Microtermolides A and B from termite-associated Streptomyces sp. and structural revision of vinylamycin

Org Lett. 2012 Jun 1;14(11):2822-5. doi: 10.1021/ol301043p. Epub 2012 May 16.

Abstract

Microtermolides A (1) and B (2) were isolated from a Streptomyces sp. strain associated with fungus-growing termites. The structures of 1 and 2 were determined by 1D- and 2D-NMR spectroscopy and high-resolution mass spectrometry. Structural elucidation of 1 led to the re-examination of the structure originally proposed for vinylamycin (3). Based on a comparison of predicted and experimental (1)H and (13)C NMR chemical shifts, we propose that vinylamycin's structure be revised from 3 to 4.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Bacterial Proteins / chemistry*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Dose-Response Relationship, Drug
  • Isoptera / microbiology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Depsipeptides
  • microtermolide A
  • microtermolide B
  • vinylamycin