Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis (Leguminosae)

Phytochemistry. 2006 Sep;67(17):1964-9. doi: 10.1016/j.phytochem.2006.06.004. Epub 2006 Jul 20.

Abstract

Five cadinane sesquiterpenes derivatives were isolated by bioassay-guided fractionation from Phomopis cassiae, an endophytic fungus isolated from Cassia spectabilis. The structures of the two diastereoisomeric 3,9,12-trihydroxycalamenenes (1, 2); 3,12-dihydroxycalamenene (3); 3,12-dihydroxycadalene (4) and 3,11,12-trihydroxycadalene (5) were established on the basis of analyses of 1D and 2D NMR and HRTOFMS experiments. Antifungal activity of the isolates was evaluated against Cladosporium sphaerospermum and Cladosporium cladosporioides, revealing 5 as the most active compound.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Ascomycota / chemistry*
  • Ascomycota / metabolism
  • Cassia / microbiology*
  • Cell Survival / drug effects
  • Cladosporium / drug effects
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • cadinane