Isolation, structure, synthesis, and antimitotic properties of combretastatins b-3 and b-4 from combretum caffrum

George Pettit, Sheo Bux Singh, Jean M. Schmidt, Margaret L. Niven, Ernest Hamel, Chii M. Lin

Research output: Contribution to journalArticle

74 Scopus citations

Abstract

Further investigation of a CH9Cl2 fraction prepared from the South African tree Combretum caffrum for substances inhibitory to the murine P-388 lymphocytic leukemia (PS system) cell line has led to the isolation of two new bibenzyls, designated combretastatins B-3 [3] and B-4 [4], accompanied by the previously known bibenzyls 7, 8, and 9. The structure of each substance was ascertained by results of mass and nmr spectral analyses and confirmed by crystal structure determination (for 7) or synthesis. Combretastatins B-3 and B-4 gave PS ED50 values of 0.4 and 1.7 ug/ml, respectively, and bibenzyls 7, 8, and 9 were comparably cell growth inhibitory against the PS cell line with ED50 results of 1.7, 2.5, and 0.25 ug/ml, respectively. All the bibenzyls caused leukemia cells to accumulate in mitosis at cytotoxic drug concentrations; however, a wide range of in vitro activity against the protein tubulin (the major component of the mitotic spindle) was observed.

Original languageEnglish (US)
Pages (from-to)517-527
Number of pages11
JournalJournal of Natural Products
Volume51
Issue number3
DOIs
StatePublished - May 1988

ASJC Scopus subject areas

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

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