Pestalofones A-E, bioactive cyclohexanone derivatives from the plant endophytic fungus Pestalotiopsis fici

Bioorg Med Chem. 2009 Jan 15;17(2):606-13. doi: 10.1016/j.bmc.2008.11.066. Epub 2008 Dec 3.

Abstract

Pestalofones A-E (1-5), five new cyclohexanone derivatives, have been isolated from cultures of the plant endophytic fungus Pestalotiopsis fici, along with the known compounds, isosulochrin (6), isosulochrin dehydrate (7), and iso-A82775C (8). The structures of 1-5 were determined by NMR spectroscopy, and the absolute configuration of 1 was assigned using the modified Mosher method. Compounds 1, 2, and 5 displayed inhibitory effects on HIV-1 replication in C8166 cells, whereas 3 and 5 showed significant antifungal activity against Aspergillus fumigatus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology
  • Aspergillus fumigatus / drug effects
  • Benzophenones
  • Cell Line
  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Cyclohexanones / pharmacology*
  • Fungi / chemistry*
  • HIV-1 / drug effects
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants / microbiology
  • Virus Replication / drug effects

Substances

  • Anti-Infective Agents
  • Benzophenones
  • Cyclohexanones
  • pestalone
  • cyclohexanone