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Khayanolides from African mahogany Khaya senegalensis (Meliaceae): A revision

文献类型：期刊论文

作者Zhang, Huaping4; Tan, Junjie5; VanDerveer, Don1; Wang, Xi3; Wargovich, Michael J.2; Chen, Feng4
刊名PHYTOCHEMISTRY
出版日期2009-01
卷号70期号:2页码:294-299
关键词Khaya senegalensis Meliaceae African mahogany Limonoid Khayanolide Structure revision 1-O-acetylkhayanolide B Khayanolide B Khayanolide E 1-O-deacetylkhayanolide E 6-Dehydroxylkhayanolide E Methyl 6-hydroxyangolensate
ISSN号0031-9422
DOI10.1016/j.phytochem.2008.12.004
文献子类Article
英文摘要Five khayanolides (1-O-acetylkhayanolide B 1, khayanolide B 2, khayanolide E 3, 1-O-deacetylkhayanolide E 4, 6-dehydroxylkhayanolide E 5) were isolated from the stem bark of African mahogany Khaya senegalensis (Meliaceae). Their structures and absolute configurations were determined through extensive spectroscopic analyses including MS, NMR, and single-crystal X-ray diffraction experiments. The results established that two previously reported khayanolicles, 1 alpha-acetoxy-2 beta,3 alpha,6,8 alpha, 14 beta-pentahydroxy-[4.2.1 (10,30).1(1.4)]-tricyclomeliac-7-oate 6 and 1 alpha,2 beta,3 alpha,6,8 alpha,14 beta-hexahydroxy-[4.2.1 (10.30).1(1,4)]-tricyclomeliac-7-oate 7, were, in fact, 1-O-acetylkhayanolide B 1 and khayanolide B 2, and that the two reported phragmalin derivatives, methyl 1 alpha-acetoxy-6,8 alpha,14 beta,30 beta-tetrahydroxy-3-oxo-[3.3.1 (10.2).1(1.4)]-tricyclomeliac-7-oate 8 and methyl 1 alpha,6,8 alpha,14 beta,30 beta-pentahydroxy-3-oxo-[3.3.1 (10.2).1(1.4)]-tricyclomeliac-7-oate 9. were, in fact, khayanolide E 3 and 1-O-deacetylkhayanolide E 4, respectively. Based on the results from this study and consideration of the biogenetic pathway, the methyl 6-hydroxyangolensate in African mahogany K. senegalensis should have a C-6 S configuration while methyl 6-hydroxyangolensate in genuine mahogany Swietenia species should have a C-6 R configuration. Published by Elsevier Ltd.
WOS关键词STEM BARK ; LIMONOIDS ; GRANDIFOLIOLA ; EXTRACTIVES ; CHEMISTRY ; SKELETON ; JUSS
资助项目National Institutes of Health (NIH), Bethesda, MD, USA[R21CA107138] ; Clemson University Vice President's Research Investment Fund[00000000]
WOS研究方向Biochemistry & Molecular Biology ; Plant Sciences
语种英语
WOS记录号WOS:000264584000019
出版者PERGAMON-ELSEVIER SCIENCE LTD
源URL[http://119.78.100.183/handle/2S10ELR8/279401]  
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Chen, Feng
作者单位1.Clemson Univ, Dept Chem, Clemson, SC 29634 USA;
2.Hollings Canc Ctr, Dept Cell & Mol Pharmacol, Charleston, SC 29425 USA
3.Clemson Univ, Dept Biochem & Genet, Clemson, SC 29634 USA;
4.Clemson Univ, Dept Food Sci & Human Nutr, Clemson, SC 29634 USA;
5.Chinese Acad Sci, State Key Lab Drug Res, Inst Mat Med, Shanghai Inst Biol Sci, Shanghai 201203, Peoples R China;
推荐引用方式
GB/T 7714		 Zhang, Huaping,Tan, Junjie,VanDerveer, Don,et al. Khayanolides from African mahogany Khaya senegalensis (Meliaceae): A revision[J]. PHYTOCHEMISTRY,2009,70(2):294-299.
APA Zhang, Huaping,Tan, Junjie,VanDerveer, Don,Wang, Xi,Wargovich, Michael J.,&Chen, Feng.(2009).Khayanolides from African mahogany Khaya senegalensis (Meliaceae): A revision.PHYTOCHEMISTRY,70(2),294-299.
MLA Zhang, Huaping,et al."Khayanolides from African mahogany Khaya senegalensis (Meliaceae): A revision".PHYTOCHEMISTRY 70.2(2009):294-299.

入库方式： OAI收割

来源：上海药物研究所

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