Cytotoxic xanthone-anthraquinone heterodimers from an unidentified fungus of the order Hypocreales (MSX 17022)

J Antibiot (Tokyo). 2012 Jan;65(1):3-8. doi: 10.1038/ja.2011.95. Epub 2011 Nov 9.

Abstract

Two new xanthone-anthraquinone heterodimers, acremoxanthone C (5) and acremoxanthone D (2), have been isolated from an extract of an unidentified fungus of the order Hypocreales (MSX 17022) by bioactivity-directed fractionation as part of a search for anticancer leads from filamentous fungi. Two known related compounds, acremonidin A (4) and acremonidin C (3) were also isolated, as was a known benzophenone, moniliphenone (1). The structures of these isolates were determined via extensive use of spectroscopic and spectrometric tools in conjunction with comparisons to the literature. All compounds (1-5) were evaluated against a suite of biological assays, including those for cytotoxicity, inhibition of the 20S proteasome, mitochondrial transmembrane potential and nuclear factor-κB.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Humans
  • Hypocreales / chemistry*
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • NF-kappa B / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Optical Rotation
  • Proteasome Endopeptidase Complex / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Xanthones / chemistry
  • Xanthones / isolation & purification*
  • Xanthones / pharmacology*

Substances

  • Anthraquinones
  • Antineoplastic Agents
  • NF-kappa B
  • Xanthones
  • Proteasome Endopeptidase Complex