Bakuchiol Dimers From Psoraleae Fructus That Inhibit Nitric Oxide Production in RAW264.7 Macrophages Cells

Bakuchiol Dimers From Psoraleae Fructus That Inhibit Nitric Oxide Production in RAW264.7 Macrophages Cells | 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 Help Center Sign In Submit a Preprint Cite Share Download PDF Research Bakuchiol Dimers From Psoraleae Fructus That Inhibit Nitric Oxide Production in RAW264.7 Macrophages Cells Qingxia Xu, Qian Lv, Lu Liu, Yingtao Zhang, Xiuwei Yang This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-706759/v1 This work is licensed under a CC BY 4.0 License Status: Under Review Version 1 posted 13 You are reading this latest preprint version Abstract Background: Dried fruit of Psoralea corylifolia L. (Psoraleae Fructus) is one of the most popular traditional Chinese medicine with treatment for nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases. Bakuchiol is main meroterpenoid with bioactive diversity from Psoraleae Fructus. Methods: Various column chromatography methods were used for isolation experiment. Structures and configurations of these compounds were determined by spectroscopic methods and single-crystal X-ray diffraction. Their inhibition on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were evaluated by the Griess reaction. Results: Twelve unpresented bakuchiol dimmers, bisbakuchiols M–U ( 1 – 9 ) and bisbakuchiol ethers A–C ( 10 – 12 ), along with five known compounds ( 13 – 17 ), were isolated from the fruits of Psoralea corylifolia L. Compounds 1 – 3 and 10 – 14 exhibited inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, and the inhibition of compound 1 (IC 50 = 11.47 ± 1.57 μM) was equal to that of L-NIL (IC 50 = 10.29 ± 1.10 μM) as a positive control. Conclusions: Seventeen bakuchiol dimers ( 1 – 17 ), including 12 undescribed dimers and 5 known compounds, were isolated. Bisbakuchiol M ( 1 ), whose other bakuchiol unit was cyclized to form a 6/6/5 tricyclic system, was a new skeleton compound. Some compounds exhibited NO inhibition activities and the inhibition of compound 1 was equal to that of L-NIL, a positive control. These findings suggested that Psoraleae Fructus provided natural anti-inflammatory constituents and bisbakuchiol M had the potential to be novel NO inhibitor. Natural Product Chemistry Psoralea corylifolia bakuchiol dimers inhibition of nitric oxide Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 1. Background The higher plant, Psoralea corylifolia L. ( Cullen corylifolia (L) Mefik) is an annual herb and belongs to family Leguminosae distributed in China, India, Malay peninsula, and Indonesia [ 1 ]. Dried fruit of P. corylifolia (Psoraleae Fructus) is one of the most popular traditional Chinese medicine (TCM) and officially listed in Chinese Pharmacopoeia [ 2 ], and it is also a natural food additive [ 3 ]. It has been used for the treatment of nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases [ 4 ]. Psoraleae Fructus contains approximately 110 compounds including coumarins, flavonoids, meroterpenoids, and benzofurans [ 5 ]. Among these, meroterpenoids are considered to be the one of characteristic and active components [ 6 , 7 ]. Bakuchiol is main meroterpenoid that consists of a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a p -disubstituted benzene ring. Structural changes including oxidation, dehydration reduction, condensation and alkylation, occur in the side chain and benzene ring, which increases structural and bioactive diversities of meroterpenoid constituents. According to a review of predecessors' researches, 22 meroterpenoids and 12 bakuchiol dimers were found from the plant [ 5 , 8 – 10 ]. In our previous researches [ 11 , 12 ], fourteen meroterpenoids and seventeen heterodimers of bakuchiol have been reported and their cytotoxicity were evaluated. Further investigation on the cyclohexane extract brought about twelve unpresented bakuchiol dimmers, bisbakuchiols M–U ( 1 – 9 ) and bisbakuchiol ethers A–C ( 10 – 12 ), along with five known compounds ( 13 – 17 ). Compound 1 was a new skeleton possessing an undescribed 6/6/5 tricyclic-4,11-dione system deriving from 2,5-dihydroxybakuchiol intramolecular cyclization, and its' plausible biosynthetic pathway was proposed. Moreover, compound 2 was a biphenyl dimer constructed by C 3 –C 3' bond and compounds 10 – 12 were rare heterodimers of bakuchiol and terpenoid. Herein the structure elucidation of these compounds and evaluation of their ability to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were discussed. 2. Materials And Methods 2.1. General experimental procedures Infrared data were recorded on a Thermo Nicolet Nexus 470 FT-IR spectrometer. Ultraviolet data were acquired on a Mapada UV-6100 double beam spectrophotometer. HRESIMS data were collected using a Waters Xevo G2 QTOF spectrometer. NMR spectra were recorded on a Bruker AVANCE III HD 400 NMR spectrometer. Optical rotations were measured on a Rudolph Autopol IV automatic polarimeter. X-ray data were collected by a Rigaku Micromax-003 X-ray single-crystal diffractometer with CuKα radiation. Open column chromatography (CC) was performed by packing silica gel (200–300 mesh, Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 gel (Pharmacia Biotek, Denmark). Thin layer chromatography (TLC) was carried out on silica gel GF254 plates (Merck, Darmstadt, Germany) with 10% H 2 SO 4 in 95% ethanol followed by heating. Reversed phase semi-preparative HPLC (RP-SP-HPLC) was accomplished using an LC3000 system (Beijing Innovation Technology Co., Ltd), equipped with a phenomenon C 18 column (21.2 mm × 250 mm, 5 µm). Cells were cultured in Sanyo MCO-15 AC carbon dioxide (CO 2 ) incubator (Sanyo Electric Co., Ltd., Osaka, Japan). HPLC grade solvents, methanol (MeOH) and acetonitrile (MeCN), were purchased from Fisher Scientific (Pittsburgh, PA, USA) and solvents, petroleum ether (PE), cyclohexane (cHE), ethyl acetate (EtOAc), chloroform (CHCl 3 ) and normal-butanol (BuOH) for column chromatography purchased from Beijing Chemical Works (Beijing, China). Dulbecco's modified Eagle's medium (DMEM), fetal bovine serum (FBS), trypsin, penicillin-streptomycin solution, phosphate buffered saline were obtained from Gibco® (Life Technologies Inc., Grand Island, NY, USA). 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT), lipopolysaccharide (LPS), Griess reagent, dimethylsulfoxide (DMSO), and L-N 6 -(1-iminoethyl)-lysine (L-NIL) were obtained from Sigma-Aldrich (St. Louis, MO, USA). The murine macrophage cell line RAW264.7 was obtained from the Cell Bank of the Chinese Academy of Sciences (Shanghai, China). 2.2. Plant material The mature fruits of Psoralea corylifolia L. were harvested from Yunnan province of People's Republic of China (GPS coordinates:23°32′N, 99°23′E) in October 2016, and authenticated by Prof. Xiu-Wei Yang of the School of Pharmaceutical Sciences, Peking University. A voucher specimen (accession number: BGZ201610) of the fruits was deposited at the State Key Laboratory of Natural Medicines and Biomimetic Drugs of Peking University. 2.3. Extraction and isolation The dried mature fruits powder (47.9 kg) was extracted with 70% aqueous ethanol under reflux. After extracted for three times (first 479 kg for 2 h, and then 384 kg for 2 h two times), the crude extract (8.2 kg, yield 17.12%) was obtained. And then, part of the residue (6.0 kg) was suspended in H 2 O (8 L) and extracted with cHE (8 L × 8), EtOAc (8 L × 8) and n -butanol (BuOH, 8 L × 8) successively and afforded corresponding extract for 1.2 kg, 2.2 kg and 0.7 kg. The cHE extract (1.0 kg) was fractionated by silica gel column (SGC, 140 mm i.d. × 800 mm) with gradient eluent (PE-EtOAc, 5:1, 3:1, 1:1, 2:3, 1:3, 0:1, v/v ) to give 26 fractions (Fr. A–Z). The Fr. B (27.2 g) was separated by SGC (55 mm i.d. × 650 mm) with a step gradient eluent of PE-EtOAc (100: 1, 50: 1, 25: 1, 7: 1, 5: 1, 3:1, 1: 1, 1:3, 0:1, v/v ) to afford 15 subfractions (Fr. B-1–Fr. B-15). Fr. B-8 (2.1 g) was separated by reversed-phase column (RPC), eluted with MeCN-H 2 O (40:60 to 100:0, v/v ), to give 13 subfractions. Fr. B-8-5 was purified by SP-RP-HPLC (MeCN-H 2 O, 95:5, v/v ), to yield compound 10 (5 mg, t R = 85 min). The Fr. C (136 g) was separated by SGC (120 mm i.d. × 600 mm) with a step gradient eluent of PE-EtOAc (100: 1, 50: 1, 20: 1, 15: 1, 10: 1, 5:1, 5: 2, 1:1, 0:1, v/v ) to afford 16 subfractions (Fr. C-1–Fr. C-16). Fr. C-4-7 was separated by Sephadex LH-20 column (SC) and purified by SP-RP-HPLC (MeCN-H 2 O, 93:7, v/v ), to yield compound 1 (230 mg, t R = 45 min) and 11 (60 mg, t R = 80 min). Fr. C-5 (20 g) was separated by RPC, eluted with MeOH-H 2 O (80:20 to 100:0, v/v ), to give 9 subfractions. Fr.C-5-9 was separated by SC and purified by SP-RP-HPLC (MeCN-H 2 O, 93:7, v/v ), to yield compound 12 (34 mg, t R = 71 min). By SP-RP-HPLC (MeCN-H 2 O, 90:10, v/v ) and preparative TLC (PE-CHCl 3 , 10:1, v/v ), compound 2 (104 mg, t R = 252 min) was obtained from Fr. C-11 (2.1 g). The Fr. D (335 g) was separated by SGC (140 mm i.d. × 800 mm) with a step gradient eluent of PE-CHCl 3 (100: 1, 50: 1, 20: 1, 10: 1, 5: 1, 4:1, 3: 1, 2: 1, 1: 1, 1:3, 0:100, v/v ) to afford 14 subfractions (Fr. D-1–Fr. D-14). Fr. D-4 (20.7 g) was separated by RPC, eluted with MeOH-H 2 O (45:55 to 100:0, v/v ), to give 13 subfractions. Fr. D-4-12 was purified by SP-RP-HPLC (MeOH-H 2 O, 93:7, v/v ), to yield compounds 8 (15 mg, t R = 131 min) and 9 (28 mg, t R = 136 min). By SP-RP-HPLC (MeCN-H 2 O, 90:10, v/v ), Fr. D-7(1.7 g)was separated to yield compounds 3 (5 mg, t R = 95 min) and 4 (2 mg, t R = 87 min). The Fr. D-9 (37 g) was separated by SGC (55 mm i.d. × 650 mm) with a step gradient eluent of PE-CHCl 3 (100: 1, 50: 1, 20: 1, 10: 1, 9: 1, 8:1, 7: 1, 6: 1, 5: 1, 4:1, 3:1, 1:1, 1:3, 0:1, v/v ) to afford 28 subfractions. By SP-RP-HPLC (MeOH-H 2 O, 92:8, v/v ), Fr. D-9-13 was separated to yield compounds 5 (11 mg, t R = 77 min), 6 (9 mg, t R = 100 min) and 7 (19 mg, t R = 110 min). Fr. D-9-25 was purified by SP-RP-HPLC (MeOH-H 2 O, 92:8, v/v ), to give compounds 13 (18 mg, t R = 86 min) and 14 (25 mg, t R = 92 min). Fr. D-9-26 was purified by SP-RP-HPLC (MeOH-H 2 O, 92:8, v/v ), to give compound 15 (15 mg, t R = 76 min). Fr. D-11 (19.2 g) was separated by RPC, eluted with MeOH-H 2 O (45:55 to 100:0, v/v ), to give 27 subfractions. The Fr. D-11-25 (5.9 g) was separated by SGC (35 mm i.d. × 500 mm) with a step gradient eluent of PE-CHCl 3 (8:1, 7: 1, 6: 1, 5: 1, 4:1, 3:1, 1:1, 1:3, 0:100, v/v ) to afford 18 subfractions. By SP-RP-HPLC (MeOH-H 2 O, 75:25, v/v ), Fr. D-11-25-12 was separated to yield compounds 16 (14 mg, t R = 286 min) and 17 (15 mg, t R = 328 min). Bisbakuchiol M ( 1 ). Brown-red needle crystals; mp 114–116 ºC; [ α ]25 D + 50.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 204 (4.85), 258 (4.80), 386 (4.28) nm; IR (KBr) ν max 3315, 2967, 2930, 1692, 1609, 1582, 1504, 1385, 1358, 1255, 1035 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 537.3004 [M + H] + (calcd for C 36 H 41 O 4 , 537.3005). Bisbakuchiol N ( 2 ). Yellow oils; [ α ]25 D + 20.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 203 (4.41), 253 (4.44) nm; IR (KBr) ν max 3319, 2966, 2924, 1703, 1633, 1603, 1496, 1409, 1373, 1231, 969 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 511.3573 [M + H] + (calcd for C 36 H 47 O 2 , 511.3576). Bisbakuchiol O ( 3 ). Yellowish oils; [ α ]25 D + 30.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 203 (4.57), 267 (4.33) nm; IR (KBr) ν max 3373, 2962, 2926, 1704, 1604, 1507, 1454, 1372, 1238, 1172, 1007 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 555.3468 [M + HCOO] − (calcd for C 37 H 47 O 4 , 555.3474). Bisbakuchiol P ( 4 ). Yellowish oils; [ α ]25 D − 26.7 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 202 (4.61), 267 (4.32) nm; IR (KBr) ν max 3381, 2968, 2927, 1703, 1604, 1507, 1452, 1375, 1240, 1172, 1000 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 509.3417 [M – H] − (calcd for C 36 H 45 O 2 , 509.3420). Bisbakuchiol Q ( 5 ). Yellowish oils; [ α ]25 D + 70.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 202 (4.76), 264 (4.55) nm; IR (KBr) ν max 3370, 2964, 2921, 1704, 1607, 1507, 1459, 1370, 1238, 1171, 1099 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 525.3364 [M – H] − (calcd for C 36 H 45 O 3 , 525.3369). Bisbakuchiol R ( 6 ). White amorphous powder; [ α ]25 D + 70.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 203 (4.57), 260 (4.35) nm; IR (KBr) ν max 3372, 2967, 2924, 1704, 1613, 1506, 1451, 1365, 1253, 1143, 1094 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 603.3676 [M + HCOO] − (calcd for C 38 H 51 O 6 , 603.3686). Bisbakuchiol S ( 7 ). White amorphous powders; [ α ]25 D + 60.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 204 (4.42), 260 (4.32) nm; IR (KBr) ν max 3373, 2968, 2925, 1705, 1614, 1506, 1450, 1364, 1235, 1143, 1082 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 557.3635 [M − H] − (calcd for C 37 H 49 O 4 , 557.3631). Bisbakuchiol T ( 8 ). Yellowish oils; [ α ]25 D − 20.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 202 (4.68), 222 (4.57), 262 (4.33) nm; IR (KBr) ν max 3395, 2967, 2921, 1702, 1588, 1507, 1450, 1375, 1267, 1171, 1010 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 525.3367 [M − H] − (calcd for C 36 H 45 O 3 , 525.3369). Bisbakuchiol U ( 9 ). Yellowish oils; [ α ]25 D + 20.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 202 (4.63), 265 (4.21) nm; IR (KBr) ν max 3387, 2966, 2922, 1703, 1587, 1507, 1451, 1374, 1267, 1171, 1009 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 1; 13 C NMR (CDCl 3 , 100 MHz), see Table 2 ; HRESIMS m/z 525.3371 [M − H] − (calcd for C 36 H 45 O 3 , 525.3369). Bakuchiol ether A ( 10 ). Yellowish oils; [ α ]25 D + 10.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 204(4.26),260(4.15) nm; IR (KBr) ν max 3424, 2969, 2929, 1712, 1603, 1505, 1453, 1369, 1224, 1136, 913 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 3 ; 13 C NMR (CDCl 3 , 100 MHz), see Table 3 ; HRESIMS m/z 445.3080 [M + Na] + (calcd for C 29 H 42 O 2 Na, 445.3083). Bakuchiol ether B ( 11 ). Yellowish oils; [ α ]25 D + 20.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 206(4.50), 265(4.45) nm; IR (KBr) ν max 3420, 2926, 2864, 1715, 1606, 1507, 1463, 1364, 1245, 1173, 969 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 3 ; 13 C NMR (CDCl 3 , 100 MHz), see Table 3 ; HRESIMS m/z 477.3713 [M + H] + (calcd for C 33 H 49 O 2 , 477.3733). Bakuchiol ether C ( 12 ). Yellowish oils; [ α ]25 D + 30.0 ( c 0.1, MeOH); UV (MeOH) λ max (log ε ): 206(4.46), 263(4.42) nm; IR (KBr) ν max 3420, 2952, 2927, 1710, 1604, 1505, 1452, 1375, 1241, 1171, 967 cm − 1 ; 1 H NMR (CDCl 3 , 400 MHz), see Table 3 ; 13 C NMR (CDCl 3 , 100 MHz), see Table 3 ; HRESIMS m/z 475.3532 [M − H] − (calcd for C 33 H 47 O 2 , 475.3576). 2.4. X-ray Crystallographic Analysis The X-ray crystallographic experiments were carried out on a XtaLAB Synergy R, HyPix diffractometer with CuKα radiation. Crystallographic data (No. CCDC 1993852) of 1 have been deposited at the Cambridge Crystallographic Data Center. Crystallographic data of 1 : C 72 H 80 O 8 , M = 1073.36, a = 13.2661(2) Å, b = 14.3761(2) Å, c = 31.3617(5) Å, α = 90°, β = 90°, γ = 90°, V = 5981.13(18) Å 3 , T = 100 K, space group P2 1 2 1 2 1 , Z = 4, µ (Cu Kα) = 0.599 mm -1 , Crystal size = 0.99 × 0.4 × 0.02 mm 3 , 2Ɵ range for data collection = 8.344 to 139.15826790°, 26790 reflections measured, 10867 independent reflections ( R int = 0.0431, R sigma =0.0446). The final R 1 value was 0.0475 ( I > 2σ(I) ). The final wR (F 2 ) value was 0.1153. Flack parameter =-0.02 (12). 2.5. ECD calculations The calculation was performed by the Gaussian 16 software. Conformation analysis were proceeded with the MMFF94s molecular mechanics force field. Optimization of the stable conformers with a Boltzmann distribution over 1% was conducted by time-dependent density functional theory (TD-DFT) at the Cam-B3LYP/6–31 + G(d, p) level for compounds 8 and 9 , with the CPCM model in MeOH. The ECD data was analysed by SpecDis v1.71 with the half-bandwidth no more than 0.3 eV. The final ECD spectra were obtained based on the Boltzmann-calculated contribution of each conformer. 2.6. Inhibition assay on NO production RAW264.7 cells were maintained in DMEM containing 10% FBS, in a constant humidity atmosphere of 5% CO 2 and 95% air at 37°C. The cells were cultivated at a density of 3 × 10 5 cells/mL for 24 h in 96-well culture plates. And then, the cells were stimulated with LPS (1 µg/mL) and treated with various concentrations (1.5625–50 µM) of assay compounds. After exposure to the compounds for 24 h, MTT (20 µ L, 5mg/mL) was added to each well [ 13 ]. Four hours later, 100 µ L of lysis solution (40 g SDS, 20 mL isopropanol, 0.4 mL concentrated HCl and 400 mL ddH 2 O) was added to dissolve the formazan crystals. Absorbances at 490 nm were measured after 10h by a Multiskan MK3 Automated Microplate Reader (Thermo-Labsystems, Franklin, MA, USA). The RAW264.7 cells were grown at a density of 3 × 10 5 cells/mL in 96-well culture plates. After 24 h, the cells were stimulated with LPS (1 µg/mL) and treated with various non-cytotoxic concentrations of assay compounds. And then, the cell culture supernatant (100 µL) was collected and reacted with the same volume of Griess reagent (100 µL) for 15 min at room temperature [ 14 ]. The absorbance was determined at 540 nm. The experiments were performed in parallel for three times, and L-NIL was used as a positive control. IC 50 (half maximal inhibitory concentration) value of each compound was defined as the concentration ( µ M) that caused 50% inhibition of NO production. The IC 50 values were calculated by the software SPSS 16.0 (SPSS Inc., Chicago, IL, USA). 3. Results Phytochemical investigation on cHE fraction of 70% ethanol extract of Psoraleae Fructus resulted in twelve unpresented bakuchiol dimmers ( 1 – 12 ) and five known compounds ( 13 – 17 ) (Fig. 1 ). Structures of these new compounds were assigned by NMR spectra and single crystal X-ray diffraction. Compounds 1 – 3 , 6 – 9 , and 13 – 17 could be detected from ultrasonic extraction of Psoraleae Fructus by LC/MS analysis, suggesting that these compounds were natural products (Fig. S94). Compound 1 was obtained as brown-red needle crystals (MeOH) with mp 114–116 ºC. It had the molecular formula C 36 H 40 O 4 , as established by HRESIMS at m/z 537.3004 [M + H] + (calcd for 609.3216). Compared with the NMR data (Tables 1 and 2 ) of bakuchiol [ 15 ], a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a p -disubstituted benzene ring in 1 were identical to that of bakuchiol. The 1 H NMR data of an another side chain of compound 1 exhibited three methyl groups at δ H 1.78 (3H, s), 1.78 (3H, s) and 1.44 (3H, s); a vinyl group at δ H 5.87 (1H, dd, J = 10.6, 7.5 Hz, H-17'), 5.19 (1H, br d, J = 3.9 Hz, Ha-18'), and 5.16 (1H, br d, J = 10.6, Hb-18'); two trisubstituted olefinic protons at δ H 5.68 (1H, s) and 7.43 (1H, s); and one methylene group at δ H 2.60 (1H, d, J = 18.7 Hz, Ha-10') and 2.46 (1H, d, J = 18.7 Hz, Hb-10'). The presence of an α,β-unsaturated ketone group was revealed by the band at 1692 cm –1 in its IR spectrum, which was confirmed by the resonance at δ C 180.4(s) in its 13 C NMR spectrum. Comparison of the 13 C NMR spectrum of 1 with those of bakuchiol, the chemical shifts of C-3 and C-5 were shifted downfield to δ C 121.4, suggesting that this substituted group was connected to C-4 of bakuchiol moiety by an ether linkage. The full assignment of 1 H and 13 C NMR resonances was supported by 1 H– 1 H COSY, DEPT, HSQC and HMBC spectral analyses. The X-ray structure was shown in Fig. 2 and confirmed the absolute configuration of 9 S ,9' S for 1 . Thus, the structure of 1 was as shown in Fig. 1 and named bisbakuchiol M. The plausible biosynthetic pathway of bisbakuchiol M was proposed (Fig. 3 ). Hydroxylation reactions occurred at the positions of C-2 and C-5 in bakuchiol to form M1. Once the 4-hydroxyl group in M1 lost a proton to generate M2-1, migrations of the double bond would start. The double bond at C-7 and C-8 would attack C-12 to form a five-membered ring, along with the generation of carbanion at C-13 (M2-2). Subsequently, the carbanion at C-13 attacked C-6 to form six-membered ring (M2-3). The proton at C-6 left, which was accompanied by electron migrations of negative ion of oxygen to produce ketone carbonyl (M3). And then, the α-proton of double bond at C-8 was easily to be hydroxylated to generate M4. The elimination reaction would follow to the generation of M5. Similarly, the hydroxylation occurred at C-11 (M6). Subsequently, 11-hydroxyl group would be oxidized to ketone carbonyl (M7). Finally, M7 and bakuchiol were condensed to produce bisbakuchiol M. Compound 2 was isolated as yellow oils. The resonances in the 1 H NMR spectrum [ δ H 7.26, d, 2.4 Hz; 6.97, d, 8.5 Hz; and 7.34, dd, 8.5, 2.4 Hz] in 2 suggested clearly the 2,5,6-nature of the aromatic protons. Compared with the NMR data of bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) in 2 was identical to that of bakuchiol. Compound 2 had a molecular formula C 36 H 46 O 2 on the basis of the HRESIMS ion at m/z 511.3573 [M + H] + . Consequently, the structure of compound 2 was unambiguously identified as a dimer comprising two bakuchiol units by a C–C linkage, and it was given the trivial name bisbakuchiol N. Compound 3 was isolated as yellowish oils with [α]25 D + 30.0, and possessed a molecular formula of C 36 H 46 O 2 by the HRESIMS ion at m/z 555.3468 [M + HCOO] − . The IR spectrum of 3 showed absorption bands at 3373, 1604, 1507, 1454, 1238, 1007 cm − 1 ascribable to hydroxyl group and ether functions and aromatic ring. Compared with the NMR data of bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a p -disubstituted benzene ring in 3 were identical to that of bakuchiol, together with a set of remaining NMR signals, which were very similar to those of psoracorylifol F characterized from the fruits of P. corylifolia [ 16 ]. However, the correlations between H-17' at δ H 6.43 and H-7' at δ H 2.89 were observed, which indicated that H-7' was α-oriented. The large coupling constant ( J = 11.7 Hz) of H-7' and H-12' indicated a trans configuration of the two methine protons. Likewise, the configuration of H-8' was confirmed β-oriented on the basis of the large coupling constant ( J = 10.6 Hz). Thus, the configuration was assigned as 7' S ,8' S ,9' S ,12' S from the occurrence of (9 S )-bakuchiol only from nature [ 17 , 18 ]. Furthermore, the HMBC cross-peaks of H-8' at δ H 4.06 with aromatic C-4 at δ C 159.7 correlation indicated that C-8' was connected to C-4 of bakuchiol moiety by an ether linkage (Fig. 4 ). According to the above data, the structure of compound 3 , named bisbakuchiol O, was established as shown in Fig. 1 . Compound 4 was also isolated as yellowish oils with [α]25 D–26.7 ( c 0.1, MeOH), and possessed the same molecular formula, C 36 H 46 O 3 , as 3 according to the HRESIMS m/z 509.3417 [M – H] − . Similarly, NMR data (Tables 1 and 2 ) for compound 4 was comparable to those of compound 3 . Compared with compound 3 , H-7' at δ H 2.96 (1H, br dd, J = 11.7, 10.5 Hz) displayed a NOE correlation with 16'-CH 3 at δ H 1.30 (1H, s), indicating that they were cofacial, and H-7' was assigned in a β-configuration. And the large coupling constants ( J = 11.7, 10.5 Hz) indicated that H-8' and H-12' were α-oriented. As a result, the configuration was confirmed as 7' R ,8' R ,9' S ,12' R . According to the above data, compound 4 was a dimer, whose C-8' of psoracorylifol F was connected to aromatic C-4 of bakuchiol moiety by an ether linkage (Fig. 4 ). Thus, the structure of compound 4 , named bisbakuchiol P, was established as shown in Fig. 1 . Compound 5 possessed the molecular formula of C 36 H 46 O 3 as determined by its HRESIMS ion at m/z 525.3364 [M–H] – . Combined with NMR data, a set of bakuchiol unit signals except for downfield shift to δ C 157.0 for C-4 and a set of psoracorylifol A unit signals [ 19 ] except for downfield shift to δ C 79.9 for C-7' were observed. In the HMBC spectrum of 5 (Fig. 4 ), a psoracorylifol A unit located at C-4 of the bakuchiol unit was verified by correlations from H-7' at δ H 5.17 to C-4 at δ C 157. These features permitted assignment of the planar structure of compound 5 as shown in Fig. 1 . In the NOESY spectrum (Fig. 5 ), correlations between H-7' at δ H 5.17 and CH 3 -16'β at δ H 1.10, H-8' at δ H 3.46 and CH 3 -16'β, indicated that H-7' and H-8' were β-oriented. Whereas H-12' at δ H 4.58 was α-oriented, which was verified by correlations from H-8' and CH 3 -15' at δ H 1.35. Thus, the absolute structure of compound 5 , named bisbakuchiol Q, was established as 9 S ,7' S ,8' S ,9' S ,12' S . Compound 6 was isolated as white amorphous powders, and possessed the molecular formula of C 37 H 50 O 4 as deduced by HREIMS m/z 603.3676 [M + HCOO] – . Combined with the various NMR experiments, a set of bakuchiol unit signals except for downfield shift to δ C 123.7 for C-3, C-5 and a set of psoracorylifol A unit signals except for downfield shift to δ C 82.9 for C-7' and δ C 82.0 for C-13' were observed. In the HMBC experiment (Fig. 4 ), a characteristic methoxyl group at δ H 3.04 (3H, s) correlated with C-7' enabled us to attach this methoxyl group to the C-7'. In NMR spectra of 6 , the signals of an exo -methylene of psoracorylifol A unit had disappeared, while a new signal for characteristic methyl group at δ H 0.49 (3H, s) and an oxygenated quaternary carbon at δ C 82.0 had appeared. Combined with the downfield shift of C-3 and C-5 of bakuchiol unit, it was obvious that two units were attached together by C 4 –O–C 13' . In the NOESY spectrum (Fig. 5 ), correlations between H-7' at δ H 4.18 and CH 3 -16'β at δ H 1.10, H-8' at δ H 3.96 and CH 3 -16'β, indicated that they were cofacial and were β-oriented. Similarly, correlations from H-8' and CH 3 -15' at δ H 0.82 supported that H-12' at δ H 3.14 was α-oriented. Finally, the structural assignment of 6 was assigned as 9 S ,7' S ,8' S ,9' S ,12' S , and compound 6 was named bisbakuchiol R. Compound 7 was isolated as white amorphous powders, and possessed the same molecular formula, C 37 H 50 O 4 , as 6 according to the HRESIMS data ( m/z 557.3635 [M – H] – ). Its 1D NMR pattern was highly overlapped to that of compound 6 , indicating their same planar structure. In the NOESY spectrum (Fig. 5 ), correlations between H-7' at δ H 4.30, H-8' at δ H 3.54, and CH 3 -16'β at δ H 1.17 indicated that they were cofacial and were β-oriented. Meanwhile, correlations from H-8' and H-12' at δ H 4.08 suggested β-orientation of H-12'. Finally, the structural assignment of 7 was 9S,7' S ,8' S ,9' S ,12' R as shown in Fig. 1 and compound 7 was named bisbakuchiol. Table 1 1 H NMR (400 MHz, CDCl 3 ; δ H , J in Hz) data for compounds 1 – 9 . Position 1 2 3 4 5 6 7 8 9 1 2 7.42 (d, 8.6) 7.26 (d, 2.4) 7.00 (d, 8.6) 6.96 (d, 8.7) 7.17 (d, 8.4) 7.19 (d, 8.6) 7.21 (d, 8.5) 6.93 (br s) 6.92 (br s) 3 7.04 (d, 8.6) 6.43 (d, 8.6) 6.36 (d, 8.7) 6.72 (d, 8.4) 6.72 (d, 8.6) 6.79 (d, 8.5) 4 5 7.04 (d, 8.6) 6.97 (d, 8.5) 6.43 (d, 8.6) 6.36 (d, 8.7) 6.72 (d, 8.4) 6.72 (d, 8.6) 6.79 (d, 8.5) 6.86, overlapped 6.85, overlapped 6 7.42 (d, 8.6) 7.34 (dd, 8.5, 2.4) 7.00 (d, 8.6) 6.96 (d, 8.7) 7.17 (d, 8.4) 7.19 (d, 8.6) 7.21 (d, 8.5) 6.85, overlapped 6.85, overlapped 7 6.33 (d, 16.2) 6.29 (d, 16.3) 6.13 (d,16.3) 6.11 (d, 16.2) 6.18 (d, 16.2) 6.25 (d, 16.2) 6.26 (d, 16.2) 6.19 (d, 16.2) 6.19 (d, 16.2) 8 6.20 (d, 16.2) 6.11 (d, 16.3) 5.95 (d, 16.3) 5.93 (d, 16.2) 5.99 (d, 16.2) 6.08 (d, 16.2) 6.09 (d, 16.2) 6.03 (d, 16.2) 6.03 (d, 16.2) 9 10 1.53 (m) 1.50 (m) 1.45 (m) 1.45 (m) 1.46 (m) 1.49 (m) 1.50 (m) 1.46 (m) 1.46 (m) 11 1.98 (m) 1.96 (m) 1.92 (m) 1.91 (m) 1.93 (m) 1.94 (m) 1.95 (m) 1.93 (m) 1.93 (m) 12 5.12 (m) 5.10 (m) 5.09 (br t, 7.1) 5.08 (br t, 6.9) 5.08 (br t, 7.3) 5.10 (br t, 7.3) 5.10 (br t, 7.3) 5.09 (br t) 5.09 (br t) 13 14 1.60 (s) 1.58 (s) 1.57 (s) 1.66 (s) 1.56 (s) 1.58 (s) 1.58 (s) 1.57 (s) 1.57 (s) 15 1.68 (s) 1.67 (s) 1.66 (s) 1.56 (s) 1.66 (s) 1.67 (s) 1.67 (s) 1.67 (s) 1.67 (s) 16 1.23 (s) 1.20 (s) 1.15 (s) 1.14 (s) 1.15 (s) 1.19 (s) 1.19 (s) 1.17 (s) 1.17 (s) 17 5.87 (dd, 17.6, 11.0) 5.88 (dd, 17.4, 10.7) 5.84 (dd, 17.2, 10.8) 5.83 (dd, 17.2, 10.8) 5.84 (dd, 17.7, 10.7) 5.87 (dd, 17.5, 10.9) 5.87 (dd, 17.5, 10.8) 5.85 (dd, 17.6, 10.7) 5.85 (dd, 17.6, 10.7) 18a 5.04 (dd, 17.6, 1.3) 5.02 (dd, 17.4, 1.4) 4.97 (dd, 17.2, 1.4) 4.97 (dd, 17.2, 1.4) 4.96 (dd, 17.7, 1.3) 5.01 (dd, 17.5, 1.3) 5.01 (dd, 17.5, 1.3) 5.01 (dd, 10.7, 1.3) 5.01 (dd, 10.7, 1.3) 18b 5.08 (dd, 11.0, 1.3) 5.04 (dd, 10.7, 1.4) 5.00 (dd, 10.8, 1.4) 5.00 (dd, 10.8, 1.4) 5.00 (dd, 10.7, 1.3) 5.03 (dd, 10.9, 1.3) 5.02 (dd, 10.8, 1.3) 4.99 (dd, 17.6, 1.3) 4.99 (dd, 17.6, 1.3) 1′ 2′ 7.26 (d, 2.4) 7.00 (d, 8.6) 7.01 (d, 8.7) 7.16 (d, 8.7) 7.24 (d, 8.5) 7.18 (d, 8.4) 7.19 (br d, 8.6) 7.16 (br d, 8.6) 3′ 5.68 (s) 6.56 (d, 8.6) 6.56 (d, 8.7) 6.71 (d, 8.7) 6.77 (d, 8.5) 6.74 (d, 8.4) 6.73 (br d, 8.6) 6.77 (br d, 8.6) 4′ 5′ 6.97 (d, 8.5) 6.56 (d, 8.6) 6.56 (d, 8.7) 6.71 (d, 8.7) 6.77 (d, 8.5) 6.74 (d, 8.4) 6.73 (br d, 8.6) 6.77 (br d, 8.6) 6′ 7.34 (dd, 8.5, 2.4) 7.00 (d, 8.6) 7.01 (d, 8.7) 7.16 (d, 8.7) 7.24 (d, 8.5) 7.18 (d, 8.4) 7.19 (br d, 8.6) 7.16 (br d, 8.6) 7′ 7.43 (s) 6.29 (d, 16.3) 2.89 (br dd, 11.7, 10.6) 2.96 (br dd, 11.7, 10.5) 5.17 (d, 2.2) 4.18 (d, 8.7) 4.30 (d, 3.0) 4.80 (d, 7.3) 4.91 (d, 6.1) 8′ 6.11 (d, 16.3) 4.06 (d, 10.6) 4.05 (d, 10.5) 3.46 (d, 2.2) 3.96 (d, 8.7) 3.54 (d, 3.0) 3.97 (d, 7.3) 4.04 (d, 6.1) 9′ 10′a 2.60 (d, 18.7) 1.50 (m) 1.98 (m) 1.72 (m) 1.86 (m) 1.76 (m) 2.32 (m) 1.76 (m) 1.55 (m) 10′b 2.46(d, 18.7) 1.56 (m) 1.64 (m) 1.62 (m) 1.76 (m) 1.49 (m) 1.30 (m) 1.44 (m) 11′a 1.96 (m) 1.79 (dd, 12.3, 3.3), 1.70 (dd, 11.8, 3.5) 1.93 (m) 1.74 (m) 1.85 (m) 1.93(m) 1.83 (m) 11′b 1.96 (m) 1.55 (dd, 12.3, 3.3) 1.60 (dd, 11.8, 3.5) 1.88 (m) 1.74 (m) 1.85 (m) 1.82 (m) 1.83 (m) 12′ 5.10 (m) 2.53 (dt, 12.3, 3.3) 2.47 (dt, 11.8, 3.5) 4.58 (m) 3.14 (m) 4.08 (dd, 3.0) 5.06 (m) 5.03 (m) 13′ 14′ 1.78 (s) 1.58 (s) 4.57 (br s), 4.54 (br s) 4.58 (br s) 4.56 (br s) 4.95 (d, 1.3) 4.91 (d, 1.3) 0.82 (s) 1.11 (s) 1.58 (s) 1.57 (s) 15′ 1.78 (s) 1.67 (s) 1.51 (s) 1.56 (s) 1.35 (s) 0.49 (s) 1.09 (s) 1.66 (s) 1.67 (s) 16′ 1.44 (s) 1.20 (s) 1.04 (s) 1.30 (s) 1.10 (s) 1.10 (s) 1.17 (s) 0.62 (s) 1.07 (s) 17′ 5.87 (dd, 10.6, 7.5) 5.88 (dd, 17.4, 10.7) 6.43 (dd, 17.2, 10.8) 5.83 (dd, 17.2, 10.8) 6.46 (dd, 17.7, 10.9) 6.15 (dd, 17.5, 10.9) 6.02 (dd, 17.5, 10.8) 5.84 (dd, 17.4, 10.8) 5.48 (dd, 17.7, 11.0) 18′a 5.19 (br d, 3.9) 5.02 (dd, 17.4, 1.4) 5.20 (dd, 17.2, 1.4) 5.20 (dd, 17.2, 1.4) 4.81 (d, 1.6) 5.14 (dd, 17.5, 1.3) 5.05 (dd, 17.5, 1.3) 18′b 5.16 (br d, 10.6) 5.04 (dd, 10.7, 1.4) 5.29 (dd, 10.8, 1.4) 5.29 (dd, 10.8, 1.4) 4.85 (d, 1.6) 4.99 (dd, 10.9, 1.3) 5.02 (dd, 10.8, 1.3) OCH3 3.04 (s) 3.16 (s) Table 2 13 C NMR (100 MHz, CDCl 3 ) data for compounds 1 – 9 . Position 1 2 3 4 5 6 7 8 9 1 136.2, C 131.6, C 130.3, C 129.9, C 130.5, C 132.7, C 132.8, C 131.3, C 131.4, C 2 127.8, CH 123.4, CH 126.6, CH 126.4, CH 126.9, CH 126.3, CH 126.4, CH 113.7, CH 113.9, CH 3 121.4, CH 128.9, C 115.9, CH 116.3, CH 115.2, CH 123.7, CH 124.0, CH 143.7, C 143.4, C 4 152.0, C 152.1, C 159.7, C 159.4, C 157.0, C 155.3, C 154.3, C 143.0, C 143.0, C 5 121.4, CH 116.7, CH 115.9, CH 116.3, CH 115.2, CH 123.7, CH 124.0, CH 116.5, CH 116.4, CH 6 127.8, CH 127.6, CH 126.6, CH 126.4, CH 126.9, CH 126.3, CH 126.4, CH 119.5, CH 119.5, CH 7 125.9, CH 126.1, CH 126.6, CH 126.7, CH 126.5, CH 126.6, CH 126.7, CH 126.5, CH 126.6, CH 8 138.9, CH 136.7, CH 135.3, CH 135.1, CH 135.7, CH 136.5, CH 136.5, CH 136.1, CH 136.1, CH 9 42.7, C 42.6, C 42.4, C 42.4, C 42.5, C 42.5, C 42.5, C 42.5, C 42.5, C 10 41.2, CH 2 41.2, CH 2 41.3, CH 2 41.3, CH 2 41.2, CH 2 41.2, CH 2 41.2, CH 2 41.3, CH 2 41.3, CH 2 11 23.2, CH 2 23.2, CH 2 23.3, CH 2 23.2, CH 2 23.5, CH 2 23.2, CH 2 23.2, CH 2 23.2, CH 2 23.2, CH 2 12 124.6, CH 124.7, CH 124.8, CH 124.8, CH 124.8, CH 124.8, CH 124.8, CH 124.8, CH 124.8, CH 13 131.4, C 131.3, C 131.2, C 131.2, C 131.2, C 131.3, C 131.3, C 131.5, C 131.4, C 14 17.7, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 17.6, CH 3 15 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 25.7, CH 3 16 23.2, CH 3 23.3, CH 3 23.3, CH 3 23.3, CH 3 23.4, CH 3 23.3, CH 3 23.3, CH 3 23.4, CH 3 23.4, CH 3 17 145.5, CH 145.8, CH 146.0, CH 146.0, CH 146.0, CH 145.9, CH 145.9, CH 145.9, CH 145.9, CH 18 112.3, CH 2 112.0, CH 2 111.7, CH 2 111.7, CH 2 111.8, CH 2 111.9, CH 2 111.9, CH 2 113.9, CH 2 111.8, CH 2 1′ 131.6, C 131.6, C 133.3, C 133.3, C 131.9, C 131.5, C 132.4, C 130.4, C 130.4, C 2′ 163.8, C 123.4, CH 126.6, CH 129.9, CH 128.0, CH 130.6, CH 128.9, CH 129.8, CH 129.6, CH 3′ 104.5, CH 128.9, C 114.7, CH 114.7, CH 115.7, CH 114.8, CH 114.8, CH 115.4, CH 115.2, CH 4′ 180.4, C 152.1, C 153.6, C 153.6, C 154.8, C 154.1, C 154.7, C 156.1, C 156.0, C 5′ 144.8, C 116.7, CH 114.7, CH 114.7, CH 115.7, CH 114.8, CH 114.8, CH 115.4, CH 115.2, CH 6′ 146.8, C 127.6, CH 126.6, CH 129.9, CH 128.0, CH 130.6, CH 128.9, CH 129.8, CH 129.6, CH 7′ 126.6, CH 126.1, CH 49.0, CH 48.1, CH 79.9, CH 82.9, CH 84.8, CH 77.4, CH 76.4, CH 8′ 122.7, C 136.7, CH 89.1, CH 87.8, CH 83.1, CH 80.5, CH 83.8, CH 81.8, CH 81.4, CH 9′ 43.5, C 42.6, C 43.5, C 42.5, C 39.0, C 38.6, C 39.2, C 43.0, C 43.6, C 10′ 51.4, CH 2 41.2, CH 2 36.6, CH 2 35.5, CH 2 34.0, CH 2 32.8, CH 2 30.7, CH 2 38.3, CH 2 38.8, CH 2 11′ 204.2, C 23.2, CH 2 27.9, CH 2 27.2, CH 2 23.2, CH 2 20.5, CH 2 20.3, CH 2 22.2, CH 2 22.2, CH 2 12′ 163.0, C 124.7, CH 51.0, CH 50.7, CH 76.0, CH 76.3, CH 78.4, CH 124.5, CH 124.6, CH 13′ 37.7, C 131.3, C 147.0, C 146.9, C 144.6, C 82.0, C 82.7, C 131.6, C 131.3, C 14′ 22.3, CH 3 17.6, CH 111.9, CH 2 112.0, CH 2 111.5, CH 2 20.9, CH 3 24.2, CH 3 17.5, CH 3 17.5, CH 3 15′ 22.5, CH 3 25.7, CH 3 19.2, CH 3 19.3, CH 3 19.3, CH 3 23.4, CH 3 21.9, CH 3 25.7, CH 3 25.7, CH 3 16′ 23.9, CH 3 23.3, CH 3 28.7, CH 3 17.1, CH 3 24.3, CH 3 24.0, CH 3 23.3, CH 3 19.9, CH 3 17.4, CH 3 17′ 142.5, CH 145.8, CH 141.2, CH 147.5, CH 143.4, CH 146.7, CH 145.8, CH 141.9, CH 141.9, CH 18′ 114.5, CH 2 112.0, CH 2 114.2, CH 2 111.6, CH 2 112.2, CH 2 111.7, CH 2 111.1, CH 2 111.8, CH 2 112.4, CH 2 OCH3 55.1 56.8 Compound 8 was also isolated as yellowish oils with [α]25 D–20.0, and had a molecular formula of C 36 H 46 O 3 according to HRESIMS at m/z 525.3367 [M – H] – (calcd for C 36 H 45 O 3 , 525.3369). The IR spectrum of 8 showed absorption bands at 3395, 1615, 1588, 1516, 1456, 1267 and 1010 cm –1 ascribable to hydroxyl group and ether functions and an aromatic ring. Its NMR spectroscopic data (Tables 1 and 2 ) was consistent with those of a known bisbakuchiol A [ 20 ], except for the chemical shifts of B ring. A set of ABX type NMR signals had disappeared in bisbakuchiol A, whereas a set of A 2 B 2 type NMR signals appeared at δ H 7.19 (2H, br d, J = 8.6 Hz, H-2', 6') and 6.73 (2H, br d, J = 8.6 Hz, H-3', 5') in compound 8 . The configuration of 8 was elucidated through NOESY experiments (Fig. 5 ), where correlations between H-8' at δ H 3.97, and 16'-CH 3 at δ H 0.62 suggested their same β-orientation. The coupling constant ( J = 7.3 Hz) between H-7' and H-8' confirmed a trans configuration of the two methine protons of the dioxane ring [ 20 ]. Thus, the configuration of 8 , named bisbakuchiol T, was established as 9 S ,7' S ,8' S ,9' S , which was supported by comparison of the calculated and experimental ECD curves (Fig. 6 ). Compound 9 was isolated as yellowish oils with [α]25 D + 10.0, and possessed the same molecular formula, C 36 H 46 O 3 , as 8 according to the HRESIMS data ( m/z 525.3371 [M – H] – ). The 1 H NMR and 13 C NMR spectral data (Tables 1 and 2 ) of 9 were quite superimposable with those of compound 8 , which clearly indicated the same skeleton as that of 8 . Likely, NOE correlations between H-7' at δ H 4.91 and 16'-CH 3 at δ H 1.07, and the coupling constant ( J = 6.1 Hz) between H-7' and H-8', indicated that the configuration of 9 was 9 S ,7' R ,8' R ,9' S , which was consistent with ECD data (Fig. 6 ). Therefore, the structure of compound 9 , named bisbakuchiol U, was established as shown in Fig. 1 . Compound 10 was also isolated as yellowish oils. Its HRESIMS data exhibited a sodium adduct ion at m/z 445.3080 [M + Na] + , establishing the molecular formula as C 29 H 42 O 2 . Comparison of 1 H and 13 C NMR spectra of 10 (Table 3 ) and known bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a p -disubstituted benzene ring of 10 were identical to that of bakuchiol. In addition, the COSY, HSQC and HMBC correlations showed the presence of 2-ethenyl-2-methyl-5-isopropanol-cyclopentan-1-ol (6-ethenyl-6-methyl-4-isopropanol-cyclopentan-5-ol) substituted group in 10 . Comparison of the 13 C NMR spectrum of 10 with those of bakuchiol, the chemical shifts of C-3 and C-5 in 10 were shifted downfield to δ C 124.5, suggesting that this substituted group was connected to C-4 of bakuchiol moiety by an ether linkage. The relative configuration was mainly assigned by NOESY spectrum. Furthermore, the signals of H-4' at δ H 2.31 and H-5' at δ H 4.01 showed an NOE correlation, whereas H-4' or H-5' and 11'-CH 3 no showed the NOE correlation in its the NOESY correlation, confirmed that both H-4' and H-5' were α-oriented. Therefore, the structure of compound 10 , named bakuchiol ether A, was defined as shown in Fig. 1 . Compound 11 showed a molecular formula of C 33 H 48 O 2 on the basis of the HRESIMS ion at m/z 477.3713 [M + H] + . Compared with the NMR data (Table 3 ) of compound 10 , a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a p -disubstituted benzene ring in 11 were identical to that of compound 10 . In addition, the COSY, HSQC and HMBC correlations in 11 showed the presence of clovane-2β,9α-diol [ 21 , 22 ] moiety with the exception of the resonances of C-1', C-2' to downfield shifts and C-3' and C-4' to highfield shifts. In the key HMBC spectrum (Fig. 4 ), correlations between H-2' at δ H 4.24 and C-4 at δ C 158.2 (s) revealed that C-4 of bakuchiol moiety was connected to C-2' of clovane-2β,9α-diol moiety by an ether linkage. Therefore, the structure of compound 11 , named bakuchiol ether B, was defined as shown in Fig. 1 . Compound 12 was isolated as yellowish oils with [α]25 D + 30.0. It showed a molecular formula of C 33 H 48 O 2 . The COSY, HSQC and HMBC correlations showed the presences of one set of the bakuchiol signals as in compound 12 and one set of the caryolane-1,9β-diol signals [ 22 ]. Comparison of the 13 C NMR spectrum of 12 with those of bakuchiol, the chemical shifts of C-3 and C-5 were shifted downfield to δ C 121.6 and the chemical shifts of C-1' was shifted downfield to δ C 80.2 in 12 , suggesting that C-1' of this caryolane-1,9β-diol moiety was connected to C-4 of bakuchiol moiety by an ether linkage. Therefore, the structure of compound 12 , named bakuchiol ether C, was defined as shown in Fig. 1 . When the quaternary carbon from the other unit was connected to bakuchiol unit by C–O–C 4 , the chemical shifts of C-3 and C-5 would shift downfield (from115 to 121 or 123 ppm) as shown in compounds 1 , 6 , 7 , 10 , 12 , 15 , 16 and 17 . Whereas, the link by CH–O–C 4 would not result in changes of δ C at C-3 and C-5 as shown in compounds 3 , 4 , 5 and 11 . Therefore, we could infer the connection position of the dimers by the carbon chemical shifts of C-3/5 in bakuchiol unit. Table 3 1 H NMR (400 MHz, CDCl 3 ; δ H , J in Hz) data and 13 C NMR (100 MHz, CDCl 3 ) data for compounds 10 – 12 . Position 10 11 12 δ H ( J in Hz) δ C δ H ( J in Hz) δ C δ H ( J in Hz) δ C 1 134.9, C 130.3, C 131.4, C 2 7.27 (d, 8.6) 126.6, CH 7.25 (d, 8.7) 127.1, CH 7.20 (d, 8.7) 126.4, CH 3 6.93 (d, 8.6) 124.5, CH 6.82 (d, 8.7) 115.9, CH 6.79 (d, 8.7) 121.6, CH 4 153.5, C 158.2, C 154.7, C 5 6.93 (d, 8.6) 124.5, CH 6.82 (d, 8.7) 115.9, CH 6.79 (d, 8.7) 121.6, CH 6 7.27 (d, 8.6) 126.6, CH 7.25 (d, 8.7) 127.1, CH 7.20 (d, 8.7) 126.4, CH 7 6.28 (d, 16.3) 126.5, CH 6.25 (d, 16.2) 126.6, CH 6.25 (d, 16.3) 126.7, CH 8 6.12 (d, 16.3) 137.1, CH 6.04 (d, 16.2) 135.5, CH 6.06 (d, 16.3) 136.0, CH 9 42.6, C 42.5, C 42.5, C 10 1.49 (m) 41.2, CH 2 1.49 (m) 41.3, CH 2 1.49 (m) 41.3, CH 2 11 1.94 (m) 23.2, CH 2 1.95 (m) 23.2, CH 2 1.95 (m) 23.2, CH 2 12 5.12 (m) 124.8, CH 5.11 (br t, 7.1) 124.8, CH 5.11 (m) 124.8, CH 13 131.3, C 131.2, C 131.3, C 14 1.58 (s) 17.7, CH 3 1.57 (s) 17.6, CH 3 1.58 (s) 17.7, CH 3 15 1.67 (s) 25.7, CH 3 1.67 (s) 25.7, CH 3 1.67 (s) 25.7, CH 3 16 1.20 (s) 23.3, CH 3 1.19 (s) 23.4, CH 3 1.19 (s) 23.4, CH 3 17 5.88 (dd, 17.4, 10.8) 145.8, CH 5.88 (dd, 17.4, 10.7) 146.1, CH 5.87 (dd, 17.4, 10.7) 146.0, CH 18a 5.10 (dd, 17.4, 1.3) 111.9, CH 2 5.01 (dd, 17.4, 1.3) 111.8, CH 2 5.01 (dd, 17.4, 1.3) 111.9, CH 2 18b 5.04 (dd, 10.8, 1.3) 5.03 (dd, 10.7, 1.3) 5.03 (dd, 10.7, 1.3) 1′ 1.25 (s), 21.8, CH 3 45.3, C 80.2, C 2′ 84.1, C 4.24 (dd, 8.3, 5.4) 86.2, CH 2.35 (ddd, 11.7, 9.1, 8.6') 40.5, CH 3′ 1.26 (s) 26.3, CH 3 1.87 (dd, 12.9, 5.4), 1.65(m) 44.0, CH 2 1.86 (dd, 9.1, 6.1), 1.72 (dd, 9.1, 8.6) 30.7, CH 2 4′ 2.31 (m) 53.7, CH 38.3, C 34.7, C 5′ 4.01 (d, 9.0) 79.8, CH 1.58 (br d, 14.8) 50.1, CH 2.04 (ddd, 11.7, 9.1, 6.1) 44.9, CH 6′ 47.8, C 1.39 (m), 1.49 (m) 20.9, CH 2 1.41 (m), 1.53 (m) 21.3, CH 2 7′ 1.61 (m), 1.52 (m) 35.1, CH 2 1.38 (m), 1.16 (m) 33.2, CH 2 1.50 (m), 1.19 (m) 36.1, CH 2 8′ 1.95 (m), 1.49 (m) 22.8, CH 2 34.7, C 39.2, C 9′ 5.95 (dd, 17.6, 10.8) 146.7, CH 3.34 (br t, 2.6) 75.0, CH 3.50 (t, 4.7) 71.8, CH 10′a 5.03 (dd, 10.8, 1.3) 112.0, CH 2 2.03 (m), 27.2, CH 2 2.01 (dddd, 15.5, 12.5, 5.5, 3.0) 28.3, CH 2 10′b 5.02 (dd, 17.6, 1.3) 1.80 (dd, 14.1, 5.1) 1.78 (ddt, 15.5, 5.5, 3.0 ) 11′a 1.10 (s) 17.2, CH 3 1.38 (m) 26.7, CH 2 1.71 (m) 37.5, CH 2 11′b 1.06 (m) 12′ 1.56 (br s), 1.02 (br s) 36.0, CH 2 1.64 (d, 16.4), 1.49 (d, 16.4) 42.1, CH 2 13′ 0.94 (s) 25.7, CH 3 1.01 (s) 20.9, CH 3 14′ 1.06 (s) 31.4, CH 3 1.00 (s) 30.3, CH 3 15′ 0.95 (s) 28.4, CH 3 0.92 (s) 26.4, CH 3 NO, an unstable biological free radical, comes of L -arginine under the action of constitutive NO synthase (cNOS) and inducible NO synthase (iNOS). NO functions as a signaling molecule participating in neurotransmission and vasodilation. However, overproduction of NO is involved in inflammatory diseases, which can be treated by NO inhibitor. Compounds 1 – 17 (3.125–50 µM) were assay inhibition effect on NO production in LPS-stimulated RAW264.7 macrophages using the Griess reaction [ 14 ]. The MTT tests demonstrated that compound 4 showed cytotoxicity at the concentration of 50 µM, whereas other compounds were not cytotoxic. L-NIL, a selective inhibitor of iNOS, was used for the positive control. Compound 1 exhibited significant inhibition of NO production with IC 50 value at the concentration of 11.47 ± 1.57 µM, which showed no significant difference with that of L-NIL (10.29 ± 1.10 µM). Compounds 2 , 3 , 10 – 12 , 16 and 17 exhibited moderate inhibitory activity with IC 50 values at the range of 15.98–27.80 µM. The IC 50 values of the other compounds were more than 50 µM, and they were ineffective against NO production. Table 5 Inhibition of 1 – 3 , 10 – 12 and 16 – 17 on NO production. Compound IC 50 ( µ M) 1 11.47 ± 1.57 2 23.52 ± 1.82 3 21.43 ± 2.04 10 27.80 ± 1.18 11 26.86 ± 1.05 12 23.54 ± 0.82 16 15.98 ± 2.30 17 24.93 ± 1.13 L-NIL 10.29 ± 1.10 4. Discussion In our previous researches, we have obtained fourteen meroterpenoids and seventeen heterodimers of bakuchiol and evaluated their cytotoxicity [ 11 , 12 ]. Further investigation on the cHE extract brought about twelve unpresented bakuchiol dimmers and their NO inhibition activities were studied. In sum, Structural changes in bakuchiol increases structural and bioactive diversity of constituents from Psoraleae Fructus. And a new skeleton compound ( 1 ) was isolated and the compound exhibited significant NO inhibition activities. 5. Conclusion Seventeen bakuchiol dimers ( 1 – 17 ), including 12 undescribed dimers and 5 known compounds, were isolated from the fruits of Psoralea corylifolia L. and their structure were identified by spectral methods and X-ray single-crystal diffraction. Bisbakuchiol M ( 1 ), whose other bakuchiol unit was cyclized to form a 6/6/5 tricyclic system, was a new skeleton compound. And the plausible biosynthetic pathway of bisbakuchiol M was proposed. Their inhibition on NO production in LPS-stimulated RAW264.7 macrophages were evaluated by the Griess reaction. Compounds 2 , 3 , 10 – 12 , 16 and 17 exhibited inhibitory activities, and the inhibition of compound 1 was equal to that of L-NIL, a positive control. These findings suggested that Psoraleae Fructus provided natural anti-inflammatory constituents and bisbakuchiol M had the potential to be novel NO inhibitor. Abbreviations TCM: Traditional Chinese medicine; NO: nitric oxide; IC 50 : half maximal inhibitory concentration; CC: open column chromatography; TLC: thin layer chromatography; RP-SP-HPLC: reversed phase semi-preparative HPLC; PE: petroleum ether; cHE: cyclohexane; EtOAc: ethyl acetate; DMEM: Dulbecco's modified Eagle's medium; FBS: fetal bovine serum; CHCl 3 : chloroform; BuOH: normal-butanol; MTT: 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide; LPS: lipopolysaccharide; DMSO: dimethylsulfoxide; L-NIL: L-N6-(1-iminoethyl)-lysine. Declarations Author's contributions XWY and YTZ designed the experiments. QXX and QL were responsible for isolation experiment. QXX finished biological activity assay. LL performed LC/MS analysis. XWY and QXX writed the manuscripit. All authors read and approved the final manuscript. Acknowledgements Not applicable. Funding This work was supported by the National Natural Science Foundation of China (81773865). Availability of data and materials All data included in this article are available from the corresponding author upon request. Consent for publication All authors have provided consent for publication in the journal of Chinese Medicine. Conflicts of Interest The authors declare no conflict of interest. References Ai TM. Medicinal Flora of China, Peking University Press, Beijing, 2016; vol. 5 , p. 585–588. Chinese Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China, Chinese Medical Science and Technology Press, Beijing, 2015, vol. 1, p. 187–188. Chino M, Sato K, Yamazaki T and Maitani T. Constituent of natural food additive hokosshi extract and an analytical method for the additive in foods. Shokuhin Eiseigaku Zasshi. 2002; 43(6):352–355. Chopra B, Dhingra AK and Dhar KL, Psoralea corylifolia L. (Buguchi) - folklore to modern evidence: review. Fitoterapia. 2013;90:44–56. Zhang XN, Zhao WW, Wang Y, Lu JJ and Chen XP. The Chemical Constituents and Bioactivities of Psoralea corylifolia Linn.: A Review . Am. J. Chin. Med. 2016;44(1):35–60. Lim SH, Ha TY, Kim SR, Ahn J, Park HJ and Kim S, Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague-Dawley rats. Br. J. Nutr. 2009;101(7):1031–1039. Kim YJ, Lim HS, Lee J and Jeong SJ. Quantitative Analysis of Psoralea corylifolia Linne and its Neuroprotective and Anti-Neuroinflammatory Effects in HT22 Hippocampal Cells and BV-2 Microglia. Molecules. 2016;21(8):1076. Lin X, Li BB, Zhang L, Li HZ, Meng X, Jiang YY, Lee HS and Cui L. Four new compounds isolated from Psoralea corylifolia and their diacylglycerol acyltransferase (DGAT) inhibitory activity. Fitoterapia. 2018;128:130–134. Sun NJ, Woo SH, Cassady JM and Snapka RM. DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia . J. Nat. Prod. 1998;61(3):362–366. Gao HTY, Lang GZ, Zang YD, Ma J, Yang JZ, Ye F, Tian JY, Gao PP, Li CJ and Zhang DM. Bioactive monoterpene phenol dimers from the fruits of Psoralea corylifolia L. Bioorg Chem. 2021;112:104924. Xu QX, Zhang YB, Liu XY, Xu W and Yang XW. Cytotoxic heterodimers of meroterpene phenol from the fruits of Psoralea corylifolia . Phytochemistry. 2020;176:112394. Xu QX, Xu Wand Yang XW. Meroterpenoids from the fruits of Psoralea corylifolia . Tetrahedron. 2020;76:131343. MosMann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods.1983;65:55–63. Cao GY, Xu W, Yang XW, Gonzalez FJ and Li F. New neolignans from the seeds of Myristica fragrans that inhibit nitric oxide production. Food Chem. 2015;173:231–237. Labbe C, Faini F, Coll J and Connolly JD. Bakuchiol derivatives from the leaves of Psoralea glandulosa . Phytochemistry. 1996;42(5):1299–1303. Xiao GD, Li XK, Wu T, Cheng ZH, Tang QJ and Zhang T. Isolation of a new meroterpene and inhibitors of nitric oxide production from Psoralea corylifolia fruits guided by TLC bioautography. Fitoterapia. 2012;83(8):1553–1557. Banerji A and Chintalwar GJ. Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia . Phytochemistry. 1983;22(9):1945–1947. Takano S, Shimazaki Y and Ogasawara K. Enantiocontrolled synthesis of natural (+)-bakuchiol. Tetrahedron Lett. 1990;31:3325–3326. Yin S, Fan CQ, Dong L and Yue JM. Psoracorylifols A–E, five novel compounds with activity against Helicobacter pylori from seeds of Psoralea corylifolia . Tetrahedron. 2006;62:2569–2575. Wu CZ, Cai XF, Dat NT, Hong SS, Han AR, Seo EK, Hwang BY, Nan JX, Lee D and Lee JJ. Bisbakuchiols A and B, novel dimeric meroterpenoids from Psoralea corylifolia . Tetrahedron Lett . 2007;48(50):8861–8864. Wang AX, Zhang Q, and Jia ZJ. A new furobenzopyranone and other constituents from Anaphalis lacteal . Pharmazie. 2004;59(10):807–811. Heymann H, Tezuka Y, Kikuchi T, and Supriyatna S. Constituents of Sindora sumatrana MIQ. III. New trans-clerodane diterpenoids from the dried pods. Chem. Pharm. Bull. 1994;42(6):138–146. Supplementary Files Supplementarymaterial.docx Cite Share Download PDF Status: Under Review Version 1 posted Review # 1 received at journal 01 Aug, 2021 Review # 2 received at journal 01 Aug, 2021 Editorial decision: Major revision 01 Aug, 2021 Review # 3 received at journal 29 Jul, 2021 Reviewer # 3 agreed at journal 24 Jul, 2021 Reviews received at journal 21 Jul, 2021 Reviewers invited by journal 21 Jul, 2021 Reviewer # 2 agreed at journal 21 Jul, 2021 Reviewer # 1 agreed at journal 20 Jul, 2021 Submission checks completed at journal 15 Jul, 2021 Editor invited by journal 15 Jul, 2021 Editor assigned by journal 14 Jul, 2021 First submitted to journal 10 Jul, 2021 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. 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Yang","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA2UlEQVRIiWNgGAWjYPACmwTGBhDNRryWNNK1HE6A0MRoMbiRY/i54Nf5POZpZwwYPpQdZuCf3YBfi+SMHGPpmX23ixln5xgwzjh3mEHizgH8WvilcwykeXtuJzYCtTDzth1mMJBIwK+FTTrH+DdvzzmIlr/EaAHaYibN8+MARAsjMVok5z8rs+ZtSAb6Ja3gYM+5dB6JGwS0GJw5vPk2zx+7PMPZyRsf/CizluOfQUALAwOHAQNjGwODYQMDwwEgl4eQeiBgf8DA8IeBQZ4IpaNgFIyCUTBCAQCJB0PapmTtWQAAAABJRU5ErkJggg==","orcid":"","institution":"Peking University Health Science Centre","correspondingAuthor":true,"submittingAuthor":false,"prefix":"","firstName":"Xiuwei","middleName":"","lastName":"Yang","suffix":""}],"badges":[],"createdAt":"2021-07-11 03:46:58","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-706759/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-706759/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":11806576,"identity":"c0bb16c4-bf72-4294-9926-9cb828caad80","added_by":"auto","created_at":"2021-07-26 14:40:43","extension":"jpg","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":1517843,"visible":true,"origin":"","legend":"Structures of compounds 1–17.","description":"","filename":"Fig1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/e40c790e36bb932ba9880248.jpg"},{"id":11806578,"identity":"37d0a1bc-c5de-452d-b0de-7ffb6a225d15","added_by":"auto","created_at":"2021-07-26 14:40:44","extension":"jpg","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":99610,"visible":true,"origin":"","legend":"X-ray ORTEP drawings of 1.","description":"","filename":"Fig2.jpg","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/c1384ed4c2095a0571da17f1.jpg"},{"id":11807089,"identity":"d220acb3-4583-418a-a76a-f23699938ddf","added_by":"auto","created_at":"2021-07-26 14:43:43","extension":"jpg","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":747463,"visible":true,"origin":"","legend":"Plausible biogenetic pathway of 1.","description":"","filename":"Fig3.jpg","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/79381b6675bbc6b27565fef3.jpg"},{"id":11807091,"identity":"1ae4cd79-e15b-4ba6-94b5-536841cb91db","added_by":"auto","created_at":"2021-07-26 14:43:44","extension":"jpg","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":1229930,"visible":true,"origin":"","legend":"Key 1H–1H COSY and HMBC correlations of 1–12.","description":"","filename":"Fig4.jpg","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/7ac1c35dcf501d0437a01641.jpg"},{"id":11806579,"identity":"31139007-374f-4fea-a281-e7e7bff8d499","added_by":"auto","created_at":"2021-07-26 14:40:44","extension":"jpg","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":2153076,"visible":true,"origin":"","legend":"Key NOESY correlations of 3–9.","description":"","filename":"Fig5.jpg","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/6afc985f7efdc56f7b9a4f72.jpg"},{"id":13705545,"identity":"374bcb5d-d91d-49b7-9a0d-ec01763b5c47","added_by":"auto","created_at":"2021-09-17 13:52:49","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":942376,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/2ff9bb08-b247-4aaa-b856-218a5898597a.pdf"},{"id":11806581,"identity":"dafe29dd-575d-46a8-8548-09054e08e9d8","added_by":"auto","created_at":"2021-07-26 14:40:46","extension":"docx","order_by":4,"title":"","display":"","copyAsset":false,"role":"supplement","size":46558123,"visible":true,"origin":"","legend":"","description":"","filename":"Supplementarymaterial.docx","url":"https://assets-eu.researchsquare.com/files/rs-706759/v1/e8d26179d31f0119174271d8.docx"}],"financialInterests":"","formattedTitle":"\u003cp\u003eBakuchiol Dimers From Psoraleae Fructus That Inhibit Nitric Oxide Production in RAW264.7 Macrophages Cells\u003c/p\u003e","fulltext":[{"header":"1. Background","content":"\u003cp\u003eThe higher plant, \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. (\u003cem\u003eCullen corylifolia\u003c/em\u003e (L) Mefik) is an annual herb and belongs to family Leguminosae distributed in China, India, Malay peninsula, and Indonesia [\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e]. Dried fruit of \u003cem\u003eP. corylifolia\u003c/em\u003e (Psoraleae Fructus) is one of the most popular traditional Chinese medicine (TCM) and officially listed in Chinese Pharmacopoeia [\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e], and it is also a natural food additive [\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e]. It has been used for the treatment of nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e]. Psoraleae Fructus contains approximately 110 compounds including coumarins, flavonoids, meroterpenoids, and benzofurans [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e]. Among these, meroterpenoids are considered to be the one of characteristic and active components [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e, \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eBakuchiol is main meroterpenoid that consists of a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a \u003cem\u003ep\u003c/em\u003e-disubstituted benzene ring. Structural changes including oxidation, dehydration reduction, condensation and alkylation, occur in the side chain and benzene ring, which increases structural and bioactive diversities of meroterpenoid constituents. According to a review of predecessors' researches, 22 meroterpenoids and 12 bakuchiol dimers were found from the plant [\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e, \u003cspan additionalcitationids=\"CR9\" citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e]. In our previous researches [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e, \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e], fourteen meroterpenoids and seventeen heterodimers of bakuchiol have been reported and their cytotoxicity were evaluated. Further investigation on the cyclohexane extract brought about twelve unpresented bakuchiol dimmers, bisbakuchiols M\u0026ndash;U (\u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e9\u003c/b\u003e) and bisbakuchiol ethers A\u0026ndash;C (\u003cb\u003e10\u003c/b\u003e\u0026ndash;\u003cb\u003e12\u003c/b\u003e), along with five known compounds (\u003cb\u003e13\u003c/b\u003e\u0026ndash;\u003cb\u003e17\u003c/b\u003e).\u003c/p\u003e \u003cp\u003eCompound \u003cb\u003e1\u003c/b\u003e was a new skeleton possessing an undescribed 6/6/5 tricyclic-4,11-dione system deriving from 2,5-dihydroxybakuchiol intramolecular cyclization, and its' plausible biosynthetic pathway was proposed. Moreover, compound \u003cb\u003e2\u003c/b\u003e was a biphenyl dimer constructed by C\u003csub\u003e3\u003c/sub\u003e\u0026ndash;C\u003csub\u003e3'\u003c/sub\u003e bond and compounds \u003cb\u003e10\u003c/b\u003e\u0026ndash;\u003cb\u003e12\u003c/b\u003e were rare heterodimers of bakuchiol and terpenoid. Herein the structure elucidation of these compounds and evaluation of their ability to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were discussed.\u003c/p\u003e"},{"header":"2. Materials And Methods","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e2.1. General experimental procedures\u003c/h2\u003e \u003cp\u003eInfrared data were recorded on a Thermo Nicolet Nexus 470 FT-IR spectrometer. Ultraviolet data were acquired on a Mapada UV-6100 double beam spectrophotometer. HRESIMS data were collected using a Waters Xevo G2 QTOF spectrometer. NMR spectra were recorded on a Bruker AVANCE III HD 400 NMR spectrometer. Optical rotations were measured on a Rudolph Autopol IV automatic polarimeter. X-ray data were collected by a Rigaku Micromax-003 X-ray single-crystal diffractometer with CuKα radiation. Open column chromatography (CC) was performed by packing silica gel (200\u0026ndash;300 mesh, Marine Chemical Ltd., Qingdao, China), Sephadex LH-20 gel (Pharmacia Biotek, Denmark). Thin layer chromatography (TLC) was carried out on silica gel GF254 plates (Merck, Darmstadt, Germany) with 10% H\u003csub\u003e2\u003c/sub\u003eSO\u003csub\u003e4\u003c/sub\u003e in 95% ethanol followed by heating. Reversed phase semi-preparative HPLC (RP-SP-HPLC) was accomplished using an LC3000 system (Beijing Innovation Technology Co., Ltd), equipped with a phenomenon C\u003csub\u003e18\u003c/sub\u003e column (21.2 mm \u0026times; 250 mm, 5 \u0026micro;m). Cells were cultured in Sanyo MCO-15 AC carbon dioxide (CO\u003csub\u003e2\u003c/sub\u003e) incubator (Sanyo Electric Co., Ltd., Osaka, Japan).\u003c/p\u003e \u003cp\u003eHPLC grade solvents, methanol (MeOH) and acetonitrile (MeCN), were purchased from Fisher Scientific (Pittsburgh, PA, USA) and solvents, petroleum ether (PE), cyclohexane (cHE), ethyl acetate (EtOAc), chloroform (CHCl\u003csub\u003e3\u003c/sub\u003e) and normal-butanol (BuOH) for column chromatography purchased from Beijing Chemical Works (Beijing, China). Dulbecco's modified Eagle's medium (DMEM), fetal bovine serum (FBS), trypsin, penicillin-streptomycin solution, phosphate buffered saline were obtained from Gibco\u0026reg; (Life Technologies Inc., Grand Island, NY, USA). 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT), lipopolysaccharide (LPS), Griess reagent, dimethylsulfoxide (DMSO), and \u003cem\u003eL-N\u003c/em\u003e\u003csup\u003e\u003cem\u003e6\u003c/em\u003e\u003c/sup\u003e-(1-iminoethyl)-lysine (L-NIL) were obtained from Sigma-Aldrich (St. Louis, MO, USA). The murine macrophage cell line RAW264.7 was obtained from the Cell Bank of the Chinese Academy of Sciences (Shanghai, China).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2. Plant material\u003c/h2\u003e \u003cp\u003eThe mature fruits of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. were harvested from Yunnan province of People's Republic of China (GPS coordinates:23\u0026deg;32\u0026prime;N, 99\u0026deg;23\u0026prime;E) in October 2016, and authenticated by Prof. Xiu-Wei Yang of the School of Pharmaceutical Sciences, Peking University. A voucher specimen (accession number: BGZ201610) of the fruits was deposited at the State Key Laboratory of Natural Medicines and Biomimetic Drugs of Peking University.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3. Extraction and isolation\u003c/h2\u003e \u003cp\u003eThe dried mature fruits powder (47.9 kg) was extracted with 70% aqueous ethanol under reflux. After extracted for three times (first 479 kg for 2 h, and then 384 kg for 2 h two times), the crude extract (8.2 kg, yield 17.12%) was obtained. And then, part of the residue (6.0 kg) was suspended in H\u003csub\u003e2\u003c/sub\u003eO (8 L) and extracted with cHE (8 L \u0026times; 8), EtOAc (8 L \u0026times; 8) and \u003cem\u003en\u003c/em\u003e-butanol (BuOH, 8 L \u0026times; 8) successively and afforded corresponding extract for 1.2 kg, 2.2 kg and 0.7 kg. The cHE extract (1.0 kg) was fractionated by silica gel column (SGC, 140 mm i.d. \u0026times; 800 mm) with gradient eluent (PE-EtOAc, 5:1, 3:1, 1:1, 2:3, 1:3, 0:1, \u003cem\u003ev/v\u003c/em\u003e) to give 26 fractions (Fr. A\u0026ndash;Z). The Fr. B (27.2 g) was separated by SGC (55 mm i.d. \u0026times; 650 mm) with a step gradient eluent of PE-EtOAc (100: 1, 50: 1, 25: 1, 7: 1, 5: 1, 3:1, 1: 1, 1:3, 0:1, \u003cem\u003ev/v\u003c/em\u003e) to afford 15 subfractions (Fr. B-1\u0026ndash;Fr. B-15). Fr. B-8 (2.1 g) was separated by reversed-phase column (RPC), eluted with MeCN-H\u003csub\u003e2\u003c/sub\u003eO (40:60 to 100:0, \u003cem\u003ev/v\u003c/em\u003e), to give 13 subfractions. Fr. B-8-5 was purified by SP-RP-HPLC (MeCN-H\u003csub\u003e2\u003c/sub\u003eO, 95:5, \u003cem\u003ev/v\u003c/em\u003e), to yield compound \u003cb\u003e10\u003c/b\u003e (5 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 85 min). The Fr. C (136 g) was separated by SGC (120 mm i.d. \u0026times; 600 mm) with a step gradient eluent of PE-EtOAc (100: 1, 50: 1, 20: 1, 15: 1, 10: 1, 5:1, 5: 2, 1:1, 0:1, \u003cem\u003ev/v\u003c/em\u003e) to afford 16 subfractions (Fr. C-1\u0026ndash;Fr. C-16). Fr. C-4-7 was separated by Sephadex LH-20 column (SC) and purified by SP-RP-HPLC (MeCN-H\u003csub\u003e2\u003c/sub\u003eO, 93:7, \u003cem\u003ev/v\u003c/em\u003e), to yield compound \u003cb\u003e1\u003c/b\u003e (230 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 45 min) and \u003cb\u003e11\u003c/b\u003e (60 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 80 min). Fr. C-5 (20 g) was separated by RPC, eluted with MeOH-H\u003csub\u003e2\u003c/sub\u003eO (80:20 to 100:0, \u003cem\u003ev/v\u003c/em\u003e), to give 9 subfractions. Fr.C-5-9 was separated by SC and purified by SP-RP-HPLC (MeCN-H\u003csub\u003e2\u003c/sub\u003eO, 93:7, \u003cem\u003ev/v\u003c/em\u003e), to yield compound \u003cb\u003e12\u003c/b\u003e (34 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 71 min). By SP-RP-HPLC (MeCN-H\u003csub\u003e2\u003c/sub\u003eO, 90:10, \u003cem\u003ev/v\u003c/em\u003e) and preparative TLC (PE-CHCl\u003csub\u003e3\u003c/sub\u003e, 10:1, \u003cem\u003ev/v\u003c/em\u003e), compound \u003cb\u003e2\u003c/b\u003e (104 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 252 min) was obtained from Fr. C-11 (2.1 g). The Fr. D (335 g) was separated by SGC (140 mm i.d. \u0026times; 800 mm) with a step gradient eluent of PE-CHCl\u003csub\u003e3\u003c/sub\u003e (100: 1, 50: 1, 20: 1, 10: 1, 5: 1, 4:1, 3: 1, 2: 1, 1: 1, 1:3, 0:100, \u003cem\u003ev/v\u003c/em\u003e) to afford 14 subfractions (Fr. D-1\u0026ndash;Fr. D-14). Fr. D-4 (20.7 g) was separated by RPC, eluted with MeOH-H\u003csub\u003e2\u003c/sub\u003eO (45:55 to 100:0, \u003cem\u003ev/v\u003c/em\u003e), to give 13 subfractions. Fr. D-4-12 was purified by SP-RP-HPLC (MeOH-H\u003csub\u003e2\u003c/sub\u003eO, 93:7, \u003cem\u003ev/v\u003c/em\u003e), to yield compounds \u003cb\u003e8\u003c/b\u003e (15 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 131 min) and \u003cb\u003e9\u003c/b\u003e (28 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 136 min). By SP-RP-HPLC (MeCN-H\u003csub\u003e2\u003c/sub\u003eO, 90:10, \u003cem\u003ev/v\u003c/em\u003e), Fr. D-7(1.7 g)was separated to yield compounds \u003cb\u003e3\u003c/b\u003e (5 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 95 min) and \u003cb\u003e4\u003c/b\u003e (2 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 87 min). The Fr. D-9 (37 g) was separated by SGC (55 mm i.d. \u0026times; 650 mm) with a step gradient eluent of PE-CHCl\u003csub\u003e3\u003c/sub\u003e (100: 1, 50: 1, 20: 1, 10: 1, 9: 1, 8:1, 7: 1, 6: 1, 5: 1, 4:1, 3:1, 1:1, 1:3, 0:1, \u003cem\u003ev/v\u003c/em\u003e) to afford 28 subfractions. By SP-RP-HPLC (MeOH-H\u003csub\u003e2\u003c/sub\u003eO, 92:8, \u003cem\u003ev/v\u003c/em\u003e), Fr. D-9-13 was separated to yield compounds \u003cb\u003e5\u003c/b\u003e (11 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 77 min), \u003cb\u003e6\u003c/b\u003e (9 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 100 min) and \u003cb\u003e7\u003c/b\u003e (19 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 110 min). Fr. D-9-25 was purified by SP-RP-HPLC (MeOH-H\u003csub\u003e2\u003c/sub\u003eO, 92:8, \u003cem\u003ev/v\u003c/em\u003e), to give compounds \u003cb\u003e13\u003c/b\u003e (18 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 86 min) and \u003cb\u003e14\u003c/b\u003e (25 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 92 min). Fr. D-9-26 was purified by SP-RP-HPLC (MeOH-H\u003csub\u003e2\u003c/sub\u003eO, 92:8, \u003cem\u003ev/v\u003c/em\u003e), to give compound \u003cb\u003e15\u003c/b\u003e (15 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 76 min). Fr. D-11 (19.2 g) was separated by RPC, eluted with MeOH-H\u003csub\u003e2\u003c/sub\u003eO (45:55 to 100:0, \u003cem\u003ev/v\u003c/em\u003e), to give 27 subfractions. The Fr. D-11-25 (5.9 g) was separated by SGC (35 mm i.d. \u0026times; 500 mm) with a step gradient eluent of PE-CHCl\u003csub\u003e3\u003c/sub\u003e (8:1, 7: 1, 6: 1, 5: 1, 4:1, 3:1, 1:1, 1:3, 0:100, \u003cem\u003ev/v\u003c/em\u003e) to afford 18 subfractions. By SP-RP-HPLC (MeOH-H\u003csub\u003e2\u003c/sub\u003eO, 75:25, \u003cem\u003ev/v\u003c/em\u003e), Fr. D-11-25-12 was separated to yield compounds \u003cb\u003e16\u003c/b\u003e (14 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 286 min) and \u003cb\u003e17\u003c/b\u003e (15 mg, \u003cem\u003et\u003c/em\u003e\u003csub\u003e\u003cem\u003eR\u003c/em\u003e\u003c/sub\u003e = 328 min).\u003c/p\u003e \u003cp\u003eBisbakuchiol M (\u003cb\u003e1\u003c/b\u003e). Brown-red needle crystals; mp 114\u0026ndash;116 \u0026ordm;C; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;50.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 204 (4.85), 258 (4.80), 386 (4.28) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3315, 2967, 2930, 1692, 1609, 1582, 1504, 1385, 1358, 1255, 1035 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 537.3004 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e41\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, 537.3005).\u003c/p\u003e \u003cp\u003eBisbakuchiol N (\u003cb\u003e2\u003c/b\u003e). Yellow oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;20.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 203 (4.41), 253 (4.44) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3319, 2966, 2924, 1703, 1633, 1603, 1496, 1409, 1373, 1231, 969 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 511.3573 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e47\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e, 511.3576).\u003c/p\u003e \u003cp\u003eBisbakuchiol O (\u003cb\u003e3\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;30.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 203 (4.57), 267 (4.33) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3373, 2962, 2926, 1704, 1604, 1507, 1454, 1372, 1238, 1172, 1007 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 555.3468 [M\u0026thinsp;+\u0026thinsp;HCOO]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e47\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, 555.3474).\u003c/p\u003e \u003cp\u003eBisbakuchiol P (\u003cb\u003e4\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D \u0026minus;\u0026thinsp;26.7 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 202 (4.61), 267 (4.32) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3381, 2968, 2927, 1703, 1604, 1507, 1452, 1375, 1240, 1172, 1000 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 509.3417 [M \u0026ndash; H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e, 509.3420).\u003c/p\u003e \u003cp\u003eBisbakuchiol Q (\u003cb\u003e5\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;70.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 202 (4.76), 264 (4.55) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3370, 2964, 2921, 1704, 1607, 1507, 1459, 1370, 1238, 1171, 1099 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 525.3364 [M \u0026ndash; H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, 525.3369).\u003c/p\u003e \u003cp\u003eBisbakuchiol R (\u003cb\u003e6\u003c/b\u003e). White amorphous powder; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;70.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 203 (4.57), 260 (4.35) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3372, 2967, 2924, 1704, 1613, 1506, 1451, 1365, 1253, 1143, 1094 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 603.3676 [M\u0026thinsp;+\u0026thinsp;HCOO]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e38\u003c/sub\u003eH\u003csub\u003e51\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e, 603.3686).\u003c/p\u003e \u003cp\u003eBisbakuchiol S (\u003cb\u003e7\u003c/b\u003e). White amorphous powders; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;60.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 204 (4.42), 260 (4.32) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3373, 2968, 2925, 1705, 1614, 1506, 1450, 1364, 1235, 1143, 1082 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 557.3635 [M\u0026thinsp;\u0026minus;\u0026thinsp;H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e49\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, 557.3631).\u003c/p\u003e \u003cp\u003eBisbakuchiol T (\u003cb\u003e8\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D \u0026minus;\u0026thinsp;20.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 202 (4.68), 222 (4.57), 262 (4.33) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3395, 2967, 2921, 1702, 1588, 1507, 1450, 1375, 1267, 1171, 1010 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 525.3367 [M\u0026thinsp;\u0026minus;\u0026thinsp;H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, 525.3369).\u003c/p\u003e \u003cp\u003eBisbakuchiol U (\u003cb\u003e9\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;20.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 202 (4.63), 265 (4.21) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3387, 2966, 2922, 1703, 1587, 1507, 1451, 1374, 1267, 1171, 1009 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;1; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 525.3371 [M\u0026thinsp;\u0026minus;\u0026thinsp;H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, 525.3369).\u003c/p\u003e \u003cp\u003eBakuchiol ether A (\u003cb\u003e10\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;10.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 204(4.26),260(4.15) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3424, 2969, 2929, 1712, 1603, 1505, 1453, 1369, 1224, 1136, 913 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 445.3080 [M\u0026thinsp;+\u0026thinsp;Na]\u003csup\u003e+\u003c/sup\u003e (calcd for C\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eNa, 445.3083).\u003c/p\u003e \u003cp\u003eBakuchiol ether B (\u003cb\u003e11\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;20.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 206(4.50), 265(4.45) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3420, 2926, 2864, 1715, 1606, 1507, 1463, 1364, 1245, 1173, 969 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 477.3713 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e (calcd for C\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e49\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e, 477.3733).\u003c/p\u003e \u003cp\u003eBakuchiol ether C (\u003cb\u003e12\u003c/b\u003e). Yellowish oils; [\u003cem\u003eα\u003c/em\u003e]25 D\u0026thinsp;+\u0026thinsp;30.0 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH); UV (MeOH) \u003cem\u003eλ\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e (log \u003cem\u003eε\u003c/em\u003e): 206(4.46), 263(4.42) nm; IR (KBr) \u003cem\u003eν\u003c/em\u003e\u003csub\u003emax\u003c/sub\u003e 3420, 2952, 2927, 1710, 1604, 1505, 1452, 1375, 1241, 1171, 967 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e; \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 400 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; \u003csup\u003e13\u003c/sup\u003eC NMR (CDCl\u003csub\u003e3\u003c/sub\u003e, 100 MHz), see Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e; HRESIMS \u003cem\u003em/z\u003c/em\u003e 475.3532 [M\u0026thinsp;\u0026minus;\u0026thinsp;H]\u003csup\u003e\u0026minus;\u003c/sup\u003e (calcd for C\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e47\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e, 475.3576).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e2.4. X-ray Crystallographic Analysis\u003c/h2\u003e \u003cp\u003eThe X-ray crystallographic experiments were carried out on a XtaLAB Synergy R, HyPix diffractometer with \u003cem\u003eCuKα\u003c/em\u003e radiation. Crystallographic data (No. CCDC 1993852) of \u003cb\u003e1\u003c/b\u003e have been deposited at the Cambridge Crystallographic Data Center.\u003c/p\u003e \u003cp\u003eCrystallographic data of \u003cb\u003e1\u003c/b\u003e: C\u003csub\u003e72\u003c/sub\u003eH\u003csub\u003e80\u003c/sub\u003eO\u003csub\u003e8\u003c/sub\u003e, \u003cem\u003eM\u003c/em\u003e\u0026thinsp;=\u0026thinsp;1073.36, \u003cem\u003ea\u003c/em\u003e\u0026thinsp;=\u0026thinsp;13.2661(2) \u0026Aring;, \u003cem\u003eb\u003c/em\u003e\u0026thinsp;=\u0026thinsp;14.3761(2) \u0026Aring;, \u003cem\u003ec\u003c/em\u003e\u0026thinsp;=\u0026thinsp;31.3617(5) \u0026Aring;, \u003cem\u003eα\u003c/em\u003e\u0026thinsp;=\u0026thinsp;90\u0026deg;, \u003cem\u003eβ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;90\u0026deg;, \u003cem\u003eγ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;90\u0026deg;, \u003cem\u003eV\u003c/em\u003e\u0026thinsp;=\u0026thinsp;5981.13(18) \u0026Aring;\u003csup\u003e3\u003c/sup\u003e, \u003cem\u003eT\u003c/em\u003e\u0026thinsp;=\u0026thinsp;100 K, space group \u003cem\u003eP2\u003c/em\u003e\u003csub\u003e\u003cem\u003e1\u003c/em\u003e\u003c/sub\u003e\u003cem\u003e2\u003c/em\u003e\u003csub\u003e\u003cem\u003e1\u003c/em\u003e\u003c/sub\u003e\u003cem\u003e2\u003c/em\u003e\u003csub\u003e\u003cem\u003e1\u003c/em\u003e\u003c/sub\u003e, \u003cem\u003eZ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;4, \u003cem\u003e\u0026micro;\u003c/em\u003e (Cu Kα)\u0026thinsp;=\u0026thinsp;0.599 mm\u003csup\u003e-1\u003c/sup\u003e, Crystal size\u0026thinsp;=\u0026thinsp;0.99 \u0026times; 0.4 \u0026times; 0.02 mm\u003csup\u003e3\u003c/sup\u003e, 2Ɵ range for data collection\u0026thinsp;=\u0026thinsp;8.344 to 139.15826790\u0026deg;, 26790 reflections measured, 10867 independent reflections (\u003cem\u003eR\u003c/em\u003e\u003csub\u003e\u003cem\u003eint\u003c/em\u003e\u003c/sub\u003e = 0.0431, \u003cem\u003eR\u003c/em\u003e\u003csub\u003e\u003cem\u003esigma\u003c/em\u003e\u003c/sub\u003e =0.0446). The final \u003cem\u003eR\u003c/em\u003e\u003csub\u003e\u003cem\u003e1\u003c/em\u003e\u003c/sub\u003e value was 0.0475 (\u003cem\u003eI\u0026thinsp;\u0026gt;\u0026thinsp;2σ(I)\u003c/em\u003e). The final \u003cem\u003ewR (F\u003c/em\u003e\u003csup\u003e\u003cem\u003e2\u003c/em\u003e\u003c/sup\u003e\u003cem\u003e)\u003c/em\u003e value was 0.1153. Flack parameter =-0.02 (12).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e2.5. ECD calculations\u003c/h2\u003e \u003cp\u003eThe calculation was performed by the Gaussian 16 software. Conformation analysis were proceeded with the MMFF94s molecular mechanics force field. Optimization of the stable conformers with a Boltzmann distribution over 1% was conducted by time-dependent density functional theory (TD-DFT) at the Cam-B3LYP/6\u0026ndash;31\u0026thinsp;+\u0026thinsp;G(d, p) level for compounds \u003cb\u003e8\u003c/b\u003e and \u003cb\u003e9\u003c/b\u003e, with the CPCM model in MeOH. The ECD data was analysed by SpecDis v1.71 with the half-bandwidth no more than 0.3 eV. The final ECD spectra were obtained based on the Boltzmann-calculated contribution of each conformer.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003e2.6. Inhibition assay on NO production\u003c/h2\u003e \u003cp\u003eRAW264.7 cells were maintained in DMEM containing 10% FBS, in a constant humidity atmosphere of 5% CO\u003csub\u003e2\u003c/sub\u003e and 95% air at 37\u0026deg;C. The cells were cultivated at a density of 3 \u0026times; 10\u003csup\u003e5\u003c/sup\u003e cells/mL for 24 h in 96-well culture plates. And then, the cells were stimulated with LPS (1 \u0026micro;g/mL) and treated with various concentrations (1.5625\u0026ndash;50 \u0026micro;M) of assay compounds. After exposure to the compounds for 24 h, MTT (20 \u003cem\u003e\u0026micro;\u003c/em\u003eL, 5mg/mL) was added to each well [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. Four hours later, 100 \u003cem\u003e\u0026micro;\u003c/em\u003eL of lysis solution (40 g SDS, 20 mL isopropanol, 0.4 mL concentrated HCl and 400 mL ddH\u003csub\u003e2\u003c/sub\u003eO) was added to dissolve the formazan crystals. Absorbances at 490 nm were measured after 10h by a Multiskan MK3 Automated Microplate Reader (Thermo-Labsystems, Franklin, MA, USA).\u003c/p\u003e \u003cp\u003eThe RAW264.7 cells were grown at a density of 3 \u0026times; 10\u003csup\u003e5\u003c/sup\u003e cells/mL in 96-well culture plates. After 24 h, the cells were stimulated with LPS (1 \u0026micro;g/mL) and treated with various non-cytotoxic concentrations of assay compounds. And then, the cell culture supernatant (100 \u0026micro;L) was collected and reacted with the same volume of Griess reagent (100 \u0026micro;L) for 15 min at room temperature [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e]. The absorbance was determined at 540 nm. The experiments were performed in parallel for three times, and L-NIL was used as a positive control. IC\u003csub\u003e50\u003c/sub\u003e (half maximal inhibitory concentration) value of each compound was defined as the concentration (\u003cem\u003e\u0026micro;\u003c/em\u003eM) that caused 50% inhibition of NO production. The IC\u003csub\u003e50\u003c/sub\u003e values were calculated by the software SPSS 16.0 (SPSS Inc., Chicago, IL, USA).\u003c/p\u003e \u003c/div\u003e"},{"header":"3. Results","content":"\u003cp\u003ePhytochemical investigation on cHE fraction of 70% ethanol extract of Psoraleae Fructus resulted in twelve unpresented bakuchiol dimmers (\u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e12\u003c/strong\u003e) and five known compounds (\u003cstrong\u003e13\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e17\u003c/strong\u003e) (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e). Structures of these new compounds were assigned by NMR spectra and single crystal X-ray diffraction. Compounds \u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e3\u003c/strong\u003e, \u003cstrong\u003e6\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e9\u003c/strong\u003e, and \u003cstrong\u003e13\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e17\u003c/strong\u003e could be detected from ultrasonic extraction of Psoraleae Fructus by LC/MS analysis, suggesting that these compounds were natural products (Fig. S94).\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e1\u003c/strong\u003e was obtained as brown-red needle crystals (MeOH) with mp 114\u0026ndash;116 \u0026ordm;C. It had the molecular formula C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e40\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, as established by HRESIMS at \u003cem\u003em/z\u003c/em\u003e 537.3004 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e (calcd for 609.3216). Compared with the NMR data (Tables\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) of bakuchiol [\u003cspan class=\"CitationRef\"\u003e15\u003c/span\u003e], a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a \u003cem\u003ep\u003c/em\u003e-disubstituted benzene ring in \u003cstrong\u003e1\u003c/strong\u003e were identical to that of bakuchiol. The \u003csup\u003e1\u003c/sup\u003eH NMR data of an another side chain of compound \u003cstrong\u003e1\u003c/strong\u003e exhibited three methyl groups at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.78 (3H, s), 1.78 (3H, s) and 1.44 (3H, s); a vinyl group at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 5.87 (1H, dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.6, 7.5 Hz, H-17'), 5.19 (1H, br d, J\u0026thinsp;=\u0026thinsp;3.9 Hz, Ha-18'), and 5.16 (1H, br d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.6, Hb-18'); two trisubstituted olefinic protons at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 5.68 (1H, s) and 7.43 (1H, s); and one methylene group at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 2.60 (1H, d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;18.7 Hz, Ha-10') and 2.46 (1H, d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;18.7 Hz, Hb-10'). The presence of an \u0026alpha;,\u0026beta;-unsaturated ketone group was revealed by the band at 1692 cm\u003csup\u003e\u0026ndash;1\u003c/sup\u003e in its IR spectrum, which was confirmed by the resonance at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 180.4(s) in its \u003csup\u003e13\u003c/sup\u003eC NMR spectrum. Comparison of the \u003csup\u003e13\u003c/sup\u003eC NMR spectrum of \u003cstrong\u003e1\u003c/strong\u003e with those of bakuchiol, the chemical shifts of C-3 and C-5 were shifted downfield to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 121.4, suggesting that this substituted group was connected to C-4 of bakuchiol moiety by an ether linkage. The full assignment of \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eC NMR resonances was supported by \u003csup\u003e1\u003c/sup\u003eH\u0026ndash;\u003csup\u003e1\u003c/sup\u003eH COSY, DEPT, HSQC and HMBC spectral analyses. The X-ray structure was shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e and confirmed the absolute configuration of 9\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e for \u003cstrong\u003e1\u003c/strong\u003e. Thus, the structure of \u003cstrong\u003e1\u003c/strong\u003e was as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and named bisbakuchiol M.\u003c/p\u003e\n\u003cp\u003eThe plausible biosynthetic pathway of bisbakuchiol M was proposed (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e). Hydroxylation reactions occurred at the positions of C-2 and C-5 in bakuchiol to form M1. Once the 4-hydroxyl group in M1 lost a proton to generate M2-1, migrations of the double bond would start. The double bond at C-7 and C-8 would attack C-12 to form a five-membered ring, along with the generation of carbanion at C-13 (M2-2). Subsequently, the carbanion at C-13 attacked C-6 to form six-membered ring (M2-3). The proton at C-6 left, which was accompanied by electron migrations of negative ion of oxygen to produce ketone carbonyl (M3). And then, the \u0026alpha;-proton of double bond at C-8 was easily to be hydroxylated to generate M4. The elimination reaction would follow to the generation of M5. Similarly, the hydroxylation occurred at C-11 (M6). Subsequently, 11-hydroxyl group would be oxidized to ketone carbonyl (M7). Finally, M7 and bakuchiol were condensed to produce bisbakuchiol M.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e2\u003c/strong\u003e was isolated as yellow oils. The resonances in the \u003csup\u003e1\u003c/sup\u003eH NMR spectrum [\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 7.26, d, 2.4 Hz; 6.97, d, 8.5 Hz; and 7.34, dd, 8.5, 2.4 Hz] in \u003cstrong\u003e2\u003c/strong\u003e suggested clearly the 2,5,6-nature of the aromatic protons. Compared with the NMR data of bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) in \u003cstrong\u003e2\u003c/strong\u003e was identical to that of bakuchiol. Compound \u003cstrong\u003e2\u003c/strong\u003e had a molecular formula C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e on the basis of the HRESIMS ion at \u003cem\u003em/z\u003c/em\u003e 511.3573 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e. Consequently, the structure of compound \u003cstrong\u003e2\u003c/strong\u003e was unambiguously identified as a dimer comprising two bakuchiol units by a C\u0026ndash;C linkage, and it was given the trivial name bisbakuchiol N.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e3\u003c/strong\u003e was isolated as yellowish oils with [\u0026alpha;]25 D\u0026thinsp;+\u0026thinsp;30.0, and possessed a molecular formula of C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e by the HRESIMS ion at \u003cem\u003em/z\u003c/em\u003e 555.3468 [M\u0026thinsp;+\u0026thinsp;HCOO]\u003csup\u003e\u0026minus;\u003c/sup\u003e. The IR spectrum of \u003cstrong\u003e3\u003c/strong\u003e showed absorption bands at 3373, 1604, 1507, 1454, 1238, 1007 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e ascribable to hydroxyl group and ether functions and aromatic ring. Compared with the NMR data of bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a \u003cem\u003ep\u003c/em\u003e-disubstituted benzene ring in \u003cstrong\u003e3\u003c/strong\u003e were identical to that of bakuchiol, together with a set of remaining NMR signals, which were very similar to those of psoracorylifol F characterized from the fruits of \u003cem\u003eP. corylifolia\u003c/em\u003e [\u003cspan class=\"CitationRef\"\u003e16\u003c/span\u003e]. However, the correlations between H-17' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 6.43 and H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 2.89 were observed, which indicated that H-7' was \u0026alpha;-oriented. The large coupling constant (\u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;11.7 Hz) of H-7' and H-12' indicated a \u003cem\u003etrans\u003c/em\u003e configuration of the two methine protons. Likewise, the configuration of H-8' was confirmed \u0026beta;-oriented on the basis of the large coupling constant (\u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;10.6 Hz). Thus, the configuration was assigned as 7'\u003cem\u003eS\u003c/em\u003e,8'\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e,12'\u003cem\u003eS\u003c/em\u003e from the occurrence of (9\u003cem\u003eS\u003c/em\u003e)-bakuchiol only from nature [\u003cspan class=\"CitationRef\"\u003e17\u003c/span\u003e, \u003cspan class=\"CitationRef\"\u003e18\u003c/span\u003e]. Furthermore, the HMBC cross-peaks of H-8' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.06 with aromatic C-4 at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 159.7 correlation indicated that C-8' was connected to C-4 of bakuchiol moiety by an ether linkage (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e). According to the above data, the structure of compound \u003cstrong\u003e3\u003c/strong\u003e, named bisbakuchiol O, was established as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e4\u003c/strong\u003e was also isolated as yellowish oils with [\u0026alpha;]25 D\u0026ndash;26.7 (\u003cem\u003ec\u003c/em\u003e 0.1, MeOH), and possessed the same molecular formula, C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, as \u003cstrong\u003e3\u003c/strong\u003e according to the HRESIMS \u003cem\u003em/z\u003c/em\u003e 509.3417 [M \u0026ndash; H]\u003csup\u003e\u0026minus;\u003c/sup\u003e. Similarly, NMR data (Tables\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) for compound \u003cstrong\u003e4\u003c/strong\u003e was comparable to those of compound \u003cstrong\u003e3\u003c/strong\u003e. Compared with compound \u003cstrong\u003e3\u003c/strong\u003e, H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 2.96 (1H, br dd, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;11.7, 10.5 Hz) displayed a NOE correlation with 16'-CH\u003csub\u003e3\u003c/sub\u003e at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.30 (1H, s), indicating that they were cofacial, and H-7' was assigned in a \u0026beta;-configuration. And the large coupling constants (\u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;11.7, 10.5 Hz) indicated that H-8' and H-12' were \u0026alpha;-oriented. As a result, the configuration was confirmed as 7'\u003cem\u003eR\u003c/em\u003e,8'\u003cem\u003eR\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e,12'\u003cem\u003eR\u003c/em\u003e. According to the above data, compound \u003cstrong\u003e4\u003c/strong\u003e was a dimer, whose C-8' of psoracorylifol F was connected to aromatic C-4 of bakuchiol moiety by an ether linkage (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e). Thus, the structure of compound \u003cstrong\u003e4\u003c/strong\u003e, named bisbakuchiol P, was established as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e5\u003c/strong\u003e possessed the molecular formula of C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e as determined by its HRESIMS ion at \u003cem\u003em/z\u003c/em\u003e 525.3364 [M\u0026ndash;H]\u003csup\u003e\u0026ndash;\u003c/sup\u003e. Combined with NMR data, a set of bakuchiol unit signals except for downfield shift to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 157.0 for C-4 and a set of psoracorylifol A unit signals [\u003cspan class=\"CitationRef\"\u003e19\u003c/span\u003e] except for downfield shift to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 79.9 for C-7' were observed. In the HMBC spectrum of \u003cstrong\u003e5\u003c/strong\u003e (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e), a psoracorylifol A unit located at C-4 of the bakuchiol unit was verified by correlations from H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 5.17 to C-4 at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 157. These features permitted assignment of the planar structure of compound \u003cstrong\u003e5\u003c/strong\u003e as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e. In the NOESY spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e), correlations between H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 5.17 and CH\u003csub\u003e3\u003c/sub\u003e-16'\u0026beta; at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.10, H-8' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.46 and CH\u003csub\u003e3\u003c/sub\u003e-16'\u0026beta;, indicated that H-7' and H-8' were \u0026beta;-oriented. Whereas H-12' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.58 was \u0026alpha;-oriented, which was verified by correlations from H-8' and CH\u003csub\u003e3\u003c/sub\u003e-15' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.35. Thus, the absolute structure of compound \u003cstrong\u003e5\u003c/strong\u003e, named bisbakuchiol Q, was established as 9\u003cem\u003eS\u003c/em\u003e,7'\u003cem\u003eS\u003c/em\u003e,8'\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e,12'\u003cem\u003eS\u003c/em\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e6\u003c/strong\u003e was isolated as white amorphous powders, and possessed the molecular formula of C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e as deduced by HREIMS \u003cem\u003em/z\u003c/em\u003e 603.3676 [M\u0026thinsp;+\u0026thinsp;HCOO]\u003csup\u003e\u0026ndash;\u003c/sup\u003e. Combined with the various NMR experiments, a set of bakuchiol unit signals except for downfield shift to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 123.7 for C-3, C-5 and a set of psoracorylifol A unit signals except for downfield shift to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 82.9 for C-7' and \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 82.0 for C-13' were observed. In the HMBC experiment (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e), a characteristic methoxyl group at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.04 (3H, s) correlated with C-7' enabled us to attach this methoxyl group to the C-7'. In NMR spectra of \u003cstrong\u003e6\u003c/strong\u003e, the signals of an \u003cem\u003eexo\u003c/em\u003e-methylene of psoracorylifol A unit had disappeared, while a new signal for characteristic methyl group at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 0.49 (3H, s) and an oxygenated quaternary carbon at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 82.0 had appeared. Combined with the downfield shift of C-3 and C-5 of bakuchiol unit, it was obvious that two units were attached together by C\u003csub\u003e4\u003c/sub\u003e\u0026ndash;O\u0026ndash;C\u003csub\u003e13'\u003c/sub\u003e. In the NOESY spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e), correlations between H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.18 and CH\u003csub\u003e3\u003c/sub\u003e-16'\u0026beta; at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.10, H-8' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.96 and CH\u003csub\u003e3\u003c/sub\u003e-16'\u0026beta;, indicated that they were cofacial and were \u0026beta;-oriented. Similarly, correlations from H-8' and CH\u003csub\u003e3\u003c/sub\u003e-15' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 0.82 supported that H-12' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.14 was \u0026alpha;-oriented. Finally, the structural assignment of \u003cstrong\u003e6\u003c/strong\u003e was assigned as 9\u003cem\u003eS\u003c/em\u003e,7'\u003cem\u003eS\u003c/em\u003e,8'\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e,12'\u003cem\u003eS\u003c/em\u003e, and compound \u003cstrong\u003e6\u003c/strong\u003e was named bisbakuchiol R.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e7\u003c/strong\u003e was isolated as white amorphous powders, and possessed the same molecular formula, C\u003csub\u003e37\u003c/sub\u003eH\u003csub\u003e50\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e, as \u003cstrong\u003e6\u003c/strong\u003e according to the HRESIMS data (\u003cem\u003em/z\u003c/em\u003e 557.3635 [M \u0026ndash; H]\u003csup\u003e\u0026ndash;\u003c/sup\u003e). Its 1D NMR pattern was highly overlapped to that of compound \u003cstrong\u003e6\u003c/strong\u003e, indicating their same planar structure. In the NOESY spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e), correlations between H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.30, H-8' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.54, and CH\u003csub\u003e3\u003c/sub\u003e-16'\u0026beta; at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.17 indicated that they were cofacial and were \u0026beta;-oriented. Meanwhile, correlations from H-8' and H-12' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.08 suggested \u0026beta;-orientation of H-12'. Finally, the structural assignment of \u003cstrong\u003e7\u003c/strong\u003e was 9S,7'\u003cem\u003eS\u003c/em\u003e,8'\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e,12'\u003cem\u003eR\u003c/em\u003e as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and compound \u003cstrong\u003e7\u003c/strong\u003e was named bisbakuchiol.\u003c/p\u003e\n\u003cdiv class=\"gridtable\"\u003e\n\u003ctable id=\"Tab1\" border=\"1\"\u003e\u003ccaption\u003e\n\u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e\n\u003cdiv class=\"CaptionContent\"\u003e\n\u003cp\u003e\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e; \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e, \u003cem\u003eJ\u003c/em\u003e in Hz) data for compounds \u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e9\u003c/strong\u003e.\u003c/p\u003e\n\u003c/div\u003e\n\u003c/caption\u003e\n\u003cthead\u003e\n\u003ctr\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003ePosition\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e1\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e2\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e3\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e4\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e5\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e6\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e7\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e8\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e9\u003c/p\u003e\n\u003c/th\u003e\n\u003c/tr\u003e\n\u003c/thead\u003e\n\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.42 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.26 (d, 2.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.00 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.96 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.17 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.19 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.21 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.93 (br s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.92 (br s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.04 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.43 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.36 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.72 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.72 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.79 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.04 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.97 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.43 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.36 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.72 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.72 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.79 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.86, overlapped\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.85, overlapped\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.42 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.34 (dd, 8.5, 2.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.00 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.96 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.17 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.19 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.21 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.85, overlapped\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.85, overlapped\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.33 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.29 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.13 (d,16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.11 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.18 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.25 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.26 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.19 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.19 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.20 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.11 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.95 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.93 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.99 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.08 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.09 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.03 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.03 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.53 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.50 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.45 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.45 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.46 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.50 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.46 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.46 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.98 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.96 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.92 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.91 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.93 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.94 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.95 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.93 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.93 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.12 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.10 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.09 (br t, 7.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.08 (br t, 6.9)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.08 (br t, 7.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.10 (br t, 7.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.10 (br t, 7.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.09 (br t)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.09 (br t)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.60 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.57 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.66 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.56 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.57 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.57 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.68 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.66 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.56 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.66 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e16\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.23 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.20 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.15 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.14 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.15 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.19 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.19 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.17 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.17 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.87 (dd, 17.6, 11.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.88 (dd, 17.4, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.84 (dd, 17.2, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.83 (dd, 17.2, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.84 (dd, 17.7, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.87 (dd, 17.5, 10.9)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.87 (dd, 17.5, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.85 (dd, 17.6, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.85 (dd, 17.6, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.04 (dd, 17.6, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.02 (dd, 17.4, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.97 (dd, 17.2, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.97 (dd, 17.2, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.96 (dd, 17.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 17.5, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 17.5, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 10.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 10.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.08 (dd, 11.0, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.04 (dd, 10.7, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.00 (dd, 10.8, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.00 (dd, 10.8, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.00 (dd, 10.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.03 (dd, 10.9, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.02 (dd, 10.8, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.99 (dd, 17.6, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.99 (dd, 17.6, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.26 (d, 2.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.00 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.01 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.16 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.24 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.18 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.19 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.16 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.68 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.56 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.56 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.71 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.77 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.74 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.73 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.77 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.97 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.56 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.56 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.71 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.77 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.74 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.73 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.77 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.34 (dd, 8.5, 2.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.00 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.01 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.16 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.24 (d, 8.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.18 (d, 8.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.19 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.16 (br d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.43 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.29 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.89 (br dd, 11.7, 10.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.96 (br dd, 11.7, 10.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.17 (d, 2.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.18 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.30 (d, 3.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.80 (d, 7.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.91 (d, 6.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.11 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.06 (d, 10.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.05 (d, 10.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.46 (d, 2.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.96 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.54 (d, 3.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.97 (d, 7.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.04 (d, 6.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u0026prime;a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.60 (d, 18.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.50 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.98 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.72 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.86 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.76 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.32 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.76 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.55 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u0026prime;b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.46(d, 18.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.56 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.64 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.62 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.76 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.30 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.44 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u0026prime;a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.96 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.79 (dd, 12.3, 3.3),\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.70 (dd, 11.8, 3.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.93 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.74 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.85 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.93(m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.83 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u0026prime;b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.96 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.55 (dd, 12.3, 3.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.60 (dd, 11.8, 3.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.88 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.74 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.85 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.82 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.83 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.10 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.53 (dt, 12.3, 3.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.47 (dt, 11.8, 3.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.58 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.14 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.08 (dd, 3.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.06 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.03 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.78 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.57 (br s),\u003c/p\u003e\n\u003cp\u003e4.54 (br s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.58 (br s)\u003c/p\u003e\n\u003cp\u003e4.56 (br s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.95 (d, 1.3)\u003c/p\u003e\n\u003cp\u003e4.91 (d, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.82 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.11 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.57 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.78 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.51 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.56 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.35 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.49 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.09 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.66 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e16\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.44 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.20 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.04 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.30 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.10 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.10 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.17 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.62 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.07 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.87 (dd, 10.6, 7.5)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.88 (dd, 17.4, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.43 (dd, 17.2, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.83 (dd, 17.2, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.46 (dd, 17.7, 10.9)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.15 (dd, 17.5, 10.9)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.02 (dd, 17.5, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.84 (dd, 17.4, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.48 (dd, 17.7, 11.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18\u0026prime;a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.19 (br d, 3.9)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.02 (dd, 17.4, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.20 (dd, 17.2, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.20 (dd, 17.2, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.81 (d, 1.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.14 (dd, 17.5, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.05 (dd, 17.5, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18\u0026prime;b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.16 (br d, 10.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.04 (dd, 10.7, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.29 (dd, 10.8, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.29 (dd, 10.8, 1.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.85 (d, 1.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.99 (dd, 10.9, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.02 (dd, 10.8, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003eOCH3\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.04 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.16 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u0026nbsp;\u003c/p\u003e\n\u003c/div\u003e\n\u003cdiv class=\"gridtable\"\u003e\n\u003ctable id=\"Tab2\" border=\"1\"\u003e\u003ccaption\u003e\n\u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e\n\u003cdiv class=\"CaptionContent\"\u003e\n\u003cp\u003e\u003csup\u003e13\u003c/sup\u003eC NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) data for compounds \u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e9\u003c/strong\u003e.\u003c/p\u003e\n\u003c/div\u003e\n\u003c/caption\u003e\n\u003cthead\u003e\n\u003ctr\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003ePosition\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e1\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e2\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e3\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e4\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e5\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e6\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e7\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e8\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e9\u003c/p\u003e\n\u003c/th\u003e\n\u003c/tr\u003e\n\u003c/thead\u003e\n\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e132.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e132.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e123.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e113.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e113.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e121.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e123.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e143.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e143.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e152.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e152.1, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e159.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e159.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e157.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e155.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e154.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e143.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e143.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e121.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e123.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e119.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e119.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e125.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e138.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e135.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e135.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e135.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e16\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e113.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e133.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e133.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e132.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e163.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e123.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e104.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e180.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e152.1, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e153.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e153.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e154.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e154.1, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e154.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e156.1, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e156.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e144.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e116.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e128.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e129.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e49.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e48.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e79.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e82.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e84.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e77.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e76.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e122.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e89.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e87.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e83.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e80.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e83.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e81.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e81.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e43.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e43.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e39.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e38.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e39.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e43.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e43.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e51.4, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e36.6, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e35.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e34.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e32.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e30.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e38.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e38.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e204.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e27.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e27.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e20.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e20.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e22.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e22.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e163.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e51.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e50.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e76.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e76.3, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e78.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e37.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e147.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e144.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e82.0, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e82.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e22.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e20.9, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e24.2, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.5, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.5, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e22.5, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e19.2, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e19.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e19.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e21.9, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e16\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.9, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e28.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.1, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e24.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e24.0, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e19.9, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e142.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e141.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e147.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e143.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e141.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e141.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e114.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.6, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.1, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.4, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003eOCH3\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e55.1\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e56.8\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003c/tbody\u003e\n\u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003e\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e8\u003c/strong\u003e was also isolated as yellowish oils with [\u0026alpha;]25 D\u0026ndash;20.0, and had a molecular formula of C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e according to HRESIMS at \u003cem\u003em/z\u003c/em\u003e 525.3367 [M \u0026ndash; H]\u003csup\u003e\u0026ndash;\u003c/sup\u003e (calcd for C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e45\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, 525.3369). The IR spectrum of \u003cstrong\u003e8\u003c/strong\u003e showed absorption bands at 3395, 1615, 1588, 1516, 1456, 1267 and 1010 cm\u003csup\u003e\u0026ndash;1\u003c/sup\u003e ascribable to hydroxyl group and ether functions and an aromatic ring. Its NMR spectroscopic data (Tables\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) was consistent with those of a known bisbakuchiol A [\u003cspan class=\"CitationRef\"\u003e20\u003c/span\u003e], except for the chemical shifts of B ring. A set of ABX type NMR signals had disappeared in bisbakuchiol A, whereas a set of A\u003csub\u003e2\u003c/sub\u003eB\u003csub\u003e2\u003c/sub\u003etype NMR signals appeared at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 7.19 (2H, br d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.6 Hz, H-2', 6') and 6.73 (2H, br d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.6 Hz, H-3', 5') in compound \u003cstrong\u003e8\u003c/strong\u003e. The configuration of \u003cstrong\u003e8\u003c/strong\u003e was elucidated through NOESY experiments (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e5\u003c/span\u003e), where correlations between H-8' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 3.97, and 16'-CH\u003csub\u003e3\u003c/sub\u003e at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 0.62 suggested their same \u0026beta;-orientation. The coupling constant (\u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.3 Hz) between H-7' and H-8' confirmed a \u003cem\u003etrans\u003c/em\u003e configuration of the two methine protons of the dioxane ring [\u003cspan class=\"CitationRef\"\u003e20\u003c/span\u003e]. Thus, the configuration of \u003cstrong\u003e8\u003c/strong\u003e, named bisbakuchiol T, was established as 9\u003cem\u003eS\u003c/em\u003e,7'\u003cem\u003eS\u003c/em\u003e,8'\u003cem\u003eS\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e, which was supported by comparison of the calculated and experimental ECD curves (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e).\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e9\u003c/strong\u003e was isolated as yellowish oils with [\u0026alpha;]25 D\u0026thinsp;+\u0026thinsp;10.0, and possessed the same molecular formula, C\u003csub\u003e36\u003c/sub\u003eH\u003csub\u003e46\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e, as \u003cstrong\u003e8\u003c/strong\u003e according to the HRESIMS data (\u003cem\u003em/z\u003c/em\u003e 525.3371 [M \u0026ndash; H]\u003csup\u003e\u0026ndash;\u003c/sup\u003e). The \u003csup\u003e1\u003c/sup\u003eH NMR and \u003csup\u003e13\u003c/sup\u003eC NMR spectral data (Tables\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e and \u003cspan class=\"InternalRef\"\u003e2\u003c/span\u003e) of \u003cstrong\u003e9\u003c/strong\u003e were quite superimposable with those of compound \u003cstrong\u003e8\u003c/strong\u003e, which clearly indicated the same skeleton as that of \u003cstrong\u003e8\u003c/strong\u003e. Likely, NOE correlations between H-7' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.91 and 16'-CH\u003csub\u003e3\u003c/sub\u003e at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 1.07, and the coupling constant (\u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;6.1 Hz) between H-7' and H-8', indicated that the configuration of \u003cstrong\u003e9\u003c/strong\u003e was 9\u003cem\u003eS\u003c/em\u003e,7'\u003cem\u003eR\u003c/em\u003e,8'\u003cem\u003eR\u003c/em\u003e,9'\u003cem\u003eS\u003c/em\u003e, which was consistent with ECD data (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e6\u003c/span\u003e). Therefore, the structure of compound \u003cstrong\u003e9\u003c/strong\u003e, named bisbakuchiol U, was established as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e10\u003c/strong\u003e was also isolated as yellowish oils. Its HRESIMS data exhibited a sodium adduct ion at \u003cem\u003em/z\u003c/em\u003e 445.3080 [M\u0026thinsp;+\u0026thinsp;Na]\u003csup\u003e+\u003c/sup\u003e, establishing the molecular formula as C\u003csub\u003e29\u003c/sub\u003eH\u003csub\u003e42\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e. Comparison of \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eC NMR spectra of \u003cstrong\u003e10\u003c/strong\u003e (Table\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e) and known bakuchiol, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a \u003cem\u003ep\u003c/em\u003e-disubstituted benzene ring of \u003cstrong\u003e10\u003c/strong\u003e were identical to that of bakuchiol. In addition, the COSY, HSQC and HMBC correlations showed the presence of 2-ethenyl-2-methyl-5-isopropanol-cyclopentan-1-ol (6-ethenyl-6-methyl-4-isopropanol-cyclopentan-5-ol) substituted group in \u003cstrong\u003e10\u003c/strong\u003e. Comparison of the \u003csup\u003e13\u003c/sup\u003eC NMR spectrum of \u003cstrong\u003e10\u003c/strong\u003e with those of bakuchiol, the chemical shifts of C-3 and C-5 in \u003cstrong\u003e10\u003c/strong\u003e were shifted downfield to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 124.5, suggesting that this substituted group was connected to C-4 of bakuchiol moiety by an ether linkage. The relative configuration was mainly assigned by NOESY spectrum. Furthermore, the signals of H-4' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 2.31 and H-5' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.01 showed an NOE correlation, whereas H-4' or H-5' and 11'-CH\u003csub\u003e3\u003c/sub\u003e no showed the NOE correlation in its the NOESY correlation, confirmed that both H-4' and H-5' were \u0026alpha;-oriented. Therefore, the structure of compound \u003cstrong\u003e10\u003c/strong\u003e, named bakuchiol ether A, was defined as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e11\u003c/strong\u003e showed a molecular formula of C\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e on the basis of the HRESIMS ion at \u003cem\u003em/z\u003c/em\u003e 477.3713 [M\u0026thinsp;+\u0026thinsp;H]\u003csup\u003e+\u003c/sup\u003e. Compared with the NMR data (Table\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e3\u003c/span\u003e) of compound \u003cstrong\u003e10\u003c/strong\u003e, a side chain (3-ethenyl-3,7-dimethyl-1,6-octadienyl) and a \u003cem\u003ep\u003c/em\u003e-disubstituted benzene ring in \u003cstrong\u003e11\u003c/strong\u003e were identical to that of compound \u003cstrong\u003e10\u003c/strong\u003e. In addition, the COSY, HSQC and HMBC correlations in \u003cstrong\u003e11\u003c/strong\u003e showed the presence of clovane-2\u0026beta;,9\u0026alpha;-diol [\u003cspan class=\"CitationRef\"\u003e21\u003c/span\u003e, \u003cspan class=\"CitationRef\"\u003e22\u003c/span\u003e] moiety with the exception of the resonances of C-1', C-2' to downfield shifts and C-3' and C-4' to highfield shifts. In the key HMBC spectrum (Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e4\u003c/span\u003e), correlations between H-2' at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e 4.24 and C-4 at \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 158.2 (s) revealed that C-4 of bakuchiol moiety was connected to C-2' of clovane-2\u0026beta;,9\u0026alpha;-diol moiety by an ether linkage. Therefore, the structure of compound \u003cstrong\u003e11\u003c/strong\u003e, named bakuchiol ether B, was defined as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eCompound \u003cstrong\u003e12\u003c/strong\u003e was isolated as yellowish oils with [\u0026alpha;]25 D\u0026thinsp;+\u0026thinsp;30.0. It showed a molecular formula of C\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e48\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e. The COSY, HSQC and HMBC correlations showed the presences of one set of the bakuchiol signals as in compound \u003cstrong\u003e12\u003c/strong\u003e and one set of the caryolane-1,9\u0026beta;-diol signals [\u003cspan class=\"CitationRef\"\u003e22\u003c/span\u003e]. Comparison of the \u003csup\u003e13\u003c/sup\u003eC NMR spectrum of \u003cstrong\u003e12\u003c/strong\u003e with those of bakuchiol, the chemical shifts of C-3 and C-5 were shifted downfield to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 121.6 and the chemical shifts of C-1' was shifted downfield to \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e 80.2 in \u003cstrong\u003e12\u003c/strong\u003e, suggesting that C-1' of this caryolane-1,9\u0026beta;-diol moiety was connected to C-4 of bakuchiol moiety by an ether linkage. Therefore, the structure of compound \u003cstrong\u003e12\u003c/strong\u003e, named bakuchiol ether C, was defined as shown in Fig.\u0026nbsp;\u003cspan class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e\n\u003cp\u003eWhen the quaternary carbon from the other unit was connected to bakuchiol unit by C\u0026ndash;O\u0026ndash;C\u003csub\u003e4\u003c/sub\u003e, the chemical shifts of C-3 and C-5 would shift downfield (from115 to 121 or 123 ppm) as shown in compounds \u003cstrong\u003e1\u003c/strong\u003e, \u003cstrong\u003e6\u003c/strong\u003e, \u003cstrong\u003e7\u003c/strong\u003e, \u003cstrong\u003e10\u003c/strong\u003e, \u003cstrong\u003e12\u003c/strong\u003e, \u003cstrong\u003e15\u003c/strong\u003e, \u003cstrong\u003e16\u003c/strong\u003e and \u003cstrong\u003e17\u003c/strong\u003e. Whereas, the link by CH\u0026ndash;O\u0026ndash;C\u003csub\u003e4\u003c/sub\u003e would not result in changes of \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e at C-3 and C-5 as shown in compounds \u003cstrong\u003e3\u003c/strong\u003e, \u003cstrong\u003e4\u003c/strong\u003e, \u003cstrong\u003e5\u003c/strong\u003e and \u003cstrong\u003e11\u003c/strong\u003e. Therefore, we could infer the connection position of the dimers by the carbon chemical shifts of C-3/5 in bakuchiol unit.\u003c/p\u003e\n\u003cdiv class=\"gridtable\"\u003e\n\u003ctable id=\"Tab3\" border=\"1\"\u003e\u003ccaption\u003e\n\u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e\n\u003cdiv class=\"CaptionContent\"\u003e\n\u003cp\u003e\u003csup\u003e1\u003c/sup\u003eH NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e; \u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e, \u003cem\u003eJ\u003c/em\u003e in Hz) data and \u003csup\u003e13\u003c/sup\u003eC NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) data for compounds \u003cstrong\u003e10\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e12\u003c/strong\u003e.\u003c/p\u003e\n\u003c/div\u003e\n\u003c/caption\u003e\n\u003cthead\u003e\n\u003ctr\u003e\n\u003cth rowspan=\"2\" align=\"left\"\u003e\n\u003cp\u003ePosition\u003c/p\u003e\n\u003c/th\u003e\n\u003cth colspan=\"2\" align=\"left\"\u003e\n\u003cp\u003e10\u003c/p\u003e\n\u003c/th\u003e\n\u003cth colspan=\"2\" align=\"left\"\u003e\n\u003cp\u003e11\u003c/p\u003e\n\u003c/th\u003e\n\u003cth colspan=\"2\" align=\"left\"\u003e\n\u003cp\u003e12\u003c/p\u003e\n\u003c/th\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e (\u003cem\u003eJ\u003c/em\u003e in Hz)\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e (\u003cem\u003eJ\u003c/em\u003e in Hz)\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eH\u003c/sub\u003e (\u003cem\u003eJ\u003c/em\u003e in Hz)\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003e\u003cem\u003e\u0026delta;\u003c/em\u003e\u003csub\u003eC\u003c/sub\u003e\u003c/p\u003e\n\u003c/th\u003e\n\u003c/tr\u003e\n\u003c/thead\u003e\n\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e134.9, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e130.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.4, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.27 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.25 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.20 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.93 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.82 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.79 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e121.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e153.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e158.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e154.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.93 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.82 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e115.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.79 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e121.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.27 (d, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.25 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e127.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7.20 (d, 8.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.4, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.28 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.25 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.6, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.25 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e126.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.12 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e137.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.04 (d, 16.2)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e135.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6.06 (d, 16.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e136.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.6, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.5, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e41.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.94 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.95 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.95 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.12 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.11 (br t, 7.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.11 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e124.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e131.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.57 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.6, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.67 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e16\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.20 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.19 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.19 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e23.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.88 (dd, 17.4, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e145.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.88 (dd, 17.4, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.87 (dd, 17.4, 10.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.10 (dd, 17.4, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 17.4, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.01 (dd, 17.4, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e111.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e18b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.04 (dd, 10.8, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.03 (dd, 10.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.03 (dd, 10.7, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.25 (s),\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e21.8, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e45.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e80.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e84.1, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.24 (dd, 8.3, 5.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e86.2, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.35 (ddd, 11.7, 9.1, 8.6')\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e40.5, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.26 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e26.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.87 (dd, 12.9, 5.4), 1.65(m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e44.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.86 (dd, 9.1, 6.1), 1.72 (dd, 9.1, 8.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e30.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.31 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e53.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e38.3, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e34.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e4.01 (d, 9.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e79.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.58 (br d, 14.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e50.1, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.04 (ddd, 11.7, 9.1, 6.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e44.9, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e6\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e47.8, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.39 (m), 1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e20.9, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.41 (m), 1.53 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e21.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e7\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.61 (m), 1.52 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e35.1, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.38 (m), 1.16 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e33.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.50 (m), 1.19 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e36.1, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e8\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.95 (m), 1.49 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e22.8, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e34.7, C\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e39.2, C\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e9\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.95 (dd, 17.6, 10.8)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e146.7, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.34 (br t, 2.6)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e75.0, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e3.50 (t, 4.7)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e71.8, CH\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u0026prime;a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.03 (dd, 10.8, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e112.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.03 (m),\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e27.2, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e2.01 (dddd, 15.5, 12.5, 5.5, 3.0)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e28.3, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e10\u0026prime;b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e5.02 (dd, 17.6, 1.3)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.80 (dd, 14.1, 5.1)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.78 (ddt, 15.5, 5.5, 3.0 )\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u0026prime;a\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.10 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e17.2, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.38 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e26.7, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.71 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e37.5, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e11\u0026prime;b\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.06 (m)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e12\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.56 (br s), 1.02 (br s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e36.0, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.64 (d, 16.4), 1.49 (d, 16.4)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e42.1, CH\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e13\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.94 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e25.7, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.01 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e20.9, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e14\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.06 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e31.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e1.00 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e30.3, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e15\u0026prime;\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\u0026nbsp;\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.95 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e28.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e0.92 (s)\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e26.4, CH\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003c/tbody\u003e\n\u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003e\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eNO, an unstable biological free radical, comes of \u003cem\u003eL\u003c/em\u003e-arginine under the action of constitutive NO synthase (cNOS) and inducible NO synthase (iNOS). NO functions as a signaling molecule participating in neurotransmission and vasodilation. However, overproduction of NO is involved in inflammatory diseases, which can be treated by NO inhibitor. Compounds \u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e17\u003c/strong\u003e (3.125\u0026ndash;50 \u0026micro;M) were assay inhibition effect on NO production in LPS-stimulated RAW264.7 macrophages using the Griess reaction [\u003cspan class=\"CitationRef\"\u003e14\u003c/span\u003e]. The MTT tests demonstrated that compound \u003cstrong\u003e4\u003c/strong\u003e showed cytotoxicity at the concentration of 50 \u0026micro;M, whereas other compounds were not cytotoxic. L-NIL, a selective inhibitor of iNOS, was used for the positive control. Compound \u003cstrong\u003e1\u003c/strong\u003e exhibited significant inhibition of NO production with IC\u003csub\u003e50\u003c/sub\u003e value at the concentration of 11.47\u0026thinsp;\u0026plusmn;\u0026thinsp;1.57 \u0026micro;M, which showed no significant difference with that of L-NIL (10.29\u0026thinsp;\u0026plusmn;\u0026thinsp;1.10 \u0026micro;M). Compounds \u003cstrong\u003e2\u003c/strong\u003e, \u003cstrong\u003e3\u003c/strong\u003e, \u003cstrong\u003e10\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e12\u003c/strong\u003e, \u003cstrong\u003e16\u003c/strong\u003e and \u003cstrong\u003e17\u003c/strong\u003e exhibited moderate inhibitory activity with IC\u003csub\u003e50\u003c/sub\u003e values at the range of 15.98\u0026ndash;27.80 \u0026micro;M. The IC\u003csub\u003e50\u003c/sub\u003e values of the other compounds were more than 50 \u0026micro;M, and they were ineffective against NO production.\u003c/p\u003e\n\u003cdiv class=\"gridtable\"\u003e\n\u003ctable id=\"Tab4\" border=\"1\"\u003e\u003ccaption\u003e\n\u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e\n\u003cdiv class=\"CaptionContent\"\u003e\n\u003cp\u003eInhibition of \u003cstrong\u003e1\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e3\u003c/strong\u003e, \u003cstrong\u003e10\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e12\u003c/strong\u003e and \u003cstrong\u003e16\u003c/strong\u003e\u0026ndash;\u003cstrong\u003e17\u003c/strong\u003e on NO production.\u003c/p\u003e\n\u003c/div\u003e\n\u003c/caption\u003e\n\u003cthead\u003e\n\u003ctr\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003eCompound\u003c/p\u003e\n\u003c/th\u003e\n\u003cth align=\"left\"\u003e\n\u003cp\u003eIC\u003csub\u003e50\u003c/sub\u003e (\u003cem\u003e\u0026micro;\u003c/em\u003eM)\u003c/p\u003e\n\u003c/th\u003e\n\u003c/tr\u003e\n\u003c/thead\u003e\n\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e1\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e11.47\u0026thinsp;\u0026plusmn;\u0026thinsp;1.57\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e2\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e23.52\u0026thinsp;\u0026plusmn;\u0026thinsp;1.82\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e3\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e21.43\u0026thinsp;\u0026plusmn;\u0026thinsp;2.04\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e10\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e27.80\u0026thinsp;\u0026plusmn;\u0026thinsp;1.18\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e11\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e26.86\u0026thinsp;\u0026plusmn;\u0026thinsp;1.05\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e12\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e23.54\u0026thinsp;\u0026plusmn;\u0026thinsp;0.82\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e16\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e15.98\u0026thinsp;\u0026plusmn;\u0026thinsp;2.30\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003e\u003cstrong\u003e17\u003c/strong\u003e\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e24.93\u0026thinsp;\u0026plusmn;\u0026thinsp;1.13\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003ctr\u003e\n\u003ctd align=\"left\"\u003e\n\u003cp\u003eL-NIL\u003c/p\u003e\n\u003c/td\u003e\n\u003ctd align=\"char\" char=\"\u0026plusmn;\"\u003e\n\u003cp\u003e10.29\u0026thinsp;\u0026plusmn;\u0026thinsp;1.10\u003c/p\u003e\n\u003c/td\u003e\n\u003c/tr\u003e\n\u003c/tbody\u003e\n\u003c/table\u003e\n\u003c/div\u003e"},{"header":"4. Discussion","content":"\u003cp\u003eIn our previous researches, we have obtained fourteen meroterpenoids and seventeen heterodimers of bakuchiol and evaluated their cytotoxicity [\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e, \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e]. Further investigation on the cHE extract brought about twelve unpresented bakuchiol dimmers and their NO inhibition activities were studied. In sum, Structural changes in bakuchiol increases structural and bioactive diversity of constituents from Psoraleae Fructus. And a new skeleton compound (\u003cb\u003e1\u003c/b\u003e) was isolated and the compound exhibited significant NO inhibition activities.\u003c/p\u003e"},{"header":"5. Conclusion","content":"\u003cp\u003eSeventeen bakuchiol dimers (\u003cb\u003e1\u003c/b\u003e\u0026ndash;\u003cb\u003e17\u003c/b\u003e), including 12 undescribed dimers and 5 known compounds, were isolated from the fruits of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. and their structure were identified by spectral methods and X-ray single-crystal diffraction. Bisbakuchiol M (\u003cb\u003e1\u003c/b\u003e), whose other bakuchiol unit was cyclized to form a 6/6/5 tricyclic system, was a new skeleton compound. And the plausible biosynthetic pathway of bisbakuchiol M was proposed. Their inhibition on NO production in LPS-stimulated RAW264.7 macrophages were evaluated by the Griess reaction. Compounds \u003cb\u003e2\u003c/b\u003e, \u003cb\u003e3\u003c/b\u003e, \u003cb\u003e10\u003c/b\u003e\u0026ndash;\u003cb\u003e12\u003c/b\u003e, \u003cb\u003e16\u003c/b\u003e and \u003cb\u003e17\u003c/b\u003e exhibited inhibitory activities, and the inhibition of compound \u003cb\u003e1\u003c/b\u003e was equal to that of L-NIL, a positive control. These findings suggested that Psoraleae Fructus provided natural anti-inflammatory constituents and bisbakuchiol M had the potential to be novel NO inhibitor.\u003c/p\u003e "},{"header":"Abbreviations","content":"\u003cp\u003eTCM: Traditional Chinese medicine; NO: nitric oxide; IC\u003csub\u003e50\u003c/sub\u003e:\u0026nbsp;half maximal inhibitory concentration;\u0026nbsp;CC:\u0026nbsp;open column chromatography; TLC: thin layer chromatography; RP-SP-HPLC: reversed phase semi-preparative HPLC; PE: petroleum ether; cHE: cyclohexane; EtOAc: ethyl acetate; DMEM: Dulbecco\u0026apos;s modified Eagle\u0026apos;s medium; FBS: fetal bovine serum; CHCl\u003csub\u003e3\u003c/sub\u003e: chloroform; BuOH: normal-butanol; MTT: 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide; LPS: lipopolysaccharide; DMSO: dimethylsulfoxide; L-NIL: L-N6-(1-iminoethyl)-lysine.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAuthor\u0026apos;s contributions\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eXWY and YTZ designed the experiments. QXX and QL were responsible for isolation experiment. QXX finished biological activity assay. LL performed LC/MS analysis. XWY and QXX writed the manuscripit. All authors read and approved the final manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgements\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eNot applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThis work was supported by the National Natural Science Foundation of China (81773865).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAvailability of data and materials\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll data included in this article are available from the corresponding author upon request.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent for publication\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll authors have provided consent for publication in the journal of Chinese Medicine.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of Interest\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare no conflict of interest.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n \u003cli\u003eAi TM. Medicinal Flora of China, Peking University Press, Beijing, 2016; vol. \u003cstrong\u003e5\u003c/strong\u003e, p. 585\u0026ndash;588.\u003c/li\u003e\n \u003cli\u003eChinese Pharmacopoeia Commission. Pharmacopoeia of the People\u0026apos;s Republic of China, Chinese Medical Science and Technology Press, Beijing, 2015, vol. 1, p. 187\u0026ndash;188.\u003c/li\u003e\n \u003cli\u003eChino M, Sato K, Yamazaki T and Maitani T.\u0026nbsp;Constituent of natural food additive hokosshi extract and an analytical method for the additive in foods.\u0026nbsp;Shokuhin Eiseigaku Zasshi. 2002; 43(6):352\u0026ndash;355.\u003c/li\u003e\n \u003cli\u003eChopra B, Dhingra AK and Dhar KL, \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. (Buguchi) - folklore to modern evidence: review.\u003cem\u003e\u0026nbsp;\u003c/em\u003eFitoterapia. 2013;90:44\u0026ndash;56.\u003c/li\u003e\n \u003cli\u003eZhang XN, Zhao WW, Wang Y, Lu JJ and Chen XP. The Chemical Constituents and Bioactivities of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e Linn.: A Review\u003cem\u003e.\u003c/em\u003e Am. J. Chin. Med. 2016;44(1):35\u0026ndash;60.\u003c/li\u003e\n \u003cli\u003eLim SH, Ha TY, Kim SR, Ahn J, Park HJ and Kim S,\u0026nbsp;Ethanol extract of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague-Dawley rats.\u0026nbsp;Br. J. Nutr.\u0026nbsp;2009;101(7):1031\u0026ndash;1039.\u003c/li\u003e\n \u003cli\u003eKim YJ, Lim HS, Lee J and Jeong SJ.\u0026nbsp;Quantitative Analysis of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e Linne and its Neuroprotective and Anti-Neuroinflammatory Effects in HT22 Hippocampal Cells and BV-2 Microglia.\u0026nbsp;Molecules. 2016;21(8):1076.\u003c/li\u003e\n \u003cli\u003eLin X, Li BB, Zhang L, Li HZ, Meng X, Jiang YY, Lee HS and Cui L. Four new compounds isolated from \u003cem\u003ePsoralea corylifolia\u003c/em\u003e and their diacylglycerol acyltransferase (DGAT) inhibitory activity. Fitoterapia. 2018;128:130\u0026ndash;134.\u003c/li\u003e\n \u003cli\u003eSun NJ, Woo SH, Cassady JM and Snapka RM. DNA polymerase and topoisomerase II inhibitors from \u003cem\u003ePsoralea corylifolia\u003c/em\u003e. J. Nat. Prod. 1998;61(3):362\u0026ndash;366.\u003c/li\u003e\n \u003cli\u003eGao HTY, Lang GZ, Zang YD, Ma J, Yang JZ, Ye F, Tian JY, Gao PP, Li CJ and Zhang DM. Bioactive monoterpene phenol dimers from the fruits of \u003cem\u003ePsoralea corylifolia\u0026nbsp;\u003c/em\u003eL. Bioorg Chem. 2021;112:104924.\u003c/li\u003e\n \u003cli\u003eXu QX, Zhang YB, Liu XY, Xu W and Yang XW. Cytotoxic heterodimers of meroterpene phenol from the fruits of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e. Phytochemistry. 2020;176:112394.\u003c/li\u003e\n \u003cli\u003eXu QX, Xu Wand Yang XW. Meroterpenoids from the fruits of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e. Tetrahedron. 2020;76:131343.\u003c/li\u003e\n \u003cli\u003eMosMann T.\u0026nbsp;Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods.1983;65:55\u0026ndash;63.\u003c/li\u003e\n \u003cli\u003eCao GY, Xu W, Yang XW, Gonzalez FJ and Li F. New neolignans from the seeds of \u003cem\u003eMyristica fragrans\u003c/em\u003e that inhibit nitric oxide production.\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003eFood Chem.\u0026nbsp;2015;173:231\u0026ndash;237.\u003c/li\u003e\n \u003cli\u003eLabbe C, Faini F, Coll J and Connolly JD. Bakuchiol derivatives from the leaves of \u003cem\u003ePsoralea glandulosa\u003c/em\u003e. Phytochemistry. 1996;42(5):1299\u0026ndash;1303.\u003c/li\u003e\n \u003cli\u003eXiao GD, Li XK, Wu T, Cheng ZH, Tang QJ and Zhang T. Isolation of a new meroterpene and inhibitors of nitric oxide production from \u003cem\u003ePsoralea corylifolia\u003c/em\u003e fruits guided by TLC bioautography.\u0026nbsp;Fitoterapia. 2012;83(8):1553\u0026ndash;1557.\u003c/li\u003e\n \u003cli\u003eBanerji A and Chintalwar GJ. Biosynthesis of bakuchiol, a meroterpene from \u003cem\u003ePsoralea corylifolia\u003c/em\u003e.\u003cem\u003e\u0026nbsp;\u003c/em\u003ePhytochemistry. 1983;22(9):1945\u0026ndash;1947.\u003c/li\u003e\n \u003cli\u003eTakano S, Shimazaki Y and Ogasawara K. Enantiocontrolled synthesis of natural (+)-bakuchiol.\u003cem\u003e\u0026nbsp;\u003c/em\u003eTetrahedron Lett. 1990;31:3325\u0026ndash;3326.\u003c/li\u003e\n \u003cli\u003eYin S, Fan CQ, Dong L and Yue JM. Psoracorylifols A\u0026ndash;E, five novel compounds with activity against Helicobacter pylori from seeds of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e. Tetrahedron. 2006;62:2569\u0026ndash;2575.\u003c/li\u003e\n \u003cli\u003eWu CZ, Cai XF, Dat NT, Hong SS, Han AR, Seo EK, Hwang BY, Nan JX, Lee D and Lee JJ. Bisbakuchiols A and B, novel dimeric meroterpenoids from \u003cem\u003ePsoralea corylifolia\u003c/em\u003e. Tetrahedron Lett\u003cem\u003e.\u003c/em\u003e 2007;48(50):8861\u0026ndash;8864.\u003c/li\u003e\n \u003cli\u003eWang AX, Zhang Q,\u0026nbsp;and\u0026nbsp;Jia ZJ. A new furobenzopyranone and other constituents from\u003cem\u003e\u0026nbsp;Anaphalis lacteal\u003c/em\u003e. Pharmazie. 2004;59(10):807\u0026ndash;811.\u003c/li\u003e\n \u003cli\u003eHeymann H, Tezuka Y, Kikuchi T, and Supriyatna S. Constituents of Sindora sumatrana MIQ. III. New trans-clerodane diterpenoids from the dried pods. Chem. Pharm. Bull. 1994;42(6):138\u0026ndash;146.\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":true,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"chinese-medicine","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"cmed","sideBox":"Learn more about [Chinese Medicine](http://cmjournal.biomedcentral.com)","snPcode":"","submissionUrl":"https://www.editorialmanager.com/cmed/default.aspx","title":"Chinese Medicine","twitterHandle":"@BioMedCentral","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"BMC/SO AJ","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Psoralea corylifolia, bakuchiol dimers, inhibition of nitric oxide","lastPublishedDoi":"10.21203/rs.3.rs-706759/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-706759/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003e\u003cstrong\u003eBackground: \u003c/strong\u003eDried fruit of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. (Psoraleae Fructus) is one of the most popular traditional Chinese medicine with treatment for nephritis, spermatorrhea, pollakiuria, asthma, and various inflammatory diseases. Bakuchiol is main meroterpenoid with bioactive diversity from Psoraleae Fructus.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eMethods:\u003c/strong\u003e Various column chromatography methods were used for isolation experiment. Structures and configurations of these compounds were determined by spectroscopic methods and single-crystal X-ray diffraction. Their inhibition on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages were evaluated by the Griess reaction.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eResults:\u003c/strong\u003e Twelve unpresented bakuchiol dimmers, bisbakuchiols M–U (\u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e9\u003c/strong\u003e) and bisbakuchiol ethers A–C (\u003cstrong\u003e10\u003c/strong\u003e–\u003cstrong\u003e12\u003c/strong\u003e), along with five known compounds (\u003cstrong\u003e13\u003c/strong\u003e–\u003cstrong\u003e17\u003c/strong\u003e), were isolated from the fruits of \u003cem\u003ePsoralea corylifolia\u003c/em\u003e L. Compounds \u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e3\u003c/strong\u003e and\u003cstrong\u003e 10\u003c/strong\u003e–\u003cstrong\u003e14\u003c/strong\u003e exhibited inhibitory activities against LPS-induced NO production in RAW264.7 macrophages, and the inhibition of compound \u003cstrong\u003e1\u003c/strong\u003e (IC\u003csub\u003e50\u003c/sub\u003e = 11.47 ± 1.57 μM) was equal to that of L-NIL (IC\u003csub\u003e50\u003c/sub\u003e = 10.29 ± 1.10 μM) as a positive control.\u003c/p\u003e\u003cp\u003e\u003cstrong\u003eConclusions: \u003c/strong\u003eSeventeen bakuchiol dimers (\u003cstrong\u003e1\u003c/strong\u003e–\u003cstrong\u003e17\u003c/strong\u003e), including 12 undescribed dimers and 5 known compounds, were isolated. Bisbakuchiol M (\u003cstrong\u003e1\u003c/strong\u003e), whose other bakuchiol unit was cyclized to form a 6/6/5 tricyclic system, was a new skeleton compound. Some compounds exhibited NO inhibition activities and the inhibition of compound \u003cstrong\u003e1\u003c/strong\u003e was equal to that of L-NIL, a positive control. These findings suggested that Psoraleae Fructus provided natural anti-inflammatory constituents and bisbakuchiol M had the potential to be novel NO inhibitor.\u003c/p\u003e","manuscriptTitle":"Bakuchiol Dimers From Psoraleae Fructus That Inhibit Nitric Oxide Production in RAW264.7 Macrophages Cells","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2021-07-26 14:40:41","doi":"10.21203/rs.3.rs-706759/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"editorInvitedReview","content":"","date":"2021-08-02T00:00:00+00:00","index":1,"fulltext":"Recommendation: Reviewer's comments unavailable due to the journal's policy.\n"},{"type":"editorInvitedReview","content":"","date":"2021-08-02T00:00:00+00:00","index":2,"fulltext":"Recommendation: Reviewer's comments unavailable due to the journal's policy.\n"},{"type":"decision","content":"Major revision","date":"2021-08-02T00:00:00+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2021-07-30T00:00:00+00:00","index":3,"fulltext":"Recommendation: Reviewer's comments unavailable due to the journal's policy.\n"},{"type":"reviewerAgreed","content":"","date":"2021-07-25T00:00:00+00:00","index":3,"fulltext":""},{"type":"editorInvitedReview","content":"","date":"2021-07-22T01:54:48+00:00","index":0,"fulltext":""},{"type":"reviewersInvited","content":"","date":"2021-07-22T00:21:48+00:00","index":"","fulltext":""},{"type":"reviewerAgreed","content":"","date":"2021-07-22T00:00:00+00:00","index":2,"fulltext":""},{"type":"reviewerAgreed","content":"","date":"2021-07-21T00:00:00+00:00","index":1,"fulltext":""},{"type":"checksComplete","content":"","date":"2021-07-15T23:00:00+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2021-07-15T23:00:00+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2021-07-14T06:56:14+00:00","index":"","fulltext":""},{"type":"submitted","content":"Chinese Medicine","date":"2021-07-10T23:46:27+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"chinese-medicine","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"cmed","sideBox":"Learn more about [Chinese Medicine](http://cmjournal.biomedcentral.com)","snPcode":"","submissionUrl":"https://www.editorialmanager.com/cmed/default.aspx","title":"Chinese Medicine","twitterHandle":"@BioMedCentral","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"BMC/SO AJ","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"5fc98a9f-aecb-4ae5-bd9e-e018217ee508","owner":[],"postedDate":"July 26th, 2021","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"under-review","subjectAreas":[{"id":5928400,"name":"Natural Product Chemistry"}],"tags":[],"updatedAt":"2021-08-31T14:35:36+00:00","versionOfRecord":[],"versionCreatedAt":"2021-07-26 14:40:41","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-706759","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-706759","identity":"rs-706759","version":["v1"]},"buildId":"GqpaHPwrfC8PjnIFayRh5","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}