Calbistrin E and two other new metabolites from an Australian isolate of Penicillium striatisporum

J Nat Prod. 2005 Apr;68(4):581-4. doi: 10.1021/np049614y.

Abstract

An Australian isolate of Penicillium striatisporum collected near Shalvey, New South Wales, exhibited selective antifungal activity against Candida albicans versus Saccharomyces cerevisiae. Bioassay-directed fractionation yielded members of the rare class of fungal metabolites known as the calbistrins. These included a new example of this structure class, calbistrin E (1), as well as the known polyenes calbistrin C (2) and deformylcalbistrin A (3). Also recovered from P. striatisporum were new triene and butenolide acids, striatisporin A (4) and striatisporolide A (5), together with the known fungal metabolites versiol (6) and (+)-hexylitaconic acid (7). Structures for all metabolites were determined by detailed spectroscopic analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Australia
  • Candida albicans / drug effects
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / isolation & purification*
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • New South Wales
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*
  • Saccharomyces cerevisiae / drug effects
  • Succinates / chemistry

Substances

  • 2-methylene-3-hexylbutanedioic acid
  • Antifungal Agents
  • Heterocyclic Compounds, 3-Ring
  • Naphthalenes
  • Succinates
  • calbistrin E
  • versiol