Synthesis and Anticancer Activity of 8-Allyl Garcinol

doi:10.6023/cjoc201701017

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2086-2093.DOI: 10.6023/cjoc201701017 Previous Articles Next Articles

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8-烯丙基山竹醇的合成及其抗癌活性研究

曹菁^a, 韩超明^a, 张桂莲^b, 周新莹^b, 李舒雯^a, 杜银端^a, 赵帅^a, 张辛燕^b, 陈新^a

a 常州大学制药与生命科学学院常州 213164;
b 首都医科大学附属北京口腔医院口腔医学研究所北京 100050

收稿日期:2017-01-09 修回日期:2017-03-25 发布日期:2017-04-10
通讯作者: 张辛燕, 陈新 E-mail:xinyanzhangzh@126.com;xinchen@cczu.edu.cn
基金资助:
国家自然科学基金（Nos.21272029，81272982）资助项目.

Synthesis and Anticancer Activity of 8-Allyl Garcinol

Cao Jing^a, Han Chaoming^a, Zhang Guilian^b, Zhou Xinying^b, Li Shuwen^a, Du Yinduan^a, Zhao Shuai^a, Zhang Xinyan^b, Chen Xin^a

a School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164;
b Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050

Received:2017-01-09 Revised:2017-03-25 Published:2017-04-10
Contact: 10.6023/cjoc201701017 E-mail:xinyanzhangzh@126.com;xinchen@cczu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21272029, 81272982).

1. Synthesis and Anticancer Activity of 8-Allyl Garcinol.PDF(1151KB)

Abstract

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-methylbut-2-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.

Key words: garcinol, Effenburger cyclization, synthesis, structural modification

Cite this article

Cao Jing, Han Chaoming, Zhang Guilian, Zhou Xinying, Li Shuwen, Du Yinduan, Zhao Shuai, Zhang Xinyan, Chen Xin. Synthesis and Anticancer Activity of 8-Allyl Garcinol[J]. Chin. J. Org. Chem., 2017, 37(8): 2086-2093.

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8-烯丙基山竹醇的合成及其抗癌活性研究

Synthesis and Anticancer Activity of 8-Allyl Garcinol

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