Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

Fredyc Díaz, Daniel Chávez, Dongho Lee, Qiuwen Mi, Hee Byung Chai, Ghee T. Tan, Leonardus B.S. Kardono, Soedarsono Riswan, Craig R. Fairchild, Robert Wild, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, A. Douglas Kinghorn

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65 Citations (Scopus)

Abstract

Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3′-dihexanoyloxy-3,6,7,4′-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation, However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lul, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.

Original languageEnglish
Pages (from-to)865-867
Number of pages3
JournalJournal of Natural Products
Volume66
Issue number6
Publication statusPublished - 2003 Jun 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Díaz, F., Chávez, D., Lee, D., Mi, Q., Chai, H. B., Tan, G. T., Kardono, L. B. S., Riswan, S., Fairchild, C. R., Wild, R., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., & Kinghorn, A. D. (2003). Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo. Journal of Natural Products, 66(6), 865-867.