Synthesis and Anticancer Activity of 8-Allyl Garcinol

被引：3

作者：

Cao, Jing ^{[1
]}

Han, Chaoming ^{[1
]}

Zhang, Guilian ^{[2
]}

Zhou, Xinying ^{[2
]}

Li, Shuwen ^{[1
]}

Du, Yinduan ^{[1
]}

Zhao, Shuai ^{[1
]}

Zhang, Xinyan ^{[2
]}

Chen, Xin ^{[1
]}

机构：

[1] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, Changzhou 213164, Peoples R China

[2] Capital Med Univ, Beijing Stomatol Hosp, Beijing Inst Dent Res, Beijing 100050, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 37卷 / 08期

基金：

中国国家自然科学基金;

关键词：

garcinol; Effenburger cyclization; synthesis; structural modification; (+/-)-CLUSIANONE; INHIBITION; APOPTOSIS;

D O I：

10.6023/cjoc201701017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Garcinol, isolated from the fruit rind of Garcinia indica, shows anti-carcinogenic and anti-inflammatory activities. However, the C(8) side chain of garcinol is so large that it may influence the bioactivity of the compound. 8-Allyl garcinol, in which the bulky side chain at C(8) position of garcinol is replaced with much smaller allyl group, was synthesized through a 12-step procedure. Starting from 1,3-cyclohexandione, the key intermediate (+/-)-1-hydroxy-5,5-dimethyl-4,6-bis(3-methylbut2- en-1-yl) bicyclo[3.3.1] non-2-ene-3,9-dione (8) was obtained via Effenburger cyclization. Through additional 5-steps, 8-allyl garcinol was prepared. The thiazolyl blue tetrazolium bromide (MTT) results indicated that 8-allyl garcinol shows strong inhibitory activity on cell proliferation of oral cancer cell lines.

引用

页码：2086 / 2093

页数：8

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