Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp

Bioorg Med Chem. 2011 Nov 15;19(22):6557-62. doi: 10.1016/j.bmc.2011.06.053. Epub 2011 Jun 26.

Abstract

Three new depsipeptides, fijimycins A-C (1-3), together with the known etamycin A (4), were isolated and identified from the fermentation broth of strain CNS-575, a Streptomyces sp. cultured from a marine sediment sample collected off Nasese, Fiji. The planar structures of the new fijimycins were assigned by combined interpretation of NMR and MS/MS spectroscopic data. These assignments were complicated by the fact that 1-3 occurred as complex amide conformational mixtures. The absolute configurations of the component amino acids were established using the Marfey's method. Fijimycins A-C, and etamycin A, were shown to possess significant in vitro antibacterial activity against three methicillin-resistant Staphylococcus aureus (MRSA) strains with MIC(100) values between 4 and 16 μg mL(-1).

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology
  • Depsipeptides / biosynthesis*
  • Depsipeptides / chemistry
  • Depsipeptides / isolation & purification*
  • Depsipeptides / pharmacology
  • Fermentation
  • Fiji
  • Macrolides / chemistry
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Nuclear Magnetic Resonance, Biomolecular
  • Streptomyces / chemistry*
  • Streptomyces / metabolism*
  • Tandem Mass Spectrometry

Substances

  • Anti-Bacterial Agents
  • Depsipeptides
  • Macrolides
  • etamycin