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Chemical Research in Chinese Universities

, Volume 34, Issue 4, pp 564–570 | Cite as

Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents

  • Kingsadingthongkham Vongdeth
  • Liqiong Ran
  • Lili Yan
  • Qiuan Wang
Article
  • 27 Downloads

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.

Keywords

Prenylated flavonoid Claisen rearrangement Antiproliferative activity Cancer cell 

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Supplementary material

40242_2018_8013_MOESM1_ESM.pdf (2.5 mb)
Synthesis and Activity Evaluation of Novel Prenylated Flavonoids as Antiproliferative Agents

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Kingsadingthongkham Vongdeth
    • 1
    • 2
  • Liqiong Ran
    • 1
  • Lili Yan
    • 1
  • Qiuan Wang
    • 1
  1. 1.College of Chemistry and Chemical EngineeringHunan UniversityChangshaP. R. China
  2. 2.Department of Chemistry, Faculty of Natural SciencesNational University of LaosVientianeLao People’s Democratic Republic

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