Synthesis and Anti-tumor Activity of Novel Garcinol Analogs

doi:10.6023/cjoc202001016

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1578-1587.DOI: 10.6023/cjoc202001016 Previous Articles Next Articles

山竹醇新类似物的合成及其抗肿瘤活性研究

周汇源^a, 吴堰霖^b, 黄典红^a, 张铭婷^a, 陈欢明^a, 钱明成^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江苏常州 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:2020-01-09 修回日期:2020-03-09 发布日期:2020-04-10
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（Nos.21272029，81772868）资助项目.

Synthesis and Anti-tumor Activity of Novel Garcinol Analogs

Zhou Huiyuan^a, Wu Yanlin^b, Huang Dianhong^a, Zhang Mingting^a, Chen Huanming^a, Qian Mingcheng^a, Zhao Shuai^a, Zhang Xinyan^b, Chen Xin^a

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

Received:2020-01-09 Revised:2020-03-09 Published:2020-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21272029, 81772868).

1. 201578S.pdf(4582KB)

Abstract

Garcinol possesses a wide range of biological activities, such as anti-inflammation, anti-tumors, anti-oxidation, induction of apoptosis and so on. In this paper, the modification of the side chains in garcinol was carried out to enhance its anti-tumor activity. Employing acetylacetone as starting material, three new analogs of garcinol were prepared by means of Michael addition, Knoevenagel condensation, and so on. Furthemore, their biological activity was assessed by methyl thiazolyl tetrazolium (MTT) method and the structure-activity relationship was analyzed. The results showed that the inhibitory activities of the three new analogs on oral squamous cell carcinoma were moderately lower than that of garcinol. Hence, the isoprenyl group at the C4 position and the allylic group at the C8 position might play vital roles for the biological activity of garcinol.

Key words: garcinol, structural modification, Michael addition, anti-tumor

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Zhou Huiyuan, Wu Yanlin, Huang Dianhong, Zhang Mingting, Chen Huanming, Qian Mingcheng, Zhao Shuai, Zhang Xinyan, Chen Xin. Synthesis and Anti-tumor Activity of Novel Garcinol Analogs[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1578-1587.

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山竹醇新类似物的合成及其抗肿瘤活性研究

Synthesis and Anti-tumor Activity of Novel Garcinol Analogs

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