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.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Actinomycetales / chemistry*
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Tumor Cells, Cultured
  • Valinomycin / chemistry
  • Valinomycin / pharmacology

Substances

  • Antineoplastic Agents
  • Peptides, Cyclic
  • montanastatin
  • Valinomycin