The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp

Org Lett. 2008 Feb 21;10(4):629-31. doi: 10.1021/ol702952n. Epub 2008 Jan 19.

Abstract

Cultivation of an obligate marine Streptomyces strain has furnished the marinopyrroles A and B, densely halogenated, axially chiral metabolites that contain an uncommon bispyrrole structure. X-ray analysis of marinopyrrole B showed that the natural product exists as an atropo-enantiomer with the M-configuration. Though configurationally stable at room temperature, M-(-)-marinopyrrole A can be racemized at elevated temperatures to yield the non-natural P-(+)-atropo-enantiomer. The marinopyrroles possess potent antibiotic activities against methicillin-resistant Staphylococcus aureus.

Publication types

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

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Drug Resistance, Bacterial / drug effects
  • Marine Biology
  • Methicillin Resistance / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / pharmacology
  • Staphylococcus aureus / drug effects*
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Pyrroles
  • marinopyrrole A
  • marinopyrrole B