Bahamaolides A and B, antifungal polyene polyol macrolides from the marine actinomycete Streptomyces sp

J Nat Prod. 2012 May 25;75(5):959-67. doi: 10.1021/np3001915. Epub 2012 May 10.

Abstract

Bahamaolides A and B (1 and 2), two new 36-membered macrocyclic lactones, were isolated from the culture of the marine actinomycete Streptomyces sp. derived from a sediment sample collected at North Cat Cay in the Bahamas. The planar structures of 1 and 2, bearing a hexaenone and nine consecutive skipped hydroxy groups, were determined by 1D and 2D NMR, mass, IR, and UV spectra. The absolute configurations of the bahamaolides were established by combined multistep chemical reactions and spectroscopic analysis. Bahamaolide A displayed significant inhibitory activity against Candida albicans isocitrate lyase and antifungal activity against various pathogenic fungi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology*
  • Bahamas
  • Candida albicans / enzymology
  • Fungi / drug effects
  • Isocitrate Lyase / drug effects
  • Isocitrate Lyase / metabolism
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology*
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polyenes / chemistry
  • Polyenes / isolation & purification*
  • Polyenes / pharmacology*
  • Streptomyces / chemistry*

Substances

  • Antifungal Agents
  • Lactones
  • Macrolides
  • Polyenes
  • bahamaolide A
  • bahamaolide B
  • Isocitrate Lyase