Ivorenoids A-F: limonoids from Khaya ivorensis

被引：15
|
作者：
Wu, Wen-Bin [1 ]
Zhang, Hua [1 ]
Liu, Hong-Chun [1 ]
Dong, Shi-Hui [1 ]
Wu, Yan [1 ]
Ding, Jian [1 ]
Yue, Jian-Min [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 22期
关键词：
Khaya ivorensis; Limonoid; Ivorenoid; Cytotoxicity; STEM BARK; MACROLIDE;
D O I：
10.1016/j.tet.2014.04.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Six new limonoids, ivorenoids A-F (1-6), along with ten known analogues, were isolated from an ethanolic extract of the stems of Khaya ivorensis. Their structures were elucidated on the basis of spectroscopic analyses. Compounds 1 and 2 possessed a rare rearranged skeleton of khayanolides and a unique gamma-lactone (C-16/C-8) replacing the common and characteristic delta-lactone D-ring (C-16/C-17) of limonoids. A mechanism of the interesting deuteration of H-2 and H-15 beta of 1, and H-15 beta of the solvent CD3OD due to the keto enol tautomerism was demonstrated. Compounds 3 and 6 showed moderate activity against HL-60 cell line with IC50 values of 15.3 and 17.5 mu M, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3570 / 3575
页数：6
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