Trichodermaketones A-D and 7-O-methylkoninginin D from the marine fungus Trichoderma koningii

J Nat Prod. 2010 May 28;73(5):806-10. doi: 10.1021/np900642p.

Abstract

Five new polyketide derivatives, 7-O-methylkoninginin D (1) and trichodermaketones A-D (2-5), together with four known compounds, koninginins A, D, E, and F, were isolated from the marine-derived fungus Trichoderma koningii. Trichodermaketones A (2) and B (3) are unprecedented polyketides with a bistetrafuran-containing tricyclic skeleton. The chemical structures and absolute configurations of compounds 1-5 were elucidated by comparing with literature data and extensive spectroscopic methods, including 2D NMR and CD spectroscopic analysis. Compounds 1-5 were evaluated for action against bacteria and fungi and for synergistic antifungal activity. Compound 2 showed synergistic antifungal activity against Candida albicans with 0.05 microg/mL ketoconazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology
  • Candida albicans / drug effects
  • Ketoconazole / pharmacology
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Trichoderma / chemistry*

Substances

  • 7-O-methylkoninginin D
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzopyrans
  • Macrolides
  • Ketoconazole