Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids
Wu, J; Zhang, S; Bruhn, T; Xiao, Q; Ding, HX; Bringmann, G; wwujun2003@yahoo.com; bringmann@chemie.uni-wuerzburg.de
2008
发表期刊CHEMISTRY-A EUROPEAN JOURNAL
ISSN0947-6539
卷号14期号:4页码:1129-1144
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.
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
关键词Antifeedant Activity Biosynthesis Configuration Determination Natural Products Xylogranatins
学科领域Chemistry, Multidisciplinary
收录类别sci
资助项目LMB
WOS记录号WOS:000252879800007
引用统计
文献类型期刊论文
条目标识符http://ir.scsio.ac.cn/handle/344004/5012
专题中科院海洋生物资源可持续利用重点实验室
通讯作者wwujun2003@yahoo.com; bringmann@chemie.uni-wuerzburg.de
推荐引用方式
GB/T 7714
Wu, J,Zhang, S,Bruhn, T,et al. Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(4):1129-1144.
APA Wu, J.,Zhang, S.,Bruhn, T.,Xiao, Q.,Ding, HX.,...&bringmann@chemie.uni-wuerzburg.de.(2008).Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids.CHEMISTRY-A EUROPEAN JOURNAL,14(4),1129-1144.
MLA Wu, J,et al."Xylogranatins F-R: Antifeedants from the chinese mangrove, Xylocarpus granatum, a new biogenetic pathway to tetranortriterpenoids".CHEMISTRY-A EUROPEAN JOURNAL 14.4(2008):1129-1144.
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