Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12

George Pettit, Yoshiaki Kamano, Haruhisa Kizu, Claude Dufresne, Cherry L. Herald, Roger J. Bontems, Jean M. Schmidt, Fred E. Boettner, Ronald A. Nieman

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Abstract

Two antineoplastic cyclic depsipeptides designated dolastatin 11(1) and dolastatin 12 (2) were isolated from the Indian Ocean sea hare Dolabella auricularia. Dolastatins 11 and 12 inhibited growth of the PS leukemia with ED50 2.7 × 10-3 and 7.5 × 10-2 μg/mL respectively. Detailed structural studies employing 400 MHz 1H,1H-COSY, 1H,13C-COSY, NOE, and HMBC experiments (in addition to acid and base hydrolysis, followed by GC-MS analysis) led to structure 1 for dolastatin 11 and to structure 2 for dolastatin 12.

Original languageEnglish (US)
Pages (from-to)553-558
Number of pages6
JournalHeterocycles
Volume28
Issue number2
StatePublished - Jan 1 1989

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Pettit, G., Kamano, Y., Kizu, H., Dufresne, C., Herald, C. L., Bontems, R. J., Schmidt, J. M., Boettner, F. E., & Nieman, R. A. (1989). Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12. Heterocycles, 28(2), 553-558.