Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp.

George Pettit, Rui Tan, Robin Pettit, Thomas H. Smith, Song Feng, Dennis L. Doubek, Linda Richert, John Hamblin, Christine Weber, Jean Chapuis

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

By utilizing a bioassay-guided separation (P388 lymphocytic leukemia and a panel of human cancer cell lines) of fermentation broths from a Kitasatospora sp. collected from a tundra soil sample taken at the shore of the Beaufort Sea, we have isolated three powerful (GI50 to 0.0006 μg/mL) cancer cell growth inhibitors (1-3) and determined their structures to be closely related cyclodepsipeptides. From 380 L fermentations of Kitasatospora sp. were obtained 2.6 mg of a new cyclodepsipeptide designated kitastatin 1 (3), accompanied by the previously known respirantin (1, 10.8 mg) and its valeryl homologue (2, 4.8 mg). The structures were determined by employment of a series of high-resolution mass and 2D NMR spectroscopic analyses. The stereochemical assignments and overall structures were confirmed by subsequent total synthesis of depsipdptide 1, as reported in the accompanying contribution.

Original languageEnglish (US)
Pages (from-to)1069-1072
Number of pages4
JournalJournal of Natural Products
Volume70
Issue number7
DOIs
StatePublished - Jul 2007

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., Tan, R., Pettit, R., Smith, T. H., Feng, S., Doubek, D. L., Richert, L., Hamblin, J., Weber, C., & Chapuis, J. (2007). Antineoplastic agents. 560. Isolation and structure of kitastatin 1 from an alaskan Kitasatospora sp. Journal of Natural Products, 70(7), 1069-1072. https://doi.org/10.1021/np068072c