Meliaceous Limonoids: Chemistry and Biological Activities

被引:393
作者
Tan, Qin-Gang [1 ,2 ]
Luo, Xiao-Dong [1 ]
机构
[1] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources W China, Kunming Inst Bot, Kunming 650204, Peoples R China
[2] Guilin Med Univ, Guilin 541004, Peoples R China
关键词
AZADIRACHTA-INDICA JUSS; A; WEST-AFRICAN TIMBERS; C-SECO LIMONOIDS; CARAPA-GUIANENSIS AUBLET; SWIETENIA-MAHAGONI JACQ; STRUCTURE BIOACTIVITY RELATIONSHIPS; PERFORMANCE LIQUID-CHROMATOGRAPHY; HELICOVERPA-ARMIGERA LEPIDOPTERA; CNAPHALOCROCIS-MEDINALIS GUENEE; GROWTH-REGULATING ACTIVITIES;
D O I
10.1021/cr9004023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Some of the important naturally occurring limonoids from Meliaceae discovered in the last six decades, from 1942 to June 30, 2010, and their various bioactivities, are discussed. The cedrelone-class limonoids are characterized as the 5,6-enol-7-one derivatives and Burke et al. presented the chemical correlation of anthothecol with hirtin. Under mildly acid conditions, the first stage of the ring-opening of havanensin gives a 15-hydroxy-14- carbonium ion, which then either undergoes Wagner-Meerwein rearrangement or loses a proton to give a 15-ketone enolate and involves participation of the oxygenated function at C-7. The photooxidation of salannin and nimbin by UV light in the presence of oxygen led to more polar unstable intermediates that rearranged on silica gel to two final products in which the furan ring had been oxidized to isomeric hydroxybutenolides.
引用
收藏
页码:7437 / 7522
页数:86
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