A new phytotoxic nonenolide from Phoma herbarum

J Nat Prod. 2003 Apr;66(4):511-4. doi: 10.1021/np020501t.

Abstract

Reinvestigation of the fermentation broth and mycelium of the fungus Phoma herbarum led to the isolation of a new phytotoxic nonenolide, namely, (7R,9R)-7-hydroxy-9-propyl-5-nonen-9-olide, which was designated with the trivial name herbarumin III (3). The known compounds herbarumins I (1) and II (2) were also obtained. The structure of 3 was elucidated by spectroscopic methods and molecular modeling. Compounds 1-3 interacted with bovine-brain calmodulin and inhibited the activation of the calmodulin-dependent enzyme cAMP phosphodiesterase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
  • Amaranthus / drug effects
  • Animals
  • Brain / drug effects
  • Calmodulin / antagonists & inhibitors*
  • Cattle
  • Cyclic Nucleotide Phosphodiesterases, Type 1
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Fungi / chemistry*
  • Heterocyclic Compounds, 1-Ring
  • Inhibitory Concentration 50
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Seeds / drug effects
  • Zea mays

Substances

  • Calmodulin
  • Enzyme Inhibitors
  • Heterocyclic Compounds, 1-Ring
  • Lactones
  • herbarumin I
  • herbarumin II
  • herbarumin III
  • 3',5'-Cyclic-AMP Phosphodiesterases
  • Cyclic Nucleotide Phosphodiesterases, Type 1