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Bioorg Chem. 2017 Apr;71:74-80. doi: 10.1016/j.bioorg.2017.01.013. Epub 2017 Jan 22.

The C8 side chain is one of the key functional group of Garcinol for its anti-cancer effects.

Author information

1
Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050, PR China.
2
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China.
3
Hua Lookeng Honors College, Changzhou University, Jiangsu 213164, PR China.
4
Beijing Institute of Dental Research, Beijing Stomatological Hospital, Capital Medical University, Beijing 100050, PR China. Electronic address: xinyanzhangzh@126.com.
5
School of Pharmaceutical Engineering and Life Sciences, Changzhou University, Jiangsu 213164, PR China. Electronic address: xinchen@cczu.edu.cn.

Abstract

Garcinol from the fruit rind of Garcinia indica shows anti-carcinogenic and anti-inflammatory properties, but its mechanism and key functional groups were still need to be identified. Our previous computer modeling suggested that the C8 side chain of Garcinol is so large that it may influence the bioactivity of the compound. 8-Me Garcinol, a derivative of Garcinol in which the bulky side chain at the C8 position of Garcinol is replaced with a much smaller methyl group, was synthesized through a 12-step procedure starting from 1,3-cyclohexanedione. The antitumor activity of Garcinol and 8-Me Garcinol was evaluated in vitro by MTT, cell cycle and cell apoptosis assays. The results showed that 8-Me Garcinol had weaker inhibitory activity on cells proliferation, and little effects on cell cycle and apoptosis in oral cancer cell line SCC15 cells when compared with Garcinol. All of the results indicated 8-Me Garcinol exerts weaker antitumor activity than Garcinol, and the C8 side chain might be an important active site in Garcinol. Changing the C8 side chain will affect the inhibitory effect of Garcinol.

KEYWORDS:

8-Me Garcinol; Garcinol; Oral squamous cell carcinoma cell; Synthesis

PMID:
28169002
DOI:
10.1016/j.bioorg.2017.01.013
[Indexed for MEDLINE]

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