Co-reporter:Yu Tang, Juan Xiong, Yike Zou, Wei Wang, Chao Huang, Hai-Yan Zhang, Jin-Feng Hu
Phytochemistry 2017 Volume 143(Volume 143) pp:
Publication Date(Web):1 November 2017
DOI:10.1016/j.phytochem.2017.07.003
•Ten hitherto unknown Lycopodium alkaloids were isolated from Lycopodium annotinum.•Their absolute configurations were determined by extensive methods.•Annotinolide F has an unusual 7,8-seco-lycopodane-derived 8,5-lactone skeleton.•Lycoannotine C is an uncommon 8,15-seco lycopodine-type alkaloid.•Lycoannotine I is the first fawcettimine alkaloid with a cleavage of the C-9/N bond.Seven lycopodine-type (annotinolide F and lycoannotines A–F), two lycodine-type (lycoannotines G and H), and one fawcettimine-type (lycoannotine I) previously undescribed naturally occurring Lycopodium alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum. Their structures and absolute configurations were determined by extensive spectroscopic methods, single-crystal X-ray diffraction, chemical transformation, and electronic circular dichroism (ECD) calculations. Among the isolates, annotinolide F, lycoannotines A and B are unusual 7,8-seco-lycopodane derivatives, and annotinolide F even further possesses a rare 8,5-lactone framework through a lactonization after the C-7/C-8 bond cleavage. Lycoannotine C is an uncommon 8,15-seco lycopodine-type alkaloid, whereas lycoannotine I represents the first example of a naturally occurring C-9/N bond cleavage product of fawcettimine-type alkaloid. Among them, only lycoannotine I was found to show considerable anti-butyrylcholinesterase (anti-BuChE) activity.Ten previously undescribed Lycopodium alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum. Among them, lycoannotine I showed anti-BuChE activity.Download high-res image (103KB)Download full-size image
Co-reporter:Chang-Ling Hu, Juan Xiong, Pei-Pei Wang, Guang-Lei Ma, ... Jin-Feng Hu
Phytochemistry Letters 2017 Volume 20(Volume 20) pp:
Publication Date(Web):1 June 2017
DOI:10.1016/j.phytol.2017.05.006
•A mass-limited sample of Pinus kwangtungensis was phytochemically investigated.•Three new and 12 known diterpenoids were isolated from this endangered plant.•The new structures were established by ECD and chemical transformations.•Two isolates were found to show PTP1 B inhibitory effects.Pinus kwangtungensis is an endangered pine species native to China. In the present study, 15 diterpenoids including three new labdane-type analogs were isolated and characterized during a pioneer phytochemical investigation on a mass-limited sample of the needles and twigs of this plant, which is growing in a Cantonese garden. The new structures, (4S,5R,9S,10R)-6-oxo-labd-7,13-dien-16,15- olid-19-oic acid (1), 15(S)-n-butoxypinusolidic acid (2), and β-d-glucopyranosyl- (4S,5R,9S,10R)-labda-8(17),13-dien-15,16-olid-19-oate (3), were established by extensive spectroscopic methods and some chemical transformations. Among the isolates, lambertianic acid (10) and cassipourol (15) showed inhibitory activities against human protein tyrosine phosphatase 1 B (PTP1B), a target for the treatment of type-II diabetes and obesity, with IC50 values of 25.5 and 11.2 μM, respectively.Download high-res image (291KB)Download full-size image
Co-reporter:Yu Tang, Juan Xiong, Jing-Jing Zhang, Wei Wang, Hai-Yan Zhang, and Jin-Feng Hu
Organic Letters 2016 Volume 18(Issue 17) pp:4376-4379
Publication Date(Web):August 15, 2016
DOI:10.1021/acs.orglett.6b02132
Three novel 7,8-seco-lycopodane-derived 8,5-lactones (annotinolides A–C, 1–3) were isolated from Lycopodium annotinum. Their structures were elucidated by spectroscopic methods and single-crystal X-ray diffraction. Compound 1 possesses an unusual cyclopropane ring constructed through a hitherto unknown C-6/C-12 bond. Compound 2 represents the first 7,8-seco-lycopodane-derived alkaloid with a rare cyclobutane ring formed by a new C-12/C-15 linkage, while the C-8/C-15 bond remains. Compound 3 contains an unprecedented 12-spiro-9,12-γ-lactone moiety. Their plausible biosynthetic pathways and antiaggregation effects on amyloid-β1–42 are also presented.
Co-reporter:Juan Xiong, Zhi-Lai Hong, Peng Xu, Yike Zou, Shang-Bo Yu, Guo-Xun Yang and Jin-Feng Hu
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 20) pp:4678-4689
Publication Date(Web):19 Apr 2016
DOI:10.1039/C6OB00731G
Twelve new ent-abietane diterpenoids, chlorabietins A–L (1–12), were isolated from the roots of Chloranthus oldhamii. Their structures and absolute configurations were determined by extensive spectroscopic analyses, X-ray diffraction, and experimental/calculated electronic circular dichroism (ECD) spectroscopy. Among the new isolates, chlorabietins D (4) and E (5) are the first two naturally occurring 8-spiro-fused 9,10-seco-ent-abietanes containing an unexpected cis-fused A/B ring system. Chlorabietin F (6) is a rare chinane-type diterpenoid featuring a hitherto unknown C-ring cleavage between C-13 and C-14, which might be derived from a common precursor of the above spiro-diterpenoid epimers 4 and 5, and their biosynthetic relationships are briefly discussed. Meanwhile, chlorabietin I (9) is the first representative of the abietane-type diterpenoids possessing a tetrahydrofurano function bridging C-6 and C-19. Chlorabietins B (2), C (3), F (6), and G (7) showed anti-neuroinflammatory effects by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells, with IC50 values ranging from 16.4 to 33.8 μM.
Co-reporter:Chang-Ling Hu;Juan Xiong;Ji-Yang Li;Li-Xin Gao;Wen-Xuan Wang;Ke-Jun Cheng;Guo-Xun Yang;Jia Li;Jin-Feng Hu
European Journal of Organic Chemistry 2016 Volume 2016( Issue 10) pp:1832-1835
Publication Date(Web):
DOI:10.1002/ejoc.201600165
Abstract
Two rare rearranged cuparane-type sesquiterpenoid C-10 epimers [beshanzuenones A (1) and B (2)] and two bisabolane-type sesquiterpenoid spirolactones [beshanzuenones C (3) and D (4)] featuring an unusual [6/6/5]-fused tricyclic ring system were isolated from the shed trunk barks of Abies beshanzuensis, one of the critically endangered plant species in the world. The structures of these four new enone-containing sesquiterpenoids were determined by spectroscopic analyses and single-crystal X-ray diffraction or electronic circular dichroism (ECD) calculations. Compounds 1 and 2 showed considerable activity against the H3N2 virus, whereas 3 and 4 exhibited significant inhibition on PTP1B.
Co-reporter:Chang-Ling Hu, Juan Xiong, Li-Xin Gao, Jia Li, Huaqiang Zeng, Yike Zou and Jin-Feng Hu
RSC Advances 2016 vol. 6(Issue 65) pp:60467-60478
Publication Date(Web):16 Jun 2016
DOI:10.1039/C6RA08986K
Rare and endangered plants have proven to be better sources for drug discovery than other botanic sources. Pinus dabeshanensis is an endangered plant listed in the China Plant Red Data Book, and has never been phytochemically investigated. In the present study, 11 new (dabeshanensins A–K, 1–11, resp.) and 28 related known naturally occurring diterpenoids were isolated from the shed trunk bark of this plant. The new structures were established by extensive spectroscopic methods and molecular modeling. Among them, dabeshanensin C (3) has an unprecedented bicyclo[3.3.1]nonane ring system (rings B and C) by oxidative cleavage of the C-6/C-7 bond followed by the formation of a new C–C bond between C-6 and C-12. The plausible biosynthetic pathway to 3 is briefly discussed. Dabeshanensins A (1) and J (10), 12-hydroxydehydroabietic acid (33), abieta-8,11,13,15-tetraen-18-oic acid (35), and 15-hydroxy-7-oxo-8,11,13-abietatrien-18-oic acid (37) showed significant inhibitory effects against the human protein tyrosine phosphatase 1B (PTP1B) enzyme, a key target for the treatment of type-II diabetes and obesity, with IC50 values ranging from 5.4 to 50.9 μM.
Co-reporter:Wei-Jia Meng, Juan Xiong, Wen-Xuan Wang, Hai-Yan Zhang, Huaqiang Zeng, Jin-Feng Hu
Tetrahedron Letters 2016 Volume 57(Issue 29) pp:3218-3221
Publication Date(Web):20 July 2016
DOI:10.1016/j.tetlet.2016.06.050
•A novel C16N2Lycopodium alkaloid (1) was isolated from Phlegmariurus fargesii.•Phlefargesiine A (1) possesses an unprecedented [6/7/6/6]-tetracyclic skeleton.•A hitherto unknown C-4–C-14 linkage was formed in compound 1.•The absolute configuration of 1 was determined by ECD and computational methods.A novel C16N2Lycopodium alkaloid, phlefargesiine A (1), was isolated from the whole plant of the club moss Phlegmariurus fargesii. The structure and absolute configuration were determined by extensive spectroscopic and computational methods. Compound 1 possesses an unprecedented [6/7/6/6]-tetracyclic framework, of which the seven-membered ring (ring B) is constructed through a hitherto unknown C-4–C-14 linkage.
Co-reporter:Yu Tang, Juan Xiong, Yike Zou, Bastien Nay, Li-Jun Wang, Jin-Feng Hu
Chinese Chemical Letters 2016 Volume 27(Issue 6) pp:969-973
Publication Date(Web):June 2016
DOI:10.1016/j.cclet.2016.02.014
One novel (named palcernuine, 1) and five known cernuane-type (2–6) alkaloids were isolated from the whole plant of Palhinhaea cernua f. sikkimensis. The structure of 1, possessing an unprecedented [5/6/6/6]-tetracyclic ring system containing two nitrogen atoms, was established on the basis of spectroscopic methods, and its absolute configuration was determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. A plausible biosynthetic pathway to 1 is proposed.One novel (palcernuine, 1) cernuane-type alkaloid was isolated from the whole plant of Palhinhaea cernua f. sikkimensis. This compound possesses an unprecedented [5/6/6/6]-tetracyclic ring system containing two nitrogen atoms.
Co-reporter:Juan Xiong;Ya Huang;Xi-Ying Wu;Xin-Hua Liu;Hui Fan;Wei Wang;Yun Zhao;Guo-Xun Yang;Hai-Yan Zhang;Jin-Feng Hu
Helvetica Chimica Acta 2016 Volume 99( Issue 1) pp:83-89
Publication Date(Web):
DOI:10.1002/hlca.201500231
Abstract
Nineteen compounds mainly including pyrrole-containing alkaloids and phytosterols were isolated from the EtOH extract of the fermented mycelia of Xylaria nigripes, a precious medicinal fungus known as Wuling Shen in Chinese. On the basis of spectroscopic methods, the structures of the new naturally occurring compounds were determined to be (4S)-3,4-dihydro-4-(4-hydroxybenzyl)-3-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (1), methyl (2S)-2-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-3-(4-hydroxyphenyl)propanoate (2), and 3-{4-[(2R)-(2,3-dihydroxy-3-methylbutoxy]phenyl}-7-hydroxy-4H-chromen-4-one (3), respectively. The absolute configurations of 1 and 2 were deduced by the observed Cotton effects in their circular dichroism (CD) spectra, whereas that of the 1,2-diol moiety in 3 was determined using the Snatzke's method. Their biological activities such as neuroprotective, anti-neuroinflammatory, and cytotoxic properties were also reported.
Co-reporter:Li-Jun Wang, Juan Xiong, Yike Zou, Qi-Bing Mei, Wen-Xuan Wang, Jin-Feng Hu
Phytochemistry Letters 2016 Volume 18() pp:202-207
Publication Date(Web):December 2016
DOI:10.1016/j.phytol.2016.10.018
•Two new sesquiterpenoids were isolated and characterized from Manglietia aromatica..•Their absolute configurations were established by experimental and calculated ECD.•The new cadinane-type sesquiterpenoid (2) exhibited inhibitory effect against PTP1B.One new bourbonane-type (1) and one new cadinane-type (2) sesquiterpenoids, along with one known aromodendrane-type (3) and five known megastigmane-type (4–8) compounds, were isolated from the leaves and twigs of Manglietia aromatica, a Chinese endangered plant that has not been previously phytochemically investigated. The structures and absolute configurations of the new isolates, (1R,4S,5S,6S,7S,10S)-4-hydroxy-bourbon-8-one (1) and (1R,6S,7S)-1-hydroxy- cadin-4,9-dien-8-one (2), were established by means of spectroscopic methods and a combination of experimental and calculated electronic circular dichroism (ECD). Among the isolates, compound 2 was found to show a moderate inhibitory effect against the human protein tyrosine phosphatase 1 B (PTP1B) enzyme, a target for the treatment of type-II diabetes and obesity, with an IC50 value of 83.5 μM.
Co-reporter:Si-Yu Liu;Peng Xu;Xiao-Ling Luo;Jin-Feng Hu;Xin-Hua Liu
Neurochemical Research 2016 Volume 41( Issue 7) pp:1570-1577
Publication Date(Web):2016 July
DOI:10.1007/s11064-016-1870-8
(7R,8S)-Dehydrodiconiferyl alcohol (DDA), a lignan isolated from the dried stems of Clematis armandii, has been found to exert potential anti-inflammatory activity in vitro. In the present study, we investigated the effects and possible mechanisms of DDA on lipopolysaccharide (LPS)-mediated inflammatory response in murine BV2 microglia. Our results revealed that non-toxic concentrations (6.25–25 μM) of DDA markedly suppressed LPS-induced production of nitric oxide, expression of inducible nitric oxide synthase and cyclooxygenase-2, and release of inflammatory factors, including tumor necrosis factor (TNF)-α, interleukin (IL)-1β, and IL-6 in a concentration dependent manner. In addition, DDA time- and concentration-dependently attenuated LPS-induced phosphorylation of c-Jun N-terminal kinase 1/2 (JNK), but not protein kinase B, p38, or extracellular signal-regulated kinase 1/2. Moreover, DDA significantly suppress LPS-mediated nuclear factor-κB (NF-κB) activation by inhibiting phosphorylation and nuclear translocation of NF-κB p65. Collectively, our results demonstrated that DDA inhibited LPS-stimulated inflammatory response in BV2 cell, at least in part, through inhibition of NF-κB activation and modulation of JNK signaling.
Co-reporter:Li-Jun Wang, Juan Xiong, Wei Wang, Hai-Yan Zhang, Guo-Xun Yang, Jin-Feng Hu
Phytochemistry Letters 2016 15() pp: 260-264
Publication Date(Web):March 2016
DOI:10.1016/j.phytol.2016.02.001
Co-reporter:Yu Tang, Juan Xiong, Yike Zou, Hai-Yan Zhang, Jin-Feng Hu
Phytochemistry 2016 Volume 131() pp:130-139
Publication Date(Web):November 2016
DOI:10.1016/j.phytochem.2016.08.010
•Twenty-six Lycopodium alkaloids, twenty previously known, were isolated from Palhinhaea cernua.•The absolute configurations of the six alkaloids hitherto unknown were determined.•Fawcettimine-type alkaloids are rare, and have trans-fused C/D-rings and are C-13 methoxylated.•Chemotaxonomy for the species in the genus Palhinhaea is briefly discussed.Four fawcettimine-type (palhicerines A–D, resp.) and two lycopodine-type (palhicerines E and F) Lycopodium alkaloids together with twenty known ones were isolated from the whole plant of Palhinhaea cernua. The structures and absolute configurations of the palhicerines A–F were determined by extensive spectroscopic methods, single-crystal X-ray diffraction analyses, chemical transformation, and electronic circular dichroism (ECD) calculations or induced electronic circular dichroism (IECD) spectra. Among the isolates, the new C/D-ring of the palhicerines A–C (trans-fused fawcettimine-type alkaloids) are rare, and each possesses a β-oriented C-16 methyl group and a distinctive tertiary methoxy group at C-13. Chemotaxonomy for differentiating species in the genus Palhinhaea is briefly discussed.Four fawcettimine-type and two lycopodine-type Lycopodium alkaloids were isolated from the whole plant of Palhinhaea cernua.
Co-reporter:Li-Jun Wang; Juan Xiong; Shu-Ting Liu; Li-Long Pan; Guo-Xun Yang;Jin-Feng Hu
Journal of Natural Products 2015 Volume 78(Issue 7) pp:1635-1646
Publication Date(Web):July 1, 2015
DOI:10.1021/acs.jnatprod.5b00195
Fourteen new ent-abietane-type diterpenoids, sessilifols A–N (1–14), and three related new norditerpenoids (15–17) were isolated from Chloranthus sessilifolius. The absolute configurations were determined by single-crystal X-ray diffraction analysis, the modified Mosher’s method, and/or the observed Cotton effects in their electronic circular dichroism spectra. Sessilifols A (1) and B (2) possess an uncommon five-membered C-ring rearranged by oxidative cleavage of the C-13/C-14 bond in abieta-7,13-diene followed by the formation of a new C–C bond between C-12 and C-14. Sessilifol C (3) is a rare 7,8-seco-9-spiro-fused ent-abietane, whereas sessilifol O (15) represents the first example of a naturally occurring 14-norabietane-type diterpenoid. Compounds 6 and 9 were found to have moderate antineuroinflammatory activities by inhibiting the nitric oxide production in lipopolysaccharide-stimulated murine BV-2 microglial cells, with IC50 values of 8.3 and 7.4 μM, respectively.
Co-reporter:Guang-Lei Ma, Guo-Xun Yang, Juan Xiong, Wen-Liang Cheng, Ke-Jun Cheng, Jin-Feng Hu
Tetrahedron Letters 2015 Volume 56(Issue 27) pp:4071-4075
Publication Date(Web):1 July 2015
DOI:10.1016/j.tetlet.2015.05.008
Two new [named salicifoxazines A (1) and B (2)] and six known dimeric tryptamine-derived alkaloids (3–8) were isolated from the leaves of Chimonanthus salicifolius. The new structures were established on the basis of extensive spectroscopic methods and chemical transformations. The absolute configuration of 1 was determined by the observed Cotton effects in its circular dichroism (CD) spectrum, whereas 2 is a pseudo-mesomer of 1. In fact, the first two naturally occurring asymmetric tetrahydro-1,2-oxazine-containing tryptamine-derived alkaloids 1 and 2 are diastereoisomers at C-3a/C-8a or at C-3a′/C-8a′. Compounds 1, 2, (−)-chimonanthine (3), and meso-chimonanthine (4) were found to show moderate cytotoxic effects against human colorectal carcinoma cells (SW-1116 and HCT-116) and/or gastric carcinoma cells (SGC-7901).
Co-reporter:Ming Li, Juan Xiong, Ya Huang, Li-Jun Wang, Yu Tang, Guo-Xun Yang, Xin-Hua Liu, Bang-Guo Wei, Hui Fan, Yun Zhao, Wen-Zhu Zhai, Jin-Feng Hu
Tetrahedron 2015 Volume 71(Issue 33) pp:5285-5295
Publication Date(Web):19 August 2015
DOI:10.1016/j.tet.2015.06.020
Two new [named xylapyrrosides A (1) and B (2)] along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the EtOH extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A1 (1a), A2 (1b) and B1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs).
Co-reporter:Juan Xiong, Zhi-Lai Hong, Li-Xin Gao, Jie Shen, Shu-Ting Liu, Guo-Xun Yang, Jia Li, Huaqiang Zeng, and Jin-Feng Hu
The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:11080-11085
Publication Date(Web):October 7, 2015
DOI:10.1021/acs.joc.5b01658
Three unprecedented phloroglucinol-diterpene adducts, chlorabietols A–C (1–3), were isolated from the roots of the rare Chloranthaceae plant Chloranthus oldhamii. They represent a new class of compounds, featuring an abietane-type diterpenoid coupled with different alkenyl phloroglucinol units by forming a 2,3-dihydrofuran ring. Their structures were elucidated by detailed spectroscopic analysis, molecular modeling studies, and electronic circular dichroism calculations. Compounds 1–3 showed inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 12.6, 5.3, and 4.9 μM, respectively.
Co-reporter:Miao Ye, Juan Xiong, Jing-Jing Zhu, Jun-Lin Hong, Yun Zhao, Hui Fan, Guo-Xun Yang, Gang Xia, and Jin-Feng Hu
Journal of Natural Products 2014 Volume 77(Issue 1) pp:178-182
Publication Date(Web):December 13, 2013
DOI:10.1021/np400838a
Six new (leonurusoleanolides E–J, 1–6) and five known (7–11) nortriterpenoids were isolated and characterized from the dried fruits of Leonurus japonicus. They all contain a distinctive 19(18→17)-abeo-28-noroleanane-type spirocylclic skeleton with a trans or a cis acyl substituent at C-3 or C-23. Similar to the previously known leonurusoleanolides A/B (7/8) and C/D (9/10), compounds 1/2 and 3/4 were also found to exist as equilibrium mixtures of trans and cis isomers. The isolated pure compounds and mixtures were evaluated for their cytotoxicity against a small panel of human cancer cell lines (BGC-823 and KE-97 gastric carcinoma, Huh-7 hepatocarcinoma, Jurkat T cell lymphoblasts, and MCF-7 breast adenocarcinoma) using the CellTiter-Glo luminescent cell viability assay method. Among them, (2α,3β,17R*,18β)-3-O-(trans-caffeoyl)-19(18→17)-abeo-28-norolean-12-ene-2,18,23-triol (leonurusoleanolide J, 6) showed the most potent cytotoxic activity, with IC50 values less than 10 μM.
Co-reporter:Li-Jun Wang;Juan Xiong;Shu-Ting Liu;Xin-Hua Liu;Jin-Feng Hu
Chemistry & Biodiversity 2014 Volume 11( Issue 6) pp:919-928
Publication Date(Web):
DOI:10.1002/cbdv.201300283
Abstract
Five new and seven known mono-sesquiterpenoids (1–5 and 6–12, resp.) together with five known lindenane-type disesquiterpenoids, 13–17, were isolated from the whole plant of Chloranthus henryi. Based on spectroscopic methods, the new structures were established to be (5S,6R,8S,10R)-6-hydroxyeudesma-4(15),7(11)-diene-12,8-olide (1), 6α-hydroxyeudesma-4(15),7(11),8(9)-triene-12,8-olide (2), 8,12-epoxy-1β-hydroxyeudesma-4(15),7,11-trien-6-one (3), 12-oxochloraniolide A (4), and (4α)-8-hydroxy-12-norcardina-6,8,10-trien-11-one (5), respectively. Among the isolates, compound 2, zederone epoxide (8), spicachlorantin G (13), chloramultilide A (14), shizukaol B (15), and spicachlorantin B (17) showed significant anti-neuroinflammatory effects by inhibiting nitric-oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells with relatively low cytotoxicity.
Co-reporter:Miao Ye, Guang-Lei Ma, Jing-Jing Su, Juan Xiong, Jin-Feng Hu
Phytochemistry Letters 2014 10() pp: 287-290
Publication Date(Web):
DOI:10.1016/j.phytol.2014.10.016
Co-reporter:Yu Tang ; Yan Fu ; Juan Xiong ; Ming Li ; Guang-Lei Ma ; Guo-Xun Yang ; Bang-Guo Wei ; Yun Zhao ; Hai-Yan Zhang ;Jin-Feng Hu
Journal of Natural Products 2013 Volume 76(Issue 8) pp:1475-1484
Publication Date(Web):August 13, 2013
DOI:10.1021/np4003355
Ten new lycodine-type alkaloids, named casuarinines A–J (1–10), along with eight known analogues (11–18), were isolated from the whole plant of Lycopodiastrum casuarinoides. The new structures were established by spectroscopic methods and chemical transformations. Casuarinines A–D (1–4) and J (10) are common lycodine alkaloids possessing four connected six-membered rings, while tricyclic casuarinines E–H (5–8) are the piperidine ring cleavage products. In particular, casuarinine I (9) has an unprecedented five-membered tetrahydropyrrole ring instead of the piperidine ring. A plausible biosynthetic pathway to 9 is proposed. Among the compounds reported, casuarinine H (8) exhibited significant neuroprotective effect against hydrogen peroxide (H2O2)-induced neuronal cell damage in human neuroblastoma SH-SY5Y cells, while casuarinines C (3) and I (9) showed moderate inhibitory activity against acetylcholinesterase (AChE).
Co-reporter:Wen-Xuan Wang, Jing-Jing Zhu, Yike Zou, Zhi-Lai Hong, Shu-Ting Liu, Ming Li, Ya Huang, Juan Xiong, Yun Zhao, Guo-Xun Yang, Gang Xia, Jin-Feng Hu
Tetrahedron Letters 2013 Volume 54(Issue 20) pp:2549-2552
Publication Date(Web):15 May 2013
DOI:10.1016/j.tetlet.2013.03.048
A novel dimeric diterpene (named trichotomone, 1) was isolated from the roots of the medicinal ornamental plant Clerodendrum trichotomum. Compound 1 is a rare phenolic ketal of a regular abietane derivative cyrtophyllone B and a rearranged abietane derivative containing a 17(15→16),18(4→3)-diabeo-abietane framework related to uncinatone. The structure was elucidated by extensive spectroscopic methods. The absolute configuration was defined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Trichotomone (1) exhibited in vitro cytotoxicities against several human cancer cell lines (A549, Jurkat, BGC-823 and 293T WT) with IC50 values ranged from 7.51 to 19.38 μM.
Co-reporter:Juan Xiong, Shu-Ting Liu, Yu Tang, Wen-Xuan Wang, Van-Binh Bui, Yun Zhao, Hui Fan, Guo-Xun Yang, Jin-Feng Hu
Phytochemistry Letters 2013 Volume 6(Issue 4) pp:586-589
Publication Date(Web):November 2013
DOI:10.1016/j.phytol.2013.07.015
•Three new and ten known sesquiterpenoids were isolated from Chloranthus elatior.•The absolute configuration of 1 was established.•Compound 3 is the first maaliane-type sesquiterpene from the genus Chloranthus.Thirteen sesquiterpenoids were isolated from the EtOH extract of the aerial parts of Chloranthus elatior. On the basis of spectroscopic methods, the structures of the new naturally occurring compounds were elucidated to be (1R,4R,5R,8S,10R)-1-hydroxy-4-methoxy-eudesm-7(11)-en-12,8-olide (1), 1αH,5βH,6αH,7αH-4β,10β,15-trihydroxyaromadendrane (2), and (1S,4S,5S,6R,7R,10S)-1,4-dihydroxymaaliane (3), respectively.
Co-reporter:Yi Zang, Juan Xiong, Wen-Zhu Zhai, Lei Cao, Sheng-Ping Zhang, Yu Tang, Ji Wang, Jing-Jing Su, Guo-Xun Yang, Yun Zhao, Hui Fan, Gang Xia, Chuan-Gui Wang, Jin-Feng Hu
Phytochemistry 2013 Volume 92() pp:137-145
Publication Date(Web):August 2013
DOI:10.1016/j.phytochem.2013.05.003
•Four hitherto unknown ergosterols were isolated from fruiting bodies of Fomes fomentarius.•Compound 2, possessing cis-fused A/B and B/C rings, is an uncommon ergosterol.•Compound 10 exhibited moderate cytotoxicities against A549, MCF-7 and NUGC-3 cells.Four (1–4) hitherto unknown and seven (5–11) known ergostane-type sterols were isolated from the EtOH extract of the dried fruiting bodies of the polypore macrofungus Fomes fomentarius. On the basis of spectroscopic analysis, the structures of polyhydroxylated sterols 1–4 were elucidated to be (22E,24R)-3β,5α,6β,14α-tetrahydroxyergosta-7,9(11),22-triene (fomentarol A, 1), (22E,24R)-3β,5β,6α,7α-tetrahydroxy-8α,9α-dihydroergosta-14,22-diene (fomentarol B, 2), (22E,24R)-3β,5α-dihydroxy-6β-ethoxyergosta-7,22-diene (fomentarol C, 3), and (22E,24S)-3β,25-dihydroxy-15α-O-β-d-glucopyranosylergosta-7,22-dien-6-one (fomentarol D, 4), respectively. Rings A/B and B/C are in turn cis-fused in compound 2, which is uncommon in natural ergostane-type sterols. The potential biogenetic relationship of 2 and other ergostane-type sterols isolated from F. fomentarius was briefly discussed. Moderate cytotoxic effects of the isolated sterols against a small panel of human cancer cell lines were also established.Eleven sterols were isolated from Fomes fomentarius. Rings A/B and B/C are in turn cis-fused in 2, which is uncommon in natural ergostane-type sterols. Their moderate cytotoxic effects were determined.
Co-reporter:Wen-Xuan Wang, Juan Xiong, Yu Tang, Jing-Jing Zhu, Ming Li, Yun Zhao, Guo-Xun Yang, Gang Xia, Jin-Feng Hu
Phytochemistry 2013 Volume 89() pp:89-95
Publication Date(Web):May 2013
DOI:10.1016/j.phytochem.2013.01.008
The roots of the medicinal ornamental plant Clerodendrum trichotomum yielded a series of rearranged abietane diterpenoids, including three 17(15 → 16)-abeo-abietane (1–3) and three 17(15 → 16),18(4 → 3)-diabeo-abietane (4–6) derivatives. Their structures were elucidated by means of spectroscopic methods. The absolute configuration of (10R,16R)-12,16-epoxy-11,14,17-trihydroxy-6-methoxy-17(15 → 16)-abieta-5,8,11,13-tetraene-7-one (1) was deduced by a combination of single crystal X-ray diffraction analysis and the observed Cotton effects in its circular dichroism (CD) spectrum. All isolates were tested for their cytotoxicities against five human cancer cell lines (BGC-823, Huh-7, KB, KE-97, and Jurkat). Among them, compounds 4, 6, 9, 10, 12, and 14, each possessing a common 17(15 → 16),18(4 → 3)-diabeo-abietane framework, were found to have remarkable cytotoxic effects with IC50 values ranging from 0.83 to 50.99 μM.Graphical abstractRearranged abietane diterpenoids (1–6) were isolated from the roots of Clerodendrum trichotomum. The absolute configuration of compound 1 was completely deduced. Compounds 4, 6, 9, 10, 12, and 14, each possessing a common 17(15 → 16),18(4 → 3)-diabeoabietane framework, exhibited remarkable cytotoxic effects against a small panel of human cancer cell lines.Highlights►Rearranged abietane diterpenoids were isolated from Clerodendrum trichotomum. ► The absolute configuration of compound 1 was ascertained. ► Compound 6 possessed a rare 3,4-epoxy moiety in its structure. ► Some isolates exhibited remarkable cytotoxic effects against human cancer cells.
Co-reporter:Zhi-Lai Hong, Juan Xiong, Shi-Biao Wu, Jing-Jing Zhu, Jun-Lin Hong, Yun Zhao, Gang Xia, Jin-Feng Hu
Phytochemistry 2013 Volume 86() pp:159-167
Publication Date(Web):February 2013
DOI:10.1016/j.phytochem.2012.10.008
Tetracyclic triterpenoids (named as altissimanins A–E, 1–5) and a terpenylated coumarin (denominated as altissimacoumarin G, 6), along with fifteen known compounds (7–21) were isolated from the bark of Ailanthus altissima. Structures of compounds 1–6 were established by spectroscopic methods and chemical transformations. Altissimanin A (1) is a tirucallane-type triterpenoid bearing an uncommon oxetane ring in the side-chain, while altissimanins D (4) and E (5) are two unprecedented dimers each consisting of one tirucallane-type and one dammarane-type triterpenoid moiety. All the isolates were evaluated for their cytotoxic effects against a small panel of human cancer cell lines.Graphical abstractTetracyclic triterpenoids (1–5) and a terpenylated coumarin (6) were isolated from the bark of Ailanthus altissima. 1 processes an uncommon oxetane ring in the C-17 side-chain. 4 and 5 are unprecedented dimers each consisting of one tirucallane-type and one dammarane-type triterpenoid moiety.Highlights► Five triterpenoids and one coumarin were isolated from Ailanthus altissima. ► Triterpenoid 1 has a rare oxetane ring in the C-17 side-chain. ► Compounds 4 and 5 are two unprecedented triterpenoid dimers. ► The cytotoxicities of the isolates against human cancer cells were evaluated.
Co-reporter:Miao Ye, Jun Zhi Ma, Juan Xiong, Shu Ting Liu, Dong Wang, Chong Gang Yuan, Ji Yan Ma, Jin Feng Hu
Chinese Chemical Letters 2012 Volume 23(Issue 10) pp:1157-1160
Publication Date(Web):October 2012
DOI:10.1016/j.cclet.2012.07.018
A new isopimarane-type diterpene (liwariverol, 1) and eight known compounds were isolated and characterized from the EtOAc extract of the whole plant of Potamogeton crispus. The structure of 1 was elucidated to be 17-hydroxy-8αH-isopimara-9(11),15-diene by means of spectroscopic methods. Among the isolates, crenulatoside A (2), an acyclic sesquiterpene glycoside, was found to have anti-oxidative activity with enhancement of the expression of the NAD(P)H:quinone oxidoreductase 1 (NQO1) in human neuroblastoma SH-SY5Y cells at 100 μmol/L after a 24-h incubation.
Co-reporter:Van-Binh Bui, Shu-Ting Liu, Jing-Jing Zhu, Juan Xiong, Yun Zhao, Guo-Xun Yang, Gang Xia, Jin-Feng Hu
Phytochemistry Letters 2012 Volume 5(Issue 3) pp:685-689
Publication Date(Web):September 2012
DOI:10.1016/j.phytol.2012.07.008
The EtOH extract of the aerial parts of Xanthium sibiricum afforded six sesquiterpene lactones (STLs), including two new eremophilanolides. The structures of the new compounds were established on the basis of spectroscopic methods and the modified Mosher's method to be the C-11 epimers of 2S,4S,5R,7R,8R-2-hydroxy-eremophil-1(10)-en-12,8-olide [11R: 1 (sibiriolide C); 11S: 2 (sibiriolide D)]. The isolated compounds were evaluated for their in vitro cytotoxicities against five human cancer cell lines (Huh-7 hepatocarcinoma, KB nasopharynx carcinoma, Jurkat T cell lymphoblast, BGC-823 and KE-97 gastric carcinoma) using the CellTiter-Glo™ luminescent cell viability assay method. Compounds 4–6, each possessing an α-methylene-γ-lactone moiety, were found to have noteworthy cytotoxic effects with IC50 values ranging from 1.1 to 18.0 μM.Graphical abstractThe EtOH extract of the aerial parts of Xanthium sibiricum afforded six sesquiterpene lactones (STLs). The structures of the two new eremophilanolides (1, 2) were established on the basis of spectroscopic methods and the modified Mosher's method to be the C-11 epimers of 2S,4S,5R,7R,8R-2-hydroxy-eremophil-1(10)-en-12,8-olide. STLs 4–6, each possessing an α-methylene-γ-lactone moiety, were found to have noteworthy in vitro cytotoxic effects against five human cancer cell lines (Huh-7, KB, Jurkat, BGC-823 and KE-97), with IC50 values ranging from 1.1 to 18.0 μM.Highlights► Two new eremophilanolides were isolated from the aerial parts of Xanthium sibiricum. ► The new structures were elucidated by spectroscopic method and the modified Mosher's method. ► Three sesquiterpene lactones exhibited remarkable cytotoxicities against human cancer cells.
Co-reporter:Jin-Feng Hu, Hui Fan, Juan Xiong, and Shi-Biao Wu
Chemical Reviews 2011 Volume 111(Issue 9) pp:5465
Publication Date(Web):June 21, 2011
DOI:10.1021/cr100435g
Co-reporter:Wen-Xuan Wang, Lei Cao, Juan Xiong, Gang Xia, Jin-Feng Hu
Phytochemistry Letters 2011 Volume 4(Issue 3) pp:271-274
Publication Date(Web):September 2011
DOI:10.1016/j.phytol.2011.04.012
One new (1) and seven (2–8) known sesquiterpenoids, four dimeric tryptamine-related alkaloids (9–12) and six glycosides (13–18) were isolated from the fruits and leaves of Chimonanthus praecox (wintersweet). Based on its spectroscopic data, the new structure of compound 1, an oppositane-type sesquiterpenoid, was elucidated to be the C-4 epimer of bullatantriol (2). All isolated compounds were evaluated for their cytotoxicities against a small panel of human cancer cell lines, and only the chimonanthine-type alkaloids (10–12) were found to have cytotoxic effects against gastric carcinoma NUGC3 and hepatocarcinoma SNU739 cancer cells, with IC50 values ranging from 10.3 to 19.7 μM.Graphical abstractOne new (1) and seven known sesquiterpenoids, four dimeric tryptamine-related alkaloids and six glycosides were isolated from the fruits and leaves of Chimonanthus praecox. Among them, the chimonanthine-type alkaloids (10–12) were found to have cytotoxicities against human gastric carcinoma NUGC3 and hepatocarcinoma SNU739 cancer cells, with IC50 values ranging from 10.3 to 19.7 μM.Highlights► We investigated the 90% EtOH extracts of the fruits and leaves of Chimonanthus praecox. ► One new and seven known sesquiterpenoids, four dimeric tryptaminerelated alkaloids and six glycosides have been identified. ► Sesquiterpenoids were isolated from this plant for the first time. ► The purified chimonanthine-type alkaloids were found to have cytotoxicities against human cancer cells.
Co-reporter:Li-Long Pan, Xi-Ling Wang, Qiu-Yang Zhang, Xiao-Ling Luo, Peng Xu, Si-Yu Liu, Jin-Feng Hu, Xin-Hua Liu
Phytomedicine (15 May 2016) Volume 23(Issue 5) pp:468-476
Publication Date(Web):15 May 2016
DOI:10.1016/j.phymed.2016.02.006
BackgroundEpidermal growth factor receptor (EGFR) is an effective molecular target for cancer treatment. Boehmenan, a lignan from the dried stems of Clematis armandii, exhibited the potent cytotoxic effects against many cancer cell lines in previous studies. However, the effects and underlying mechanism of boehmenan on non-small cell lung cancer (NSCLC) remains unclear.PurposeThe present study was designed to determine the in vitro anti-cancer properties and underlying molecular mechanisms of boehmenan on A549 NSCLC cells.Study design/methodsCellular viability and chemoattractive properties of macrophages were investigated by using MTT and transwell migration assay, respectively. Mitochondrial membrane potential (ΔΨm), apoptotic ratio, and cell cycle were measured by flow cytometry. Protein expression was visualized by Western blot using specific antibodies.ResultsBoehmenan concentration-dependently suppressed proliferation and induced G1 phase arrest in A549 NSCLC cells, which were accompanied by reduction of migration, colony formation and increase of apoptosis in A549 cells. In addition, boehmenan treatment markedly modulated apoptosis-related protein (p53, p21, cleaved caspase 3, and cleaved PARP) and cyclin D1 expression and induced ΔΨm collapse in a concentration dependent manner. Furthermore, boehmenan concentration-dependently inhibited EGF-induced activation of EGFR and its downstream signaling molecules, including MEK, Akt, ERK1/2, and STAT3.ConclusionTaken together, our results suggested that boehmenan-mediated anti-tumor property was mediated by modulation of mitochondria and EGFR signaling pathway in A549 NSCLC cells.Download high-res image (119KB)Download full-size image
Co-reporter:Li-Long Pan, Qiu-Yang Zhang, Xiao-Ling Luo, Juan Xiong, Peng Xu, Si-Yu Liu, Jin-Feng Hu, Xin-Hua Liu
Phytomedicine (15 May 2016) Volume 23(Issue 5) pp:541-549
Publication Date(Web):15 May 2016
DOI:10.1016/j.phymed.2016.02.018
Background(7R, 8S)-9-Acetyl-dehydrodiconiferyl alcohol (ADDA), a novel lignan compound isolated from Clematis armandii Franch (Ranunculaceae) stems, has been found to exert potential anti-inflammatory activities in vitro.PurposeTo investigate the pharmacological effects and molecular mechanisms of ADDA on lipopolysaccharide (LPS)-induced activation and migration of macrophages.Study design/methodsMacrophages were stimulated with LPS in the presence or absence of ADDA. Expression of inflammatory mediators, including cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), and nitric oxide (NO) were measured by Western blot and commercial NO detection kit. Cellular viability and chemotactic properties of macrophages were investigated using MTT and transwell migration assays. The activation and expression of mitogen activated protein kinases, nuclear factor-κB (NF-κB), protein kinase B (Akt), Src, and focal adhesion kinase (FAK) were analyzed by Western blot.ResultsNon-toxic concentrations (12.5–50 µM) of ADDA concentration-dependently inhibited expression/release of inflammatory mediators (COX-2, iNOS, and NO), suppressed Akt and c-jun N-terminal kinase 1/2 (JNK) phosphorylation, and NF-κB activation in LPS-stimulated macrophages. In addition, ADDA blocked LPS-mediated macrophage migration and this was associated with inhibition of LPS-induced Src and FAK phosphorylation as well as Src expression in a concentration dependent manner. Notably, the inhibitory effects of ADDA on iNOS, NO, and Src could be mimicked by a Src inhibitor PP2 or an iNOS inhibitor l-NMMA.ConclusionOur results suggested that ADDA attenuated LPS-induced inflammatory responses in macrophages and cell migration, at least in part, through inhibition of NF-κB activation and modulation of iNOS/Src/FAK axis.Download high-res image (117KB)Download full-size image
Co-reporter:Juan Xiong, Van-Binh Bui, Xin-Hua Liu, Zhi-Lai Hong, Guo-Xun Yang, Jin-Feng Hu
Journal of Ethnopharmacology (14 May 2014) Volume 153(Issue 3) pp:737-743
Publication Date(Web):14 May 2014
DOI:10.1016/j.jep.2014.03.036
Ethnopharmacological relevanceThe dried stems of Clematis armandii (Caulis clematidis armandii), named “Chuan-Mu-Tong” in Chinese Pharmacopoeia, have been traditionally used as an herbal remedy mainly for inflammation-associated diseases. The Aim of the study is to identify the potential anti-neuroinflammatory components from Clematis armandii.Materials and methodsThe ethanol extract of “Chuan-Mu-Tong” was suspended in H2O and exhaustively extracted with CH2Cl2. The CH2Cl2 fraction was successively subjected to column chromatography (CC) over silica gel, Sephadex LH-20, and semi-preparative HPLC. The structures of the isolated compounds were identified by spectroscopic methods and by comparison with those reported in the literature. Their anti-neuroinflammatory activities were evaluated by inhibitory effects on pro-inflammatory mediators [e.g. nitric oxide (NO) and tumor necrosis factor-alpha (TNF-α)] in lipopolysaccharide (LPS)-activated BV-2 cells.ResultsOne new and sixteen known lignans were isolated and characterized. The absolute configuration of the new lignan, (7R,8S)-9-acetyl-dehydrodiconiferyl alcohol (1), was elucidated by a combination of 1D/2D NMR techniques and the Electronic Circular Dichroism (ECD) spectroscopy based on the empirical helicity rules. The anti-neuroinflammatory bioassay showed that compounds 1, (7R,8S)-dehydrodiconiferyl alcohol (2), erythro-guaiacylglycerol-β-coniferyl ether (5), and threo-guaiacylglycerol-β-coniferyl ether (6) displayed significant inhibitory effects on NO production. Among them, neolignans 1 and 2 exhibited more potent activities than the positive control (NG-monomethyl-l-arginine, l-NMMA), with an IC50 value of 9.3 and 3.9 μM, respectively. Moreover, both 1 and 2 were also found to concentration-dependently suppress the TNF-α release in LPS-stimulated BV-2 cells.ConclusionThe results revealed that lignans are the major components of “Chuan-Mu-Tong”, and their anti-neuroinflammatory activities strongly support the traditional application of this herb medicine on inflammation. Moreover, the dihydrobenzo[b]furan neolignans 1 and 2 as well as Caulis clematidis armandii could be further exploited as new therapeutic agents to treat inflammation-mediated neurodegenerative and aging-associated diseases.Download high-res image (153KB)Download full-size image
Co-reporter:Guang-Lei Ma; Juan Xiong; Guo-Xun Yang; Li-Long Pan; Chang-Ling Hu; Wei Wang; Hui Fan; Qiu-Hua Zhao; Hai-Yan Zhang;Jin-Feng Hu
Journal of Natural Products () pp:
Publication Date(Web):
DOI:10.1021/acs.jnatprod.6b00061
Nine unexpected new flavonol glycoside cyclodimers in the truxinate (1–7, biginkgosides A–G, respectively) or truxillate [biginkgosides H (8) and I (9)] forms were isolated as minor components from the extract of Ginkgo biloba leaves. The new dimers possess an unusual cyclobutane ring formed by a [2+2]-cycloaddition between two symmetric (for compounds 1–5 and 7–9) or nonsymmetric (for 6) flavonol coumaroyl glucorhamnosides. A plausible biosynthetic pathway for these new compounds based on the frontier molecular orbital theory of cycloaddition reactions is briefly discussed. An antineuroinflammatory screening revealed that biginkgosides E (5) and H (8) inhibited nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells, with IC50 values of 2.91 and 17.23 μM, respectively. Additionally, biginkgoside F (6) showed a significant neuroprotective effect (34.3% increase in cell viability at 1 μM) against Aβ25–35-induced cell viability decrease in SH-SY5Y neuroblastoma cells.
Co-reporter:Juan Xiong, Zhi-Lai Hong, Peng Xu, Yike Zou, Shang-Bo Yu, Guo-Xun Yang and Jin-Feng Hu
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 20) pp:NaN4689-4689
Publication Date(Web):2016/04/19
DOI:10.1039/C6OB00731G
Twelve new ent-abietane diterpenoids, chlorabietins A–L (1–12), were isolated from the roots of Chloranthus oldhamii. Their structures and absolute configurations were determined by extensive spectroscopic analyses, X-ray diffraction, and experimental/calculated electronic circular dichroism (ECD) spectroscopy. Among the new isolates, chlorabietins D (4) and E (5) are the first two naturally occurring 8-spiro-fused 9,10-seco-ent-abietanes containing an unexpected cis-fused A/B ring system. Chlorabietin F (6) is a rare chinane-type diterpenoid featuring a hitherto unknown C-ring cleavage between C-13 and C-14, which might be derived from a common precursor of the above spiro-diterpenoid epimers 4 and 5, and their biosynthetic relationships are briefly discussed. Meanwhile, chlorabietin I (9) is the first representative of the abietane-type diterpenoids possessing a tetrahydrofurano function bridging C-6 and C-19. Chlorabietins B (2), C (3), F (6), and G (7) showed anti-neuroinflammatory effects by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells, with IC50 values ranging from 16.4 to 33.8 μM.
![(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo-[2,1-c][1,4]oxazine]-6'-carbaldehyde](http://img.cochemist.com/ccimg/1324000/1323902-17-5.png)
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![5,9,11-trihydroxy-3,3-dimethyl-3H-pyrano[3,2-a]xanthen-12-one](http://img.cochemist.com/ccimg/50900/50875-24-6_b.png)
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![ethyl 3-[3-chloro-4-({4-[cyclohexyl(methyl)carbamoyl]phenyl}amino)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl]benzoate](http://img.cochemist.com/ccimg/6900/6899-87-2_b.png)
![(3aS,5S,6aR,7aS,12aS)-5-methyltetradecahydro-11H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizin-11-one](http://img.cochemist.com/ccimg/6900/6880-84-8.png)
![(3aS,5S,6aR,7aS,12aS)-5-methyltetradecahydro-11H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizin-11-one](http://img.cochemist.com/ccimg/6900/6880-84-8_b.png)
![(3R,3aR,5R,6aR,7aS,12aS)-3-hydroxy-5-methyltetradecahydro-11H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizin-11-one](http://img.cochemist.com/ccimg/6900/6871-55-2.png)
![(3R,3aR,5R,6aR,7aS,12aS)-3-hydroxy-5-methyltetradecahydro-11H-pyrido[1',2':3,4]pyrimido[2,1,6-de]quinolizin-11-one](http://img.cochemist.com/ccimg/6900/6871-55-2_b.png)
![(3aR,3a'R,8aR,8a'R)-1,1'-dimethyl-2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole](http://img.cochemist.com/ccimg/5600/5545-89-1.png)
![(3aR,3a'R,8aR,8a'R)-1,1'-dimethyl-2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole](http://img.cochemist.com/ccimg/5600/5545-89-1_b.png)
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