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学科主题: Chemistry, Multidisciplinary
题名: Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids
作者: Wu, J ; Zhang, S ; Bruhn, T ; Xiao, Q ; Ding, HX ; Bringmann, G
通讯作者: wwujun2003@yahoo.com ; bringmann@chemie.uni-wuerzburg.de
关键词: antifeedant activity ; biosynthesis ; configuration determination ; natural products ; xylogranatins
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2008
卷: 14, 期:4, 页:1129-1144
收录类别: sci
部门归属: [Wu, Jun; Zhang, Si] Chinese Acad Sci, Guangdong Key Lab Marine Mat Med, S China Sea Inst Oceanol, Guangzhou 510301, Peoples R China; [Bruhn, Torsten; Bringmann, Gerhard] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany; [Xiao, Qiang; Ding, Haixin] Jiangxi Sci & Technol Normal Univ, Inst Organ Chem, Nanchang 330013, Peoples R China
项目归属: LMB
摘要: Thirteen limonoids with a new carbon skeleton, the xylogranatins F-R (1-13), have been isolated from the seeds of a Chinese mangrove, Xylocarpus granatum; two recently reported compounds, xylogranatins C and D were also isolated. Their structures were elucidated on the basis of spectroscopic data and chemical methods. The absolute configurations of these compounds were determined by using the modified Mosher MTPA ester method and by quantum chemical circular dichroism (CD) calculations. Xylogranatins F-Q are the first aromatic B-ring limonoids found in nature. They belong to two substructural classes, of which one (1-3) contains a pyridine ring while the other one (412) contains a central furan core. Xylogranatins C and R can be considered to be key biosynthetic intermediates, while xylogranatin D, the only limonoid found so far with a carbon skeleton that conatains a C-30-C-9 linkage, is apparently an artifact. The structures of these compounds suggest a new biogenetic pathway to tetranortriterpenoids. Xylogranatins F, G and R were found to exhibit marked antifeedant activity against the third instar larvae of Mythimna separata (Walker) at a concentration of 1 mg mL(-1). The most potent compound tested was xylogranatin G. Its AFC(50) (concentration for 50% antifeedant activity) values at the exposure times of 24 and 48 h were 0.31 and 0.30 mg mL(-1), respectively.
WOS记录号: WOS:000252879800007
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内容类型: 期刊论文
URI标识: http://ir.scsio.ac.cn/handle/344004/5012
Appears in Collections:中科院海洋生物资源可持续利用重点实验室_期刊论文

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Wu, J; Zhang, S; Bruhn, T; Xiao, Q; Ding, HX; Bringmann, G.Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids,CHEMISTRY-A EUROPEAN JOURNAL,2008,14(4):1129-1144
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