Antineoplastic agents. 510. Isolation and structure of dolastatin 19 from the Gulf of California sea hare Dolabella auricularia

George Pettit, Jun-Ping Xu, Dennis L. Doubek, Jean Chapuis, Jean M. Schmidt

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

The Gulf of California shell-less mollusc Dolabella auricularia has been found to contain a new 14-membered macrocyclic lactone linked to a 2,4-di-O-methyl-L-α-rhamnopyranoside, designated dolastatin 19 (1). The new cancer cell growth inhibitor (1, 8.33 × 10-8% yield) was obtained by bioassay (P388 lymphocytic leukemia and human cancer cell lines) directed isolation, accompanied by debromoaplysiatoxin (9.17 × 10 -7% yield) and anhydrodebromoaplysiatoxin (2.0 × 10 -7% yield). The structures were determined on the basis of analyses of high-resolution mass spectra and high-field NMR data. All the relative stereochemistry for the chiral centers was designated by utilizing NMR techniques.

Original languageEnglish (US)
Pages (from-to)1252-1255
Number of pages4
JournalJournal of Natural Products
Volume67
Issue number8
DOIs
StatePublished - Aug 2004

ASJC Scopus subject areas

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

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