Isolation and Structure Elucidation of Parnafungins C and D, Isoxazolidinone-Containing Antifungal Natural Products

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1224-7. doi: 10.1016/j.bmcl.2008.12.081. Epub 2008 Dec 25.

Abstract

Parnafungins, natural products containing an isoxazolidinone ring, have been isolated from Fusarium larvarum and have been shown to be potent inhibitors of the fungal polyadenosine polymerase. The extraction and analysis of fermentation broths of taxonomically related organisms identified as closely related Fusarium spp. produce not only parnafungin A and B, but also significant quantities of two related components. These members of the paranfungin family of natural products have been isolated and the structure of each has been elucidated. While structurally analogous to parnafungin A, parnafungin C is further elaborated by methylation of a phenolic hydroxyl group, and parnafungin D has both the methyl phenol ether as well as an epoxide in the xanthone ring system. Parnafungin C and D have potent, broad spectrum antifungal activity and also have been shown to target fungal mRNA cleavage and polyadenylation.

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology*
  • Biological Products / chemistry
  • Biological Products / isolation & purification*
  • Biological Products / pharmacology*
  • Candida albicans / drug effects
  • Fusarium / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxazolidinones / chemistry
  • Oxazolidinones / isolation & purification*
  • Oxazolidinones / pharmacology*

Substances

  • Antifungal Agents
  • Biological Products
  • Oxazolidinones
  • parnafungin C
  • parnafungin D