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

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Abstract

Further investigation of a CH2Cl2 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
StatePublished - 1988

Fingerprint

Combretum caffrum
Bibenzyls
Combretum
Antimitotic Agents
cell lines
lymphocytic leukemia
mitotic spindle apparatus
synthesis
crystal structure
tubulin
leukemia
mitosis
cell growth
Cells
Lymphoid Leukemia
Cell Line
drugs
Spindle Apparatus
mice
Cell growth

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Isolation, structure, synthesis, and antimitotic properties of combretastatins B-3 and B-4 from Combretum caffrum. / Pettit, George; Singh, Sheo Bux; Schmidt, Jean M.; Niven, Margaret L.; Hamel, Ernest; Lin, Chii M.

In: Journal of Natural Products, Vol. 51, No. 3, 1988, p. 517-527.

Research output: Contribution to journalArticle

Pettit, George ; Singh, Sheo Bux ; Schmidt, Jean M. ; Niven, Margaret L. ; Hamel, Ernest ; Lin, Chii M. / Isolation, structure, synthesis, and antimitotic properties of combretastatins B-3 and B-4 from Combretum caffrum. In: Journal of Natural Products. 1988 ; Vol. 51, No. 3. pp. 517-527.
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