Co-reporter:Xiao-Xiao LU, Yi-Fan JIANG, Hong LI, Ying-Ye OU, ... Yun-Yi ZHANG
Chinese Journal of Natural Medicines 2017 Volume 15, Issue 7(Volume 15, Issue 7) pp:
Publication Date(Web):1 July 2017
DOI:10.1016/S1875-5364(17)30074-2
Lipopolysaccharides (LPS) contamination in herbal crude polysaccharides is inevitable. The present study was performed to explore the effect of polymyxin B on abolishing the influence of LPS contamination in mononuclear cells. LPS was pretreated with polymyxin B sulfate (PB) at different concentrations for 1, 5 or 24 h, and then used to stimulate RAW264.7 and mouse peritoneal macrophages (MPMs). The nitric oxide (NO) and tumor necrosis factor-α (TNF-α) in cell culture supernatant, as the indications of cell response, were assayed. Bupleurum chinensis polysaccharides (BCPs) with trace amount contamination of LPS was treated with PB. 30 μg·mL−1 of PB, treating LPS (10 and 1 000 ng·mL−1 in stimulating RAW264.7 and MPMs respectively) at 37 °C for 24 h, successfully abolished the stimulating effect of LPS on the cells. When the cells were stimulated with LPS, BCPs further promoted NO production. However, pretreated with PB, BCPs showed a suppression of NO production in MPMs and no change in RAW264.7. In the in vitro experiments, LPS contamination in polysaccharide might bring a great interference in assessing the activity of drug. Pretreatment with PB (30 μg·mL−1) at 37 °C for 24 h was sufficient to abolish the effects of LPS contamination (10 and 1 000 ng·mL−1).
Co-reporter:Xin-Xin XIE, Ze-Jing JIANG, Zhi-Hong CHENG, Dao-Feng CHEN
Chinese Journal of Natural Medicines 2017 Volume 15, Issue 8(Volume 15, Issue 8) pp:
Publication Date(Web):1 August 2017
DOI:10.1016/S1875-5364(17)30090-0
The kaurenoic acid-type diterpenoids in Acanthopanacis Cortex have been reported to be the major active components. However, the diterpenoids are present as position isomers that exacerbate the challenges in obtaining standards compounds. Little work has been done on the quantitative analysis of the diterpenoids in the herb. In the present study, two diterpenoid isomers ent-16βH,17-isovalerate-kauran-19-oic acid (1) and ent-16βH,17-methyl butanoate-kauran-19-oic acid (2) with high purity were separated by analytical HPLC, followed by recrystallization in acetone. Furthermore, an HPLC-ELSD method was developed and validated for simultaneous determination of 1 and 2 in 9 batches of Acanthopanacis Cortex samples. The HPLC separation and quantification was achieved in 40 min using an Agela Promosil C18 column eluted with a gradient of water and acetonitrile. The calibration curves showed good linearity (r2 ≥ 0.999 9) within the test ranges. The LOD ranged from 0.407 2 to 0.518 0 μg and LOQ ranged from 1.018 0 to 1.295 0 μg. The precisions (%RSD) were within 1.47% for the two isomers. The recovery of the assay was in the range of 98.78%–99.11% with RSD values less than 2.76%. It is the first time to establish a quantitative HPLC method for the analysis of the bioactive kaurenoic acid isomers in the herb.
Co-reporter:Qun Sun, Nai-Yu Xu, Qi-Run Li, Shi Yao, Meng Li, He-Ran Li, Jian Zhang, Dao-Feng Chen
Journal of Functional Foods 2017 Volume 38, Part A(Volume 38, Part A) pp:
Publication Date(Web):1 November 2017
DOI:10.1016/j.jff.2017.09.006
•One new compound and nineteen known compounds were isolated and characterized.•Ten compounds and total flavonoids exhibited anti-complementary activities in vitro.•Six compounds and total flavonoids inhibited α-glucosidase activity in vitro.•Total flavonoids showed antihyperglycaemic effects on STZ-induced diabetic mice.•G. hypoleucum could be used as functional food applications for diabetics.Gnaphalium hypoleucum DC is used as a wild vegetable, named “Qing Ming Cai”, as well as a folk medicine in China. One new compound, Gnaphaliin C, and nineteen known compounds were isolated and indentified from G. hypoleucum, total flavonoids were analyzed by UHPLC-Q-TOF/MS. The α-glucosidase inhibitory and anti-complementary activities of all compounds and total flavonoids were evaluated. Total flavonoids and ten compounds exhibited anti-complementary activities. Total flavonoids and six compounds inhibited α-glucosidase. The antihyperglycaemic effects of total flavonoids were investigated by streptozotocin (STZ)-induced diabetic mice. Total flavonoids improved the glucose tolerance and decreased blood sugar, increased muscle glycogen content, decreased the levels of triacylglycerol (TG) and total cholesterol (TC), enhanced superoxide dismutase (SOD) activity and decreased malondialdehyde (MDA) level in diabetic mice. G. hypoleucum and its total flavonoids could be used as functional food for diabetics.
Co-reporter:Pin Jiang, Yan Lu, Daofeng Chen
Journal of Pharmaceutical and Biomedical Analysis 2016 Volume 131() pp:263-271
Publication Date(Web):30 November 2016
DOI:10.1016/j.jpba.2016.08.040
•A simple method for the authentication of Wuweizi and Nan-wuweizi in herbal patent drugs was established using TLC, HPLC and HPLC–MS.•Through the establishment of a statistical model using the peak area of Anwulignan/Schisandrin in HPLC, the adulteration ratio of Nan-wuweizi in Wuweizi (w/w), as well as in FHKSP, can be determined.•Two of the 36 patent drugs that were checked did not conform to the labeled Schisandra species; the ratio of Nan-wuweizi in the mixtures (w/w) were both 100%.Authentication of species is crucial for ensuring the safety and efficacy of herbal medicines. The fruits of Schisandra chinensis and S. sphenanthera have been used for the same traditional Chinese drug, Wuweizi, but are found to be quite different according to their constituents, pharmacological effects, and qualities. These two fruits have been recorded as Schisandrae Chinensis Fructus (Wuweizi) and Schisandrae Sphenantherae Fructus (Nan-wuweizi), respectively, by Chinese Pharmacopoeia, 2000 edition. However, Nan-wuweizi is often found to be taken as Wuweizi in some Chinese patent drugs intentionally or by mistake because of its lower price and similar characteristics to Wuweizi. In this study, the selection and validation of special chemical markers for the identification of Schisandra species were established by HPLC-DAD-MS profiling analysis. Simple TLC and HPLC methods were proposed for the accurate determination of Nan-wuweizi from Wuweizi in Chinese patent medicines, using schisandrin and anwulignan as the identifying markers for Wuweizi and Nan-wuweizi, respectively. Through the establishment of a statistical model, adulterated or misused ratios of Nan-wuweizi in Wuweizi (w/w), as well as in Fenghan Kesou pills, can be determined. The limit of detection of Nan-wuweizi in a mixture (w/w) using both TLC and HPLC methods is 5% (mixed crude drugs of 50 mg and 5 g in a 1000 g prescribed amount). The constructed statistical model relating the HPLC peak area ratio (anwulignan/schisandrin) and adulteration ratio is suitable for mixed crude drugs and Fenghan Kesou pills, and the two fitting equations have a good correlation (r = 0.9979). Furthermore, 36 commercial Chinese patent medicines containing Wuweizi or Nan-wuweizi according to their labels were checked by these methods, and Nan-wuweizi was detected in Renshen Wuweizi Granules and Fenghan Kesou Pills. The ratios of Nan-wuweizi in these mixtures (w/w) were 100:0 for both, which does not comply with the statutory prescription. This study provided a simple and reliable method to prevent the adulteration or misuse of Nan-wuweizi in crude drugs and patent medicines of Wuweizi.
Co-reporter:Min Yan; Yan Lu; Chin-Ho Chen; Yu Zhao; Kuo-Hsiung Lee
Journal of Natural Products 2015 Volume 78(Issue 11) pp:2712-2718
Publication Date(Web):November 12, 2015
DOI:10.1021/acs.jnatprod.5b00660
Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D–J, 1–7) and 12 known (8–19) daphnane diterpenoids. The structures and relative configurations of 1–7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1α-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06–1.1 nM and selectivity index values of more than 10 000.
Co-reporter:Wei-Hua Song, Zhi-Hong Cheng, and Dao-Feng Chen
Journal of Natural Products 2014 Volume 77(Issue 1) pp:42-48
Publication Date(Web):December 30, 2013
DOI:10.1021/np400571x
Six new (1–6) and 19 known monoterpenoid glucosides were isolated from the root bark of Paeonia suffruticosa. The monoterpenoid glucosides 1, 2, 7, 10–19, and 22 exhibited anticomplement effects with CH50 and AP50 values ranging from 0.14 to 2.67 mM and 0.25 to 3.67 mM, respectively. In a mechanistic study, suffrupaeoniflorin A (1) interacted with C1q, C3, C5, and C9, while galloylpaeoniflorin (12) and galloyloxypaeoniflorin (19) acted on C1q, C3, and C5 components in the complement activation cascade.
Co-reporter:Qi Wang, Tzu-Hsuan Chen, Kenneth F. Bastow, Susan L. Morris-Natschke, Kuo-Hsiung Lee, and Dao-Feng Chen
Journal of Natural Products 2013 Volume 76(Issue 3) pp:305-310
Publication Date(Web):October 8, 2012
DOI:10.1021/np300532p
Five new highly oxygenated oplopane sesquiterpenes, songaricalarins A–E (1–5), and two known analogues (6 and 7) were isolated from the roots and rhizomes of Ligularia songarica. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques, and the structure of 1 was confirmed by single-crystal X-ray diffraction. All compounds were evaluated for in vitro cytotoxic activity against cultured A-549, MCF-7, KB, and KBVIN cells, and 4 exhibited cytotoxicity with EC50 values of 4.9, 0.8, 3.4, and 3.2 μg/mL, respectively.
Co-reporter:Xiao-Qin Cheng;Lu-Jin Song;Hong Li;Hongye Di;Yun-Yi Zhang
Inflammation 2012 Volume 35( Issue 5) pp:1715-1722
Publication Date(Web):2012 October
DOI:10.1007/s10753-012-9489-7
Radix Bupleuri is a traditional Chinese herb frequently used in the prescriptions for the treatment of inflammatory diseases. This study was to determine whether the crude polysaccharides isolated from the roots of Bupleurum smithii var. parvifolium (BPs) had beneficial effects on a “two-hit” acute lung injury model in rats. A two-hit lung injury model characterized by hemorrhagic shock followed by reperfusion and intratracheal lipopolysaccharide (1 mg kg−1) administration was established in Wistar rats. Drugs and saline were administered 30 min after the start of resuscitation. The two-hit acute lung injury model was successfully established. After oral administration, all BPs groups ameliorated pathological injury with lessened complement C3c deposit in lung. BPs 10 and 20 mg kg−1 diminished the ratio of wet-to-dry weight. In bronchoalveolar lavage (BAL) fluids, the protein concentration, the leukocytes counts, and the lung myeloperoxidase were significantly reduced. BPs also mediated the decreases in interleukin-6 and tumor necrosis factor-α in BAL fluids and in sera. Furthermore, BPs 20 mg kg−1 decreased the total complement hemolytic activity. BPs had beneficial effects on two-hit acute lung injury. The mechanisms of BPs on inflammatory disease might relate to its inhibitory effect on increased production of proinflammatory mediators and on overactivation of complement.
Co-reporter:Zehao Huang;Yan Lu;Yinan Liu;Kenneth F. Bastow;Kuohsiung Lee;Daofeng Chen
Helvetica Chimica Acta 2011 Volume 94( Issue 3) pp:519-527
Publication Date(Web):
DOI:10.1002/hlca.201000259
Abstract
Kadsufolins A–D (1–4, resp.), four new dibenzocyclooctane-type lignans, were isolated from the roots and stems of Kadsura oblongifolia, together with eleven known lignans. Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR techniques. The compounds were also evaluated for cytotoxic activity against human tumor cell lines A549 (lung carcinoma), DU145 (prostate carcinoma), KB (epidermoid carcinoma of the nasopharynx), and HCT-8 (ileocecal carcinoma). Kadsufolin A (1), kadsufolin D (4), angeloylbinankadsurin A, and heteroclitin B were found to show cytotoxic activities against A549, DU145, KB and HCT-8 with GI50 values of 5.1–20.0 μg/ml.
Co-reporter:Qi Wang, Tzu-Hsuan Chen, Kenneth F. Bastow, Kuo-Hsiung Lee and Dao-Feng Chen
Journal of Natural Products 2010 Volume 73(Issue 2) pp:139-142
Publication Date(Web):January 14, 2010
DOI:10.1021/np900489h
Four new bisabolane sesquiterpenes, altaicalarins A−D (1−4), and three known analogues (5−7) were isolated from the roots and rhizomes of Ligularia altaica. The structures were elucidated by spectroscopic methods including 2D NMR techniques, and the structure of 1 was confirmed by single-crystal X-ray diffraction. The isolated compounds were also evaluated for cytotoxic activity against human lung carcinoma (A-549), human breast adenocarcinoma (MCF-7), epidermoid carcinoma of the nasopharynx (KB), and vincristine-resistant nasopharyngeal (KBVIN) cell lines, and 1 was found to show significant cytotoxicity, with EC50 values of 3.4, 0.8, 1.0, and 0.9 μg/mL, respectively.
Co-reporter:Wen-Hui Ma, Hai Huang, Pei Zhou and Dao-Feng Chen
Journal of Natural Products 2009 Volume 72(Issue 4) pp:676-678
Publication Date(Web):February 19, 2009
DOI:10.1021/np8007864
Three carotane-type sesquiterpenoids, schisanwilsonenes A (1), B (2), and C (3), were isolated from the fruits of Schisandra wilsoniana. Their structures and relative configurations were elucidated on the basis of spectroscopic methods including 2D-NMR techniques, and the structure of 1 was confirmed by a single-crystal X-ray diffraction experiment. Schisanwilsonene A, at 50 μg/mL, exhibited antiviral activity, inhibiting HBsAg and HBeAg secretion by 76.5% and 28.9%.
Co-reporter:Yan Lu, Dao-Feng Chen
Journal of Chromatography A 2009 Volume 1216(Issue 11) pp:1980-1990
Publication Date(Web):13 March 2009
DOI:10.1016/j.chroma.2008.09.070
Wuweizi (Fructus Schisandrae) is classified in traditional Chinese medicine as a superior drug, and has been used for thousands of years. Modern pharmacological research has demonstrated that most of the biological actions and pharmacological effects of Wuweizi can be attributed to its lignan constituents, particularly the dibenzocyclooctadiene-type lignans, which can lower the serum glutamate-pyruvate transaminase (SGPT) level, inhibit platelet aggregation, and show antioxidative, calcium antagonism, antitumor-promoting, and anti-HIV (human immunodeficiency virus) effects. The dried ripe fruits of both Schisandra chinensis and Schisandra sphenanthera have long been used as Wuweizi, although their chemical constituents and contents of the bioactive components are quite different. Since 2000, they have been accepted as two different crude drugs, Bei-Wuweizi and Nan-Wuweizi, respectively, by the Chinese Pharmacopoeia. In order to provide a useful reference for good quality control of Wuweizi, many studies on the chemical constituents, pharmacological effects, identification and quality control methods of the two drugs have been reported in the literature and are summarized herein. Particular attention was given to the different methodologies developed for the qualitative and quantitative analysis of the major bioactive lignans. In our opinion, thin-layer chromatography (TLC) is the most simple and convenient method for identification of these two crude drugs, and high-performance liquid chromatography with UV detection (HPLC–UV) is the preferred method for quantitative analysis based on the bioactive lignans. Some newly developed methods, particularly hyphenated chromatographic-analytical techniques, are effective in determination of the lignans that occur in low content and those difficult to be fully separated with HPLC.
Co-reporter:Hongwei Zhu, Hongye Di, Yunyi Zhang, Jianwen Zhang, Daofeng Chen
Carbohydrate Research 2009 Volume 344(Issue 11) pp:1319-1324
Publication Date(Web):27 July 2009
DOI:10.1016/j.carres.2009.05.001
Bioactivity-guided fractionation of a hot-water extract from the stem bark of Eucommia ulmoides led to the isolation of a homogeneous polysaccharide EWDS-2, which was identified as a highly branched protein-bound polysaccharide with average molecular weight between 1000 and 2000 kDa, composed of Glc, Gal, Ara, and Rha in the ratio of 2.2:1.0:0.4:0.2, along with traces of Man and 6.55% of protein. The main linkages of the residues of EWDS-2 include terminal, 1,3-linked, 1,4-linked, 1,2,6-linked, 1,3,6-linked Glc; 1,6-linked, 1,2,6-linked, 1,3,4-linked, 1,4,6-linked Gal; 1,5-linked, 1,3,5-linked Ara; terminal and 1,2,5-linked Rha. The bioassay revealed that EWDS-2 inhibits complement activation on both the classic and alternative pathways with CH50 and AP50 values of 282 ± 11 μg/mL and 144 ± 17 μg/mL, respectively. Preliminary mechanism studies indicate that EWDS-2 inhibits the activation of the complement system by interacting with C1q, C1r, C1s, C2, C3, C4, C5, and C9. The results suggested that EWDS-2 could be valuable for the treatment of diseases associated with the excessive activation of the complement system.EWDS-2, a protein-bound polysaccharide isolated from the stem bark of Eucommia ulmoides, inhibited complement activation on both the classic and alternative pathways with CH50 and AP50 values of 282 ± 11 μg/mL and 144 ± 17 μg/mL, respectively, by interacting with C1q, C1r, C1s, C2, C3, C4, C5, and C9.
Co-reporter:Wen-Hui Ma, Yan Lu, Hai Huang, Pei Zhou, Dao-Feng Chen
Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 17) pp:4958-4962
Publication Date(Web):1 September 2009
DOI:10.1016/j.bmcl.2009.07.078
Seven new dibenzocyclooctane lignans, schisanwilsonins A–G (1–7), were isolated from the fruits of Schisandra wilsoniana, together with five known lignans (8–12). The structures of these new compounds were elucidated by spectroscopic methods including 2D-NMR techniques. The 12 lignans were tested for anti-hepatitis B virus (HBV) activity in vitro. Schisanwilsonin D (4), schisantherin C (9), deoxyschizandrin (10) and (+)-gomisin K3 (11) showed anti-HBV activity. 9 exhibited the most potent anti-HBV activity with potency against HBsAg and HBeAg secretion by 59.7% and 34.7%, respectively, at 50 μg/mL.
Co-reporter:Xiaolin Ma;Yan Lu ;Daofeng Chen
Helvetica Chimica Acta 2009 Volume 92( Issue 1) pp:72-77
Publication Date(Web):
DOI:10.1002/hlca.200800038
Co-reporter:Wenhui Ma;Xiaolin Ma;Yan Lu ;Daofeng Chen
Helvetica Chimica Acta 2009 Volume 92( Issue 4) pp:709-715
Publication Date(Web):
DOI:10.1002/hlca.200800363
Co-reporter:Guohong Yang ;Daofeng Chen
Chemistry & Biodiversity 2008 Volume 5( Issue 7) pp:1419-1424
Publication Date(Web):
DOI:10.1002/cbdv.200890130
Abstract
A new 3,3″-biflavanone, isosikokianin A (1), was isolated from the roots of Stellera chamaejasme, together with eleven known compounds. Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR techniques. Sikokianin A, chamaechromone, and quercetin showed in vitro antiviral activity against HBsAg secretion.
Co-reporter:Guohong Yang ;Daofeng Chen
Chemistry & Biodiversity 2008 Volume 5( Issue 9) pp:1718-1722
Publication Date(Web):
DOI:10.1002/cbdv.200890160
Abstract
Five alkaloids, 5,6-dihydro-6-methoxynitidine (1), dictamnine (2), γ-fagarine (3), skimmianine (4), and 5-methoxydictamnine (5), were isolated from the roots of Zanthoxylum nitidum. Their structures and configurations were elucidated by spectroscopic methods and X-ray analysis. Compounds 1, 4, and 5 showed in vitro antiviral effect against hepatitis B virus, and compounds 2, 3, and 5 demonstrated marked antimitotic and antifungal activity.
Co-reporter:Peilan Ding;Daofeng Chen
Helvetica Chimica Acta 2007 Volume 90(Issue 11) pp:2236-2244
Publication Date(Web):16 NOV 2007
DOI:10.1002/hlca.200790232
Two new flavanones, tonkinochromanes D (1) and E (2), and a new chalcone, tonkinochromane F (3), were isolated from the roots and rhizomes of Sophora tonkinensis. Their structures were elucidated by spectroscopic methods, including 2D-NMR and circular-dichroism (CD) techniques, in combination with HR-MS analysis. Compounds 1–3, as well the previously reported tonkinochromanes A–C, were shown by LC-MS analysis to be ‘artifacts’ resulting from acid-catalyzed electrophilic cyclization of isoprenyl side chains during extraction.
Co-reporter:Wenhui Ma;Xiaolin Ma;Hai Huang;Pei Zhou;Daofeng Chen
Chemistry & Biodiversity 2007 Volume 4(Issue 5) pp:966-972
Publication Date(Web):18 MAY 2007
DOI:10.1002/cbdv.200790087
Two new dibenzocyclooctane lignans, kadsurindutins A (1) and B (2), were isolated from the stems of Kadsura induta, together with the known, structurally related lignans schisantherin L (3), schisantherin P (4), kadsulignan L (5), and neokadsuranin (6). Their structures and configurations were elucidated by spectroscopic methods (UV, ORD, CD, IR, 1D- and 2D-NMR) in combination with mass-spectrometric (HR-MS) techniques. Compounds 1, 5, and 6 showed in vitro antiviral effects on hepatitis B virus.
Co-reporter:Qi Wang;Daofeng Chen
Helvetica Chimica Acta 2007 Volume 90(Issue 12) pp:2432-2437
Publication Date(Web):14 DEC 2007
DOI:10.1002/hlca.200790251
Three new compounds, (5β,9β)-guaia-6,10(14)-dien-9-ol (=rel-(1R,3aS,5R,8aR)-1,2,3,3a,4,5,6,8a-octahydro-1-methyl-4-methylene-7-(1-methylethyl)azulen-5-ol; 1), 6-acetyl-8-methoxy-2,3-dimethylchromen-4-one (=6-acetyl-8-methoxy-2,3-dimethyl-4H-1-benzopyran-4-one; 2), and (2S)-3′-hydroxy-5′,7-dimethoxyflavanone (=(2S)-2,3-dihydro-2-(3-hydroxy-5-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 3) were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compounds. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques.
Co-reporter:Zhengwei Jia;Yan Lu;Zhixin Liao;Daofeng Chen
Helvetica Chimica Acta 2007 Volume 90(Issue 6) pp:1236-1243
Publication Date(Web):22 JUN 2007
DOI:10.1002/hlca.200790124
Two new triterpene lactones, polysperlactones A (2) and B (3), were isolated from the stems of Kadsura polysperma, together with the known compounds heteroclitalactone D (1) and schisanlactone E (4). Their structures were elucidated by spectroscopic methods, including 2D-NMR and HR-MS techniques. The configuration of 1 was confirmed by X-ray analysis. Compounds 2 and 3 are members of a rare class of 3,4-secolanostane metabolites with ring-expanded or cyclized structures, respectively.
Co-reporter:Pei-Lan Ding, Zhi-Xin Liao, Hai Huang, Pei Zhou, Dao-Feng Chen
Bioorganic & Medicinal Chemistry Letters 2006 Volume 16(Issue 5) pp:1231-1235
Publication Date(Web):1 March 2006
DOI:10.1016/j.bmcl.2005.11.073
(+)-12α-Hydroxysophocarpine (8), a new quinolizidine alkaloid was isolated from the roots of Sophora flavescens, together with 10 known quinolizidine alkaloids, (+)-oxymatrine (1), (+)-matrine (2), (+)-9α-hydroxymatrine (3), (+)-allomatrine (4), (+)-oxysophocarpine (5), (−)-sophocarpine (6), (−)-9α-hydroxysophocarpine (7), (+)-lehmannine (9), (−)-13,14-dehydrosophoridine (10), and (−)-anagyrine (11). Their structures were elucidated by spectroscopic methods, and the stereochemistry of 8 was confirmed by X-ray analysis. These alkaloids were tested for anti-hepatitis B virus (HBV) activity in vitro, compounds 5, 6, 9, and 10 showed significant anti-HBV activity with inhibitory potency against HBsAg secretion at 48.3–79.3% and that against HBeAg secretion at 24.6–34.6%.(+)-12α-Hydroxysophocarpine, a new quinolizidine alkaloid was isolated from the roots of Sophora flavescens, together with 10 known quinolizidine alkaloids. (+)-Oxysophocarpine, (−)-sophocarpine, (+)-lehmannine and (−)-13,14-dehydrosophoridine showed significant anti-HBV activity in vitro.
Co-reporter:Peilan Ding;Daofeng Chen
Helvetica Chimica Acta 2006 Volume 89(Issue 1) pp:103-110
Publication Date(Web):19 JAN 2006
DOI:10.1002/hlca.200690000
Two new flavanones, tonkinochromanes A (1) and B (2), and a new chalcone, tonkinochromane C (3), were isolated from the roots and rhizomes of Sophora tonkinensis. Their structures were elucidated by spectroscopic methods including 2D-NMR and MS experiments. Of the three isoprenyl substituents in these compounds on rings A and B, one to two were found to be ring-fused in the form of either dihydro- or regular 2,2-dimethyl-2H-pyran moieties.
Co-reporter:Yan Lu;Daofeng Chen
Helvetica Chimica Acta 2006 Volume 89(Issue 5) pp:895-901
Publication Date(Web):24 MAY 2006
DOI:10.1002/hlca.200690092
Three new dibenzocyclooctane-type lignans, kadsutherins A–C (1–3), were isolated from the stems of two Kadsura species. Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR and HR-MS techniques. Kadsutherin C (3) is the first dibenzocyclooctane lignan without an oxygen-containing substituent at C(2).
Co-reporter:Shou-Zhou Zhang;Yan-Han Wang;Jian-Ping Gao
Chemistry & Biodiversity 2006 Volume 3(Issue 3) pp:359-369
Publication Date(Web):23 MAR 2006
DOI:10.1002/cbdv.200690039
The chloroplast mat-K region and rpL16 intron region were sequenced for 14 species of Schisandraceae, representing both genera KadsuraKaempf. ex Juss. and SchisandraMichx, to discuss the phylogeny of this family. Analyses were performed both in separate and combined sequence data sets (including the rbc-L sequence), with Illicium angustispealum A. C. Smith as the out-group. The results showed that the Schisandraceae are monophyletic. In all the analyses, Schisandra propinqua var. chinensisOliva and Schisandra plena A. C. Smith were nested within Kadsura, which implies that the genera Kadsura and Schisandra are closely related. They might have originated from a common ancestor, but then evolved via different routes. The result inferred from the combined data showed a greater resolution within Schisandra than those from the two separate data sets. High bootstrap values supported the monophyly of most subgenera according to Law's system (1996). A combination of morphological, anatomical, and chemical analyses indicates that S. chinensis and S. rubriflora may be the primitive taxa in Schisandra.
Co-reporter:Pei-lan Ding;Yun-qiu Yu
Phytochemical Analysis 2005 Volume 16(Issue 4) pp:257-263
Publication Date(Web):5 JUL 2005
DOI:10.1002/pca.829
A simple, rapid and reliable high-performance capillary electrophoresis method has been developed to determine quantitatively the alkaloid content of Sophora tonkinensis, a Chinese herb commonly known as shan-dou-gen. A total of seven quinolizidine alkaloids (cytisine, sophocarpine, matrine, lehmannine, sophoranol, oxymatrine and oxysophocarpine) could be readily separated within 15 min. The running buffer was 50 mM phosphate buffer (pH 2.5) containing 1% hydroxypropyl-β-cyclodextrin and 3.3% isopropanol in water. The applied voltage was 25 kV, the capillary temperature was 25°C, the detection wavelength was 200 nm and scopolamine butylbromide was used as internal standard. The method was used to analyse the chemical constituents of two commercial alternatives to shan-dou-gen. The alkaloid constituents of authentic shan-dou-gen gave a specific HPCE electropherogram that could be used to distinguish the drug from potential substitutes. Furthermore, the content of oxymatrine and the total content of the seven quinolizidine alkaloids could be used as quantitative markers in order to assess the quality of S. tonkinensis. Copyright © 2005 John Wiley & Sons, Ltd.
Co-reporter:Zhengwei Jia;Zhixin Liao;Daofeng Chen
Helvetica Chimica Acta 2005 Volume 88(Issue 8) pp:2288-2293
Publication Date(Web):23 AUG 2005
DOI:10.1002/hlca.200590163
Yunnankadsurins A and B (1 and 2, resp.), two new dibenzocyclooctene-type lignans, were isolated from the aqueous extract of Kadsura spp. Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR techniques.
Co-reporter:Jun Deng;Daofeng Chen;Zhixin Liao
Helvetica Chimica Acta 2005 Volume 88(Issue 10) pp:2675-2682
Publication Date(Web):28 OCT 2005
DOI:10.1002/hlca.200590208
Three new polyoxypregnane glycosides, marsdenosides I–K (1–3), were isolated from the stem of Marsdenia tenacissima. The structures were elucidated on the basis of in-depth spectroscopic analyses, and by means of chemical evidence. Marsdenoside I (= (3β,5α,11α,12β,14β,17α,20R)-3-[(2,6-dideoxy-4-O-(6-deoxy-3-O-methyl-β-D-allopyranosyl)-3-O-methyl-β-D-arabino-hexopyranosyl)oxy]-8,20 : 11,20-diepoxypregnane-12,14-diol; 1) is the first C21 steroidal glycoside with a rigid cage. Also, the isolation of 1 demonstrated that tenacigenin A (1a) is a true natural product as well, rather than an artifact.
Co-reporter:Jun Deng, Zhixin Liao, Daofeng Chen
Phytochemistry 2005 Volume 66(Issue 9) pp:1040-1051
Publication Date(Web):May 2005
DOI:10.1016/j.phytochem.2005.03.018
Eight polyoxypregnane glycosides, marsdenosides A–H, were isolated from the CHCl3-soluble fraction of the ethanolic extract of the stem of Marsdenia tenacissima, along with six known glycosides and two known polyoxypregnane aglycones. Three polyoxypregnanes, 12β-O-2-methylbutyryl-tenacigenin A, 11α,12β-di-O-acetyltenacigenin B, and 11α-O-tigloyltenacigenin B were also obtained. Their structures were established on the basis of spectroscopic analysis and chemical evidence.From the CHCl3 extract of the stem of Marsdenia tenacissima, eight polyoxypregnane glycosides were isolated. The structures were elucidated by spectroscopic analysis and chemical evidence.
Co-reporter:Daofeng Chen;Min Chen;Zhixin Liao
Helvetica Chimica Acta 2004 Volume 87(Issue 6) pp:1368-1376
Publication Date(Web):24 JUN 2004
DOI:10.1002/hlca.200490124
Four new dibenzocyclooctene-type lignans, named renchangianins A–D (1–4), were isolated from the stems of Kadsura renchangiana. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques. Renchangianin D (4) possesses a spiro[dibenzocyclooctene-6,2′-oxirane] parent structure previously unknown in plants of the Schisandraceae family.
Co-reporter:Peilan Ding;Daofeng Chen;Kenneth F. Bastow;Alexer K. Nyarko;Xihong Wang;Kuo-Hsiung Lee
Helvetica Chimica Acta 2004 Volume 87(Issue 10) pp:2574-2580
Publication Date(Web):21 OCT 2004
DOI:10.1002/hlca.200490230
Three new flavonoids, which are isoprenylated by fused 2,2-dimethyl-3,4-dihydro-2H-pyran moieties, were isolated from the roots of Sophora flavescens and named flavenochromanes A–C (1–3). Their structures were elucidated by spectroscopic methods, including 2D-NMR techniques. Flavenochromane C (3) showed strong cytotoxic activity against A549 (lung carcinoma), 1A9 (ovarian carcinoma), KB (epidermoid carcinoma of the nasopharynx), and KB-Vin (drug-resistant variant KB) cell lines with IC50 values ≤1.7 μM, and significant activity against the MCF-7 (breast adenocarcinoma) cell line with an IC50 value of 3.6 μM. Flavenochromane B (2) displayed slightly lower inhibitory effects (IC50 3.2–6.9 μM) as compared with 3.
Co-reporter:Li-Bo Zhou, Dao-Feng Chen
Steroids (January 2008) Volume 73(Issue 1) pp:83-87
Publication Date(Web):1 January 2008
DOI:10.1016/j.steroids.2007.09.002
Two new steroidal saponins with a new aglycone moiety, aspafiliosides E (1) and F (2), were isolated from the roots of Asparagus filicinus Buch.–Ham. Their structures were fully elucidated on the basis of detailed spectroscopic study and chemical analysis.
Co-reporter:Chunjun Chu, Huiling Ren, Naiyu Xu, Long Xia, Daofeng Chen, Jian Zhang
Journal of Ethnopharmacology (5 June 2016) Volume 185() pp:263-271
Publication Date(Web):5 June 2016
DOI:10.1016/j.jep.2016.03.022
Ethnopharmacological relevanceEupatorium lindleyanum DC. is widely used for its efficiency in treating cough, tracheitis and tonsillitis. Acute lung injury (ALI) induced by lipopolysaccharide (LPS) in mice was used to investigate therapeutic effects and possible mechanism of the sesquiterpenes fraction of E. lindleyanum DC. (EUP-SQT).Materials and methodsMice were orally administrated with EUP-SQT (15, 30 and 60 mg/kg) per day for 7 days consecutively before LPS challenge. The lung specimens and bronchoalveolar lavage fluid (BALF) were harvested for histopathological examinations and biochemical analysis at 6 h and 24 h after LPS challenge. The level of complement 3 (C3) and complement 3c (C3c) in serum was quantified by a sandwich ELISA kit.ResultsPretreatment with EUP-SQT could significantly decrease lung wet-to-dry weight (W/D) ratio, nitric oxide (NO) and protein concentration in BALF, which was exhibited together with the lowered myeloperoxidase (MPO) activity, the increased superoxide dismutase (SOD) activity and down-regulation the level of tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1β (IL-1β) in ALI model. Additionally, EUP-SQT attenuated lung histopathological changes and significantly reduced complement deposition with decreasing the level of C3 and C3c in serum.ConclusionsThese results showed that EUP-SQT significantly attenuated LPS-induced ALI via reducing productions of pro-inflammatory mediators and decreasing the level of complement, indicating it as a potential therapeutic agent for ALI.Download high-res image (244KB)Download full-size image
Co-reporter:Dongsheng Du, Yan Lu, Zhihong Cheng, Daofeng Chen
Journal of Ethnopharmacology (4 December 2016) Volume 193() pp:345-353
Publication Date(Web):4 December 2016
DOI:10.1016/j.jep.2016.08.034
Ethnopharmacological relevanceThe spikes of Prunella vulgaris have long been used as a traditional Chinese medicine to treat various inflammation-related diseases. The aim of this study was to isolate and characterize homogenous polysaccharides from this herb and to evaluate their anticomplement activity.Materials and methodsAnticomplement activity-guided fractionation of the hot water extract of P. vulgaris was performed by DEAE-cellulose and size-exclusion chromatography, yielding two homogeneous polysaccharides PW-PS1 and PW-PS2. The homogeneity, molecular weight, monosaccharide composition and linkage of the two polysaccharides were determined in addition to other chemical characterizations. The anticomplement activity of the polysaccharides was evaluated and expressed as 50% hemolytic inhibition concentration through the classical pathway (CH50 value) and alternative pathway (AP50 value). The preliminary mechanism for the complement activation cascade was also assessed.ResultsPW-PS1 and PW-PS2 were both branched acidic polysaccharides. PW-PS1 was composed of Ara, Xyl, and 4-methoxy-Glc A in a ratio of 1.0: 2.6: 0.8. The main linkages of the sugar residues of PW-PS1 included terminal β-d-Xylp, 1,4-linked β-d-Xylp, 1,3-linked α-d-Arap, 1,3,5-linked α-d-Arap, and terminal 4-methoxy-α-d-Glcp A. PW-PS2 was composed of Rha, Ara, Xyl, Gal, and Gal A in a ratio of 0.6: 1.0: 1.3: 1.8: 3.4. The main linkages between the sugar residues of PW-PS2 included terminal Araf, 1,4-linked β-d-Xylp, 1,3-linked α-d-Rhap, terminal α-d-Galp, and 1,4,6-linked α-d-Galp. PW-PS1 and PW-PS2 inhibited complement activation through both the classical and alternative pathways with CH50 values of 0.28 and 0.13 mg/mL, respectively, and AP50 values of 0.40 and 0.35 mg/mL, respectively. Preliminary mechanism studies using complement component-depleted sera showed that PW-PS1 acted on the C1q, C3, and C9 components and that PW-PS2 acted on the C1q, C2, C3, C5, and C9 components.ConclusionOur study suggested that PW-PS1 and PW-PS2 could be valuable for the treatment of diseases associated with the excessive activation of the complement system.Download high-res image (156KB)Download full-size image
Co-reporter:Jun-yun Xie, Hong-ye Di, Hong Li, Xiao-qin Cheng, Yun-yi Zhang, Dao-feng Chen
Phytomedicine (15 January 2012) Volume 19(Issue 2) pp:130-137
Publication Date(Web):15 January 2012
DOI:10.1016/j.phymed.2011.08.057
Bupleurum chinense DC had hepato-protective, anti-inflammatory, antipyretic, analgesic, and immunomodulatory effect in traditional Chinese medicine. This study was to determine whether the crude polysaccharides isolated from the roots of Bupleurum chinense DC (BCPs) attenuated lipopolysaccharide (LPS)-induced acute lung injury in mice. Mice were challenged with LPS intratracheally 2 h before BCPs (20, 40 and 80 mg/kg) administration. The bronchoalveolar lavage fluid (BALF) was collected 24 h after LPS challenge. Treatment with BCPs reduced lung wet-to-dry weight ratio. The elevated number of total cells and protein concentration in BALF was reduced. The increased level of myeloperoxidase (MPO), tumor necrosis factor-α (TNF-α) in BALF, and serum nitric oxide (NO) were also inhibited. BCPs significantly attenuated lung injury with improved lung morphology and reduced complement deposition. These results suggested that the effect of BCPs against ALI might be related with its inhibitory effect on excessive activation of complement and on the production of proinflammatory mediators.
Co-reporter:Quan Wen, Yan Lu, Zhi Chao, Dao-feng Chen
Bioorganic & Medicinal Chemistry Letters (15 February 2017) Volume 27(Issue 4) pp:
Publication Date(Web):15 February 2017
DOI:10.1016/j.bmcl.2017.01.007
•Five new ursane and oleanane triterpenoids were isolated from the roots of Ilex asprella.•Several triterpenoids were found to show anticomplement activity.•The targets of the bioactive triterpenoids in complement activation cascade were identified.Five new (1–5) and twenty-eight known (6–33) triterpenoids were isolated from the roots of Ilex asprella. The structures of the new compounds were elucidated by the detailed spectral analysis. The ursane and oleanane triterpenoids were found to show anticomplement activity with some structure-activity relationships. Several triterpenoids (1–3, 6–7) exhibited potent anticomplement activity with the CH50 and AP50 values of 0.058–0.131 mg/mL and 0.080–0.444 mg/mL, respectively. It was found that caffeoyl group could enhance activity remarkably, followed by coumaroyl and feruloyl group. The 28-carboxyl group was also important to anticomplement activity for the triterpenoids. However, the triterpenoids with lactone ring (4, 9–14) exhibited weak activity and triterpenoid glycosides (5, 23–33) showed no inhibition. The targets of several bioactive triterpenoids in complement activation cascade were identified as well.
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![[(3S,6aR,6bS,8aR,11R,12S,12aS,14aS,14bS)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] hexadecanoate](http://img.cochemist.com/ccimg/22300/22255-10-3_b.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy-](http://img.cochemist.com/ccimg/21500/21453-69-0.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2,6-dimethoxy-](http://img.cochemist.com/ccimg/21500/21453-69-0_b.png)
![Benzo[f]-1,3-benzodioxolo[6,5,4-cd]indol-5(6H)-one,8-methoxy-](http://img.cochemist.com/ccimg/13400/13395-02-3.png)
![Benzo[f]-1,3-benzodioxolo[6,5,4-cd]indol-5(6H)-one,8-methoxy-](http://img.cochemist.com/ccimg/13400/13395-02-3_b.png)
![(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate](http://img.cochemist.com/ccimg/1700/1617-68-1.png)
![(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate](http://img.cochemist.com/ccimg/1700/1617-68-1_b.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-](http://img.cochemist.com/ccimg/500/487-36-5.png)
![Phenol,4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-](http://img.cochemist.com/ccimg/500/487-36-5_b.png)
![5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-36-4.png)
![5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/480-36-4_b.png)
![Furo[2,3-b]quinoline,4,7,8-trimethoxy-](http://img.cochemist.com/ccimg/100/83-95-4.png)
![Furo[2,3-b]quinoline,4,7,8-trimethoxy-](http://img.cochemist.com/ccimg/100/83-95-4_b.png)
![5,8-Epoxybenzo[3,4]cycloocta[1,2-f][1,3]benzodioxole,5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (5S,6S,7R,8R,13aS)-](http://img.cochemist.com/ccimg/163700/163660-06-8.png)
![5,8-Epoxybenzo[3,4]cycloocta[1,2-f][1,3]benzodioxole,5,6,7,8-tetrahydro-1,2,3,13-tetramethoxy-6,7-dimethyl-, (5S,6S,7R,8R,13aS)-](http://img.cochemist.com/ccimg/163700/163660-06-8_b.png)
![b-D-Glucopyranoside, (3b,5b,25S)-spirostan-3-yl O-a-L-arabinopyranosyl-(1®6)-O-[b-D-xylopyranosyl-(1®4)]-](http://img.cochemist.com/ccimg/131200/131123-73-4.png)
![b-D-Glucopyranoside, (3b,5b,25S)-spirostan-3-yl O-a-L-arabinopyranosyl-(1®6)-O-[b-D-xylopyranosyl-(1®4)]-](http://img.cochemist.com/ccimg/131200/131123-73-4_b.png)
![2-Butenoic acid,2-methyl-,(5S,6S,7S)-5,6,7,8-tetrahydro-6-hydroxy-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-5-ylester, (2E)-](http://img.cochemist.com/ccimg/65000/64938-51-8.png)
![2-Butenoic acid,2-methyl-,(5S,6S,7S)-5,6,7,8-tetrahydro-6-hydroxy-1,2,3,13-tetramethoxy-6,7-dimethylbenzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-5-ylester, (2E)-](http://img.cochemist.com/ccimg/65000/64938-51-8_b.png)
![13,14-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole (non-preferred name)](http://img.cochemist.com/ccimg/61400/61301-33-5.png)
![13,14-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole (non-preferred name)](http://img.cochemist.com/ccimg/61400/61301-33-5_b.png)
![(6R,7S)-1,2,11,12-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene-3,10-diol](http://img.cochemist.com/ccimg/66300/66280-25-9.png)
![(6R,7S)-1,2,11,12-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulene-3,10-diol](http://img.cochemist.com/ccimg/66300/66280-25-9_b.png)
![(6R,7R,8R)-1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-8-yl acetate](http://img.cochemist.com/ccimg/51700/51670-40-7.png)
![(6R,7R,8R)-1,2,3,13-tetramethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3',4']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxol-8-yl acetate](http://img.cochemist.com/ccimg/51700/51670-40-7_b.png)
![2-Butenoic acid,2-methyl-,(6R,7R,8R,14aS)-5,6,7,8-tetrahydro-2,3-dimethoxy-6,7-dimethyl-1-oxo-1H,14H-benzo[1,8]cycloocta[1,2,3-cd][1,3]dioxolo[4,5-g]benzofuran-8-ylester, (2Z)-](http://img.cochemist.com/ccimg/140400/140369-76-2.png)
![2-Butenoic acid,2-methyl-,(6R,7R,8R,14aS)-5,6,7,8-tetrahydro-2,3-dimethoxy-6,7-dimethyl-1-oxo-1H,14H-benzo[1,8]cycloocta[1,2,3-cd][1,3]dioxolo[4,5-g]benzofuran-8-ylester, (2Z)-](http://img.cochemist.com/ccimg/140400/140369-76-2_b.png)
![(6S,7R)-2,3,10,11,12-pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-1-ol](http://img.cochemist.com/ccimg/69400/69363-14-0.png)
![(6S,7R)-2,3,10,11,12-pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-1-ol](http://img.cochemist.com/ccimg/69400/69363-14-0_b.png)
![b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-tetrahydro-5-hydroxy-5b-[[(4-hydroxy-3-methoxybenzoyl)oxy]methyl]-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl](http://img.cochemist.com/ccimg/172800/172705-25-8.png)
![b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-tetrahydro-5-hydroxy-5b-[[(4-hydroxy-3-methoxybenzoyl)oxy]methyl]-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl](http://img.cochemist.com/ccimg/172800/172705-25-8_b.png)
![Dibenz[cd,f]indol-4(5H)-one,1-hydroxy-2-methoxy-](http://img.cochemist.com/ccimg/112600/112501-42-5.png)
![Dibenz[cd,f]indol-4(5H)-one,1-hydroxy-2-methoxy-](http://img.cochemist.com/ccimg/112600/112501-42-5_b.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one, 3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-](/data/chemimg/2052900/88497-81-8.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one, 3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-](/data/chemimg/2052900/88497-81-8_b.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one, 10-(acetyloxy)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-](/data/chemimg/1952200/73061-92-4.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one, 10-(acetyloxy)-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-](/data/chemimg/1952200/73061-92-4_b.png)
![16aH-1,6:2,6-Diepoxybenz[7,8]oxireno[5,6]azuleno[8,1-bc]oxacyclotridecin-16,16a,17-triol, eicosahydro-17a-(hydroxymethyl)-4,14,15-trimethyl-2-(1-](/data/chemimg/1315300/66107-37-7.png)
![16aH-1,6:2,6-Diepoxybenz[7,8]oxireno[5,6]azuleno[8,1-bc]oxacyclotridecin-16,16a,17-triol, eicosahydro-17a-(hydroxymethyl)-4,14,15-trimethyl-2-(1-](/data/chemimg/1315300/66107-37-7_b.png)
![16aH-1,6:2,6-Diepoxybenz[7,8]oxireno[5,6]azuleno[8,1-bc]oxacyclotridecin-7,16,16a,17-tetrol, 4-[(benzoyloxy)methyl]eicosahydro-17a-(hydroxymethyl)-](/data/chemimg/597800/60796-70-5.png)
![16aH-1,6:2,6-Diepoxybenz[7,8]oxireno[5,6]azuleno[8,1-bc]oxacyclotridecin-7,16,16a,17-tetrol, 4-[(benzoyloxy)methyl]eicosahydro-17a-(hydroxymethyl)-](/data/chemimg/597800/60796-70-5_b.png)
![Dibenz[cd,f]indol-4(5H)-one,1,2-dimethoxy-](http://img.cochemist.com/ccimg/54000/53948-09-7.png)
![Dibenz[cd,f]indol-4(5H)-one,1,2-dimethoxy-](http://img.cochemist.com/ccimg/54000/53948-09-7_b.png)
![Dibenz[cd,f]indol-4(5H)-one,2-hydroxy-1-methoxy-](http://img.cochemist.com/ccimg/54000/53948-07-5.png)
![Dibenz[cd,f]indol-4(5H)-one,2-hydroxy-1-methoxy-](http://img.cochemist.com/ccimg/54000/53948-07-5_b.png)
![2-METHYL-2-PROPANYL 3-{[(6-CHLORO-3-PYRIDAZINYL)AMINO]METHYL}-1-P<WBR />IPERIDINECARBOXYLATE](http://img.cochemist.com/ccimg/38000/37905-08-1.png)
![2-METHYL-2-PROPANYL 3-{[(6-CHLORO-3-PYRIDAZINYL)AMINO]METHYL}-1-P<WBR />IPERIDINECARBOXYLATE](http://img.cochemist.com/ccimg/38000/37905-08-1_b.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one,3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-2-(1E,3E)-1,3-tridecadien-1-yl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10aR)-](http://img.cochemist.com/ccimg/33500/33465-16-6.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one,3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-2-(1E,3E)-1,3-tridecadien-1-yl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10aR)-](http://img.cochemist.com/ccimg/33500/33465-16-6_b.png)
![2-Cyclohexen-1-one,4-hydroxy-4-[(1E,3R)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-, (4S)-](http://img.cochemist.com/ccimg/23600/23526-45-6.png)
![2-Cyclohexen-1-one,4-hydroxy-4-[(1E,3R)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-, (4S)-](http://img.cochemist.com/ccimg/23600/23526-45-6_b.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one,3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-2-nonyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10aR)-](http://img.cochemist.com/ccimg/1500/1404-62-2.png)
![6H-2,8b-Epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-one,3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-5,5a-dihydroxy-4a-(hydroxymethyl)-7,9-dimethyl-10a-(1-methylethenyl)-2-nonyl-,(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10aR)-](http://img.cochemist.com/ccimg/1500/1404-62-2_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/482-39-3.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one](http://img.cochemist.com/ccimg/500/482-39-3_b.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9_b.png)
![b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-tetrahydro-5-hydroxy-5b-[[(4-hydroxybenzoyl)oxy]methyl]-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl,6-(3,4,5-trihydroxybenzoate)](http://img.cochemist.com/ccimg/145900/145898-93-7.png)
![b-D-Glucopyranoside,(1aR,2S,3aR,5R,5aR,5bS)-tetrahydro-5-hydroxy-5b-[[(4-hydroxybenzoyl)oxy]methyl]-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl,6-(3,4,5-trihydroxybenzoate)](http://img.cochemist.com/ccimg/145900/145898-93-7_b.png)
