Advertisement

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

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 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

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

References

  1. [1]
    Raffa D., Maggio B., Raimondi M. V., Plescia F., Daidone G., Eur. J. Med. Chem., 2017, 142, 213CrossRefGoogle Scholar
  2. [2]
    Verma A. K., Pratap R., Tetrahydron, 2012, 68(41), 8523CrossRefGoogle Scholar
  3. [3]
    Vogel S., Ohmayer S., Brunner G., Heilmann J., Bioorg. Med. Chem., 2008, 16(8), 4286CrossRefGoogle Scholar
  4. [4]
    Lei Q., Zhang S., Liu M., Li J., Zhang X., Long Y., Mol. Divers., 2017, 21(4), 957CrossRefGoogle Scholar
  5. [5]
    Dong X., Liu Y., Yan J., Jiang C., Chen J., Liu T., Hu Y., Bioorg. Med. Chem., 2008, 16(17), 8151CrossRefGoogle Scholar
  6. [6]
    Neves M. P., Cidade H., Pinto M., Silva A. M. S., Gales L., Damas A. M., Lima R.T., Vasconcelos M. H., Nascimento M. S. J., Eur. J. Med. Chem., 2011, 46(6), 2562CrossRefGoogle Scholar
  7. [7]
    Wen Z., Zhang Y., Wang X., Zeng X., Hu Z., Liu Y., Xie Y., Liang G., Zhu J., Luo H., Xu B., Eur. J. Med. Chem., 2017, 133, 227CrossRefGoogle Scholar
  8. [8]
    Basabe P., de Roman M., Marcos I. S., Diez D., Blanco A., Bodero O., Mollinedo F., Eur. J. Med. Chem., 2010, 45(9), 4258CrossRefGoogle Scholar
  9. [9]
    Wang C., Wu P., Shi J. F., Jiang Z. H., Wei X. Y., Eur. J. Med. Chem., 2015, 100, 139CrossRefGoogle Scholar
  10. [10]
    Jung A. H., Jin E. S., Choi J. R., Manh T. H., Kim S. Y., Min S. B., Son K. Y., Ahn R. B., Kim W. B., Sohn S. S., Choi S. J., Arch. Pharm. Res., 2011, 34(12), 2087CrossRefGoogle Scholar
  11. [11]
    Zhang B., Duan D., Ge C., Yao J., Liu Y., Li X., Fang J., J. Med. Chem., 2015, 58(4), 1795CrossRefGoogle Scholar
  12. [12]
    Chen M., Shi L., Tang J., Wang Q. A., Chem. Res. Chinese Universities, 2016, 32(5), 754CrossRefGoogle Scholar
  13. [13]
    Nguyen V. S., Li W., Li Y., Wang Q. A., Med. Chem. Res., 2017, 26, 1585CrossRefGoogle Scholar
  14. [14]
    Nguyen V. S., Shi L., Wang S. C., Wang Q. A., Anti-cancer Agents Med. Chem., 2017, 17(1), 137CrossRefGoogle Scholar
  15. [15]
    Liu J. D., Chen L., Cai S. L., Wang Q. A., Carbohyd. Res., 2012, 357, 41CrossRefGoogle Scholar
  16. [16]
    Wu Z., Cai S. L., Fan W. J., Wang Q. A., Chin. J. Org. Chem., 2012, 32(7), 1296CrossRefGoogle Scholar
  17. [17]
    Ou L., Han S., Ding W., Che Z., Ye Z., Yang H., Zhang G., Lou Y., Chen J., Yu Y., Mol. Divers., 2011, 15(3), 665CrossRefGoogle Scholar
  18. [18]
    Pinhey J. T., Southwell I. A., Aust. J. Chem., 1973, 26(2), 409CrossRefGoogle Scholar
  19. [19]
    Song Y. P., Xin Z. Y., Wan Y. M., Li J. B., Ye B. P., Xue X. W., Eur. J. Med. Chem., 2015, 90, 695CrossRefGoogle Scholar

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

Personalised recommendations