Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. II. Physico-chemical properties and structure elucidation

J Antibiot (Tokyo). 1997 Apr;50(4):330-3. doi: 10.7164/antibiotics.50.330.

Abstract

The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH:ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (1a) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (1a), which was obtained as a 1:5 inseparable mixture of the two isomers (Z)-1a and (E)-1a, in addition contains a furan. Their structures were determined by mass spectrometry and NMR spectroscopy, and 2D heteronuclear correlation experiments permitted the assignment of all NMR signals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Antifungal Agents / chemistry*
  • Benzofurans / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxepins*
  • Stereoisomerism

Substances

  • Acetates
  • Antifungal Agents
  • Benzofurans
  • Oxepins
  • pterulinic acid
  • pterulone