Structural and stereochemical studies of alpha-methylene-gamma-lactone-bearing cembrane diterpenoids from a South China Sea Soft Coral Lobophytum crassum
文献类型：期刊论文
| 作者 | Zhang, Wen1,2; Krohn, Karsten2; Ding, Jian1 ; Miao, Ze-Hong1; Zhou, Xiu-Hong1; Chen, Si-Han1; Pescitelli, Gennaro3; Salvadori, Piero3; Kurtan, Tibor4; Guo, Yue-Wei1
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| 刊名 | JOURNAL OF NATURAL PRODUCTS
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| 出版日期 | 2008-06 |
| 卷号 | 71期号:6页码:961-966 |
| ISSN号 | 0163-3864 |
| DOI | 10.1021/np800081p |
| 文献子类 | Article |
| 英文摘要 | Four new alpha-methylene-gamma-lactone-bearing cembranoids, 20-acetylsinularolide B (6), presinularolide B (7), 3-dehydroxy-lpresinularolide B (8), and 3-dehydroxyl-20-acetylpresinularolide B (9), together with five known analogues, sinularolides B-E (1-4) and 20-acetylsinularolide C (5), were isolated from a South China Sea soft coral Lobophytum crassum. Their structures and relative stereochemistry were established by a combination of detailed spectroscopic data analysis and chemical correlations. The structures of 1-9 were further confirmed by an X-ray diffraction study on a single crystal of sinularolide B (1). The absolute configurations of sinularolide B (1) and presinularolide B (7) were determined by a novel solid-state CD/TDDFT approach and by a modified Mosher's method, respectively. This study also revealed that the coupling constant between the lactonic methine protons ((3)J(1,2)) varies considerably with different functional groups on the cembrane ring and that the determination of the stereochemistry of lactone ring fusion based on this coupling constant is risky. In a bioassay, sinularolides B and C (1 and 2) and new cembranoids 7 and 8 showed in vitro cytotoxicity against the tumor cell lines A-549 and P-388. |
| WOS关键词 | GORGONIAN EUNICEA-SUCCINEA ; STATE CD/TDDFT APPROACH ; ABSOLUTE-CONFIGURATION ; CLAVULARIA-KOELLIKERI ; SECONDARY METABOLITES ; SARCOPHYTON-LATUM ; NATURAL-PRODUCTS ; NMR APPLICATION ; MOSHER METHOD ; PHOMA SP |
| WOS研究方向 | Plant Sciences ; Pharmacology & Pharmacy |
| 语种 | 英语 |
| WOS记录号 | WOS:000257227200007 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/272907]  |
| 专题 | 天然药物化学研究室 中科院受体结构与功能重点实验室 新药研究国家重点实验室 |
| 通讯作者 | Guo, Yue-Wei |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Univ Gesamthsch Paderborn, Dept Chem, D-33098 Paderborn, Germany; 3.Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy; 4.Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary |
| 推荐引用方式 GB/T 7714 | Zhang, Wen,Krohn, Karsten,Ding, Jian,et al. Structural and stereochemical studies of alpha-methylene-gamma-lactone-bearing cembrane diterpenoids from a South China Sea Soft Coral Lobophytum crassum[J]. JOURNAL OF NATURAL PRODUCTS,2008,71(6):961-966. |
| APA | Zhang, Wen.,Krohn, Karsten.,Ding, Jian.,Miao, Ze-Hong.,Zhou, Xiu-Hong.,...&Guo, Yue-Wei.(2008).Structural and stereochemical studies of alpha-methylene-gamma-lactone-bearing cembrane diterpenoids from a South China Sea Soft Coral Lobophytum crassum.JOURNAL OF NATURAL PRODUCTS,71(6),961-966. |
| MLA | Zhang, Wen,et al."Structural and stereochemical studies of alpha-methylene-gamma-lactone-bearing cembrane diterpenoids from a South China Sea Soft Coral Lobophytum crassum".JOURNAL OF NATURAL PRODUCTS 71.6(2008):961-966. |
入库方式： OAI收割
来源：上海药物研究所
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