Cyclopenicillone, a unique cyclopentenone from the cultures of Penicillium decumbens

Chem Commun (Camb). 2011 Oct 7;47(37):10413-5. doi: 10.1039/c1cc12079d. Epub 2011 Aug 11.

Abstract

Cyclopenicillone (1), possessing a unique 2,5-dimethylcyclopent-2-enone carbon skeleton, has been isolated from the cultures broth of the fungus Penicillium decumbens. The structure and absolute configuration of 1 were elucidated using a combination of NMR spectroscopy, CD data and computational approaches. Cyclopenicillone (1) demonstrated a dose-dependent (10-100 μM) inhibition against LPS-induced NO production in RAW264.7 macrophages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Culture Techniques*
  • Cyclopentanes / chemistry*
  • Cyclopentanes / isolation & purification
  • Cyclopentanes / metabolism
  • Cyclopentanes / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Models, Molecular
  • Molecular Conformation
  • Nitric Oxide / biosynthesis
  • Penicillium / growth & development*
  • Penicillium / metabolism

Substances

  • Cyclopentanes
  • Lipopolysaccharides
  • cyclopenicillone
  • Nitric Oxide
  • cyclopentenone