Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856

J Antibiot (Tokyo). 2003 Feb;56(2):114-22. doi: 10.7164/antibiotics.56.114.

Abstract

The coprophilic ascomycete Coniochaeta ellipsoidea DSM 13856 forms the new antibiotic coniosetin (1) in surface cultures grown on a medium containing malt extract and oatmeal. The structure of the compound C25H35NO4, MW 413, was determined by 2D-NMR and mass spectrometric studies. Coniosetin belongs to the class of tetramic acids; it consists of a substituted aliphatic bicyclic ring system linked to a tetramic acid subunit through a carbonyl center. The absolute configuration was determined by measuring its circular dichroism spectrum and comparing the data with those of equisetin. Coniosetin has a pronounced antibacterial and antifungal action, inhibiting even multi drug-resistant strains of Staphylococcus aureus at a concentration of 0.3 microg/ml, though it is inactive against Gram-negative bacteria.

MeSH terms

  • Anti-Bacterial Agents / biosynthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Ascomycota / chemistry
  • Ascomycota / metabolism*
  • Chromatography, High Pressure Liquid
  • Circular Dichroism
  • Fermentation
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Molecular Weight
  • Naphthalenes / chemistry*
  • Naphthalenes / isolation & purification
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Optical Rotation
  • Pyrrolidinones / chemistry*
  • Pyrrolidinones / isolation & purification
  • Pyrrolidinones / metabolism
  • Pyrrolidinones / pharmacology
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Staphylococcus aureus / metabolism

Substances

  • Anti-Bacterial Agents
  • Naphthalenes
  • Pyrrolidinones
  • coniosetin