Co-reporter:Zhen-Hui Wang, Xiao-Chi Ma, Guo-Yu Li, Chao Niu, Yue-Ping Ma, Rena Kasimu, Jian Huang, Jin-Hui Wang
Phytochemistry Letters 2014 Volume 9() pp:153-157
Publication Date(Web):September 2014
DOI:10.1016/j.phytol.2014.06.001
•Four new phenolic glucosides were isolated from Curculigo orchioides Gaertn.•Antiosteoporotic effects were evaluated for the isolated phenolic glycosides.•Chlorophenolic glucosides have better antiosteoporotic activity than phenolic glycosides.Three new chlorophenolic glucosides, curculigine K (1), curculigine L (2), curculigine J (3) and one new phenolic glycoside, curculigoside I (4), together with two known phenolic glycosides (5, 6) were isolated from the dried rhizomes of Curculigo orchioides Gaertn. Their structures were elucidated by extensive spectroscopic techniques (IR, UV, MS, 1D and 2D NMR). The isolated chlorophenolic glycosides were evaluated for antiosteoporotic activity against MC3T3-E1 cell line by using MTT assays. Compounds 1 and 2 showed moderate antiosteoporotic activity with the proliferation rate of 10.6–13.9%.
Co-reporter:Jin Lu, Guoyu Li, Jian Huang, Cui Zhang, Lan Zhang, Ke Zhang, Pingya Li, Ruichao Lin, Jinhui Wang
Phytochemistry 2014 Volume 104() pp:79-88
Publication Date(Web):August 2014
DOI:10.1016/j.phytochem.2014.04.020
•Twenty-two lathyrane-type diterpenoids were isolated.•The configuration of 1 was confirmed by X-ray crystallographic and CD spectrum analyses.•A putative biosynthetic pathway leading to these compounds was proposed.•Cytotoxic activity of the isolated compounds was evaluated.Ten lathyrane-type diterpenoids named Euphorbia Factor L12–L21 (1–10) and twelve known diterpenoids (11–22) were isolated from seeds of Euphorbia lathyris. The structures of these compounds were determined by extensive spectroscopic (UV, IR, HRESIMS, 1D and 2D NMR) analyses. In addition, the configuration of Euphorbia Factor L12 (1) was further confirmed by X-ray crystallographic and circular dichroism (CD) analyses. A putative biogenetic relationship to these compounds was proposed. Cytotoxicity of the isolated compounds against C6 and MCF-7 cell lines were evaluated. Compounds 1, 5, 7, 12 and 17 exhibited considerable cytotoxic activities (IC50 12.4–36.2 μM).Twenty-two lathyrane-type diterpenoid derivatives (ten previously unknown) were isolated from seeds of Euphorbia lathyris, and their structures were established by extensive spectroscopic interpretation. A putative biogenetic relationship to the isolated compounds was proposed. Cytotoxic activity against cancer cell lines (C6, MCF-7, Hela and HepG2) was evaluated.
Co-reporter:He Meng, Guoyu Li, Jian Huang, Ke Zhang, Xiuyan Wei, Yueping Ma, Cui Zhang, Jinhui Wang
Phytochemistry 2013 Volume 86() pp:151-158
Publication Date(Web):February 2013
DOI:10.1016/j.phytochem.2012.10.013
Eight sesquiterpenoids, named Ferulaeone A–H (1–8), and seven known sesquiterpenoid derivatives were isolated from the roots of Ferula ferulaeoides (Steud.) Korov. Their structures were established by comprehensive spectroscopic analysis, and biosynthetic pathways leading to these compounds were proposed. The cytotoxicity of all these isolates against HepG2, MCF-7, and C6 cancer cell lines was evaluated and compounds 6–11, 13 exihibited various degrees of cytotoxic effect. Among them, compounds 9–11 displayed the highest potency against C6 with IC50 values 34, 36, and 31 μM, respectively.Graphical abstractFifteen sesquiterpenoid derivatives (eight previously unknown) were isolated from roots of Ferula ferulaeoides (Steud.) Korov., and their structures were established. Biosynthetic pathways leading to these compounds were also proposed. The cytotoxicity of all these isolates against HepG2, MCF-7, and C6 cancer cell lines was evaluated.Highlights► Fifteen sesquiterpenoid derivatives were isolated. ► Biosynthetic pathways leading to these compounds were proposed. ► The cytotoxicity of all these isolates was evaluated.
Co-reporter:Shuo Shen, Guoyu Li, Jian Huang, Yong Tan, Chaojun Chen, Bu Ren, Ga Lu, Cui Zhang, Xian Li, Jinhui Wang
Biochemical Systematics and Ecology 2012 Volume 45() pp:183-187
Publication Date(Web):December 2012
DOI:10.1016/j.bse.2012.07.034
Phytochemical investigation on Fritillaria pallidiflora led to the isolations of one new steroidal alkaloid, (20R,22R,23R,25R)-3β,23-dihydroxy-N-methyl-veratram-13(17)-en-6-one (14) and fifteen known compounds: five steroidal saponins (1–5), three phenolic glucosides (6–8), three nucleoside compounds (9–11), one amino acid (12), four steroidal alkaloids (13–16). Compounds 12, 14 were isolated from F. pallidiflora for the first time. Compounds 1–6 were isolated from the genus Fritillaria for the first time and compounds 7–8 were isolated from the family Liliaceae for the first time. The chemotaxonomic significance of these compounds was summarized.Graphical abstractOne new steroidal alkaloid, (20R,22R,23R,25R)-3β,23-dihydroxy-N-methyl-veratram-13(17)-en-6-one (14) together with fifteen known compounds, was isolated from Fritillaria pallidiflora Schrenk.Highlights► One new steroidal alkaloid was isolated from Fritillaria pallidiflora Schrenk. ► Two phenolic glucosides were firstly found in the family Liliaceae. ► Five steroidal saponins were firstly obtained from the genus Fritillaria. ► The chemotaxonomic significance of these compounds was discussed.
Co-reporter:Hong-Ying Gao;Guo-Yu Li;Jin-Hui Wang
Helvetica Chimica Acta 2012 Volume 95( Issue 7) pp:1108-1113
Publication Date(Web):
DOI:10.1002/hlca.201100454
Abstract
Alopecurin A, an alkaloid with an unprecedented skeleton, was isolated from the seeds of Sophora alopecuroides L. The absolute configuration and structure of this compound was identified as (3S,12R)-3-hydroxy-1,7-diazatricyclo[10.4.0.13,7]heptadecane-11,16,17-trione (=(7S,15aR)-decahydro-7-hydroxy-6H-7,11-methano-4H-pyrido[1,2-a][1,7]diazacyclododecine-4,15,16(12H)-trione). The structure and absolute configuration was elucidated by spectroscopic methods, mainly HR-ESI-TOF-MS, IR, 1D-NMR (1H- and 13C-NMR), 2D-NMR (COSY, NOESY, HSQC, HMBC), and particularly X-ray crystal-diffraction and CD spectral analysis.
Co-reporter:Qing Peng, Guoyu Li, Yueping Ma, Jian Huang, Xiuyan Wei, Jinhui Wang
Biochemical Systematics and Ecology 2012 Volume 43() pp:64-66
Publication Date(Web):August 2012
DOI:10.1016/j.bse.2012.02.021
Phytochemical investigation of the dried roots of Euphorbia kansui resulted in the isolation of three flavonoids (1-3), three diterpenoids (4-6) and five triterprnoids (7-11). Among them, three compounds (1-3) were firstly isolated from the family Euphorbiaceae. Others were reported in the genus Euphorbia, in which three compounds (8-11) were firstly isolated from the E. kansui. The chemotaxonomic significance of these compounds was summarized.Highlights► Eleven secondary metabolites were isolated from the dried roots of Euphorbia kansui. ► Two chalcones and one flavanone were firstly obtained from the Euphorbiaceae. ► It is the first report that the four triterpenoids were obtained from E. Kansui. ► The presence of these compounds may be useful for chemotaxonomic studies.
Co-reporter:Yue-Ping Ma;Ning Li;Jian Gao;Ke-Ling Fu;Ying Qin;Guo-Yu Li;Jin-Hui Wang
Helvetica Chimica Acta 2011 Volume 94( Issue 10) pp:1881-1887
Publication Date(Web):
DOI:10.1002/hlca.201100120
Abstract
A new peroxy-multiflorane triterpene ester, (3α,5α,8α,20α)-5,8-epidioxymultiflora-6,9(11)-diene-3,29-diol 3,29-dibenzoate (1), was isolated from the processed seeds of Trichosanthes kirilowii, together with the two known related derivatives 2 and 3, and the two known steroids 4 and 5. Compounds 2, 4, and 5 were isolated from the genus Trichosanthes for the first time. The structure of compound 1 was established by NMR, HR-MS, and CD analyses. Compounds 1–3 were tested for their in vitro cytotoxicity against human-tumor cell lines (Hela, HL-60, and MCF-7) and anti-inflammatory activity (LPS-induced B lymphocyte cells) with the MTT method.
Co-reporter:Hong-ying Gao, Guo-yu Li, Jin-hui Wang
Journal of Chromatography B 2011 Volume 879(15–16) pp:1121-1125
Publication Date(Web):1 May 2011
DOI:10.1016/j.jchromb.2011.03.031
A sensitive and accurate method for the simultaneous determination of five alkaloids, namely 9α-hydroxymatrine (M1), matrine (M2), sophoridine (M3), oxymatrine (M4), alopecurin A (M5) in different parts (seed, legume, stem, and root) and different harvest times of Sophora alopecuroides L. was developed by high performance liquid chromatography (HPLC) with photodiode array detector (PDA) for the first time. The separation by gradient elution was achieved on Scienhome Kromasil C18 (4.6 × 250 mm, 5 μm) column at 30 °C with acetonitrile (A)/0.1% phosphatic acid + 0.1% triethylamine (B) as the mobile phase. The detection wavelength was 205 nm. The optimized method provided a good linear relation (r ≥ 0.9993 for all the target compounds), satisfactory precision (RSD values less than 2.3%) and good recovery (96.4–103.6%). The limits of detection ranged between 0.11 × 10−3 and 4.70 × 10−3 μg for the different analytes. The method was successfully applied to analysis and quality control of alkaloid extracts from the traditional Chinese herbal drugs of S. alopecuroides L.
Co-reporter:Yue Hu;Xiao-Dong Li;Guo-Yu Li;Ning Li;Wen-Jian Zuo;Yi-Mei Zeng;He Meng;Xian Li;Jin-Hui Wang
Helvetica Chimica Acta 2010 Volume 93( Issue 5) pp:
Publication Date(Web):
DOI:10.1002/hlca.200900350
Abstract
Two new sesquiterpenoids, ferulactones A and B (1 and 2, resp.), have been isolated from the roots of Ferula ferulaeoides (Steud.) Korov. Their structures and relative configurations were established by analysis of spectroscopic data. Their absolute configuration was assigned by application of the CD technique.
Co-reporter:He Meng, Guoyu Li, Ronghua Dai, Yuepin Ma, Ke Zhang, Cui Zhang, Xian Li, Jinhui Wang
Biochemical Systematics and Ecology 2010 Volume 38(Issue 6) pp:1220-1223
Publication Date(Web):December 2010
DOI:10.1016/j.bse.2010.12.023
Phytochemical investigations of the rhizomes of Atractylodes chinensis (DC.) Koidz. resulted in the isolation of four sesquiterpenes (1–4), five polyacetylenes (5–9), oleanolic acid (10), and 5-hydromethyl furaldehyde (11). Among them, seven compounds (3, 5–10) were firstly isolated from the A. chinensis, and all have been reported in the genus Atractylodes except compound 10. The chemotaxonomic significance of these compounds was summarized.Research highlights► Atractylodes chinensis (DC.) Koidz. has been showed to contain sesquiterpenes, polyacetylenes, oleanolic acid, and 5-hydromethyl furaldehyde. ► Discuss the chemotaxomic marker for genus Atractylodes. ► Five species of Atractylodes were similar in the sesquiterpenes and polyacetylenes. ► Oleanolic acid can be used to differentiate A. chinensis from A. lancea, A. koreana, A. ovata, and A. japonica.
Co-reporter:Wen Jian Zuo, Yi Mei Zeng, Yue Hu, He Meng, Zhen Hui Wang, Jin Hui Wang
Chinese Chemical Letters 2009 Volume 20(Issue 11) pp:1331-1334
Publication Date(Web):November 2009
DOI:10.1016/j.cclet.2009.07.002
A new compound, kudinoside LZ2 (1), was isolated from the leaves of Ilex kudincha. Its structure was elucidated by the combination of one- and two-dimensional NMR analysis, HR–ESI–MS, CD spectrum measurement and chemical evidences.
Co-reporter:Yi-Mei Zeng;Wen-Jian Zuo;Min-Ge Sun;He Meng;Qing-Hui Wang;Jin-Hui Wang;Xian Li
Helvetica Chimica Acta 2009 Volume 92( Issue 7) pp:
Publication Date(Web):
DOI:10.1002/hlca.200800419
Abstract
Three new Daphne diterpenes, yuanhuaoate A (1), yuanhuaoate B (2), and yuanhuaoate C (3), were isolated from the buds of Daphne genkwaSieb. etZucc. processed by rice vinegar. Their structures and relative configurations were established by analysis of spectroscopic data. Their absolute configurations were assigned by the CD technique, applied for the first time to Daphne diterpenes.
Co-reporter:Shuang Song, Lu Sun, Lei Yuan, Tiemin Sun, Yun Zhao, Wenjian Zuo, Yue Cong, Xian Li, Jinhui Wang
Journal of Chromatography A 2008 Volume 1179(Issue 2) pp:125-130
Publication Date(Web):1 February 2008
DOI:10.1016/j.chroma.2007.11.092
Using nonchiral high-performance liquid chromatography (HPLC) coupled with a circular dichroism (CD) detector, we developed a new method to determine the enantiomeric excess (e.e.) of glucose derivatized with chromophores (p-bromobenzoate). This method is suitable for microscale analysis of glycoside and saccharide. As an application of this method, the enantiomeric excess of the component glucose of a glucan was assayed.
Co-reporter:Yu-Bo Zhou;Jin-Hui Wang;Xiang-Mei Li;Xiao ChunFu;Zhen Yan;Yue Cong;Xian Li
Helvetica Chimica Acta 2008 Volume 91( Issue 7) pp:1244-1250
Publication Date(Web):
DOI:10.1002/hlca.200890135
Abstract
The phytochemical investigation of the methanolic extract of the root of Ilex pubescensHook. et Arn. furnished six compounds including three new compounds, ilexin A (1), ilexin B (2), and ilexin C (3), besides vanillic acid, vanillin, and caffeic acid. Compounds 1 and 2 were identified as 2-phenylethyl alcohol derivatives, while compound 3 is a lignan derivative. The structures of these compounds have been elucidated by the combination of the analysis of NMR and MS data, CD spectra, and chemical evidences.
Co-reporter:William Jia;Yue Cong;Jing Chen;Shuang Song;Jin-Hui Wang;Yu-Hui Yang
Helvetica Chimica Acta 2007 Volume 90(Issue 5) pp:1038-1042
Publication Date(Web):18 MAY 2007
DOI:10.1002/hlca.200790087
Two new steroidal alkaloids, neoverapatuline (1) and (1β,3α,5β)-1,3-dihydroxyjervanin-12-en-11-one (2), together with the four known compounds, veratramine (3), rubijervine (4), veratrosine (5), and veratroylzygadenine (6), were isolated from the roots and rhizomes of Veratrum nigrum L. Their structures were established through combined analyses of physicochemical properties and spectroscopic evidence. All compounds 1–6 were tested for their cytotoxicities in vitro against the human glioma cell line SF188.
![26-O-beta-D-glucopyranosyl-(25R)-furost-5-en-3beta,20alpha,26-triol 3-O-beta-D-xylopyranosyl(1->4)-[alpha-L-rhamnopyranosyl(1->2)]-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/1383600/1383540-06-4.png)
![26-O-beta-D-glucopyranosyl-(25R)-furost-5-en-3beta,20alpha,26-triol 3-O-beta-D-xylopyranosyl(1->4)-[alpha-L-rhamnopyranosyl(1->2)]-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/1383600/1383540-06-4_b.png)
![26-O-beta-D-glucopyranosyl-3beta,26-dihydroxyl-20,22-seco-(25R)-furost-5-en-20,22-dione 3-O-beta-D-xylopyranosyl(1->4)-[alpha-L-rhamnopyranosyl(1->2)]-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/1383600/1383540-05-3.png)
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![2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-[ 6-deoxy-3-O-(4-hydroxy-3,5-dimethoxybenzoyl)-α-L-mannopyranosyl]- β-D-galactopyranoside](http://img.cochemist.com/ccimg/852700/852638-61-0_b.png)
![3-chloro-4-[(4-methyl-1-piperazinyl)methyl]-Benzenamine](http://img.cochemist.com/ccimg/943400/943320-67-0.png)
![3-chloro-4-[(4-methyl-1-piperazinyl)methyl]-Benzenamine](http://img.cochemist.com/ccimg/943400/943320-67-0_b.png)
![Benzenamine, 3-chloro-4-[(4-ethyl-1-piperazinyl)methyl]-](http://img.cochemist.com/ccimg/853300/853298-98-3.png)
![Benzenamine, 3-chloro-4-[(4-ethyl-1-piperazinyl)methyl]-](http://img.cochemist.com/ccimg/853300/853298-98-3_b.png)
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![Morpholine, 4-[[4-nitro-2-(trifluoromethyl)phenyl]methyl]-](/data/chemimg/1933600/694499-28-0_b.png)
![Benzamide, 4-[4-[(4-methylphenyl)amino]-1-phthalazinyl]-](http://img.cochemist.com/ccimg/375900/375830-70-9.png)
![Benzamide, 4-[4-[(4-methylphenyl)amino]-1-phthalazinyl]-](http://img.cochemist.com/ccimg/375900/375830-70-9_b.png)
![4H-Cyclopenta[a]cyclopropa[f]cycloundecen-4-one,4a,8-bis(acetyloxy)-7-(benzoyloxy)-1,1a,4a,5,6,7,7a,8,9,10,11,11a-dodecahydro-1,1,3,6-tetramethyl-9-methylene-,(1aR,2E,4aR,6S,7S,7aR,8R,11aS)-rel-(+)-](http://img.cochemist.com/ccimg/219000/218916-52-0.png)
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![1-Propanone,3-[2-hydroxy-5-[3-(2-hydroxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-4-methoxyphenyl]-1-(4-hydroxyphenyl)-](http://img.cochemist.com/ccimg/163600/163565-66-0.png)
![1-Propanone,3-[2-hydroxy-5-[3-(2-hydroxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propyl]-4-methoxyphenyl]-1-(4-hydroxyphenyl)-](http://img.cochemist.com/ccimg/163600/163565-66-0_b.png)
![L-Alaninamide,N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-1-(carboxymethyl)-3-fluoro-2-oxopropyl]-](http://img.cochemist.com/ccimg/161500/161401-82-7.png)
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![2-Propenoic acid, 3-[2-[(1E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]-, (2E)-](/data/chemimg/103800/158732-59-3.png)
![2-Propenoic acid, 3-[2-[(1E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]-, (2E)-](/data/chemimg/103800/158732-59-3_b.png)
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![2-(3,5-DIMETHOXYPHENYL)-6-ETHYL-5-METHYLPYRAZOLO[1,5-A]PYRIMIDIN-7-OL](http://img.cochemist.com/ccimg/149800/149707-75-5_b.png)
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![Ethanone,1-[3-(3,6-dihydroxy-2-methylbenzoyl)-2,4-dihydroxyphenyl]-](http://img.cochemist.com/ccimg/115900/115834-34-9_b.png)
![2(5H)-Furanone, 4-methyl-5-[(phenylmethoxy)methyl]-, (S)-](http://img.cochemist.com/ccimg/112900/112837-16-8.png)
![2(5H)-Furanone, 4-methyl-5-[(phenylmethoxy)methyl]-, (S)-](http://img.cochemist.com/ccimg/112900/112837-16-8_b.png)
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![Benzene, 1,1'-[1-(1-propenyl)-1,3-propanediyl]bis-](http://img.cochemist.com/ccimg/103300/103240-91-1_b.png)
![2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID](http://img.cochemist.com/ccimg/76400/76376-43-7.png)
![2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID](http://img.cochemist.com/ccimg/76400/76376-43-7_b.png)
![2,3-DIHYDRO-2,7-DIMETHYLFURO[2,3-C]PYRIDINE](http://img.cochemist.com/ccimg/69100/69022-82-8.png)
![2,3-DIHYDRO-2,7-DIMETHYLFURO[2,3-C]PYRIDINE](http://img.cochemist.com/ccimg/69100/69022-82-8_b.png)
![b-D-Glucopyranoside, (3b,25R)-spirost-5-en-3-ylO-6-deoxy-a-L-mannopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®4)]-](http://img.cochemist.com/ccimg/55700/55659-75-1.png)
![b-D-Glucopyranoside, (3b,25R)-spirost-5-en-3-ylO-6-deoxy-a-L-mannopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®4)]-](http://img.cochemist.com/ccimg/55700/55659-75-1_b.png)
![(1S,4aR,5R,7S,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate](http://img.cochemist.com/ccimg/53000/52916-96-8.png)
![(1S,4aR,5R,7S,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate](http://img.cochemist.com/ccimg/53000/52916-96-8_b.png)
![Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-](http://img.cochemist.com/ccimg/33500/33495-30-6.png)
![Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-](http://img.cochemist.com/ccimg/33500/33495-30-6_b.png)
![Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-](http://img.cochemist.com/ccimg/25000/24903-95-5.png)
![Bicyclo[3.1.1]heptan-2-one, 6,6-dimethyl-](http://img.cochemist.com/ccimg/25000/24903-95-5_b.png)
![[1,1'-Biphenyl]-3,3',4,4'-tetracarboxylic acid](/data/chemimg/2200/22803-05-0.png)
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