Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1

George R. Pettit, Zbigniew Cichacz, Jozsef Barkoczy, Ann Christine Dorsaz, Delbert L. Herald, Michael D. Williams, Dennis L. Doubek, Jean M. Schmidt, Larry P. Tackett, Daniel C. Brune, Ronald L. Cerny, John N.A. Hooper, Gerald J. Bakus

Research output: Contribution to journalArticle

76 Scopus citations

Abstract

A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 µg/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.

Original languageEnglish (US)
Pages (from-to)260-267
Number of pages8
JournalJournal of Natural Products
Volume56
Issue number2
DOIs
StatePublished - Feb 1993

ASJC Scopus subject areas

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

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    Pettit, G. R., Cichacz, Z., Barkoczy, J., Dorsaz, A. C., Herald, D. L., Williams, M. D., Doubek, D. L., Schmidt, J. M., Tackett, L. P., Brune, D. C., Cerny, R. L., Hooper, J. N. A., & Bakus, G. J. (1993). Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1. Journal of Natural Products, 56(2), 260-267. https://doi.org/10.1021/np50092a011