eDipsacus asper\u003c/em\u003e on hydrogen peroxide-induced cell death in SH-SY5Y human cells [\u003cspan citationid=\"CR50\" class=\"CitationRef\"\u003e50\u003c/span\u003e]. In another study it is reported that 1,5-dicaffeoylquinic acid (cynarin) downregulates the expression of inducible nitric oxide synthase, expressed under conditions of inflammation, sepsis, or oxidative stress, in human coronary smooth muscle cells [\u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e51\u003c/span\u003e]. In addition, the dicaffeoyl quinic acid cynarin affects the survival, growth, and stress response of normal, immortalized, and cancerous human cells [\u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e52\u003c/span\u003e]. Protective effects of cynarin against hepatoxicity effects of cyclophosphamide, an important anticancer drug which belongs to the class of alkylating agents, as well as its antihypertensive and vasodilator effects have been observed in \u003cem\u003ein vivo\u003c/em\u003e studies [\u003cspan citationid=\"CR53\" class=\"CitationRef\"\u003e53\u003c/span\u003e, \u003cspan citationid=\"CR54\" class=\"CitationRef\"\u003e54\u003c/span\u003e]. \u003cem\u003eArtemisia\u003c/em\u003e spp., which were able to accumulate various isomers of caffeoyl- and dicaffeoylquinic acid, could thus represent a valuable source of these potentially bioactive compounds. A further characterization to reveal the precise identity of the various isomers accumulated by the five species is thus required.\u003c/p\u003e\u003c/div\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e6.4 Looking for a new artemisinin source\u003c/h2\u003e \u003cp\u003e \u003cdiv class=\"BlockQuote\"\u003e \u003cp\u003eThe sesquiterpene lactone artemisinin and its semi-synthetic derivatives are very important from a pharmaceutical perspective for their anti-malarial properties. Isolated from \u003cem\u003eA. annua\u003c/em\u003e plants, artemisinin earned in short time the status of most potent antimalarial drug and recently new evidence of many other bioactivities (e,g, anticancer, anti-inflammatory and antiviral) have emerged [\u003cspan citationid=\"CR55\" class=\"CitationRef\"\u003e55\u003c/span\u003e]. For this reason, a great interest arose in the search for artemisinin-rich \u003cem\u003eA. annua\u003c/em\u003e ecotypes and towards the manipulation of its biosynthetic pathway through different biotechnological tools [\u003cspan citationid=\"CR56\" class=\"CitationRef\"\u003e56\u003c/span\u003e]. Moreover, since antimalarial activity was reported for different \u003cem\u003eArtemisia\u003c/em\u003e species [\u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e], many studies have been conducted to find alternative natural sources for artemisinin within the \u003cem\u003eArtemisia\u003c/em\u003e genus. Despite artemisinin was demonstrated to occur in different amounts in \u003cem\u003eA. dubia\u003c/em\u003e [\u003cspan citationid=\"CR58\" class=\"CitationRef\"\u003e58\u003c/span\u003e], \u003cem\u003eA. scoparia\u003c/em\u003e [\u003cspan citationid=\"CR59\" class=\"CitationRef\"\u003e59\u003c/span\u003e], \u003cem\u003eA. cina\u003c/em\u003e [\u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e60\u003c/span\u003e], \u003cem\u003eA. vachanica\u003c/em\u003e and \u003cem\u003eA. dracunculus\u003c/em\u003e [\u003cspan citationid=\"CR61\" class=\"CitationRef\"\u003e61\u003c/span\u003e], \u003cem\u003eA. verlotiorum\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e [\u003cspan citationid=\"CR62\" class=\"CitationRef\"\u003e62\u003c/span\u003e], the major source of this metabolite still remains \u003cem\u003eA. annua\u003c/em\u003e [\u003cspan citationid=\"CR63\" class=\"CitationRef\"\u003e63\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003c/p\u003e \u003cp\u003eIn this work we explored the capacity of the \u003cem\u003eArtemisia\u003c/em\u003e plants collected in the province of Verona to produce the antimalaria lead drug artemisinin and related compounds from its biosynthesis pathway. We therefore performed an LC-MS analysis in positive ionization mode, which is more suitable for the ionization of sesquiterpenoid molecules, and we searched for the final products of the pathway (artemisinin and arteannuin B) and their immediate precursors (dihydroartemisinic acid and artemisinic acid, respectively). Their identification was made through the comparison of \u003cem\u003em/z\u003c/em\u003e values, fragmentation patterns and retention times with those of the respective reference standards (Table\u0026nbsp;\u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e). The relative comparison of their levels within the leaves of the five \u003cem\u003eArtemisia\u003c/em\u003e species is reported in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab5\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eMetabolites from the artemisinin pathway with their MS features searched in LC-MS ESI\u003csup\u003e+\u003c/sup\u003e analysis.\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"7\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eMetabolite\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eFormula\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eRt (min)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eNeutral\u003c/p\u003e \u003cp\u003emass (Da)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003e[M\u0026thinsp;+\u0026thinsp;Na]\u003csup\u003e+\u003c/sup\u003e\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eMS/MS\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eArteannuin B\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e20\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e12.14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e248.141\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e249.14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e271.131\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e231.138 [M\u0026thinsp;+\u0026thinsp;H-H\u003csub\u003e2\u003c/sub\u003eO];\u003c/p\u003e \u003cp\u003e185.134 [M\u0026thinsp;+\u0026thinsp;H-H\u003csub\u003e2\u003c/sub\u003eO-2CH\u003csub\u003e3\u003c/sub\u003e-O]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eArtemisinin\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e12.98\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e282.147\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e283.154\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e305.136\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e247.133 [M\u0026thinsp;+\u0026thinsp;H-2H\u003csub\u003e2\u003c/sub\u003eO]; \u003c/p\u003e \u003cp\u003e265.144 [M\u0026thinsp;+\u0026thinsp;H-H\u003csub\u003e2\u003c/sub\u003eO]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eArtemisinic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e14.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e234.162\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e235.169\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e217.159 [M\u0026thinsp;+\u0026thinsp;H-H\u003csub\u003e2\u003c/sub\u003eO];\u003c/p\u003e \u003cp\u003e199.149 [M\u0026thinsp;+\u0026thinsp;H-2H\u003csub\u003e2\u003c/sub\u003eO]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDihydroartemisinic acid\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e14.75\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e236.178\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e237.185\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e219.175 [M\u0026thinsp;+\u0026thinsp;H-H\u003csub\u003e2\u003c/sub\u003eO]\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"BlockQuote\"\u003e \u003cp\u003e \u003cem\u003eA. annua\u003c/em\u003e is the only species reporting detectable levels of artemisinin. Interestingly, the precursor of artemisinin, dihydroartemisinic acid, is present not only in \u003cem\u003eA. annua\u003c/em\u003e but also in \u003cem\u003eA. alba\u003c/em\u003e and \u003cem\u003eA. verlotiorum\u003c/em\u003e. Arteannuin B, the final metabolite of a parallel pathway that originates from artemisinic aldehyde, was detected at high levels in \u003cem\u003eA. annua\u003c/em\u003e and at considerably lower levels in \u003cem\u003eA. absinthium\u003c/em\u003e and \u003cem\u003eA. alba\u003c/em\u003e but was absent in \u003cem\u003eA. verlotiorum\u003c/em\u003e. The precursor of both arteannuin B and artemisinin, artemisinic acid, is present in \u003cem\u003eA. annua\u003c/em\u003e, as expected, but we did not detect it in \u003cem\u003eA. absinthium\u003c/em\u003e nor \u003cem\u003eA. alba\u003c/em\u003e, despite the fact that arteannuin B has been detected in both species. \u003cem\u003eA. vulgaris\u003c/em\u003e does not produce any of the metabolites from the selected pathway.\u003c/p\u003e \u003cp\u003eAccording to the literature, the presence of artemisinin has been recently reported in \u003cem\u003eA. verlotiorum\u003c/em\u003e [\u003cspan citationid=\"CR62\" class=\"CitationRef\"\u003e62\u003c/span\u003e], \u003cem\u003eA. absinthium\u003c/em\u003e [\u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e] and \u003cem\u003eA. vulgaris\u003c/em\u003e [\u003cspan citationid=\"CR62\" class=\"CitationRef\"\u003e62\u003c/span\u003e]. On the other hand, we reported for the first time the presence of artemisinin intermediates in \u003cem\u003eA. alba\u003c/em\u003e, thus furtherly increasing the number of sesquiterpene compounds (e.g. germacrane and eudesmane) that were previously reported in this species [\u003cspan citationid=\"CR64\" class=\"CitationRef\"\u003e64\u003c/span\u003e]. Although we did not detect traces of artemisinin, the presence of the precursor, dihydroartemisinic acid, and side product of the pathway, arteannuin B, indicates that genes of artemisinin biosynthetic pathway are all expressed in these plants, since the last step of artemisinin biosynthesis is a non-enzymatic photooxidative process [\u003cspan citationid=\"CR65\" class=\"CitationRef\"\u003e65\u003c/span\u003e]. One possible explanation for the absence of artemisinin could be the sampling time. It has been reported that peak in artemisinin content in \u003cem\u003eA. annua\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e corresponds to the budding stage, while for \u003cem\u003eA. absinthium\u003c/em\u003e maximum accumulation is reached during the flowering stage [\u003cspan additionalcitationids=\"CR67\" citationid=\"CR66\" class=\"CitationRef\"\u003e66\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR68\" class=\"CitationRef\"\u003e68\u003c/span\u003e]. All the plants used in this work were sampled during their vegetative stage. This could have prevented the artemisinin detection in species with lower levels of this metabolite. However, results obtained in this work strengthen the hypothesis that the artemisinin biosynthetic pathway may be an ancestral characteristic shared within plants belonging to \u003cem\u003eArtemisia\u003c/em\u003e [\u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003c/p\u003e \u003c/div\u003e"},{"header":"Experimental section","content":"\u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003e7.1 Plant material\u003c/h2\u003e \u003cp\u003eThe five selected \u003cem\u003eArtemisia\u003c/em\u003e species were sampled independently throughout three growing seasons in June of the years 2019, 2020, 2021 from three hills and mountain areas in the province of Verona. The formal identification of plant material was performed by Sebastiano Andreatta (from the \u0026ldquo;Museo di Storia Naturale\u0026rdquo; of Verona), the plants were given the barcode number and a voucher specimen of each species is available at the publicly available herbarium present in the \u0026ldquo;Museo di Storia Naturale\u0026rdquo; of Verona (Supplementary Table\u0026nbsp;3). Sampling complied with relevant institutional, national and international guidelines and legislations.\u003c/p\u003e \u003cp\u003eIn each sampling site, plants were collected from three distinct spots (\u003cem\u003ei.e.\u003c/em\u003e three different plant populations representing three biological replicates), far enough to avoid the sampling of plant populations deriving from the same genetic source. For each replicate, leaves and stems were collected from at least 5 individuals and pooled together according to the organ. The samples were immediately frozen in dry ice and then stored at -80\u0026deg;C. The frozen plant material was homogenized in liquid nitrogen using an IKA A11 basic mill (IKA, Germany).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003e7.2 Chemicals and reagents\u003c/h2\u003e \u003cp\u003eReference standard of artemisinin was purchased from Sigma-Aldrich (St. Louis, USA). Reference standards of arteannuin B and artemisinic acid were purchased from Biosynth\u0026reg; Carbosynth (Bratislava, Slovakia). Reference standard of dihydroartemisinic acid was purchased from Toronto Reasearch Chemical (Toronto, Canada). Methanol, acetonitrile and water (all LC-MS grade) were purchased from Honeywell (Charlotte, USA). Formic acid (LC-MS grade) was purchased from Biosolve Chimie (Dieuze, France). Trolox and DPPH were purchased, respectively, from Sigma-Aldrich and Thermo Fisher Scientific.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec10\" class=\"Section2\"\u003e \u003ch2\u003e7.3 Metabolites extraction\u003c/h2\u003e \u003cp\u003e100 mg of frozen powder were extracted in 1.5 ml methanol, mixed vigorously for 30 sec, sonicated at 40 KHz in an ultrasonic bath Sonica\u0026reg; Ultrasonic Cleaner (SOLTEC, Milan, Italy) at 4\u0026deg;C for 15 min and centrifuged (16000 \u003cem\u003eg\u003c/em\u003e, 15 min, 4\u0026deg;C). The supernatants were opportunely diluted in 100% methanol. Just before the analysis, the samples were diluted 1:2 (V:V) with ultrapure water (Honeywell, USA). The final mixtures were passed through Minisart RC4 filters (0.2 \u0026micro;m pores) (Sartorious, G\u0026ouml;ttingen, Germany) and 1 \u0026micro;l was injected into the UPLC device.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec11\" class=\"Section2\"\u003e \u003ch2\u003e7.4 UPLC-ESI-MS analysis\u003c/h2\u003e \u003cp\u003e \u003cdiv class=\"BlockQuote\"\u003e \u003cp\u003eAn Acquity I Class UPLC system (Waters, Milford, USA) with a BEH C18 column (Waters), coupled online with a PDA (photo-diode array) and to a Xevo G2-XS qTOF mass spectrometer (Waters), equipped with an electrospray ionization (ESI) source were used. The extracts were injected through a cooled autosampler (8\u0026deg;C) and a flow rate of 0.350 ml/min was used. The mobile phases were 0.1% formic acid in water (solvent A) and acetonitrile (solvent B), and the elution gradient was as follows: 0-1min, 1% B; 1\u0026ndash;10 min, 1 to 40% B ; 10-13.50 min, 40 to 70% B; 13.50\u0026ndash;15.00 min, 70 to 90% B; 15.00-16.50 min, 90 to 100% B; 16.50\u0026ndash;20 min 100% B; 20-20.1, 100 to 1% B; 20.1\u0026ndash;25 min, 1% B (initial conditions).\u003c/p\u003e \u003cp\u003eThe sample analysis sequence was randomized. A quality control (QC) prepared by mixing equal part of all the extracts was analyzed along the whole experiment every ten sample analysis. The ion source parameters were the following: capillary voltage 0.8 Kv, sampling cone voltage 40 V, source offset voltage 80 V, source temperature 120\u0026deg;C, desolvation temperature 500\u0026deg;C, cone gas flow rate 50 l/h and desolvation gas flow rate 1000 l/h. Nitrogen gas was used for the nebulizer and in desolvation whereas argon was used to generate collision-induced dissociation. MS data were acquired in continuum in both negative and positive ionization mode within the range 50-2000 \u003cem\u003em/z\u003c/em\u003e using a fixed collision energy of 35 V. Data were acquired through the Mass Lynx v4.2 software (Waters).\u003c/p\u003e \u003c/div\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec12\" class=\"Section2\"\u003e \u003ch2\u003e7.5 Processing of LC-MS data and metabolites identification\u003c/h2\u003e \u003cp\u003eThe chromatograms were manually inspected through Mass Lynx software. Metabolites were identified by relying on \u003cem\u003em/z\u003c/em\u003e value of the monoisotopic molecular ion, retention time and MS/MS fragmentation pattern by comparison with an in-house library of authentic standard. When no standard compounds were available, the identification was tentatively assigned comparing \u003cem\u003em/z\u003c/em\u003e, isotopic ratio, fragmentation pattern and UV/vis absorbance spectra with those reported in scientific literature and public databases (Chemspider, Human Metabolome Database, Lotus Natural Products, MassBank, MoNA, Pubchem, etc.). In particular, for the characterization of caffeoyl ester derivatives and various glycosides the following neutral losses (Da) were considered: 132.042 (pentose), 146.058 (deoxyhexose), 162.032 (caffeic acid moiety), 162.053 (hexose),\u003c/p\u003e \u003cp\u003eThe chromatograms acquired in negative ionization mode were processed with Progenesis QI software (Waters) to obtain the Feature Quantification Matrix (FQM; Supplementary File 1).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec13\" class=\"Section2\"\u003e \u003ch2\u003e7.6 Antioxidant assays\u003c/h2\u003e \u003cp\u003eThe same methanolic extracts used for UPLC-ESI-MS analysis were used for determination of antioxidant activity \u003cem\u003ein vitro\u003c/em\u003e by FRAP and DPPH assays in transparent 96-well microplates.\u003cdiv class=\"BlockQuote\"\u003e\u003cp\u003eA FRAP solution was prepared mixing in a ratio of 10:1:1 (V:V:V) the following reagents: FRAP buffer (3.1 g/l sodium acetate trihydrate, 16 ml/l acetic acid pH 3.6), 10 mM TPTZ (2,4,6-tri(2-pyridyl)-1,2,5-triazine) in HCl 40 Mm, FeCl\u003csub\u003e3\u003c/sub\u003e*6H\u003csub\u003e2\u003c/sub\u003eO 20Mm, The test was carried out mixing 200 \u0026micro;l of the FRAP solution to 20 \u0026micro;l of the sample, or solutions of Trolox at different concentrations or methanol (blank). Methanolic extracts of samples were diluted 1:20 for leaves and in a range from 1:3 to 1:10 for stems. Each sample was tested in three technical replicates. The microplate was incubated at 37\u0026deg;C in the dark for 15 min and then kept cooling at room temperature for 4 min. The absorbance was measured at 593 nm using the Infinite 200 PRO plate reader (Tecan, M\u0026auml;nnedorf, Switzerland).\u003c/p\u003e\u003cp\u003e1 mM DPPH stock solution was freshly prepared in methanol at least 2 hours before the assay. 100 \u0026micro;M of working solution was prepared diluting 1:10 (V:V) in 70% methanol the DPPH solution. 200 \u0026micro;l of the DPPH solution were added to 20 \u0026micro;l of the sample, \u003cem\u003ei.e.\u003c/em\u003e diluted plant extracts or solutions of Trolox at different concentrations or methanol (blank). Methanolic extracts were diluted in a range from 1:10 to 1:20 and from 1:3 to 1:10 for leaves and stems, respectively. Each sample was tested in three technical replicates. The microplate was incubated at 25\u0026deg;C in the dark for 30 min and then the absorbance was measured at 517 nm using the Infinite 200 PRO plate reader (Tecan).\u003c/p\u003e\u003cp\u003eThe compound Trolox, a water-soluble Vitamin E analogue, was used as reference antioxidant in order to express the antioxidant power of the plant extracts, expressed as Trolox Equivalent Antioxidant Capacity (TEAC), whose unit is mmol of Trolox Equivalent for Kg (mmol/kg). 20 \u0026micro;l of Trolox solutions with concentrations spanning from 500 \u0026micro;M to 5 \u0026micro;M was added to 200 \u0026micro;l of FRAP or DPPH solution to generate a Trolox calibration curve in each assay.\u003c/p\u003e\u003c/div\u003e\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec14\" class=\"Section2\"\u003e \u003ch2\u003e7.7 Statistical analysis\u003c/h2\u003e \u003cp\u003eThe FQM and antioxidant (TEAC values) data were analyzed with SIMCA-P software (Umetrics, Sweden) for multivariate statistical analysis in order to look for relationships among the in-vitro antioxidant activity of the plant extracts and their metabolite composition. The \u003cem\u003em/z\u003c/em\u003e features (i.e. the metabolites) of the dataset were assigned as X variables (Pareto scaling) and the antioxidant activity as Y variables (UV scaling). Orthogonal Partial Least Square (OPLS) analysis was used. Metabolites putatively responsible for the antioxidant activity were identified by inspection of the column loading plot; only metabolites showing a pq(corr) value\u0026thinsp;\u0026gt;\u0026thinsp;0.8 (arbitrary threshold) were considered correlated with antioxidant activity. All statistical calculations were performed using the GraphPad Prism version 8.0 software (GraphPad Software, San Diego, California USA). The means values\u0026thinsp;\u0026plusmn;\u0026thinsp;SD (n\u0026thinsp;=\u0026thinsp;3) are reported in the figures. Statistical analyses were conducted using One or Two-way Anova followed by Tukey\u0026rsquo;s Test.\u003c/p\u003e \u003c/div\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgments\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis work was funded by European UNion - NextGenerationEU in the framework of \u0026nbsp;National Biodiversity Future Center and by the University of Verona with the call \u0026ldquo;Joint Project 2019\u0026rdquo;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflict of interest\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare no conflict of interest.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData Availability\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAll data generated or analysed during this study are included in this published article [and its supplementary information files]\u003c/strong\u003e\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eOyemitan IA. 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Molecules 2022;27:2314. https://doi.org/10.3390/molecules27072314.\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Artemisia spp., bioprospection, antioxidants, dicaffeoylquinic acids, sesquiterpenes, artemisinin","lastPublishedDoi":"10.21203/rs.3.rs-3604409/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-3604409/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eSpecies from genus \u003cem\u003eArtemisia\u003c/em\u003e are widely distributed throughout temperate regions of the northern hemisphere and many cultures have a long-standing traditional use of these plants as herbal remedies, liquors, cosmetics, spices, etc. Nowadays, the discovery of new plant-derived products to be used as food supplements or drugs has been pushed by the exploitation of bioprospection approaches. Often driven by the knowledge derived from the ethnobotanical use of plants, bioprospection explores the existing biodiversity through integration of modern omics techniques with targeted bioactivity assays.\u003c/p\u003e\n\u003cp\u003eIn this work we set up a bioprospection plan to investigate the phytochemical diversity and the potential bioactivity of five \u003cem\u003eArtemisia\u003c/em\u003especies with recognized ethnobotanical tradition (\u003cem\u003eA. absinthium\u003c/em\u003e, \u003cem\u003eA. alba\u003c/em\u003e, \u003cem\u003eA. annua\u003c/em\u003e, \u003cem\u003eA. verlotiorum\u003c/em\u003e and \u003cem\u003eA. vulgaris\u003c/em\u003e), growing wild in the natural areas of the Verona province. We characterized the specialized metabolomes of the species (including sesquiterpenoids from the artemisinin biosynthesis pathway) through an LC-MS based untargeted approach and, in order to identify potential bioactive metabolites, we correlated their composition with the \u003cem\u003ein vitro\u003c/em\u003e antioxidant activity. We propose as potential bioactive compounds several isomers of caffeoyl and feruloyl quinic acid esters (e.g. dicaffeoylquinic acids, feruloylquinic acids and caffeoylferuloylquinic acids), which strongly characterize the most antioxidant species \u003cem\u003eA. verlotiorum\u003c/em\u003e and \u003cem\u003eA. annua\u003c/em\u003e. Morevoer, in this study we report for the first time the occurrence of sesquiterpenoids from the artemisinin biosynthesis pathway in the species \u003cem\u003eA. alba\u003c/em\u003e.\u003c/p\u003e","manuscriptTitle":"Bioprospecting of Artemisia genus: from artemisinin to other potentially bioactive compounds","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2023-11-17 18:43:04","doi":"10.21203/rs.3.rs-3604409/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2024-01-24T10:15:46+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-01-23T10:03:39+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-01-11T10:47:41+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"3010eb82-957e-42b5-8860-4b767057b17c","date":"2024-01-09T17:16:14+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"bb571818-7266-45a5-8fa0-4f41fc0cbfb6","date":"2023-12-27T10:36:00+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2023-12-21T11:11:58+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2023-12-13T11:04:01+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2023-11-15T12:44:00+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2023-11-15T12:39:52+00:00","index":"","fulltext":""},{"type":"submitted","content":"Scientific Reports","date":"2023-11-13T09:52:50+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"12c73e7b-0b8e-4179-9949-373a6f7ee84b","owner":[],"postedDate":"November 17th, 2023","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[{"id":26353445,"name":"Biological sciences/Chemical biology/Metabolomics"},{"id":26353446,"name":"Biological sciences/Plant sciences"}],"tags":[],"updatedAt":"2024-03-04T15:15:39+00:00","versionOfRecord":{"articleIdentity":"rs-3604409","link":"https://doi.org/10.1038/s41598-024-55128-z","journal":{"identity":"scientific-reports","isVorOnly":false,"title":"Scientific Reports"},"publishedOn":"2024-02-27 15:01:55","publishedOnDateReadable":"February 27th, 2024"},"versionCreatedAt":"2023-11-17 18:43:04","video":"","vorDoi":"10.1038/s41598-024-55128-z","vorDoiUrl":"https://doi.org/10.1038/s41598-024-55128-z","workflowStages":[]},"version":"v1","identity":"rs-3604409","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-3604409","identity":"rs-3604409","version":["v1"]},"buildId":"rHA-KDH7Qsr4HCuvH75dn","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}