Quinofuracins A-E, produced by the fungus Staphylotrichum boninense PF1444, show p53-dependent growth suppression

J Nat Prod. 2015 Feb 27;78(2):188-95. doi: 10.1021/np500581m. Epub 2015 Jan 22.

Abstract

Quinofuracins A-E, novel anthraquinone derivatives containing β-D-galactofuranose that were isolated from the fungus Staphylotrichum boninense PF1444, induced p53-dependent cell death in human tumor cells. The structures of quinofuracins A-E, including absolute configurations, were elucidated by extensive spectroscopic analysis and chemical transformation studies. Quinofuracins were classified into three groups according to the aglycone moieties. 5'-Oxoaverantin was present in quinofuracins A-C, whereas averantin and versicolorin B were identified in quinofuracins D and E, respectively. These quinofuracins induced p53-dependent growth suppression in human glioblastoma LNZTA3 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Ascomycota / chemistry*
  • Cell Death / drug effects
  • Drug Screening Assays, Antitumor
  • Glioblastoma / drug therapy
  • Humans
  • Japan
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Tumor Suppressor Protein p53 / drug effects
  • Tumor Suppressor Protein p53 / metabolism*

Substances

  • 5'-oxoaverantin
  • Anthraquinones
  • Antineoplastic Agents
  • Tumor Suppressor Protein p53
  • versicolorin C