Antineoplastic agents. Part 409: Isolation and structure of montanastatin from a terrestrial actinomycete

  • Bioorg Med Chem. 1999 May;7(5):895-9. doi: 10.1016/s0968-0896(99)00024-3.
G R Pettit  1 ,  R Tan ,  N Melody ,  J M Kielty ,  R K Pettit ,  D L Herald ,  B E Tucker ,  L P Mallavia ,  D L Doubek ,  J M Schmidt
Affiliations
  • 1. Cancer Research Institute and Department of Chemistry, Arizona State University, Tempe 85287-2404, USA.
PMID: 10400343 DOI: 10.1016/s0968-0896(99)00024-3
Abstract

A Montana soil actinomycete, Streptomyces anulatus, produced (1 x 10(-2)% yield) a new Cancer cell growth inhibitory cyclooctadepsipeptide named montanastatin (1) accompanied by the potent anticancer Antibiotic valinomycin (2) in very high (5.1%) yields. Valinomycin but not montanastatin inhibited growth of a number of pathogenic bacteria and fungi. Interpretation of high-field (500 MHz) NMR and high-resolution FAB mass spectral data allowed assignment of the structure cyclo-(D-Val-L-Lac-L-Val-D-Hiv) to montanastatin. Valinomycin (2) was also isolated from actinomycetes cultured from a tree branch and animal feces collected in Malaysia. Streptomyces exfoliatus, isolated from the tree branch, was found to contain valinomycin in 1.6% yield, while the fecal isolate, S. anulatus, gave valinomycin in 0.9% yield.

Products