Quercinol, an anti-inflammatory chromene from the wood-rotting fungus Daedalea quercina (Oak Mazegill)

Bioorg Med Chem Lett. 2007 May 1;17(9):2558-60. doi: 10.1016/j.bmcl.2007.02.008. Epub 2007 Feb 7.

Abstract

The fungus Daedalea quercina (oak mazegill) was examined for its capability of producing antioxidative and anti-inflammatory compounds. Bioactivity guided fractionation of the extract from a mycelial culture led to the isolation of quercinol, which was identified as (-)-(2S)-2-hydroxymethyl-2-methyl-6-hydroxychromene 1 by NMR and X-ray analyses. The cryptic hydroquinone 1 shows a broad anti-inflammatory activity against cyclooxygenase 2 (COX-2), xanthine oxidase (XO), and horseradish peroxidase (HRP) at micromolar concentrations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / pharmacology*
  • Basidiomycota / metabolism*
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry*
  • Benzopyrans / pharmacology
  • Chemistry, Pharmaceutical / methods*
  • Crystallography, X-Ray
  • Cyclooxygenase 2 / chemistry
  • Cyclooxygenase Inhibitors / pharmacology
  • Drug Design
  • Horseradish Peroxidase / antagonists & inhibitors
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Conformation
  • Xanthine Oxidase / antagonists & inhibitors

Substances

  • Anti-Inflammatory Agents
  • Benzopyrans
  • Cyclooxygenase Inhibitors
  • quercinol
  • Horseradish Peroxidase
  • Cyclooxygenase 2
  • Xanthine Oxidase