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ABSTRACT: Chemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of two innovanoside dimers ( and ) with an unusual four-membered cyclobutane ring, together with the isoinnovanoside . Their chemical structures and configurations were elucidated by extensive spectral analysis and synthesis.
Chemical Communications 05/2013; · 6.17 Impact Factor
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ABSTRACT: A phytochemical investigation of the branches and leaves of Cephalotaxus lanceolata resulted in the isolation of three new cephalotaxus alkaloids, cephalancetines A, B, and D (1, 2, and 4, resp.), together with ten known alkaloids, 3 and 5-13. The structures of the alkaloids were elucidated on the basis of spectroscopic analyses, including 1D- and 2D-NMR, and HR-ESI-MS, and single-crystal X-ray diffraction. All isolated compounds were tested for their cytotoxicities against four human tumor cell lines, A549, HCT116, SK-BR-3, and HepG2. Compounds 12 and 13 showed remarkable activities against A549, HCT116, and HepG2 cell lines.
Chemistry & Biodiversity 04/2013; 10(4):584-95. · 1.80 Impact Factor
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Bo Li,
De-Yun Kong, Yun-Heng Shen,
Ka-Li Fu,
Rong-Cai Yue,
Zhu-Zhen Han,
Hu Yuan,
Qing-Xin Liu,
Lei Shan,
Hui-Liang Li,
Xian-Wen Yang,
Wei-Dong Zhang
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ABSTRACT: A phytochemical investigation of the cone of Pseudolarix amabilis led to the isolation of pseudolarenone (), a structurally novel pentacyclic (5/11/5/6/5) nortriterpenoid lactone with an unprecedented carbon skeleton featuring a unique bicyclo[8.2.1]tridecane core. Its structure and absolute configurations were elucidated by spectroscopic analysis and single crystal X-ray diffraction (CuK(α)).
Chemical Communications 01/2013; · 6.17 Impact Factor
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Bo Li,
De-Yun Kong, Yun-Heng Shen,
Hu Yuan,
Rong-Cai Yue,
Yi-Ren He,
Lu Lu,
Lei Shan,
Hui-Liang Li,
Ji Ye,
Xian-Wen Yang,
Juan Su,
Run-Hui Liu,
Wei-Dong Zhang
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ABSTRACT: Pseudolaridimers A (1) and B (2), two unprecedented heterodimers formed via a [4 + 2] Diels-Alder cycloaddition between a cycloartane triterpenoid unit and a labdane diterpenoid unit, were isolated from the cones of Pseudolarix amabilis. Their structures were established by extensive analysis of HRESIMS and NMR spectra. The absolute configuration of 1 was determined by single crystal X-ray diffraction (CuK(α)) of its methyl esterified derivative. Pseudolaridimer A (1) showed strong cytotoxicity against HCT116, ZR-75-30, and HL-60 human tumor cell lines, with IC(50) values 9.62, 7.84, 8.29 μg/mL, respectively. Pseudolaridimer B (2) only exhibited potent inhibition against the HL-60 cell line with an IC(50) value of 7.50 μg/mL.
Organic Letters 10/2012; · 5.86 Impact Factor
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Sheng Lin,
Zhong-Xiao Zhang,
Tao Chen,
Ji Ye,
Wei-Xing Dai,
Lei Shan,
Juan Su, Yun-Heng Shen,
Hui-Liang Li,
Run-Hui Liu,
Xi-Ke Xu,
Hui Wang,
Wei-Dong Zhang
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ABSTRACT: HPLC-PDA-MS and TLC analysis were used to look for minor cytotoxic chlorinated valepotriates from whole plants of Valeriana jatamansi (syn. Valeriana wallichii DC.). This resulted in isolation of 15 chlorinated valepotriates, designated as chlorovaltrates A-O, together with six known analogues, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1,5-dihydroxyvalechlorine, volvaltrate B, chlorovaltrate, rupesin B, (1S,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5-hydroxyvalechlorine, and (1R,3R,5R,7S,8S,9S)-3,8-epoxy-1-O-ethyl-5-hydroxyvalechlorine. Their structures were elucidated by spectroscopic methods including homo- and heteronuclear two-dimensional NMR experiments. Chlorovaltrates K-N, chlorovaltrate and rupesin B showed moderate cytotoxicity against lung adenocarcinoma (A 549), metastatic prostate cancer (PC-3M), colon cancer (HCT-8) and hepatoma (Bel 7402) cell lines with IC(50) values of 0.89-9.76μM.
Phytochemistry 10/2012; · 3.35 Impact Factor
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Planta Medica 09/2012; 78(14):E23. · 2.15 Impact Factor
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ABSTRACT: Three new alkaloids (1-3), together with ten known alkaloids, were isolated from the ethanolic extract of the whole plants of Lycopodium japonicum Thunb. Their structures were elucidated on the basis of spectroscopic analysis, including MS and NMR methods. All alkaloids isolated were assayed for cytotoxic activity against four human cancer cell lines and acetylcholinesterase (AChE) inhibitory activity. No alkaloid showed either cytotoxic activity against four human cancer cell lines or acetylcholinesterase (AChE) inhibitory activity.
Chemical & pharmaceutical bulletin 08/2012; · 1.70 Impact Factor
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Chemistry of Natural Compounds 05/2012; 45(6):927-928. · 1.03 Impact Factor
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ABSTRACT: A new stilbene glycoside, 5-methylresveratrol-3,4′-O-β-D-diglucopyranoside (1), was isolated from the n-butanol fraction of the rhizomes of Veratrum dahuricum, together with five known stilbenoids: resveratrol-3-O-β-D-glycoside (2), 4′-methylresveratrol-3-O-β-D-glycoside (3), oxyresveratrol-4′-O-β-D-glycoside (4), oxyresveratrol-3-O-β-D-glycoside (5), and oxyresveratrol-3,4′-O-β-D-diglycoside (6), and found for the first time in the investigated plant. The structures of six isolates were identified on the basis of
1D and 2D NMR data. Compounds 1–6 showed platelet aggregation inhibition, and compound 1 had an IC50 value of 383.6 μM against platelet aggregation induced by AA.
Chemistry of Natural Compounds 05/2012; 45(3):325-329. · 1.03 Impact Factor
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ABSTRACT: A high performance liquid chromatography coupled with evaporative light scattering detection (HPLC–ELSD) and electrospray
ionization multistage mass spectrometry (HPLC–ESI–MSn), respectively, has been performed for the simultaneous determination of six steroidal alkaloids, including pseudojervine,
veratrosine, jervine, veratramine, 3-veratroylzygadenine, 3-angeloylzygadenine, in Veratrum dahuricum collected in different seasons. The plants were soaked in methanol and extracted ultrasonically. The six steroidal alkaloids
were obtained by silica gel column chromatography, eluting with gradient petroleum and acetyl acetate. The intra-day and inter-day
precisions of the method were evaluated and were less than 1.4%. The content of steroidal alkaloids in the plant varied significantly
from spring to autumn, confirming the necessity to control the quality of V. dahuricum during its preparation and application.
Chromatographia 04/2012; 67(1):15-21. · 1.20 Impact Factor
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Chemistry of Natural Compounds 04/2012; 46(2):305-307. · 1.03 Impact Factor
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Chemistry of Natural Compounds 04/2012; 46(1):109-111. · 1.03 Impact Factor
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ABSTRACT: Incarvilleatone (1), an unprecedented dimeric cyclohexylethanoid analog with a racemic nature, was isolated from the whole plant of Incarvillea younghusbandii. HPLC chiral separation of 1 gave two enantiomers (-)-incarvilleatone and (+)-incarvilleatone. The structure of 1 was established by spectroscopic methods and single crystal X-ray diffraction. The absolute configurations of enantiomers were determined by quantum mechanical calculation. (-)-Incarvilleatone exhibited a potent inhibitory effect against NO production in LPS-induced RAW264.7 macrophages.
Organic Letters 04/2012; 14(8):1954-7. · 5.86 Impact Factor
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ABSTRACT: Argutalactone (1), a novel sesquiterpenoid lactone featuring an unprecedented 6/5/7 rigid skeleton, was isolated from the roots of Incarvillea arguta. The structure and relative configuration of 1 were established by extensive analysis of spectroscopic data. The absolute configuration of 1 was determined as 2R,5S,10R,12S based on the analysis of biogenetical transformation, comparison of the optical rotation with literature data, and comparison of the experimental circular dichroism spectrum with the calculated electronic circular dichroism spectra.
Journal of Asian natural products research 03/2012; 14(5):496-502. · 0.61 Impact Factor
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ABSTRACT: Four new sesquiterpene lactones, (1 S,5 R,6 S,7 S,8 R,9 R,10 S,11 S)-6-acetoxy-9-hydroxy-4-oxo-pseudoguai-2(3)-en-12,8-olide, (1 S,2 R,5 R,6 S,7 R,8 S,10 R)-6-acetoxy-2-ethoxy-4-oxo-pseudoguai-11(13)-en-12,8-olide, (1 S,2 R,5 R,6 S,7 R,8 S,10 R)-6-acetoxy-2-hydroxy-4-oxo-pseudoguai-11(13)-en-12,8-olide, and 14-acetoxy-1 β,5 α,7 αH-4 β-hydroxy-guai-9(10),11(13)-dien-12,8 α-olide, along with 26 known sesquiterpene lactones, were isolated from the whole plants of Inula hookeri C. B. Clarke. Their structures were established based on spectroscopic methods including HRESIMS, 1D and 2D NMR, and CD techniques. All compounds were evaluated for their cytotoxic activities against HepG2, HeLa, PC-3, and MGC-803 cell lines by CCK-8 assay. Some of the isolates, especiallly pseudoguaianolides and guaianolides, exhibited significant cytotoxicities against these four examined cell lines.
Planta Medica 01/2012; 78(5):465-71. · 2.15 Impact Factor
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Jun-Mian Tian,
Si-Sheng Ou-Yang,
Xu Zhang,
Ying-Tong Di,
Hua-Liang Jiang,
Hong-Lin Li,
Wei-Xing Dai,
Ke-Yu Chen,
Mai-Li Liu,
Xiao-Jiang Hao, Yun-Heng Shen,
Cheng Luo,
Wei-Dong Zhang
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ABSTRACT: Tunicyclin E (1), a new cyclic heptapeptide, cyclo(Pro1–Ser2–Trp3–Leu4–Val5–Gly6–Ser7), was isolated from the root of Psammosilene tunicoides. The presence of two sets of resonance signals in its NMR spectra (1a:1b, [similar]3 : 1 abundance) indicated that it has two conformations in solution, while only one conformation was found in its crystal state by X-ray diffraction. To explore the molecular basis of the two conformations of 1 in solution and their interconversion mechanism, X-ray diffraction, NMR experiments, and theoretical calculations were performed. The results disclosed that two conformers of 1 in solution were derived from the cis/trans isomers of the Ser7–Pro1 peptide bond (1a, trans; 1b, cis). The fast interconversion of the two conformations in solution is explained by an intramolecular catalysis mechanism and solvent effects. Furthermore, the existence of several unusual pseudo turns characterized for the first time plays a key role for dominant trans conformation in solution.
RSC Advanced. 01/2012; 2:1126-35.
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ABSTRACT: Cyclopenicillone (1), possessing a unique 2,5-dimethylcyclopent-2-enone carbon skeleton, has been isolated from the cultures broth of the fungus Penicillium decumbens. The structure and absolute configuration of 1 were elucidated using a combination of NMR spectroscopy, CD data and computational approaches. Cyclopenicillone (1) demonstrated a dose-dependent (10-100 μM) inhibition against LPS-induced NO production in RAW264.7 macrophages.
Chemical Communications 08/2011; 47(37):10413-5. · 6.17 Impact Factor
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ABSTRACT: Investigation of the ethanol extract of the whole plant of Ainsliaea macrocephala led to the isolation of five new sesquiterpenoids, namely ainsliadimer C (1), ainsliadimer D (2), ainsliaolide B (3), ainsliatone B (4), and ainsliaolide C (5), together with seventeen known sesquiterpenes and sesquiterpene glycosides (6- 22). Their structures were elucidated by spectroscopic methods. The relative stereochemistry of ainsliadimers C (1) and D (2) were further confirmed by single crystal X-ray diffraction analysis. Total extract of A. macrocephala and compounds 1- 22 were tested for inhibitory activity against the production of nitric oxide in RAW 264.7 cells stimulated by LPS, as well as for cytotoxicity against RAW 264.7 macrophages. Of all samples tested, purified compounds 4, 7, and 12 strongly inhibited the production of nitric oxide with IC50 values of 8.78, 2.50, and 7.11 µM, and simultaneously showed low cytotoxicity against RAW 264.7 macrophages.
Planta Medica 03/2011; 77(13):1545-50. · 2.15 Impact Factor
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Xian-Wen Yang,
Yong-Li Li,
Su-Mei Li, Yun-Heng Shen,
Jun-Mian Tian,
Zhi-Jun Zhu,
Lin Feng,
Liang Wu,
Sheng Lin,
Ning Wang,
Yonghong Liu,
Wei-Dong Zhang
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ABSTRACT: A systematic phytochemical investigation of the aerial parts of Abies georgei yielded nine new and 72 known compounds, including four monoterpenes, four sesquiterpenes, 25 flavonones, 14 lignans, and 34 other chemical constituents. The new compounds included two monoterpenes (1 and 2), two sesquiterpenes (3 and 4), three flavonones (5, 6, and 7), and two other components (8 and 9). Their chemical structures were established on the basis of various spectroscopic data. All the isolates were tested for antitumor and anti-inflammatory activities. The new compound 9,4'-dihydroxy-5,7-dimethoxy-8-methylchalcone (7) demonstrated a moderate antiproliferative effect on QGY-7703 tumor cells (IC (50) = 17.6 µg/mL). The known compound isoferulaldehyde (67) exhibited the strongest inhibitory activity against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 macrophages (IC (50) = 19.0 µg/mL). Abies georgei may be a significant source of beneficial pharmaceutical compounds.
Planta Medica 11/2010; 77(7):742-8. · 2.15 Impact Factor
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Annalen der Chemie und Pharmacie 10/2010; 2010(34):6531 - 6534. · 3.10 Impact Factor
