Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents

doi:10.1007/s40242-018-8013-5

Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (4): 564-570.doi: 10.1007/s40242-018-8013-5

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Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents

Kingsadingthongkham VONGDETH^1,2, RAN Liqiong¹, YAN Lili¹, WANG Qiuan¹

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Department of Chemistry, Faculty of Natural Sciences, National University of Laos, Vientiane P. O. BOX 7322 Lao P. D. R

Received:2018-01-12 Online:2018-08-01 Published:2018-05-07
Contact: WANG Qiuan E-mail:wangqa@hnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.J1210040, 21173074).

Abstract

Abstract: Twenty prenylated flavonoids 1-20 were synthesized by glycoside hydrolysis, dehydrogenation, selective O-methylation, O-prenylation and Claisen rearrangement reaction, from abundant and inexpensive natural flavonoids naringin, hespiredin, quercetin and myricetin. Among them, 1-7, 10-15 and 17-20 are novel compounds, the natural product 3,3',4',7-tetramethoxy-8-prenyl-5-hydroxy flavonoid(16) was synthesized in a high yield. Their antiprolirative activities were evaluated in vitro on a panel of three human cancer cell lines(HeLa, HCC1954 and SK-OV-3). The results show that most of the target compounds displayed moderate to potent antiprolirative activities against the three cancer cells with half maximal inhibitory concentration(IC₅₀) values from 0.49 μmol/L to 95.07 μmol/L. Among them, 3',4',7-trimethoxyl-5-hydroxyl-8-prenyl flavonoid(12) exhibited the strongest antiprolirative activity against the three cancer cells mentioned above with IC₅₀ values of 0.91-7.08 μmol/L. 3',7-Dimethoxy-5-O-prenyl flavone(6) and 3',4',7-trimethoxy-5-O-prenyl flavone(10) showed selective antiproliferative activity against HCC1954 cells with IC₅₀ value of 0.49 and 5.32 μmol/L, respectively.

Key words: Prenylated flavonoid, Claisen rearrangement, Antiproliferative activity, Cancer cell

Kingsadingthongkham VONGDETH, RAN Liqiong, YAN Lili, WANG Qiuan. Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents[J]. Chemical Research in Chinese Universities, 2018, 34(4): 564-570.

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Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents

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