Bouvardin and Deoxybouvardin, Antitumor Cyclic Hexapeptides from Bouvardia ternifolia (Rubiaceae)

D. Jolad Shivanand, Joseph J. Hoffmann, Sterling J. Torrance, Richard M. Wiedhopf, Jack R. Cole, Satish K. Arora, Robert B. Bates, Robin L. Gargiulo, George R. Kriek

Research output: Contribution to journalArticlepeer-review

197 Scopus citations

Abstract

Bouvardin (C40H48N6O10) and deoxybouvardin (C40H48N6O9), both of which show high antitumor activity in the 3PS, B1, and KB systems, were isolated from the methanol extract of Bouvardia ternifolia (Rubiaceae). An x-ray study on bouvardin containing a methanol of crystallization (P212121, a=9.009 (3), b=12.623 (4), c=42.970 (19) Å, Z=4) and hydrolytic studies showed it to be Ia, a cyclic hexapeptide composed of two L-alanines, a D-alanine, and three modified N-methyl-L-tyrosines. The most unusual feature is a 14-membered ring formed by oxidative coupling of the phenolic oxygen of one tyrosine with a carbon ortho to the phenolic hydroxyl group of an adjacent tyrosine. Spectral comparison with bouvardin indicated deoxybouvardin to be Ib, identical with bouvardin except for the lack of a β-hydroxyl group on one of the tyrosines.

Original languageEnglish (US)
Pages (from-to)8040-8044
Number of pages5
JournalJournal of the American Chemical Society
Volume99
Issue number24
DOIs
StatePublished - Jan 1 1977

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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