Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

Phytochemistry. 2004 Feb;65(4):469-73. doi: 10.1016/j.phytochem.2003.09.022.

Abstract

Phytochemical examination of the methanolic extract of fruit bodies of the Xylariaceous ascomycete fungus Hypoxylon fuscum led to the isolation of two azaphilone derivatives named daldinins E and F together with two known compounds daldinin C and 4,5,4',5'-tetrahydroxy-1:1'-binaphthyl using a combination of reversed phase HPLC and high performance gel permeation chromatography. Their structures were determined by 2D NMR, MS, IR, UV, and CD spectroscopy. Their antioxidative activities were also estimated by an indication of a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging effect. The chemosystematics of Hypoxylon is discussed.

MeSH terms

  • Ascomycota / chemistry*
  • Ascomycota / metabolism
  • Aza Compounds / chemistry
  • Aza Compounds / isolation & purification
  • Aza Compounds / metabolism
  • Aza Compounds / pharmacology
  • Benzopyrans / chemistry*
  • Benzopyrans / isolation & purification
  • Benzopyrans / metabolism
  • Benzopyrans / pharmacology
  • Biphenyl Compounds
  • Cyclization
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / metabolism
  • Free Radical Scavengers / pharmacology
  • Free Radicals / antagonists & inhibitors
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Picrates / antagonists & inhibitors

Substances

  • Aza Compounds
  • Benzopyrans
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Free Radicals
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl