Co-reporter:Chang-An Geng, Xiao-Yan Huang, Yun-Bao Ma, Bo Hou, Tian-Ze Li, Xue-Mei Zhang, and Ji-Jun Chen
Journal of Natural Products April 28, 2017 Volume 80(Issue 4) pp:959-959
Publication Date(Web):February 22, 2017
DOI:10.1021/acs.jnatprod.6b00938
(±)-Uncarilins A and B (1a/1b and 2a/2b), two pairs of unusual dimeric isoechinulin-type enantiomers with a symmetric four-membered core, were isolated from Uncaria rhynchophylla driven by LCMS-IT-TOF analyses. Their structures were elucidated by extensive 1D and 2D NMR spectra, X-ray diffraction, and ECD spectroscopic data. (−)-Uncarilin B (2a) showed activities on MT1 and MT2 receptors with agonistic rates of 11.26% and 52.44% at a concentration of 0.25 mM.
Co-reporter:Xinglong Chen, Aixue Zuo, Zhentao Deng, Xiaoyan Huang, Xuemei Zhang, Changan Geng, Tianze Li, Jijun Chen
Fitoterapia 2017 Volume 122(Volume 122) pp:
Publication Date(Web):1 October 2017
DOI:10.1016/j.fitote.2017.09.009
Seven new phenolic glycosides including two heterocyclic phenolic derivatives orcinosides I-J (1–2) and five chlorophenolic glycosides curculigines J-N (3–7), together with nineteen known compounds were isolated from the rhizome of Curculigo orchioides. Based on extensive spectroscopic analyses (UV, IR, HRESIMS, 1D and 2D NMR), the structures of the new compounds were identified. Orcinoside I (1) and J (2) displayed xanthine oxidase inhibitory activities with IC50 values 0.25 and 0.62 mM respectively.Download high-res image (121KB)Download full-size image
Co-reporter:Chang-Li SUN, Chang-An GENG, Xiao-Yan HUANG, Yun-Bao MA, ... Ji-Jun CHEN
Chinese Journal of Natural Medicines 2017 Volume 15, Issue 6(Volume 15, Issue 6) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/S1875-5364(17)30070-5
5-Hydroxytryptamine 2C (5-HT2C) receptor is one of the major targets of anti-obesity agents, due to its role in regulation of appetite. In the present study, the 70% EtOH extract of the roots of Bupleurum chinense was revealed to have agonistic activity on 5-HT2C receptor, and the subsequent bioassay-guided isolation led to identification of several saikosaponins as the active constituents with 5-HT2C receptor agonistic activity in vitro and anti-obesity activity in vivo. The new compound, 22-oxosaikosaponin d (1), was determined by extensive spectroscopic analyses (HR-ESI-MS, IR, and 1D and 2D NMR). The primary structure-activity relationship study suggested that the intramolecular ether bond between C-13 and C-28 and the number of sugars at C-3 position were closely related to the 5-HT2C receptor agonistic activity. Saikosaponin a (3), the main saponin in B. chinense, showed obviously agonistic activity on 5-HT2C receptor with an EC50 value of 21.08 ± 0.33 μmol·L−1 in vitro and could reduce food intake by 39.1% and 69.2%, and weight gain by 13.6% and 16.4%, respectively, at 3.0 and 6.0 mg·kg−1 in vivo. This investigation provided valuable information for the potential use of B. chinense as anti-obesity agent.
Co-reporter:Tian-Ze Li, Chang-An GengXiu-Juan Yin, Tong-Hua Yang, Xing-Long Chen, Xiao-Yan Huang, Yun-Bao Ma, Xue-Mei Zhang, Ji-Jun Chen
Organic Letters 2017 Volume 19(Issue 3) pp:
Publication Date(Web):January 26, 2017
DOI:10.1021/acs.orglett.6b03801
The first catalytic asymmetric total synthesis of (+)- and (−)-paeoveitol has been accomplished in 42% overall yield via a biomimetic hetero-Diels–Alder reaction. The chiral phosphoric acid catalyzed hetero-Diels–Alder reaction showed excellent diastereo- and enantioselectivity (>99:1 dr and 90% ee); two rings and three stereocenters were constructed in a single step to produce (−)-paeoveitol on a scale of 452 mg. This strategy enabled us to selectively synthesize both paeoveitol enantiomers from the same substrates by simply changing the enantiomer of the catalyst.
Co-reporter:Xiu-Juan Yin;Chang-An Geng;Xing-Long Chen
Natural Products and Bioprospecting 2017 Volume 7( Issue 2) pp:215-223
Publication Date(Web):20 March 2017
DOI:10.1007/s13659-017-0124-z
Sixteen tropinone derivatives were prepared, and their antitumor activities against five human cancer cells (HL-60, A-549, SMMC-7721, MCF-7 and SW480) were evaluated with MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxy methoxyphenyl)-2-(4-sulfopheny)-2H-tetrazolium] assay. Most of the derivatives exhibited better activities compared with tropinone at the concentration of 40 μM. Particularly, derivative 6 showed significant activities with IC50 values of 3.39, 13.59, 6.65, 13.09 and 12.38 μM respectively against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cells, which suggested more potent activities than that of cis-dichlorodiamineplatinum (DDP).
Co-reporter:Xiu-Juan Yin, Chang-An Geng, Xiao-Yan Huang, Hao Chen, Yun-Bao Ma, Xing-Long Chen, Chang-Li Sun, Tong-Hua Yang, Jun Zhou, Xue-Mei Zhang and Ji-Jun Chen
RSC Advances 2016 vol. 6(Issue 51) pp:45059-45063
Publication Date(Web):20 Apr 2016
DOI:10.1039/C6RA06748D
Twenty-three tropine derivatives as new melatonin receptor (MT1 and MT2) agonists were synthesized and evaluated on HEK293 cells in vitro. Derivatives 1f, 1i, 1j, 1m–1s and 1t exhibited increased agonisting activities on MT1 and MT2 receptors compared to the substrate tropine. Particularly, compound 1r showed significant agonistic activities on MT1 and MT2 receptors with EC50 values of 0.20 and 0.24 mM, respectively. The preliminary structure–activity relationships (SARs) of tropine derivatives were summarized for further investigation on melatonin receptor agonists.
Co-reporter:Chang-An Geng
Natural Products and Bioprospecting 2016 Volume 6( Issue 6) pp:297-303
Publication Date(Web):2016 December
DOI:10.1007/s13659-016-0114-6
Swerilactones H–K (1–4) as four unprecedented secoiridoid trimers represent a new type of natural product, which has attracted much interest of natural chemists due to their novel skeletons and promising bioactivity. In order to well understand their MS fragmentation behaviors, they were investigated by electrospray ionization ion-trap time-of-flight multistage product ion mass spectrometry (ESI-IT-TOF-MSn) for the first time. The protonated molecules ([M+H]+) of swerilactones J and K, and deprotonated molecules ([M−H]−) of swerilactones H, J and K were readily observed in the conventional single-stage mass spectra (MS); however only the [M+Cl]− ion for swerilactone I was obtained in negative mode. Based on the MSn study, the fragmentation pathways of swerilactones H and I in negative mode, and swerilactones J and K in both positive and negative modes were proposed. The neutral losses of H2O, CO, CO2 and C2H4O moieties are the particular elimination from the precursor ions due to the presence of hydroxyl, δ-lactone and 1-O-ethyl moieties in their structures, of which the retro-Diels–Alder cleavage was the most particular dissociation. The fragment ions at m/z 341 and 291 in negative mode can be considered as the diagnostic ions for secoiridoid trimers. This investigation will provide valuable information for their fast characterization from complicated natural mixtures and extensive understanding their structural architectures.
Co-reporter:Chang-An Geng, Xing-Long Chen, Xiao-Yan Huang, Yun-Bao Ma, Kang He, Ning-Jia Zhou, Tuan-Wu Cao, Xue-Mei Zhang, Ji-Jun Chen
Tetrahedron Letters 2015 Volume 56(Issue 17) pp:2163-2166
Publication Date(Web):22 April 2015
DOI:10.1016/j.tetlet.2015.03.057
One unusual secoiridoid trimer, namely sweriyunnanlactone A (1), was isolated from Swertia yunnanensis under the guidance of LC–MS analysis. Sweriyunnanlactone A with a phenyl ring (ring F) was the first example of secoiridoid trimer featuring a C28 skeleton. Its structure was determined by extensive HRESIMS, 1D and 2D NMR spectroscopic data, and GIAO 13C NMR calculation. Compound 1 showed weak inhibition on HBV DNA replication with an IC50 value of 60.76 μM (SI = 12.6) on HepG 2.2.15 cell line in vitro.
Co-reporter:Yong Zhao, Chang-An Geng, Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Tuan-Wu Cao, Kang He, Hao Wang, Xue-Mei Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 7) pp:1509-1514
Publication Date(Web):1 April 2015
DOI:10.1016/j.bmcl.2015.02.024
p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure–activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a–2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.
Co-reporter:Chang-An Geng, Xiao-Yan Huang, Yun-Bao Ma, Xue-Mei Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 7) pp:1568-1571
Publication Date(Web):1 April 2015
DOI:10.1016/j.bmcl.2015.02.009
Twenty-four derivatives of erythrocentaurin (ET) were synthesized and evaluated for their anti-HBV activities on HepG 2.2.15 cell line in vitro. Eight compounds 1, 2, 5, 8, 9, 1e, 1k, and 1m increased activity against HBV DNA replication with the SI values higher than 11. In particular, derivatives 1e and 1k exhibited the most potent inhibition on HBV DNA replication with the IC50 values of 0.026 mM (SI >70.8) and 0.045 mM (SI >36.0), respectively. The primary structure–activity relationships (SARs) of ET derivatives were summarized for exploring potent anti-HBV agents.
Co-reporter:Wen-Juan Liang, Chang-An Geng, Xue-Mei Zhang, Hao Chen, Cai-Yan Yang, Guang-Qing Rong, Yong Zhao, Hong-Bo Xu, Hao Wang, Ning-Jia Zhou, Yun-Bao Ma, Xiao-Yan Huang, and Ji-Jun Chen
Organic Letters 2014 Volume 16(Issue 2) pp:424-427
Publication Date(Web):December 31, 2013
DOI:10.1021/ol403315d
(+)-Paeoveitol and (−)-paeoveitol, a pair of new norditerpene enantiomers, were isolated from the root of Paeonia veitchii. Their structures and absolute configurations were determined on the basis of extensive analysis of 1D and 2D NMR spectra, crystal X-ray diffraction, and electronic circular dichroism (ECD). A possible biogenesis involving two molecules of paeoniflorin was postulated.
Co-reporter:Chang-An Geng, Xing-Long Chen, Ning-Jia Zhou, Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Xue-Mei Zhang, and Ji-Jun Chen
Organic Letters 2014 Volume 16(Issue 2) pp:370-373
Publication Date(Web):December 20, 2013
DOI:10.1021/ol403198d
(±)-Sweriledugenin A, a pair of novel enantiomeric lactones, were isolated from Swertia leducii under the guidance of LC-MS investigation. The enantiomeric separation was achieved by HPLC on a chiral column. Their structures were determined by extensive NMR spectra, X-ray, and quantum calculations. (+)-Sweriledugenin A and (−)-sweriledugenin A showed activities inhibiting HBV DNA replication with the IC50 values of 36.86 and 26.55 μM on the HepG 2.2.15 cell line in vitro.
Co-reporter:Chang-An Geng, Hao Chen, Xing-Long Chen, Xue-Mei Zhang, Li-Gong Lei, Ji-Jun Chen
International Journal of Mass Spectrometry 2014 Volume 361() pp:9-22
Publication Date(Web):15 March 2014
DOI:10.1016/j.ijms.2014.01.021
•The first time LC–DAD/MSn investigation on S. guangxiense led to the identification of 50 compounds.•Cyanogenic glycosides, triterpenoids, phenolic sulfates and organic acids are the main constituents.•This paper is valuable for understanding the chemical profiles and taxonomic position of S. guangxiense.Saniculiphyllum guangxiense as a highly distinctive species within Saxifragaceae is fallen to the critically endangered category, whose chemical and taxonomic information is still little-known. The first time LC–DAD/MSn investigation on S. guangxiense led to the detection and characterization of 50 compounds, involving cyanogenic glycosides, phenolic sulfates, triterpenoids, amino acids, phenylpropanoids, aromatic derivatives, lignans, flavonoids, nucleosides, fatty acids and carbohydrate, based on their fragmentation characteristics, UV spectra or comparison with the reference compounds. The collision induced dissociation (CID) fragmentation patterns for several types of compounds were also concluded. The main constituents of S. guangxiense were revealed as cyanogenic glycosides, triterpenoids, phenolic sulfates and organic acids, which were very different from other Saxifragaceae plants. This paper will provide valuable information for understanding its chemical profiles and taxonomic position in Saxifragaceae from a chemotaxonomic point of view.
Co-reporter:Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Chang-An Geng, Yong Zhao, Li-Jun Wang, Rui-Hua Guo, Wen-Juan Liang, Xue-Mei Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 10) pp:2353-2359
Publication Date(Web):15 May 2014
DOI:10.1016/j.bmcl.2014.03.060
Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07 μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal log P value of 1.78 and log D values. Structure–activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07 μM and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal log P value of 1.78 and log D values. Structure–activity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs.
Co-reporter:Hao Chen;Li-Jun Wang;Yun-Bao Ma;Xiao-Yan Huang
Natural Products and Bioprospecting 2014 Volume 4( Issue 3) pp:163-174
Publication Date(Web):2014 June
DOI:10.1007/s13659-014-0018-2
28 Derivatives of panaxadiol (PD) and panaxatriol were synthesized and evaluated for their anti-HBV activity on HepG 2.2.15 cells, of which 17 derivatives inhibited HBV DNA replication. Compounds 4, 9, 10, 14, and 15 showed moderate activity against HBV DNA replication with IC50 values ranged from 7.27 to 28.21 μM compared with PD. In particular, 3-O-2′-thenoyl panaxadiol (4) inhibited not only HBV DNA replication (IC50 = 16.5 μM, SI > 115.7) but also HBsAg (IC50 = 30.8 μM, SI > 62.0) and HBeAg (IC50 = 18.2 μM, SI > 105.14) secretions. Their structure–activity relationships were discussed for guiding future research toward the discovery of new anti-HBV agents.
Co-reporter:Hong-Ling Wang, Tuan-Wu Cao, Fu-Qiang Jiang, Chang-An Geng, Xue-Mei Zhang, Xiao-Yan Huang, Li-Jun Wang, Kang-He, Hao-Chen, Wen-Juan Liang, Guang-Qing Rong, Ji-Jun Chen
Tetrahedron Letters 2013 Volume 54(Issue 21) pp:2710-2712
Publication Date(Web):22 May 2013
DOI:10.1016/j.tetlet.2013.03.057
Swerpunilactones A (1) and B (2), two novel xanthone and secoiridoid heterodimers, together with their presumed biosynthetic precursors (±)-gentiolactone (3), bellidifolin (4), and norbellidifolin (5), were isolated from the whole plants of Swertia species. A plausible biogenetic pathway for swerpunilactones A and B was proposed. In vitro anti-hepatitis B virus assay on the Hep G 2.2.15 cell line showed that both compounds 1 and 2 exhibited activities against the secretion of HBsAg (IC50 = 0.25 and 0.29 mM), HBeAg (IC50 = 0.86 and 0.31 mM), and HBV DNA replication (IC50 = 0.18 and 0.19 mM).
Co-reporter:Chang-An Geng, Yun-Bao Ma, Ji-Jun Chen
Chinese Chemical Letters 2013 Volume 24(Issue 3) pp:236-238
Publication Date(Web):March 2013
DOI:10.1016/j.cclet.2013.01.042
One unusual dimeric tropane alkaloid, bishyoscyamine, was isolated from the roots of Anisodus acutangulus, whose structure including the absolute stereochemistry was unambiguously determined based on extensive 1D NMR and 2D NMR, HR-ESI-MS [α]D and CD spectroscopic analyses. To our knowledge, bishyoscyamine is the first example of tropane alkaloid dimer condensed by a CN bond.One unusual tropane alkaloid dimer, bishyoscyamine, was isolated from the roots of Anisodus acutangulus.
Co-reporter:Rui-Hua Guo, Chang-An Geng, Xiao-Yan Huang, Yun-Bao Ma, Quan Zhang, Li-Jun Wang, Xue-Mei Zhang, Rong-Ping Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 5) pp:1201-1205
Publication Date(Web):1 March 2013
DOI:10.1016/j.bmcl.2013.01.024
A series of hemslecin A derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely, inhibiting the secretion of hepatitis B surface antigen (HBsAg), hepatitis B e antigen (HBeAg), and HBV DNA replication on HepG 2.2.15 cells. Most of the derivatives showed enhanced anti-HBV activities, of which compounds A1–A7, B5, C and E exhibited significant activities inhibiting HBV DNA replication with IC50 values of 2.8–11.6 μM, comparable to that of the positive control, tenofovir. Compounds A1–A3, A5, B5, and C displayed low cytotoxicities, which resulted in high SI values of 89.7, 55.6, 77.8, >83.4, >55.8, and >150.5, respectively.
Co-reporter:Zhi-Yong Jiang, Wen-Feng Liu, Xue-Mei Zhang, Jie Luo, Yun-Bao Ma, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 7) pp:2123-2127
Publication Date(Web):1 April 2013
DOI:10.1016/j.bmcl.2013.01.118
In the screening search for Hepatitis B virus inhibitory agents from medicinal plants, the ethanol extract of Piper longum Linn. was found to possess superior anti-HBV activity in vitro. Bioassay-guided fractionation coupled with repeated purification resulted in the isolation of four new compounds, involving two new glycosides longumosides A (1) and B (2) and two new amide alkaloids erythro-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (3), threo-1-[1-oxo-9(3,4-methylenedioxyphenyl)-8,9-dihydroxy-2E-nonenyl]-piperidine (4), as well as two compounds 3β,4α-dihydroxy-2-piperidinone (5), 5,6-dihydro-2(1H)-pyridinone (6) from natural source for the first time. The structures of the four new compounds were determined by extensive analyses of the MS, IR, 1D and 2D NMR data. Besides, the compounds 2–6, together with the known compounds 7–11 obtained previously, were assayed for their anti-HBV activity by using Hep G 2.2.15 cell line in vitro. Results suggested the compound piperine (7) possessed remarkable inhibitory HBV activity, against the secretion of hepatitis B virus surface antigen (HBsAg) and hepatitis B virus e antigen (HBeAg) with the Selectivity Index (SI) values of 15.7 and 16.8, respectively.
Co-reporter:Chang-An Geng;Xue-Mei Zhang;Yun-Bao Ma
Natural Products and Bioprospecting 2013 Volume 3( Issue 5) pp:243-249
Publication Date(Web):2013 October
DOI:10.1007/s13659-013-0059-y
Co-reporter:Li-Jun Wang, Chang-An Geng, Yun-Bao Ma, Jie Luo, Xiao-Yan Huang, Hao Chen, Ning-Jia Zhou, Xue-Mei Zhang, Ji-Jun Chen
European Journal of Medicinal Chemistry 2012 Volume 54() pp:352-365
Publication Date(Web):August 2012
DOI:10.1016/j.ejmech.2012.05.012
Forty-six conjugated derivatives of caudatin with substituted cinnamic acids were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the derivatives exhibited potent anti-HBV activity, especially inhibiting the HBV DNA replication with the IC50 values from 2.44 to 22.89 μΜ. Compound 18 showed significant activity against the secretion of HBsAg, HBeAg, and HBV DNA replication with IC50 values of 5.52, 5.52, 2.44 μΜ, respectively, and had good safety (LD50 > 1250 mg/kg) according to the acute toxicity study. Preliminary mechanism investigation suggested that compound 18 exerted antivirus effects via interfering HBV X promoter and enhancer I to influence HBV transcriptions.Graphical abstractForty-six conjugated derivatives of caudatin with cinnamic acids bearing various substituents were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated. Most of the derivatives exhibited potent anti-HBV activity, especially inhibiting the HBV DNA replication with the IC50 values from 2.44 to 22.89 μΜ. Compound 18 could influence HBV transcriptions by inhibiting the activity of HBV X promoter (Xp) and enhancing the activity of HBV enhancer I (ENI).Highlights► Conjugated derivatives of caudatin with cinnamic acids were synthesized. ► Most of the derivatives exhibited potent anti-HBV activity. ► The compound 18 exerted antivirus effects by interfering HBV promoters and enhancers. ► The mechanism of compound 18 is different from those of the nucleoside analogs.
Co-reporter:Chang-An Geng, Yun-Bao Ma, Xue-Mei Zhang, Shu-Ying Yao, Duo-Qing Xue, Rong-Ping Zhang, and Ji-Jun Chen
Journal of Agricultural and Food Chemistry 2012 Volume 60(Issue 33) pp:8197-8202
Publication Date(Web):July 27, 2012
DOI:10.1021/jf302639b
Mulberrofuran G (1) and isomulberrofuran G (2), a pair of isomeric Diels–Alder-type adducts, were isolated from the root bark of Morus alba L. Isomulberrofuran G (2) as a new IIB-type Diels–Alder-type adduct, was elucidated by extensive 1H, 13C, and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectroscopic analyses. A fragmentation study on compounds 1 and 2 was performed by high-resolution electrospray ionization (ESI) multistage tandem mass spectrometry linked with ion-trap (IT) and time-of-flight (TOF) mass analyzers (ESI–MSn/IT–TOF) in negative mode, which resulted in obviously different fragmentations. In the MS2 experiments, the characteristic ions at m/z 451 and 439 could be revealed as their respective diagnostic ions. Mulberrofuran G (1) showed moderate activity, inhibiting hepatitis B virus (HBV) DNA replication with the IC50 value of 3.99 μM, according to the anti-HBV assay on the HepG 2.2.15 cell line in vitro.
Co-reporter:Li-Jun Wang, Chang-An Geng, Yun-Bao Ma, Xiao-Yan Huang, Jie Luo, Hao Chen, Rui-Hua Guo, Xue-Mei Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry 2012 Volume 20(Issue 9) pp:2877-2888
Publication Date(Web):1 May 2012
DOI:10.1016/j.bmc.2012.03.023
A series of caudatin derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the 3-O-substituted caudatin derivatives showed effective anti-HBV activity. Among the tested compounds, six compounds (2e–2h, 2l, 2r) exhibited significantly inhibitory activity against HBV DNA replication with IC50 values in the range of 2.82–7.48 μM. Interestingly, two compounds (2e, 2f) had potent activity inhibiting not only the secretion of HBsAg (IC50 = 18.68 μM, 21.71 μM), HBeAg (IC50 = 13.16 μM, 33.73 μM), but also HBV DNA replication (IC50 = 7.48 μM, 3.63 μM). The structure–activity relationships (SARs) of caudatin derivatives had been discussed, which were useful for caudatin derivatives to be explored and developed as novel anti-HBV agents.A series of caudatin derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the 3-O-substituted caudatin derivatives showed effective anti-HBV activity. Two compounds (2e, 2f) had potent activity inhibiting not only the secretion of HBsAg, HBeAg, but also HBV DNA replication. The structure–activity relationships (SARs) of caudatin derivatives had been discussed.
Co-reporter:Li-Jun Wang, Chang-An Geng, Yun-Bao Ma, Xiao-Yan Huang, Jie Luo, Hao Chen, Xue-Mei Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 10) pp:3473-3479
Publication Date(Web):15 May 2012
DOI:10.1016/j.bmcl.2012.03.081
Fifty-seven derivatives of glycyrrhetinic acid (GA) were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Among them, sixteen compounds showed greater anti-HBV activity than GA, especially, compounds 29, 32, 35, 41 exhibited significantly inhibitory activities against HBV DNA replication with IC50 values of 5.71, 5.36, 8.90 and 9.08 μM, respectively. The structure–activity relationships (SARs) of GA derivatives were discussed for exploring novel anti-HBV agents.Fifty-seven derivatives of glycyrrhetinic acid (GA) were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Among them, sixteen compounds showed greater anti-HBV activity than GA, especially, compounds 29, 32, 35, 41 exhibited significantly inhibitory activities against HBV DNA replication with IC50 values of 5.71, 5.36, 8.90 and 9.08 μM, respectively. The structure–activity relationships (SARs) of GA derivatives had been discussed.
Co-reporter:Yong Shen;Hong-Lian Ai;Tuan-Wu Cao;Jian-Jun Wang;Shu-Hui Zi;Xue-Mei Zhang
Helvetica Chimica Acta 2012 Volume 95( Issue 3) pp:509-513
Publication Date(Web):
DOI:10.1002/hlca.201100353
Abstract
Three new C19-diterpenoid alkaloids, named aconitramines A (1), B (2), and C (3), were isolated from Aconitum transsectum. By UV, IR, 1D- and 2D-NMR, and MS analyses, their structures were elucidated as 18-methoxyvilmoraconitine, 18-demethoxydolichotine A, and 18-demethoxydolichotine B. Compound 1 is the second known C19-diterpenoid alkaloid with a three-membered ring formed by C(8), C(9), and C(10).
Co-reporter:Chang-An Geng;Xiao-Yan Huang;Li-Gong Lei;Xue-Mei Zhang
Chemistry & Biodiversity 2012 Volume 9( Issue 8) pp:1508-1516
Publication Date(Web):
DOI:10.1002/cbdv.201100270
Abstract
The first phytochemical investigation on Saniculiphyllum guangxiense resulted in the isolation of two new triterpenoids, 16β-hydroxybryodulcosigenin (3) and 3α-O-feruloylolean-12-en-27-oic acid (6), together with six known compounds, menisdaurin (1), purshianin (2), oleanolic acid (4), 3β-hydroxyolean-12-en-27-oic acid (5), β-sitosterol (7), and daucosterol (8), which were characterized by extensive spectroscopic analyses and in one case by X-ray diffraction. According to this primary investigation, S. guangxiense is rich in nitrile glucosides and triterpenoids, of which menisdaurin (1; 0.06%) and purshianin (2; 0.015%) are the main constituents. Compounds 1–6 were assayed for their anti-hepatitis B virus (HBV) activities against the secretion of HBsAg and HBeAg, as well as HBV DNA replication on Hep G 2.2.15 cell line in vitro. The most active compound, menisdaurin (1), inhibits HBV DNA replication with an IC50 value of 0.32 mM (SI>11.97).
Co-reporter:Rui-Hua Guo, Quan Zhang, Yun-Bao Ma, Jie Luo, Chang-An Geng, Li-Jun Wang, Xue-Mei Zhang, Jun Zhou, Zhi-Yong Jiang, Ji-Jun Chen
European Journal of Medicinal Chemistry 2011 Volume 46(Issue 1) pp:307-319
Publication Date(Web):January 2011
DOI:10.1016/j.ejmech.2010.11.019
A series of novel 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one derivatives were synthesized and evaluated for anti-hepatitis B virus (anti-HBV) activities in vitro to explore their structure–activity relationships (SARs). Most of the synthesized compounds possessed potent anti-HBV activity, of which the promising compound 44 exhibited significantly inhibitory potency against the secretion of hepatitis surface antigen (HBsAg) (IC50 = 0.010 mM, SI > 135), hepatitis e antigen (HBeAg) (IC50 = 0.026 mM, SI > 51) and the replication of HBV DNA (IC50 = 0.045 mM). Preliminary mechanism study suggested compound 44 could mainly enhance the transcript activity of HBV ENI (enhancer I), EN-II (enhancer II).6-Chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl)quinolin-2(1H)-one analogues were synthesized and evaluated for the anti-HBV activities in vitro. Most of compounds possessed potent activities, of which the promising compound 44 exhibited significantly inhibitory activities.Research highlights► We synthesized a series of new non-nucleoside 6-chloro-4-(2-chlorophenyl)-3-(2-hydroxyethyl) quinolin-2(1H)-one analogues via chemical modifications on N-1, C-2, and hydroxyethyl moiety. ► These analogues were further evaluated their anti-HBV activities to explore their structure-activity relationships. ► Preliminary mechanism study suggested the promising compound 44 could mainly enhance the transcript activity of HBV ENI (enhancer I), ENII (enhancer II).
Co-reporter:Chang-An Geng ; Xue-Mei Zhang ; Yun-Bao Ma ; Jie Luo
Journal of Natural Products 2011 Volume 74(Issue 8) pp:1822-1825
Publication Date(Web):August 8, 2011
DOI:10.1021/np200256b
Swerilactones L–O (1–4), four unusual secoiridoids with unprecedented C12 and C13 skeletons, were isolated from the traditional Chinese herb Swertia mileensis. Compounds 1 and 2 had moderate inhibitory activities against the secretion of hepatitis B virus surface antigen (IC50 = 1.47 and 1.20 mM, with SI < 1 and 1.53, respectively) and hepatitis B virus e antigen (IC50 = 0.88 and >2.69 mM, with SI 1.62 and <1, respectively) in an antihepatitis B virus assay on the Hep G 2.2.15 cell line in vitro.
Co-reporter:Rui-Hua Guo, Quan Zhang, Yun-Bao Ma, Xiao-Yan Huang, Jie Luo, Li-Jun Wang, Chang-An Geng, Xue-Mei Zhang, Jun Zhou, Zhi-Yong Jiang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry 2011 Volume 19(Issue 4) pp:1400-1408
Publication Date(Web):15 February 2011
DOI:10.1016/j.bmc.2011.01.006
A series of 4-aryl-6-chloro-quinoline derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities, namely the abilities to inhibit the secretion of HBV surface antigen (HBsAg), HBV e antigen (HBeAg), and replication of HBV DNA in HepG 2.2.15 cells. Most of the compounds exhibited moderate inhibitory activity against the secretion of HBsAg and HBeAg. Nine compounds (3, 5, 6, 7, 10, 14, 17, 20, 24) showed significant inhibition against HBV DNA replication with IC50 values in the range of 4.4–9.8 μM, which were comparative to that of positive control tenofovir. Of them, compounds 10, 17, and 20 had low cytotoxicities, resulting in high SI values, >551.2, >143.7, and >284.5, respectively.A series of non-nucleoside 4-aryl-6-chloro-quinoline derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in HepG2.2.15 cells. Most of the compounds exhibited moderate inhibitory activity against the secretion of HBsAg and HBeAg. Nine compounds (3, 5, 6, 7, 10, 14, 17, 20, 24) showed significant inhibition against HBV DNA replication with IC50 values in the range of 4.4–9.8 μM. Of them, compounds 10, 17, and 20 had low cytotoxicities, resulting in high SI values, >551.2, >143.7, and >284.5, respectively.
Co-reporter:Yong Shen;Ai-Xue Zuo;Zhi-Yong Jiang;Xue-Mei Zhang;Hong-Ling Wang
Helvetica Chimica Acta 2011 Volume 94( Issue 2) pp:268-272
Publication Date(Web):
DOI:10.1002/hlca.201000187
Abstract
Hemsleyaconitines F and G (1 and 2, resp.) were isolated from the EtOH extract of Aconitum hemsleyanum. Their structures were elucidated by extensive analyses of the IR, 1D- and 2D-NMR, and MS data. The two C19-diterpenoid alkaloids 1 and 2 possess a novel skeleton, featuring a five-membered D-ring between C(9), C(13), C(14), C(15), and C(16), which is quite different from the previously isolated six-membered D-ring analogs.
Co-reporter:Yong Shen;Ai-Xue Zuo;Zhi-Yong Jiang;Xue-Mei Zhang;Hong-Ling Wang
Helvetica Chimica Acta 2011 Volume 94( Issue 1) pp:122-126
Publication Date(Web):
DOI:10.1002/hlca.201000152
Abstract
Two new C20-diterpenoid alkaloids, named aconicarchamines A and B (1 and 2, resp.), were isolated from Aconitum carmichaelii. By UV, IR, MS, and 1D- and 2D-NMR analyses, their structures were elucidated as 14,17-dihydro-14,17-dihydroxyajabicine and 15-O-acetyllassiocarpine. Compound 1 is the third C20-diterpenoid alkaloid with the lycoctine skeleton bearing an exocyclic C-atom at C(14).
Co-reporter:Chang-An Geng;Li-Jun Wang;Xue-Mei Zhang;Yun-Bao Ma;Xiao-Yan Huang;Jie Luo;Rui-Hua Guo;Jun Zhou;Yong Shen;Ai-Xue Zuo;Zhi-Yong Jiang; Ji-Jun Chen
Chemistry - A European Journal 2011 Volume 17( Issue 14) pp:3893-3903
Publication Date(Web):
DOI:10.1002/chem.201003180
Abstract
Swerilactones H–K (1–4), which are four novel lactones with an unprecedented C29 skeleton, were isolated from Swertia mileensis (Qing-Ye-Dan), an endemic Chinese herb used for treating viral hepatitis. Their structures were determined by extensive spectroscopic and X-ray crystallographic diffraction analyses. Swerilactones H–K exhibit potent anti-hepatitis B virus activity against HBV DNA replication with IC50 values ranging from 1.53 to 5.34 μM. For the first time, a plausible biogenetic pathway for swerilactones H–K, together with the previously reported swerilactones A–D is proposed. From a biogenetic point of view, swerilactones A–D are ascribed as secoiridoid dimers, and swerilactones H–K as secoiridoid trimers.
Co-reporter:Kang He;Yun-Bao Ma;Chang-An Geng;Xue-Mei Zhang
Natural Products and Bioprospecting 2011 Volume 1( Issue 1) pp:48-51
Publication Date(Web):2011 August
DOI:10.1007/s13659-011-0009-5
Co-reporter:Chang-An Geng, Xue-Mei Zhang, Yun-Bao Ma, Zhi-Yong Jiang, Jie Luo, Jun Zhou, Hong-Ling Wang, Ji-Jun Chen
Tetrahedron Letters 2010 Volume 51(Issue 18) pp:2483-2485
Publication Date(Web):5 May 2010
DOI:10.1016/j.tetlet.2010.02.156
Swerilactones E (1), F (2), and G (3), three unusual lactones with a phenyl group, were isolated from the traditional Chinese herb of Swertia mileensis. Their structures were determined based on extensive spectroscopic analysis and X-ray single crystal crystallography. Our anti-HBV assay on the Hep G 2.2.15 cell line in vitro showed that compounds 1 and 2 exhibited significant inhibitory activities against the secretion of HBsAg with IC50 of 0.22 and 0.70 mM and HBeAg with IC50 of 0.52 and >6.78 mM, respectively.
Co-reporter:Ai-Xue Zuo;Yong Shen;Zhi-Yong Jiang;Xue-Mei Zhang;Jun Zhou;Jun Lü
Helvetica Chimica Acta 2010 Volume 93( Issue 3) pp:504-510
Publication Date(Web):
DOI:10.1002/hlca.200900240
Abstract
Three new phenolic glucosides named orcinosides A, B, and C (1, 2, and 3, resp.) were isolated in low yields (4.0×10−6, 11.5×10−6, 4.5×10−6%, resp.) from the rhizomes of Curculigo orchioides. Their structures were elucidated by comprehensive spectroscopic analyses including FAB-MS, HR-ESI-MS, IR, and 1D- and 2D-NMR (HSQC, HMBC) data. Compounds 1–3 contained two orcinol-glucoside moieties linked through a CH2 group.
Co-reporter:Yong Shen;Ai-Xue Zuo;Zhi-Yong Jiang;Xue-Mei Zhang;Hong-Ling Wang
Helvetica Chimica Acta 2010 Volume 93( Issue 3) pp:482-489
Publication Date(Web):
DOI:10.1002/hlca.200900228
Abstract
Five new C19-diterpenoid alkaloids, named hemsleyaconitines A–E (1–5, resp.), were isolated from Aconitum hemsleyanumPritz. By UV, IR, MS, 1D- and 2D-NMR analyses, their structures were elucidated as 18-dehydroxygeniculatine D (1), 6-hydroxy-14-O-veratroylneoline (2), 14-O-acetyl-8-ethoxysachaconitine (3), 18-veratroylkaracoline (4) and 8-O-ethylaustroconitine B (5).
Co-reporter:Yong Shen;Ai-Xue Zuo;Zhi-Yong Jiang;Xue-Mei Zhang;Hong-Ling Wang
Helvetica Chimica Acta 2010 Volume 93( Issue 5) pp:863-869
Publication Date(Web):
DOI:10.1002/hlca.200900297
Abstract
Four new C19-nor-diterpenoid alkaloids, named brachyaconitines A–D (1–4), were isolated from the roots of Aconitum brachypodumDiels. Their structures were elucidated as 3-O-acetyl-20-deethyl-20-formylaconitine (1), 3-O-acetyl-19,20-didehydro-20-deethylaconitine (2), 3-O-acetyl-8-de(acetyloxy)-7,8,17,20-tetradehydro-20-deethyl-7,17-secoaconitine (3), and 1-O-methylflavaconitine (4) by means of MS, IR, 1D- and 2D-NMR analyses. The structure of compound 1 was confirmed by an X-ray diffraction experiment.
Co-reporter:Chang-An Geng, Zhi-Yong Jiang, Yun-Bao Ma, Jie Luo, Xue-Mei Zhang, Hong-Ling Wang, Yong Shen, Ai-Xue Zuo, Jun Zhou and Ji-Jun Chen
Organic Letters 2009 Volume 11(Issue 18) pp:4120-4123
Publication Date(Web):August 12, 2009
DOI:10.1021/ol901592f
Swerilactones A (1) and B (2), two novel lactones with an unprecedented 6/6/6/6/6 pentacyclic ring system, were isolated from the traditional Chinese herb of Swertia mileensis with activity against the hepatitis virus. Their structures and relative stereochemistry were elucidated based on spectroscopic methods and further confirmed by X-ray single crystal diffraction analysis. In vitro antihepatitis B virus (HBV) assay on Hep G 2.2.15 cell line showed that compound 1 inhibited HBsAg and HBeAg secretion with IC50 values of 3.66 and 3.58 mM, respectively.
Co-reporter:Chang-An Geng, Xue-Mei Zhang, Yong Shen, Ai-Xue Zuo, Ji-Feng Liu, Yun-Bao Ma, Jie Luo, Jun Zhou, Zhi-yong Jiang and Ji-Jun Chen
Organic Letters 2009 Volume 11(Issue 21) pp:4838-4841
Publication Date(Web):October 2, 2009
DOI:10.1021/ol901881w
Swerilactones C (1) and D (2), two novel diastereomeric lactones with an unprecedented 6/6/6/6/6 pentacyclic ring system, were isolated from the traditional Chinese herb Swertia mileensis. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic methods and further confirmed by X-ray single-crystal diffraction analysis. In vitro antihepatitis B virus (HBV) assay on the Hep G 2.2.15 cell line showed that both compounds 1 and 2 exhibited inhibitory activities against the secretion of HBsAg (IC50 = 1.24 and 2.96 mM, respectively) and HBeAg (IC50 = 0.77 and 1.47 mM, respectively).
Co-reporter:Quan Zhang, Zhi-Yong Jiang, Jie Luo, Ji-Feng Liu, Yun-Bao Ma, Rui-Hua Guo, Xue-Mei Zhang, Jun Zhou, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 8) pp:2148-2153
Publication Date(Web):15 April 2009
DOI:10.1016/j.bmcl.2009.02.122
Chemical modifications were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure–activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg >90, SIHBeAg >93).Chemical modifications were performed on hydroxyl groups at C-11,23,24,25 positions and C-13(17) double bond of alisol A for structure–activity relationship study. Forty-one derivatives of alisol A were synthesized and assayed for their in vitro anti-hepatitis B virus (HBV) activities and cytotoxicities. Of them, 14 compounds were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells, and the most promising compound 25 exhibited high activities against secretion of HBsAg (IC50 = 0.028 mM), HBeAg (IC50 = 0.027 mM) and remarkable selective indices (SIHBsAg >90, SIHBeAg >93).
Co-reporter:Quan Zhang, Zhi-Yong Jiang, Jie Luo, Yun-Bao Ma, Ji-Feng Liu, Rui-Hua Guo, Xue-Mei Zhang, Jun Zhou, Wei Niu, Fei-Fei Du, Li Li, Chuan Li, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 23) pp:6659-6665
Publication Date(Web):1 December 2009
DOI:10.1016/j.bmcl.2009.10.006
Thirty-two tetra-acylated derivatives of alisol A were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities and cytotoxicities in vitro. Among the series of alisol A derivatives examined, five analogues were active against HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) secretion in HepG 2.2.15 cells. These results also provide interesting structure–activity relationships of tetra-acylalisol A derivatives. Compounds tetra-acetyl alisol A (A1), tetra-methoxyacetyl alisol A (A23), and tetra-ethoxyacetyl alisol A (A24) exhibited high activities against secretion of HBsAg with IC50 values of 0.0048, 0.0044, and 0.014 mM, respectively, HBeAg with IC50 values of 0.011, 0.012, and 0.018 mM, respectively, and remarkable selective index values SIHBsAg >333, SIHBeAg >145; SIHBsAg = 209, SIHBeAg = 77; and SIHBsAg >200, SIHBeAg >156, respectively. Additional studies in rats showed that compound A1 has favorable pharmacokinetic prosperities for further development purpose, with elimination half-time (t1/2) of 1.63 h and oral bioavailability (F) of 40.9%.Thirty-two tetra-acylated alisol A derivatives were synthesized and evaluated for their anti-HBV activities and cytotoxicities in vitro. Among them, compounds A1, A23, and A24 exhibited high activities against secretion of HBV surface antigen with IC50 values of 0.0048, 0.0044, and 0.014 mM, respectively, HBV e antigen with IC50 values of 0.011, 0.012, and 0.018 mM, respectively, and remarkable selective index values of SIHBsAg >333, SIHBeAg >145; SIHBsAg = 209, SIHBeAg = 77; and SIHBsAg >200, SIHBeAg >156, respectively. Additional studies in rats showed that compound A1 has favorable pharmacokinetic prosperities for further development purpose, with elimination half-time (t1/2) of 1.63 h and oral bioavailability (F) of 40.9%.
Co-reporter:Meng-Hong Yan, Pi Cheng, Zhi-Yong Jiang, Yun-Bao Ma, Xue-Mei Zhang, Feng-Xue Zhang, Liu-Meng Yang, Yong-Tang Zheng and Ji-Jun Chen
Journal of Natural Products 2008 Volume 71(Issue 5) pp:760-763
Publication Date(Web):April 9, 2008
DOI:10.1021/np070479+
Four new hasubanane-type alkaloids, periglaucines A–D (1–4), and three known alkaloids, norruffscine (5), (−)-8-oxotetrahydropalmatine (6), and (−)-8-oxocanadine (7), were isolated from the aerial parts of Pericampylus glaucus. Their structures were elucidated on the basis of extensive NMR and EIMS data, and that of periglaucine A (1) was confirmed by single-crystal X-ray diffraction. Alkaloids 1–4 inhibited hepatitis B virus (HBV) surface antigen (HBsAg) secretion in Hep G2.2.15 cells. (−)-8-Oxotetrahydropalmatine (6) possessed a high selectivity index (SI = 22.4) for HBsAg secretion of the Hep G2.2.15 cell line with an IC50 value of 0.14 mM. Norruffscine (5) and (−)-8-oxotetrahydropalmatine (6) exhibited inhibitory activity against human immunodeficiency virus (HIV-1) with EC50 values of 10.9 and 14.1 µM in C8166 cells (SI = 45.7 and 18.8), respectively.
Co-reporter:Pi Cheng, Quan Zhang, Yun-Bao Ma, Zhi-Yong Jiang, Xue-Mei Zhang, Feng-Xue Zhang, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2008 Volume 18(Issue 13) pp:3787-3789
Publication Date(Web):1 July 2008
DOI:10.1016/j.bmcl.2008.05.065
A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).3-Hydroxylethyl-4-aryl-6-chloro-quinolin-2-ones (5a–c) exhibited inhibitory activities on the secretion of HBsAg and HBeAg in HBV infected Hep G2.2.15 cells.
Co-reporter:Pi Cheng, Ning Huang, Zhi-Yong Jiang, Quan Zhang, Yong-Tang Zheng, Ji-Jun Chen, Xue-Mei Zhang, Yun-Bao Ma
Bioorganic & Medicinal Chemistry Letters 2008 Volume 18(Issue 7) pp:2475-2478
Publication Date(Web):1 April 2008
DOI:10.1016/j.bmcl.2008.02.040
A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1–36) were synthesized via Pictet–Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1IIIB in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 μM respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 μM, which resulted in SI values larger than 95, 159, and 130 respectively.The syntheses and anti-HIV activities of 1-aryl-tetrahydroisoquinoline analogs were described in this paper. Compounds 6, 24, and 36 showed potent anti-HIV activities with TI values larger than 95, 159, and 130, respectively.
Co-reporter:Pi Cheng, Yun-bao Ma, Shu-ying Yao, Quan Zhang, En-jun Wang, Meng-hong Yan, Xue-mei Zhang, Feng-xue Zhang, Ji-jun Chen
Bioorganic & Medicinal Chemistry Letters 2007 Volume 17(Issue 19) pp:5316-5320
Publication Date(Web):1 October 2007
DOI:10.1016/j.bmcl.2007.08.027
Two new alkaloids, hypserpanines A and B (1, 11), together with eleven known compounds, phenolbetain (2), acutumine (3), acutumidine (4), dechloroacutumine (5), dauricumine (6), dauricumidine (7), pronuciferine (8), glaziovine (9), S-reticuline (10), magnoflorine (12) and laurifoline(13), were isolated from Hypserpa nitida Miers. (Menispermaceae) and chemically elucidated through spectral analyses. All the isolated alkaloids were evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. The most active compound, dauricumidine (7), exhibited an IC50 value of 0.450 mM (SI = 4.13) on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line.Hypserpanines A and B together with 11 known alkaloids were isolated from Hypserpa nitida and evaluated for their anti-HBV activities in vitro.
Co-reporter:Pi Cheng, Zhi-Yong Jiang, Rui-Rui Wang, Xue-Mei Zhang, Qian Wang, Yong-Tang Zheng, Jun Zhou, Ji-Jun Chen
Bioorganic & Medicinal Chemistry Letters 2007 Volume 17(Issue 16) pp:4476-4480
Publication Date(Web):15 August 2007
DOI:10.1016/j.bmcl.2007.06.008
A variety of N-acetyl-β-aryl-1,2-didehydroethylamines were synthesized by direct reduction–acetylation of β-aryl-nitroolefins and assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the first time. Compound 7a exhibited a TI value of >13.2 with CC50 value of >0.787 mM in C8166 cells. This structure–activity relationship (SAR) study provided a new lead for design and discovery of more potent and selective analogues act as NNRTIs.Compounds 4 and 7 were assayed as NNRTIs against HIV-1 for the first time. Compound 7a (Ar = 2-Br-phenyl) exhibited a TI value of >13.2 (CC50 > 0.787 mM) in C8166 cells.
Co-reporter:Zhi-Yong Jiang;Xue-Mei Zhang;Jun Zhou
Helvetica Chimica Acta 2005 Volume 88(Issue 2) pp:297-303
Publication Date(Web):18 FEB 2005
DOI:10.1002/hlca.200590011
Four new triterpenoid glycosides named asiaticoside C (1), D (2), E (3), and F (4) were isolated from the BuOH fraction of the EtOH extract of whole plants of Centella asiatica, together with three known compounds, asiaticoside (5), madecassoside (6), and scheffuroside B (7). Based on FAB-MS, IR, 1H- and 13C-NMR, and 2D-NMR data (HMQC, HMBC, COSY), the structures of the new compounds were determined as (2α,3β,4α)-23-(acetyloxy)-2,3-dihydroxyurs-12-en-28-oic acid O-α-L-rhamnopyranosyl-(14)-O-β-D-glucopyranosyl-(16)-β-D-glucopyranosyl ester (1), (2α,3β)-2,3-dihydroxyurs-12-en-28-oic acid O-α-L-rhamnopyranosyl-(14)-O-β-D-glucopyranosyl-(16)-β-D-glucopyranosyl ester (2), asiatic acid 6-O-β-D-glycopyranosyl-β-D-glucopyranosyl ester (3), (3β,4α)-3,23-dihydroxyurs-12-en-28-oic acid O-α-L-rhamnopyranosyl-(14)-O-β-D-glucopyranosyl-(16)-β-D-glucopyranosyl ester (4).
Co-reporter:Xinglong Chen, Changan Geng, Xiuqiong Zhang, Tianze Li, Jijun Chen
International Journal of Mass Spectrometry (March 2017) Volume 414() pp:70-79
Publication Date(Web):March 2017
DOI:10.1016/j.ijms.2017.01.004
Co-reporter:Chang-Li Sun, Chang-An Geng, Xing-Long Chen, Tong-Hua Yang, Xiu-Juan Yin, Xiao-Yan Huang, Hua Peng, Ji-Jun Chen
Fitoterapia (June 2016) Volume 111() pp:42-48
Publication Date(Web):1 June 2016
DOI:10.1016/j.fitote.2016.04.003
The preliminary LC–MS investigation on the stems of Nouelia insignis manifested the existence of diterpenoids. As a result, 15 ent-kaurane diterpenoids, including 7 new glycosides (nouelosides A–G, 1–7), were isolated under the direction of LC–MS analysis. The new compounds were determined by extensive spectroscopic analysis including HRESIMS, 1D and 2D NMR data and chemical methods. Compounds 6 and 15 with the exo-methylene cyclopentanone functional group exhibited obvious nitric oxide production inhibitory activity with IC50 values of 3.84 ± 0.20 and 3.19 ± 0.25 μM.Download high-res image (211KB)Download full-size image
Co-reporter:Yong Zhao, Chang-An Geng, Yun-Bao Ma, Xiao-Yan Huang, Hao Chen, Tuan-Wu Cao, Kang He, Hao Wang, Xue-Mei Zhang, Ji-Jun Chen
Journal of Ethnopharmacology (28 October 2014) Volume 156() pp:147-154
Publication Date(Web):28 October 2014
DOI:10.1016/j.jep.2014.08.043
Ethnopharmacological relevanceHepatitis B induced by HBV is a serious health problem. Artemisia capillaris (Yin-Chen) has long been used to treat hepatitis in traditional Chinese medicine. Coumarins, flavonoids and organic acids were revealed as its hepatoprotective and choleretic components, but its anti-HBV active components remain unknown. This current study focused on its anti-HBV active constituents by various chromatographic methods.Material and methodsLC/MS and bioassay-guided fractionation on the active extract of Artemisia capillaris led to the isolation of nine chlorogenic acid analogues. Structures of the isolates were elucidated by MS/MS and NMR techniques. Anti-HBV assay was performed on HepG 2.2.15 cell line in vitro: reduction of HBsAg and HBeAg secretions was measured by an ELISA method; inhibition of HBV DNA replication was monitored by real-time quantitative PCR and cellular toxicity was assessed by a MTT method.ResultsThe 90% ethanol extract of Artemisia capillaris (Fr. AC) showed significantly inhibitory activity on HBV DNA replication with an IC50 value of 76.1±3.9 μg/mL and low cytotoxic effects (SI>20.1). To clarify its active constituents, the extract was further separated into 3 sub-fractions (AC-1, AC-2 and AC-3), of which Fr. AC-2 was the most active fraction against HBeAg secretion and HBV DNA replication with IC50 values of 44.2±2.8 and 23.2±1.9 μg/mL. Nine chlorogenic acid analogues were detected from the active part (Fr. AC-2) by a LC/MS technique and further separated by a HPLC method. The isolates were determined as chlorogenic acid (1), cryptochlorogenic acid (2), neochlorogenic acid (3), 3,5-dicaffeoylquinic acid (4), 4,5-dicaffeoylquinic acid (5), 3,4-dicaffeoylquinic acid (6), chlorogenic acid methyl ester (7), cryptochlorogenic acid methyl ester (8), neochlorogenic acid methyl ester (9). Compounds 1–6 possessed potent activity against HBV DNA replication with IC50 values in the range of 5.5±0.9–13.7±1.3 μM. Di-caffeoyl analogues (4–6) also exhibited activity against the secretions of HBsAg and HBeAg. Esterified analogues (7–9) showed dramatically decreased anti-HBV activity, indicating that carboxyl group is closely associated to the anti-HBV activity.ConclusionsThis investigation was focused on the active fractions of Artemisia capillaris and their active compositions, which showed that Fr. AC-2 was the main active section of Artemisia capillaris and chlorogenic acid analogues were the main constituents contributing to its anti-HBV activity. These results support the ethnopharmacological use of Artemisia capillaris as anti-HBV agents.Download high-res image (335KB)Download full-size image
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![2-[4-[2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxy-propyl)-7-methoxy-2-benzofuranyl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol](http://img.cochemist.com/ccimg/623600/623584-31-6_b.png)
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![4H-1-Benzopyran-4-one, 2-[3-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-2,4-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-, (2S)-](/data/chemimg/2245300/174423-30-4.png)
![4H-1-Benzopyran-4-one, 2-[3-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-2,4-dihydroxyphenyl]-2,3-dihydro-5,7-dihydroxy-, (2S)-](/data/chemimg/2245300/174423-30-4_b.png)
![1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-3-methoxy-, (3S,4aS,5R,6S)-](http://img.cochemist.com/ccimg/118700/118627-52-4.png)
![1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-3-methoxy-, (3S,4aS,5R,6S)-](http://img.cochemist.com/ccimg/118700/118627-52-4_b.png)
![Pyrrolidine,1-[(2E,8E)-9-(1,3-benzodioxol-5-yl)-1-oxo-2,8-nonadienyl]- (9CI)](http://img.cochemist.com/ccimg/117200/117137-67-4.png)
![Pyrrolidine,1-[(2E,8E)-9-(1,3-benzodioxol-5-yl)-1-oxo-2,8-nonadienyl]- (9CI)](http://img.cochemist.com/ccimg/117200/117137-67-4_b.png)
![1-[1-oxo-5-(3,4-methylenedioxyphenyl)-2E-pentenyl]-pyrrolidine](http://img.cochemist.com/ccimg/117200/117137-65-2.png)
![1-[1-oxo-5-(3,4-methylenedioxyphenyl)-2E-pentenyl]-pyrrolidine](http://img.cochemist.com/ccimg/117200/117137-65-2_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)
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![1,3-Propanediol, 2-[2,6-dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3,5-](/data/chemimg/2078400/97465-75-3.png)
![1,3-Propanediol, 2-[2,6-dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3,5-](/data/chemimg/2078400/97465-75-3_b.png)
![2-[2,6-Dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol](http://img.cochemist.com/ccimg/97500/97465-73-1.png)
![2-[2,6-Dimethoxy-4-[tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol](http://img.cochemist.com/ccimg/97500/97465-73-1_b.png)
![3aH-Benzo[3,4][2]benzopyrano[1,8-bc][1]benzopyran-4,11-diol,8a-(2,4-dihydroxyphenyl)-1,8a,13b,13c-tetrahydro-6-(6-hydroxy-2-benzofuranyl)-2-methyl-,(3aS,8aS,13bS,13cR)-](http://img.cochemist.com/ccimg/87100/87085-00-5.png)
![3aH-Benzo[3,4][2]benzopyrano[1,8-bc][1]benzopyran-4,11-diol,8a-(2,4-dihydroxyphenyl)-1,8a,13b,13c-tetrahydro-6-(6-hydroxy-2-benzofuranyl)-2-methyl-,(3aS,8aS,13bS,13cR)-](http://img.cochemist.com/ccimg/87100/87085-00-5_b.png)
![3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-,(2R,3S,4S)-](http://img.cochemist.com/ccimg/83400/83327-19-9.png)
![3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-,(2R,3S,4S)-](http://img.cochemist.com/ccimg/83400/83327-19-9_b.png)
![PIPERIDINE, 1-[(2E,4E)-5-(4-HYDROXYPHENYL)-1-OXO-2,4-PENTADIENYL]-](http://img.cochemist.com/ccimg/76800/76733-91-0.png)
![PIPERIDINE, 1-[(2E,4E)-5-(4-HYDROXYPHENYL)-1-OXO-2,4-PENTADIENYL]-](http://img.cochemist.com/ccimg/76800/76733-91-0_b.png)
![4H,8H-Benzo[1,2-b:3,4-b']dipyran-4-one, 2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-2-buten-1-yl)-](/data/chemimg/624700/62596-29-6.png)
![4H,8H-Benzo[1,2-b:3,4-b']dipyran-4-one, 2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-2-buten-1-yl)-](/data/chemimg/624700/62596-29-6_b.png)
![Urs-12-en-28-oic acid, 3-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (3β)-](/data/chemimg/1251500/50627-73-1.png)
![Urs-12-en-28-oic acid, 3-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-, (3β)-](/data/chemimg/1251500/50627-73-1_b.png)
![7H-Furo[3,2-g][1]benzopyran-7-one,9-[[(2R)-3,3-dimethyl-2-oxiranyl]methoxy]-4-methoxy-](http://img.cochemist.com/ccimg/26100/26091-79-2.png)
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![4-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one](http://img.cochemist.com/ccimg/26100/26091-73-6.png)
![4-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one](http://img.cochemist.com/ccimg/26100/26091-73-6_b.png)
![6H,7H-[1]Benzopyrano[4,3-b][1]benzopyran-7-one,3,8,10-trihydroxy-11-(3-methyl-2-buten-1-yl)-6-(2-methyl-1-propen-1-yl)-,stereoisomer](http://img.cochemist.com/ccimg/19300/19275-51-5.png)
![6H,7H-[1]Benzopyrano[4,3-b][1]benzopyran-7-one,3,8,10-trihydroxy-11-(3-methyl-2-buten-1-yl)-6-(2-methyl-1-propen-1-yl)-,stereoisomer](http://img.cochemist.com/ccimg/19300/19275-51-5_b.png)
![(S)-3,9-Dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,10-diol](http://img.cochemist.com/ccimg/16600/16562-13-3.png)
![(S)-3,9-Dimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline-2,10-diol](http://img.cochemist.com/ccimg/16600/16562-13-3_b.png)
![1H,3H-Furo[3,4-c]furan-3a(4H)-ol,1,4-bis(1,3-benzodioxol-5-yl)dihydro-, (1S,3aS,4R,6aR)-](http://img.cochemist.com/ccimg/13100/13040-46-5.png)
![1H,3H-Furo[3,4-c]furan-3a(4H)-ol,1,4-bis(1,3-benzodioxol-5-yl)dihydro-, (1S,3aS,4R,6aR)-](http://img.cochemist.com/ccimg/13100/13040-46-5_b.png)
![[(1s,4ar,5s,7as)-5-hydroxy-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate](http://img.cochemist.com/ccimg/11100/11027-63-7.png)
![[(1s,4ar,5s,7as)-5-hydroxy-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate](http://img.cochemist.com/ccimg/11100/11027-63-7_b.png)
![(6aR)-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol](http://img.cochemist.com/ccimg/6900/6871-21-2.png)
![(6aR)-1-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol](http://img.cochemist.com/ccimg/6900/6871-21-2_b.png)
![6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, (6aR,12aR)-](http://img.cochemist.com/ccimg/2100/2035-15-6.png)
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![Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-](http://img.cochemist.com/ccimg/600/530-53-0.png)
![Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-](http://img.cochemist.com/ccimg/600/530-53-0_b.png)
![3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol](http://img.cochemist.com/ccimg/600/530-22-3.png)
![3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol](http://img.cochemist.com/ccimg/600/530-22-3_b.png)
![7H-Furo[3,2-g][1]benzopyran-7-one,9-[(2R)-2,3-dihydroxy-3-methylbutoxy]-4-methoxy-](http://img.cochemist.com/ccimg/500/482-25-7.png)
![7H-Furo[3,2-g][1]benzopyran-7-one,9-[(2R)-2,3-dihydroxy-3-methylbutoxy]-4-methoxy-](http://img.cochemist.com/ccimg/500/482-25-7_b.png)
![[2,3'-Biindolinylidene]-2',3-dione](http://img.cochemist.com/ccimg/500/479-41-4.png)
![[2,3'-Biindolinylidene]-2',3-dione](http://img.cochemist.com/ccimg/500/479-41-4_b.png)
![(2beta,2'alpha,3beta,3'alpha)-2,2',3,3'-tetrahydro-2'-(4-hydroxy-3-methoxyphenyl)-3,3'-bis(hydroxymethyl)-7,7'-dimethoxy-5-[(1E)-3-oxoprop-1-en-1-yl] [2,5'-bibenzofuran]](http://img.cochemist.com/ccimg/1314900/1314868-59-1.png)
![(2beta,2'alpha,3beta,3'alpha)-2,2',3,3'-tetrahydro-2'-(4-hydroxy-3-methoxyphenyl)-3,3'-bis(hydroxymethyl)-7,7'-dimethoxy-5-[(1E)-3-oxoprop-1-en-1-yl] [2,5'-bibenzofuran]](http://img.cochemist.com/ccimg/1314900/1314868-59-1_b.png)
![2-Propenoic acid, 3-[4-(sulfooxy)phenyl]-](http://img.cochemist.com/ccimg/376400/376374-66-2.png)
![2-Propenoic acid, 3-[4-(sulfooxy)phenyl]-](http://img.cochemist.com/ccimg/376400/376374-66-2_b.png)
![Ethanone, 1-[4-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]phenyl]-](http://img.cochemist.com/ccimg/149500/149475-53-6.png)
![Ethanone, 1-[4-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]phenyl]-](http://img.cochemist.com/ccimg/149500/149475-53-6_b.png)
![Cyclopentaneaceticacid, 2-[(2Z)-5-hydroxy-2-penten-1-yl]-3-oxo-, (1R,2S)-](http://img.cochemist.com/ccimg/124700/124649-26-9.png)
![Cyclopentaneaceticacid, 2-[(2Z)-5-hydroxy-2-penten-1-yl]-3-oxo-, (1R,2S)-](http://img.cochemist.com/ccimg/124700/124649-26-9_b.png)
![2-[2,6-Dimethoxy-4-[tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol](http://img.cochemist.com/ccimg/97400/97399-82-1.png)
![2-[2,6-Dimethoxy-4-[tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol](http://img.cochemist.com/ccimg/97400/97399-82-1_b.png)
![(2E)-3-[3-(sulfooxy)phenyl]prop-2-enoic acid](http://img.cochemist.com/ccimg/86400/86321-30-4.png)
![(2E)-3-[3-(sulfooxy)phenyl]prop-2-enoic acid](http://img.cochemist.com/ccimg/86400/86321-30-4_b.png)
![2-Propenoic acid,3-[3-methoxy-4-(sulfooxy)phenyl]-](http://img.cochemist.com/ccimg/86400/86321-29-1.png)
![2-Propenoic acid,3-[3-methoxy-4-(sulfooxy)phenyl]-](http://img.cochemist.com/ccimg/86400/86321-29-1_b.png)
![(2Z)-2-[(4S,6R)-4-hydroxy-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-cyclohex-2-enylidene]acetonitrile](http://img.cochemist.com/ccimg/67800/67765-58-6.png)
![(2Z)-2-[(4S,6R)-4-hydroxy-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-cyclohex-2-enylidene]acetonitrile](http://img.cochemist.com/ccimg/67800/67765-58-6_b.png)
![2(5H)-Furanone, 3-[(1E)-2-[(1R,4aS,5R,6R,8aR)-6-(acetyloxy)-5-[(acetyloxy)methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]-](/data/chemimg/3771000/42895-60-3.png)
![2(5H)-Furanone, 3-[(1E)-2-[(1R,4aS,5R,6R,8aR)-6-(acetyloxy)-5-[(acetyloxy)methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]-](/data/chemimg/3771000/42895-60-3_b.png)
![Phenol, 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-](/data/chemimg/53300/40957-99-1.png)
![Phenol, 2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]-](/data/chemimg/53300/40957-99-1_b.png)
![TERT-BUTYL 8-CHLORO-2,3-DIHYDRO-1H-BENZO[E][1,4]DIAZEPINE-4(5H)-CARBOXYLATE](http://img.cochemist.com/ccimg/38500/38489-76-8.png)
![TERT-BUTYL 8-CHLORO-2,3-DIHYDRO-1H-BENZO[E][1,4]DIAZEPINE-4(5H)-CARBOXYLATE](http://img.cochemist.com/ccimg/38500/38489-76-8_b.png)
![Pregn-5-en-20-one,12-[[(2E)-3,4-dimethyl-1-oxo-2-pentenyl]oxy]-3,8,14,17-tetrahydroxy-, (3b,12b,14b,17a)-](http://img.cochemist.com/ccimg/38400/38395-02-7.png)
![Pregn-5-en-20-one,12-[[(2E)-3,4-dimethyl-1-oxo-2-pentenyl]oxy]-3,8,14,17-tetrahydroxy-, (3b,12b,14b,17a)-](http://img.cochemist.com/ccimg/38400/38395-02-7_b.png)
![SODIUM (2S)-2-[(2,2-DICHLOROACETYL)AMINO]-3-HYDROXY-PROPANOATE](http://img.cochemist.com/ccimg/34500/34425-25-7.png)
![SODIUM (2S)-2-[(2,2-DICHLOROACETYL)AMINO]-3-HYDROXY-PROPANOATE](http://img.cochemist.com/ccimg/34500/34425-25-7_b.png)
![2,2'-[(2,4-DIMETHYL-3-PENTANYL)IMINO]DIETHANOL](http://img.cochemist.com/ccimg/32900/32811-40-8.png)
![2,2'-[(2,4-DIMETHYL-3-PENTANYL)IMINO]DIETHANOL](http://img.cochemist.com/ccimg/32900/32811-40-8_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)
![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)
![(1s,3r,4r,5r)-3,4-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic Acid](http://img.cochemist.com/ccimg/14600/14534-61-3.png)
![(1s,3r,4r,5r)-3,4-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic Acid](http://img.cochemist.com/ccimg/14600/14534-61-3_b.png)
![Ethanone,1-[4-(benzoyloxy)phenyl]-](http://img.cochemist.com/ccimg/1600/1523-18-8.png)
![Ethanone,1-[4-(benzoyloxy)phenyl]-](http://img.cochemist.com/ccimg/1600/1523-18-8_b.png)
![Ethanone, 1-[4-(b-D-glucopyranosyloxy)phenyl]-](http://img.cochemist.com/ccimg/600/530-14-3.png)
![Ethanone, 1-[4-(b-D-glucopyranosyloxy)phenyl]-](http://img.cochemist.com/ccimg/600/530-14-3_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)
