Unique metabolites of Pestalotiopsis fici suggest a biosynthetic hypothesis involving a Diels-Alder reaction and then mechanistic diversification

Chem Commun (Camb). 2010 Jan 21;46(3):460-2. doi: 10.1039/b918330b. Epub 2009 Nov 13.

Abstract

Chloropupukeanolides A (1) and B (2), unprecedented spiroketal peroxides, and chloropupukeanone A (3), three highly functionalized metabolites featuring a chlorinated pupukeanane core, were isolated from an endophytic fungus Pestalotiopsis fici, with 1 showing significant anti-HIV-1 and cytotoxic effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Furans / isolation & purification
  • Furans / pharmacology
  • HIV-1 / drug effects
  • Heterocyclic Compounds, 2-Ring / chemistry
  • Heterocyclic Compounds, 2-Ring / isolation & purification
  • Heterocyclic Compounds, 2-Ring / pharmacology
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Peroxides / chemistry
  • Peroxides / isolation & purification
  • Peroxides / pharmacology
  • Sesquiterpenes
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology
  • Xylariales / chemistry*
  • Xylariales / metabolism

Substances

  • Anti-HIV Agents
  • Antineoplastic Agents
  • Furans
  • Heterocyclic Compounds, 2-Ring
  • Peroxides
  • Sesquiterpenes
  • Spiro Compounds
  • chloropupukeanolide
  • chloropupukeanone
  • spiroketal