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 journalArticle

38 Citations (Scopus)

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

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antineoplastic agents
Gulf of California
Oceans and Seas
Antineoplastic Agents
Nuclear magnetic resonance
Molluscs
Lymphoid Leukemia
Growth Inhibitors
Stereochemistry
Bioassay
Mollusca
Lactones
Biological Assay
Neoplasms
lymphocytic leukemia
shell (molluscs)
Cells
stereochemistry
lactones

ASJC Scopus subject areas

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

Cite this

Antineoplastic agents. 510. Isolation and structure of dolastatin 19 from the Gulf of California sea hare Dolabella auricularia. / Pettit, George; Xu, Jun-Ping; Doubek, Dennis L.; Chapuis, Jean; Schmidt, Jean M.

In: Journal of Natural Products, Vol. 67, No. 8, 08.2004, p. 1252-1255.

Research output: Contribution to journalArticle

Pettit, George ; Xu, Jun-Ping ; Doubek, Dennis L. ; Chapuis, Jean ; Schmidt, Jean M. / Antineoplastic agents. 510. Isolation and structure of dolastatin 19 from the Gulf of California sea hare Dolabella auricularia. In: Journal of Natural Products. 2004 ; Vol. 67, No. 8. pp. 1252-1255.
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