Identification of two new acetylated Iridoids from Scrophularia umbrosa rhizome

Identification of two new acetylated Iridoids from Scrophularia umbrosa rhizome | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Identification of two new acetylated Iridoids from Scrophularia umbrosa rhizome Elhameh Nikkhah, Abbas Delazar, Maryam Saadat This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4268794/v1 This work is licensed under a CC BY 4.0 License Status: Under Review Version 1 posted 3 You are reading this latest preprint version Abstract Scrophularia umbrosa is a medicinal plant used as a traditional herb. This plant is one of the native species of Iran and consists of about 200 species of herbaceous flowering plants, commonly known as ‘figwort’. Many iridoid glycosides have been found in the Scrophularia genus. In this research work the methanolic extracts of Scrophularia umbrosa (S. umbrosa) rhizome was studied. For this first methanolic extract of rhizome powder was subjected to the HPLC in which two materials was detected in 220 nm and was separated. In continue 1D and 2D NMR technique has been employed for the identification of the active components. finally phytochemical investigations of the S. umbrosa rhizome indicate the presence of two new acetylated iridoid glycosides, 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin. HNMR and CNMR were the main apparatuse to identification of these compounds which has been shown medicinal property, in rhizome of Scrophularia umbrosa. Scrophularia umbrosa iridoids HPLC NMR. Figures Figure 1 Figure 2 1. Introduction Multitude plants from the Scrophularia genus have been used as medicinal herbs in Asian countries. Water figwort with the scientific name “ Scrophularia umbrosa Dumort ” is one of the native species of the Scrophularia genus from Iran. The species of Scrophularia are distributed in the north-west, west, north, north-east, central mountainous region, and scarcely south of Iran [ 1 ]. Chemotaxonomic studies are useful as markers of several genera in various plant families, such as aucuboside and harpagide of Scrophularia (Scrophulariaceae) [ 2 ]. Iridoids, natural heterocyclic monoterpenoids, are secondary metabolites of herbal Flora and nautical fauna, which are widely distributed in herbs, medicinal and ornamental plants, particularly in their green parts. They have also found in some edible fruits, such as berries, noni, olive, Japanese cornel, haskap berry, kousa dogwood, cornelian cherry, and guelder rose [ 3 ]. Iridoids are found in a large number of plant families usually as glycosides [ 4 ]. Their presence has also been reported in insects. Iridodial is a substance which are produced by the Iridomyrmex detectus ants, the source from which the name ‘iridoids’ is derived [ 3 , 5 ]. As safe materials, they can be used in healthy diet, disease treatment and prevention, which showed significance properties such as antioxidative, antidiabetic, neuroprotective, anti-inflammatory, anti-atherogenic, antihypertensive, anti-depression, cardioprotective, liver-protecting, anti-cancer, antimicrobial activity and etc [ 3 , 5 – 11 ]. In addition, they have a listed application in cosmetic preparations [ 12 ]. Moreover, in vitro , in vivo , and clinical studies suggests they may help limit the aging and general tissue damage [ 3 ]. Because of their poor chemical stability, they are highly susceptible to degradation, which has limited their identification, extraction, functions and activities. Therefore, comparative studies and analysis on the function and structure of iridoids are challenging and difficult [ 11 ]. In the present study conducted on this species of Scrophularia , we report the isolation and structural elucidation of two new acetylated iridoids. 2. Material and Methods 2.1. Chemicals HPLC grade methanol (MeOH) is the only chemical used in this work and it was purchased from Merck (sigma-Aldrich, USA). Tri-distilled water was used throughout the experiments. 2.2. Plant Material The plant material was collected as our previously described method [ 13 ]. Briefly, the rhizome parts of Scrophularia umbrosa were collected during the flowering period from Mishodaghi Mountain in East Azarbaijan province. The plant's identity was confirmed by anatomical examination compared with the herbarium specimens (voucher Nos. Tbz-Fph-762) retained in the Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran [ 13 ]. 2.3. Extraction All extraction and fractionation processes are performed according to our previously described paper [ 14 ]. Briefly, 100 g of the dried and ground rhizomes of mentioned plant were extracted in MeOH using Soxhlet and then concentrated by rotary evaporator at 45 ºC. 2.4. HPLC method of fractionation To isolate phytochemicals of methanolic extract, they were subjected to reversed phase preparative HPLC (preparative pump 1800, Knauer, Germany), with a photodiode array detector (PDA), under the following conditions: a Reprosil 100 C18 (250 mm length, 20 mm i.d, particle size 10 µm, Dr. Maisch, Germany) column and the mobile phase of MeOH: water (60:40) was applied for 60% sep-pak fraction in a 55 min run at a flow rate of 8 mL/min and a detection wavelength of 220 nm. 2.5. Identification Bruker Spectrospin 400 MHz NMR-spectrometer was used for HNMR and CNMR characterization of pure compounds. The information obtained is as follows: Compound No.1: H- NMR (400MHz, DMSO): δ 5 (s, 1H, H-1), 6.37 (d, 1H, J = 5.83 Hz, H-3), 5.16 (bdd, 1H, H-4), 2.80 (s,1H, H-5), 4.44 (s,1H, H-6), 5.82 (s, 1H, H-7), 2.80 (s, 1H, H-9), 4.16 (b, 1H, H-10a), 4.20 (b, 1H, H-10b), 4.5 (d, 1H, J = 7.9 Hz, H-1'), 4.83 (m, 1H, H-1''), 5.22 (dd, 1H, J = 10.18 and 3.4 Hz, H-2''), 1.17 (d, 1H, J = 6.12 Hz, H-6''), 7.7 (d, 1H, H-2'''), 7.43 (1H, H-3'''), 7.43 (1H, H-4'''), 7.43 (1H, H-5'''), 7.7 (d, 1H, H-6'''), 6.55 (d, 1H, J = 16 Hz, H-7'''), 7.58 (d, 1H, J = 16 Hz, H-8'''), 2.01 (s, 3H, H-Acyl), 2.12 (s, 3H, H-Acyl). Compound No.1: C NMR spectral data (DMSO):95.29 (C-1), 140.78 (C-3), 104.07 (C-4), 42.00 (C-5), 87.57(C-6), 124.67 (C-7), 149.8 (C-8), 46.83(C-9), 59.53(C-10), 98.02(C-1'), 73.41(C-2'), 76.63 (C-3'), 70.09 (C-4'), 77.25 (C-5'), 61.00 (C-6'), 96.29(C-1''), 68.88 (C-2''), 69.38 (C-3''), 70.44 (C-4''), 66.26 (C-5''), 17.39(C-6''), 133.72 (C-1'''), 129.04 (C-2'''), 128.65 (C-3'''), 130.89 (C-4'''), 128.65 (C-5'''), 129.04 (C-6'''), 117.03 (C-7'''), 145.67 (C-8'''), 165.38(C-C = O), 169.71 and 20.58(C-Acyl1), 169.83 and 20.72 (C-Acyl). Compound No.2: 1H- NMR (400MHz, DMSO): δ 4.84 (s, 1H, H-1), 6.37 (d, 1H, J = 5.8 Hz, H-3), 5.05 (m, 1H, H-4), 2.81 (s,1H, H-5), 4.44 (s,1H, H-6), 5.82 (s, 1H, H-7), 2.81 (s, 1H, H-9), 4.17 (b, 1H, H-10a), 4.20 (b, 1H, H-10b), 4.5 (d, 1H, J = 7.8 Hz, H-1'), 4.99 (b, 1H, H-1''), 5.16 (dd, 1H, J = 10.18 and 3.1 Hz, H-2''), 1.14 (d, 1H, J = 6.05 Hz, H-6''), 7.69 (d, 1H, J = 8.9 Hz, H-2'''), 6.97 (d, 1H, J = 8.6 Hz, H-3'''), 6.97 (d, 1H, J = 8.6 Hz, H-5'''), 7.69 (d, 1H, J = 8.9 Hz, H-6'''), 6.49 (d, 1H, J = 16 Hz, H-7'''), 7.66 (d, 1H, J = 16 Hz, H-8'''), 3.79 (s, 3H, H-OMe), 1.88 (s, 3H, H-Acyl), 2.11 (s, 3H, H-Acyl). Compound No.2: C NMR spectral data (DMSO): 95.35 (C-1), 140.82 (C-3), 104.08 (C-4), 42.07 (C-5), 87.66(C-6), 124.74 (C-7), 149.77 (C-8), 46.86(C-9), 59.56(C-10), 98.02(C-1'), 73.43(C-2'), 76.65 (C-3'), 70.09 (C-4'), 77.27 (C-5'), 61.05 (C-6'), 96.36(C-1''), 68.85 (C-2''), 69.3 (C-3''), 70.09 (C-4''), 66.42 (C-5''), 17.42(C-6''), 126.47 (C-1'''), 130.51 (C-2'''), 114.47 (C-3'''), 161.43 (C-4'''), 114.47 (C-5'''), 130.51 (C-6'''), 113.6 (C-7'''), 145.66 (C-8'''), 165.79(C-C = O), 55.41(C-OMe), 169.8 and 20.52(C-Acyl1), 169.86 and 20.74 (C-Acyl). 3. Results and Discussion The chemical structures of two compounds which shown in Fig. 1 were established mainly by spectroscopic methods. Compound No.1 was obtained as a yellow solid and compound No.2 was achieved as a brownish yellow solid. A comparison of their 1 H and 13 CNMR spectra indicated that the structure of compound No.1 is the same as No.2 without the methoxy group. According to 1 H-NMR spectrum of compound No.1, the presence of two trans olefinic protons with δ H 6.55 (d, J = 16 Hz) and δ H 7.58 (d, J = 16 Hz), and also the peaks with 2-proton integration of δ H 7.72 (m) represents the positions of 2 and 6 in the benzene ring. Moreover, chemical shift of δ H 7.41–7.43 (3H) indicates the positions of 3, 4, and 5 in the benzene rings. In general, these observations indicate the presence of a no substitutions in the positions of 2, 3, 4, 5, and 6 of benzene ring. As illustrated in 1 H-NMR spectrum of compound No.2, the presence of two pairs of ortho coupled aromatic protons of δ H 7.69 (d, J = 8.9 Hz) and δ H 6.97 (d, J = 8.6 Hz), two trans olefinic protons of δ H 6.49 (d, J = 16 Hz) and δ H 7.66 (d, J = 16 Hz), and one aromatic methoxy group of δ H 3.79 clearly prove that the acyl moiety is the trans-p-methoxycinnamoyl group. The presence of two peaks of δ H 1.88 (s) and δ H 2.11 (s) in the 1 H-NMR spectrum of compound No.2, represents presence of two acetyl groups; which were indicated by two peaks of δH 2.01 (s) and δH 2.12 (s) in the 1H-NMR spectrum of compound No.1. To identify the position of these acetyl groups, 2DNMR complementary spectra of HMBC and HSQC method was applied. According to Fig. 2 , two groups of acetyls are located on carbon 2 and carbon 3 of rhamnose. So, the site of esterification was determined to be the 4"-position of the ramnopyranosyl moiety in two compounds. As a result, the structure of the new compound No.1 was introduced as 6-O [2', 3' diacyl-4'-O-Trans -cynamoyl]-α-L-rhamnopyranosyl-aucubin and the structure of the compound No.2 was determined as be6-O [2', 3' diacyl-4'-O- trans- p-methoxycinamoyl]-α-L rhamnopyranosyl-aucubin. Based on the spectrum data and suggested structure, compound No.2 is derived from a compound known as unbuloside [ 15 , 16 ]. Moreover, the extracted information from the HSQC and HMBC spectra of Compound No. 2 are presented in Table 1 . Table 2 shows the iridoids and other materials which were extracted and identified according to previously reported documents. This data shows that the substances reported in this work are extracted and identified for the first time and similar case of these compounds was not found in literature. Table 1 Extracted information from the HSQC and HMBC spectra of Compound No. 2 in the CHD 3 O solvent HMBC** HSQC* 3 J CH 2 J CH δ C (ppm) δ H (ppm) 1 C-5, C-3, C-8, C-4, C-1´ C-9 96.76 4.97 3 C-5,C-1 C-4 140.58 6.37 4 C-6,C-1, C-9 C-5, C-3 103.77 5.15 5 - - 42.62 2.92 6 - - 88.36 4.5 7 C-5, C-9 C-8 125.28 5.92 8 - - 148.82 - 9 C-7 C-8,C-5,C-1 46.67 2.98 a10 C-7 C-8 59.90 4.22 b10 C-7 C-8 - 4.40 ´1 - C-2´ 98.46 4.71 ´2 - - 73.42 3.25 ´3 - C-4´ 76.38 3.4 ´4 - C-5´, C-3´ 70.06 3.30 ´5 - - 76.74 3.33 a´6 - C-5´ 61.1 3.66 b´6 - C-5´ - 3.88 ´´1 C-6, C-5´´, C-3´´ C-2´´ 96.76 4.96 ´´2 C-4´´, C acetyl - 69.22 5.33 ´´3 C acetyl C-4´´ 69.9 5.23 ´´4 C-2´´, C-6´´, C-9´´´ C-3´´ 70.59 5.17 ´´5 - C-4´´, C-6´´ 66.81 4.1 ´´6 C-4´´ - 16.38 1.25 ´´´1 - - 126.69 - ´´´2 C-4´´´, β - 129.78 7.59 ´´´3 C-1´´´ C-4´´´ 114.04 6.98 ´´´4 - - 161.96 - ´´´5 C-1´´´ C-4´´´ 114.04 6.98 ´´´6 C-4´´´, β - 129.78 7.59 α C-1´´´ β, C-9´´´ 113.51 6.39 β C-2´´´, C-6´´´, C-9´´´ α 145.97 7.69 C = O - - 166.52 - MeO C-4´´´ - 54.41 3.85 Acetyl - - 169.86 - - - 19.15 1.94 Acetyl - - 169.798 - - C = O 19.26 2.18 *(Heteronuclear Single-Quantum Correlation) ** (Heteronuclear Multiple Bond Correlation) Table 2 the compounds which were extracted from Scrophularia umbrosa according to reported literature Name of compound (s) Extraction solvent Part of plant Ref. Aucubin, lamalbide methanol Rhizome [ 17 ] Essential oil methanol aerial parts [ 1 ] Umbrosides, iridoid glycosides, phenylethanoid glycosides 40% ethanol whole plant [ 18 ] Aucubin, Luteolin-7-O-Rutinoside Methanol, DCM Aerial Parts and Seed [ 19 ] Unduloside methanol aerial parts [ 20 ] Conclusion In conclusion according to information obtained from HPLC, HNMR, CNMR, HSQC, and HMBC, two new acetylated Iridoids named from methanolic extraction of Scrophularia umbrosa rhizome were extracted and identified successfully. These materials are called 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin (No.1) and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin (No.2). Conclusion In conclusion according to information obtained from HPLC, HNMR, CNMR, HSQC, and HMBC, two new acetylated Iridoids named from methanolic extraction of Scrophularia umbrosa rhizome were extracted and identified successfully. These materials are called 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin (No.1) and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin (No.2). Declarations Acknowledgments This article has written based on a Ph.D. thesis registered in Drug Applied Research Center of Tabriz University of Medical Sciences (No. 91.75). My grateful thanks are extended to Mrs. Dr. asnaashari, for her advice and assistance in keeping my progress on schedule. I also thank the pharmacognosy laboratory technician (Mrs. Bamed) for helping to provide resources for the implementation of the program. Competing interests: The authors declare there are no competing interests. Funding Declaration Drug Applied Research Center of Tabriz University of Medical Sciences, Iran, grant number: 91.75 Data availability No datasets were generated or analyzed during the current study. References Nikkhah, E., S. Asnaashari, H. Babaei, F. Heshmati Afshar, and A. 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Nikkhah, E., F. Heshmati Afshar, H. Babaei, P. Asgharian, and A. Delazar, Iran J Pharm Res , 2018. 17(2): p. 685-694. Han, M.-F., X. Zhang, L.-Q. Zhang, and Y.-M. Li, Phytochemistry Letters , 2018. 28: p. 37-41, https://doi.org/10.1016/j.phytol.2018.09.011. Nikkhah, E., F. Heshmati Afshar, H. Babaei, A. Delazar, and P. Asgharian, Jundishapur J Nat Pharm Prod , 2018. 13(2): p. e65054, 10.5812/jjnpp.65054. Skaltsounis, A.L., E. Tsitsa-Tzardis, C. Demetzos, and C. Harvala, Journal of Natural Products , 1996. 59(7): p. 673-675, 10.1021/np960181b. Additional Declarations No competing interests reported. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-4268794","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":295031926,"identity":"651262a0-907c-4063-8948-a50852732a75","order_by":0,"name":"Elhameh Nikkhah","email":"","orcid":"","institution":"Maragheh University of medical science","correspondingAuthor":false,"prefix":"","firstName":"Elhameh","middleName":"","lastName":"Nikkhah","suffix":""},{"id":295031928,"identity":"25f3d048-f54b-44bf-8704-86726107325d","order_by":1,"name":"Abbas Delazar","email":"","orcid":"","institution":"Tabriz University of Medical Sciences","correspondingAuthor":false,"prefix":"","firstName":"Abbas","middleName":"","lastName":"Delazar","suffix":""},{"id":295031930,"identity":"48a8a478-34c1-4533-8428-ad19e73d9707","order_by":2,"name":"Maryam Saadat","email":"data:image/png;base64,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","orcid":"","institution":"Maragheh University of medical science","correspondingAuthor":true,"prefix":"","firstName":"Maryam","middleName":"","lastName":"Saadat","suffix":""}],"badges":[],"createdAt":"2024-04-15 09:47:58","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-4268794/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-4268794/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":55534500,"identity":"56397818-dcaf-4cfe-be2b-83db3de44a16","added_by":"auto","created_at":"2024-04-29 16:17:39","extension":"jpg","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":51216,"visible":true,"origin":"","legend":"\u003cp\u003eStructure of 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin (No.1) and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin (No.2)\u003c/p\u003e","description":"","filename":"1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-4268794/v1/aa5003b33d7a040d03705c23.jpg"},{"id":55534501,"identity":"077d486d-7da5-471d-b267-df6af87fe31a","added_by":"auto","created_at":"2024-04-29 16:17:39","extension":"jpg","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":23547,"visible":true,"origin":"","legend":"\u003cp\u003eHMBC spectra of Compound No. 2 in the CHD\u003csub\u003e3\u003c/sub\u003eO solvent\u003c/p\u003e","description":"","filename":"2.jpg","url":"https://assets-eu.researchsquare.com/files/rs-4268794/v1/a858692c3366d6dc889b3446.jpg"},{"id":55535759,"identity":"b85597d0-3dbc-463f-82fb-d7eb9fad9fb0","added_by":"auto","created_at":"2024-04-29 16:25:40","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":310867,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4268794/v1/9c00db2a-0158-4076-ae24-2d7ebee2d1f8.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Identification of two new acetylated Iridoids from Scrophularia umbrosa rhizome","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eMultitude plants from the \u003cem\u003eScrophularia\u003c/em\u003e genus have been used as medicinal herbs in Asian countries. Water figwort with the scientific name \u0026ldquo;\u003cem\u003eScrophularia umbrosa Dumort\u003c/em\u003e\u0026rdquo; is one of the native species of the \u003cem\u003eScrophularia\u003c/em\u003e genus from Iran. The species of \u003cem\u003eScrophularia\u003c/em\u003e are distributed in the north-west, west, north, north-east, central mountainous region, and scarcely south of Iran [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e]. Chemotaxonomic studies are useful as markers of several genera in various plant families, such as aucuboside and harpagide of \u003cem\u003eScrophularia\u003c/em\u003e (Scrophulariaceae) [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eIridoids, natural heterocyclic monoterpenoids, are secondary metabolites of herbal Flora and nautical fauna, which are widely distributed in herbs, medicinal and ornamental plants, particularly in their green parts. They have also found in some edible fruits, such as berries, noni, olive, Japanese cornel, haskap berry, kousa dogwood, cornelian cherry, and guelder rose [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e]. Iridoids are found in a large number of plant families usually as glycosides [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Their presence has also been reported in insects. Iridodial is a substance which are produced by the \u003cem\u003eIridomyrmex detectus\u003c/em\u003e ants, the source from which the name \u0026lsquo;iridoids\u0026rsquo; is derived [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e, \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eAs safe materials, they can be used in healthy diet, disease treatment and prevention, which showed significance properties such as antioxidative, antidiabetic, neuroprotective, anti-inflammatory, anti-atherogenic, antihypertensive, anti-depression, cardioprotective, liver-protecting, anti-cancer, antimicrobial activity and etc [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e, \u003cspan additionalcitationids=\"CR6 CR7 CR8 CR9 CR10\" citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e]. In addition, they have a listed application in cosmetic preparations [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e]. Moreover, \u003cem\u003ein vitro\u003c/em\u003e, \u003cem\u003ein vivo\u003c/em\u003e, and clinical studies suggests they may help limit the aging and general tissue damage [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eBecause of their poor chemical stability, they are highly susceptible to degradation, which has limited their identification, extraction, functions and activities. Therefore, comparative studies and analysis on the function and structure of iridoids are challenging and difficult [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e]. In the present study conducted on this species of \u003cem\u003eScrophularia\u003c/em\u003e, we report the isolation and structural elucidation of two new acetylated iridoids.\u003c/p\u003e"},{"header":"2. Material and Methods","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1. Chemicals\u003c/h2\u003e \u003cp\u003eHPLC grade methanol (MeOH) is the only chemical used in this work and it was purchased from Merck (sigma-Aldrich, USA). Tri-distilled water was used throughout the experiments.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2. Plant Material\u003c/h2\u003e \u003cp\u003eThe plant material was collected as our previously described method [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. Briefly, the rhizome parts of Scrophularia umbrosa were collected during the flowering period from Mishodaghi Mountain in East Azarbaijan province. The plant's identity was confirmed by anatomical examination compared with the herbarium specimens (voucher Nos. Tbz-Fph-762) retained in the Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3. Extraction\u003c/h2\u003e \u003cp\u003eAll extraction and fractionation processes are performed according to our previously described paper [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e]. Briefly, 100 g of the dried and ground rhizomes of mentioned plant were extracted in MeOH using Soxhlet and then concentrated by rotary evaporator at 45 \u0026ordm;C.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e2.4. HPLC method of fractionation\u003c/h2\u003e \u003cp\u003eTo isolate phytochemicals of methanolic extract, they were subjected to reversed phase preparative HPLC (preparative pump 1800, Knauer, Germany), with a photodiode array detector (PDA), under the following conditions: a Reprosil 100 C18 (250 mm length, 20 mm i.d, particle size 10 \u0026micro;m, Dr. Maisch, Germany) column and the mobile phase of MeOH: water (60:40) was applied for 60% sep-pak fraction in a 55 min run at a flow rate of 8 mL/min and a detection wavelength of 220 nm.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e2.5. Identification\u003c/h2\u003e \u003cp\u003eBruker Spectrospin 400 MHz NMR-spectrometer was used for HNMR and CNMR characterization of pure compounds. The information obtained is as follows:\u003c/p\u003e \u003cp\u003eCompound No.1: H- NMR (400MHz, DMSO): δ 5 (s, 1H, H-1), 6.37 (d, 1H, J\u0026thinsp;=\u0026thinsp;5.83 Hz, H-3), 5.16 (bdd, 1H, H-4), 2.80 (s,1H, H-5), 4.44 (s,1H, H-6), 5.82 (s, 1H, H-7), 2.80 (s, 1H, H-9), 4.16 (b, 1H, H-10a), 4.20 (b, 1H, H-10b), 4.5 (d, 1H, J\u0026thinsp;=\u0026thinsp;7.9 Hz, H-1'), 4.83 (m, 1H, H-1''), 5.22 (dd, 1H, J\u0026thinsp;=\u0026thinsp;10.18 and 3.4 Hz, H-2''), 1.17 (d, 1H, J\u0026thinsp;=\u0026thinsp;6.12 Hz, H-6''), 7.7 (d, 1H, H-2'''), 7.43 (1H, H-3'''), 7.43 (1H, H-4'''), 7.43 (1H, H-5'''), 7.7 (d, 1H, H-6'''), 6.55 (d, 1H, J\u0026thinsp;=\u0026thinsp;16 Hz, H-7'''), 7.58 (d, 1H, J\u0026thinsp;=\u0026thinsp;16 Hz, H-8'''), 2.01 (s, 3H, H-Acyl), 2.12 (s, 3H, H-Acyl).\u003c/p\u003e \u003cp\u003eCompound No.1: C NMR spectral data (DMSO):95.29 (C-1), 140.78 (C-3), 104.07 (C-4), 42.00 (C-5), 87.57(C-6), 124.67 (C-7), 149.8 (C-8), 46.83(C-9), 59.53(C-10), 98.02(C-1'), 73.41(C-2'), 76.63 (C-3'), 70.09 (C-4'), 77.25 (C-5'), 61.00 (C-6'), 96.29(C-1''), 68.88 (C-2''), 69.38 (C-3''), 70.44 (C-4''), 66.26 (C-5''), 17.39(C-6''), 133.72 (C-1'''), 129.04 (C-2'''), 128.65 (C-3'''), 130.89 (C-4'''), 128.65 (C-5'''), 129.04 (C-6'''), 117.03 (C-7'''), 145.67 (C-8'''), 165.38(C-C\u0026thinsp;=\u0026thinsp;O), 169.71 and 20.58(C-Acyl1), 169.83 and 20.72 (C-Acyl).\u003c/p\u003e \u003cp\u003eCompound No.2: 1H- NMR (400MHz, DMSO): δ 4.84 (s, 1H, H-1), 6.37 (d, 1H, J\u0026thinsp;=\u0026thinsp;5.8 Hz, H-3), 5.05 (m, 1H, H-4), 2.81 (s,1H, H-5), 4.44 (s,1H, H-6), 5.82 (s, 1H, H-7), 2.81 (s, 1H, H-9), 4.17 (b, 1H, H-10a), 4.20 (b, 1H, H-10b), 4.5 (d, 1H, J\u0026thinsp;=\u0026thinsp;7.8 Hz, H-1'), 4.99 (b, 1H, H-1''), 5.16 (dd, 1H, J\u0026thinsp;=\u0026thinsp;10.18 and 3.1 Hz, H-2''), 1.14 (d, 1H, J\u0026thinsp;=\u0026thinsp;6.05 Hz, H-6''), 7.69 (d, 1H, J\u0026thinsp;=\u0026thinsp;8.9 Hz, H-2'''), 6.97 (d, 1H, J\u0026thinsp;=\u0026thinsp;8.6 Hz, H-3'''), 6.97 (d, 1H, J\u0026thinsp;=\u0026thinsp;8.6 Hz, H-5'''), 7.69 (d, 1H, J\u0026thinsp;=\u0026thinsp;8.9 Hz, H-6'''), 6.49 (d, 1H, J\u0026thinsp;=\u0026thinsp;16 Hz, H-7'''), 7.66 (d, 1H, J\u0026thinsp;=\u0026thinsp;16 Hz, H-8'''), 3.79 (s, 3H, H-OMe), 1.88 (s, 3H, H-Acyl), 2.11 (s, 3H, H-Acyl).\u003c/p\u003e \u003cp\u003eCompound No.2: C NMR spectral data (DMSO): 95.35 (C-1), 140.82 (C-3), 104.08 (C-4), 42.07 (C-5), 87.66(C-6), 124.74 (C-7), 149.77 (C-8), 46.86(C-9), 59.56(C-10), 98.02(C-1'), 73.43(C-2'), 76.65 (C-3'), 70.09 (C-4'), 77.27 (C-5'), 61.05 (C-6'), 96.36(C-1''), 68.85 (C-2''), 69.3 (C-3''), 70.09 (C-4''), 66.42 (C-5''), 17.42(C-6''), 126.47 (C-1'''), 130.51 (C-2'''), 114.47 (C-3'''), 161.43 (C-4'''), 114.47 (C-5'''), 130.51 (C-6'''), 113.6 (C-7'''), 145.66 (C-8'''), 165.79(C-C\u0026thinsp;=\u0026thinsp;O), 55.41(C-OMe), 169.8 and 20.52(C-Acyl1), 169.86 and 20.74 (C-Acyl).\u003c/p\u003e \u003c/div\u003e"},{"header":"3. Results and Discussion","content":"\u003cp\u003eThe chemical structures of two compounds which shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e were established mainly by spectroscopic methods. Compound No.1 was obtained as a yellow solid and compound No.2 was achieved as a brownish yellow solid. A comparison of their \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eCNMR spectra indicated that the structure of compound No.1 is the same as No.2 without the methoxy group. According to \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of compound No.1, the presence of two trans olefinic protons with δ\u003csub\u003eH\u003c/sub\u003e 6.55 (d, J = 16 Hz) and δ\u003csub\u003eH\u003c/sub\u003e 7.58 (d, J = 16 Hz), and also the peaks with 2-proton integration of δ\u003csub\u003eH\u003c/sub\u003e 7.72 (m) represents the positions of 2 and 6 in the benzene ring. Moreover, chemical shift of δ\u003csub\u003eH\u003c/sub\u003e 7.41–7.43 (3H) indicates the positions of 3, 4, and 5 in the benzene rings. In general, these observations indicate the presence of a no substitutions in the positions of 2, 3, 4, 5, and 6 of benzene ring. As illustrated in \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of compound No.2, the presence of two pairs of ortho coupled aromatic protons of δ\u003csub\u003eH\u003c/sub\u003e 7.69 (d, J = 8.9 Hz) and δ\u003csub\u003eH\u003c/sub\u003e 6.97 (d, J = 8.6 Hz), two trans olefinic protons of δ\u003csub\u003eH\u003c/sub\u003e 6.49 (d, J = 16 Hz) and δ\u003csub\u003eH\u003c/sub\u003e 7.66 (d, J = 16 Hz), and one aromatic methoxy group of δ\u003csub\u003eH\u003c/sub\u003e 3.79 clearly prove that the acyl moiety is the trans-p-methoxycinnamoyl group. The presence of two peaks of δ\u003csub\u003eH\u003c/sub\u003e 1.88 (s) and δ\u003csub\u003eH\u003c/sub\u003e 2.11 (s) in the \u003csup\u003e1\u003c/sup\u003eH-NMR spectrum of compound No.2, represents presence of two acetyl groups; which were indicated by two peaks of δH 2.01 (s) and δH 2.12 (s) in the 1H-NMR spectrum of compound No.1. To identify the position of these acetyl groups, 2DNMR complementary spectra of HMBC and HSQC method was applied. According to Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, two groups of acetyls are located on carbon 2 and carbon 3 of rhamnose. So, the site of esterification was determined to be the 4\"-position of the ramnopyranosyl moiety in two compounds. As a result, the structure of the new compound No.1 was introduced as 6-O [2', 3' diacyl-4'-O-Trans -cynamoyl]-α-L-rhamnopyranosyl-aucubin and the structure of the compound No.2 was determined as be6-O [2', 3' diacyl-4'-O- trans- p-methoxycinamoyl]-α-L rhamnopyranosyl-aucubin. Based on the spectrum data and suggested structure, compound No.2 is derived from a compound known as unbuloside [\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e, \u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e]. Moreover, the extracted information from the HSQC and HMBC spectra of Compound No. 2 are presented in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e shows the iridoids and other materials which were extracted and identified according to previously reported documents. This data shows that the substances reported in this work are extracted and identified for the first time and similar case of these compounds was not found in literature.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e\u003cdiv class=\"gridtable\"\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\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\u003eExtracted information from the HSQC and HMBC spectra of Compound No. 2 in the CHD\u003csub\u003e3\u003c/sub\u003eO solvent\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e\u003ccolgroup cols=\"5\"\u003e\u003c/colgroup\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e\u0026nbsp;\u003c/th\u003e\u003cth align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003eHMBC**\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003eHSQC*\u003c/p\u003e \u003c/th\u003e\u003c/tr\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003csup\u003e3\u003c/sup\u003eJ\u003csub\u003eCH\u003c/sub\u003e\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003csup\u003e2\u003c/sup\u003eJ\u003csub\u003eCH\u003c/sub\u003e\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eδ\u003csub\u003eC\u003c/sub\u003e (ppm)\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003eδ\u003c/b\u003e\u003csub\u003e\u003cb\u003eH\u003c/b\u003e\u003c/sub\u003e \u003cb\u003e(ppm)\u003c/b\u003e\u003c/p\u003e \u003c/th\u003e\u003c/tr\u003e\u003c/thead\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-5, C-3, C-8, C-4, C-1´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-9\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e96.76\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.97\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-5,C-1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e140.58\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e6.37\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-6,C-1, C-9\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-5, C-3\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e103.77\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e5.15\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e42.62\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e2.92\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e88.36\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.5\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-5, C-9\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-8\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e125.28\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e5.92\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e148.82\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-7\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-8,C-5,C-1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e46.67\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e2.98\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003ea10\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-7\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-8\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e59.90\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.22\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eb10\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-7\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-8\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.40\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-2´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e98.46\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.71\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´2\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e73.42\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.25\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´3\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e76.38\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.4\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´4\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-5´, C-3´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e70.06\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.30\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´5\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e76.74\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.33\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003ea´6\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-5´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e61.1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.66\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eb´6\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-5´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.88\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-6, C-5´´, C-3´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-2´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e96.76\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.96\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´2\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-4´´, C\u003csub\u003eacetyl\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e69.22\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e5.33\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´3\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC\u003csub\u003eacetyl\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e69.9\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e5.23\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´4\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-2´´, C-6´´, C-9´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-3´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e70.59\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e5.17\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´5\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4´´, C-6´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e66.81\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e4.1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´6\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-4´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e16.38\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e1.25\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´1\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e126.69\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´2\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-4´´´, β\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e129.78\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e7.59\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´3\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-1´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e114.04\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e6.98\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´4\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e161.96\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´5\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-1´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC-4´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e114.04\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e6.98\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e´´´6\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-4´´´, β\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e129.78\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e7.59\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eα\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-1´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eβ, C-9´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e113.51\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e6.39\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eβ\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-2´´´, C-6´´´, C-9´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eα\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e145.97\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e7.69\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC = O\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e166.52\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eMeO\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eC-4´´´\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e54.41\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e3.85\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eAcetyl\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e169.86\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e19.15\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e1.94\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eAcetyl\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e169.798\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e-\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eC = O\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e19.26\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e\u003cb\u003e2.18\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/div\u003e \u003cp\u003e\u003c/p\u003e \u003cp\u003e*(Heteronuclear Single-Quantum Correlation)\u003c/p\u003e \u003cp\u003e** (Heteronuclear Multiple Bond Correlation)\u003c/p\u003e \u003cp\u003e \u003c/p\u003e\u003cdiv class=\"gridtable\"\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\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\u003ethe compounds which were extracted from Scrophularia umbrosa according to reported literature\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e\u003ccolgroup cols=\"4\"\u003e\u003c/colgroup\u003e\u003cthead\u003e\u003ctr\u003e\u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eName of compound (s)\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eExtraction solvent\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003ePart of plant\u003c/p\u003e \u003c/th\u003e\u003cth align=\"left\" colname=\"c4\"\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\u003eAucubin, lamalbide\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003emethanol\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eRhizome\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\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\u003eEssential oil\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003emethanol\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eaerial parts\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003ctr\u003e\u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eUmbrosides, iridoid glycosides, phenylethanoid glycosides\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e40% ethanol\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003ewhole plant\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\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\u003eAucubin, Luteolin-7-O-Rutinoside\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eMethanol, DCM\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eAerial Parts and Seed\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\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\u003eUnduloside\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003emethanol\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eaerial parts\u003c/p\u003e \u003c/td\u003e\u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e[\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]\u003c/p\u003e \u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/div\u003e \u003cp\u003e\u003c/p\u003e \u003cp name=\"removable\"\u003e \u003cb\u003eConclusion\u003c/b\u003e \u003c/p\u003e \u003cp name=\"removable\"\u003eIn conclusion according to information obtained from HPLC, HNMR, CNMR, HSQC, and HMBC, two new acetylated Iridoids named from methanolic extraction of Scrophularia umbrosa rhizome were extracted and identified successfully. These materials are called 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin (No.1) and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin (No.2).\u003c/p\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn conclusion according to information obtained from HPLC, HNMR, CNMR, HSQC, and HMBC, two new acetylated Iridoids named from methanolic extraction of Scrophularia umbrosa rhizome were extracted and identified successfully. These materials are called 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin (No.1) and 6- O [2', 3’ diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin (No.2).\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgments\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis article has written based on a Ph.D. thesis registered in Drug Applied Research Center of Tabriz University of Medical Sciences (No. 91.75). My grateful thanks are extended to Mrs. Dr. asnaashari, for her advice and assistance in keeping my progress on schedule. I also thank the pharmacognosy laboratory technician (Mrs. Bamed) for helping to provide resources for the implementation of the program.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eCompeting interests: \u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare there are no competing interests.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding Declaration\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eDrug Applied Research Center of Tabriz University of Medical Sciences, Iran, grant number: \u0026nbsp;91.75\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData availability\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eNo datasets were generated or analyzed during the current study.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eNikkhah, E., S. Asnaashari, H. Babaei, F. Heshmati Afshar, and A. Delazar, \u003cem\u003eResearch Journal of Pharmacognosy\u003c/em\u003e, 2017. 4(1): p. 41-50.\u003c/li\u003e\n\u003cli\u003ede Santos Galindez, J., L. Fernandez Matellano, and A.M. Diaz Lanza, \u003cem\u003eZ Naturforsch C\u003c/em\u003e, 2001. 56(7-8): p. 513-20.\u003c/li\u003e\n\u003cli\u003ePrzybylska, D., A.Z. Kucharska, and T. Sozański, \u003cem\u003eFood Reviews International\u003c/em\u003e, 2023. 39(9): p. 6447-6477, 10.1080/87559129.2022.2117375.\u003c/li\u003e\n\u003cli\u003eDinda, B., S. Debnath, and Y. Harigaya, \u003cem\u003eChem Pharm Bull\u003c/em\u003e, 2007. 55(2): p. 159-222.\u003c/li\u003e\n\u003cli\u003eDinda, B., \u003cem\u003ePharmacology and Applications of Naturally Occurring Iridoids\u003c/em\u003e. 2019.\u003c/li\u003e\n\u003cli\u003eViljoen, A., N. Mncwangi, and I. Vermaak, \u003cem\u003eCurr Med Chem\u003c/em\u003e, 2012. 19(14): p. 2104-27, 10.2174/092986712800229005.\u003c/li\u003e\n\u003cli\u003eBas, E., M.C. Recio, S. M\u0026aacute;\u0026ntilde;ez, R.M. 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Harvala, \u003cem\u003eJournal of Natural Products\u003c/em\u003e, 1996. 59(7): p. 673-675, 10.1021/np960181b.\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"Scrophularia umbrosa, iridoids, HPLC, NMR.","lastPublishedDoi":"10.21203/rs.3.rs-4268794/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4268794/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eScrophularia umbrosa is a medicinal plant used as a traditional herb. This plant is one of the native species of Iran and consists of about 200 species of herbaceous flowering plants, commonly known as \u0026lsquo;figwort\u0026rsquo;. Many iridoid glycosides have been found in the Scrophularia genus. In this research work the methanolic extracts of Scrophularia umbrosa (S. umbrosa) rhizome was studied. For this first methanolic extract of rhizome powder was subjected to the HPLC in which two materials was detected in 220 nm and was separated. In continue 1D and 2D NMR technique has been employed for the identification of the active components. finally phytochemical investigations of the S. umbrosa rhizome indicate the presence of two new acetylated iridoid glycosides, 6- O [2', 3'diacyl-4'-O-Trans-cynamoyl]-α-L-rhamnopyranosyl-aucubin and 6- O [2', 3\u0026rsquo; diacyl-4'-O-Trans-p-methoxycinamoyl]-α-L-rhamnopyranosyl-aucubin. HNMR and CNMR were the main apparatuse to identification of these compounds which has been shown medicinal property, in rhizome of Scrophularia umbrosa.\u003c/p\u003e","manuscriptTitle":"Identification of two new acetylated Iridoids from Scrophularia umbrosa rhizome","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-04-29 16:17:34","doi":"10.21203/rs.3.rs-4268794/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"editorAssigned","content":"","date":"2024-04-24T13:43:46+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2024-04-24T09:47:20+00:00","index":"","fulltext":""},{"type":"submitted","content":"Structural Chemistry","date":"2024-04-15T09:46:46+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"95fb53f8-2e26-42a1-b26d-c41ee2116e18","owner":[],"postedDate":"April 29th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"under-review","subjectAreas":[],"tags":[],"updatedAt":"2024-04-29T16:17:34+00:00","versionOfRecord":[],"versionCreatedAt":"2024-04-29 16:17:34","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-4268794","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-4268794","identity":"rs-4268794","version":["v1"]},"buildId":"J0_U0BvcaRcwD8yVFaRlm","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}