The leupyrrins: a structurally unique family of secondary metabolites from the myxobacterium Sorangium cellulosum

J Nat Prod. 2003 Sep;66(9):1203-6. doi: 10.1021/np030109v.

Abstract

The structurally unique leupyrrins A1 (1), A2 (2), B1 (3), B2 (4), C (5), and D (6) were isolated as one of three groups of secondary metabolites from Sorangium cellulosum strains So ce705 and So ce690. An unusually substituted gamma-butyrolactone ring and pyrrole and oxazoline rings are embedded in a nonsymmetric macrodiolide core structure, giving rise to compounds 1-6 as members of a novel class of secondary metabolites. Leupyrrin A1 (1) shows good biological activity against various fungi and eukaryotic cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification*
  • 4-Butyrolactone / pharmacology
  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Cells, Cultured / drug effects
  • Fibroblasts / drug effects
  • Fungi / drug effects
  • Italy
  • Mice
  • Molecular Structure
  • Myxococcales / chemistry*
  • Myxococcales / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxazoles / chemistry
  • Oxazoles / isolation & purification*
  • Oxazoles / pharmacology
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / pharmacology

Substances

  • Antifungal Agents
  • Oxazoles
  • Pyrroles
  • leupyrrin A1
  • 4-Butyrolactone