Identification of elaiophylin derivatives from the marine-derived actinomycete Streptomyces sp. 7-145 using PCR-based screening

J Nat Prod. 2013 Nov 22;76(11):2153-7. doi: 10.1021/np4006794. Epub 2013 Oct 28.

Abstract

A PCR-based genetic screening experiment targeting the dTDP-glucose-4,6-dehydratase gene revealed that a marine sediment-derived strain, Streptomyces sp. 7-145, had the potential to produce glycosidic antibiotics. Chemical investigation of culture extracts of this strain yielded two new 6-deoxyhexose-containing antibiotics, 11',12'-dehydroelaiophylin (1) and 11,11'-O-dimethyl-14'-deethyl-14'-methylelaiophylin (2), together with four known elaiophylin analogues (3-6). Their structures were determined by extensive NMR, MS, and CD analyses. Compounds 1, 3, 4, and 6 showed good antibacterial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci pathogens.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Marine Biology
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polymerase Chain Reaction
  • Streptomyces / chemistry*
  • Vancomycin / pharmacology

Substances

  • 11',12'-dehydroelaiophylin
  • 11,11'-O-dimethyl-14'-deethyl-14'-methylelaiophylin
  • Anti-Bacterial Agents
  • Macrolides
  • elaiophylin
  • Vancomycin