Chinese Journal of Organic Chemistry >
Synthesis and Anticancer Activity of 8-Allyl Garcinol
Received date: 2017-01-09
Revised date: 2017-03-25
Online published: 2017-04-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21272029, 81272982).
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
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]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2086 -2093 . DOI: 10.6023/cjoc201701017
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