Biotransformation of the fungal toxin fomannoxin by conifer cell cultures

Biol Chem. 1997 Aug;378(8):915-21. doi: 10.1515/bchm.1997.378.8.915.

Abstract

Fomannoxin [(+/-)-5-Formyl-2-isopropenyl-2,3-dihydrobenzofurane] is a phytotoxic secondary metabolite, which is produced by the forest pathogenic basidiomycete Heterobasidion annosum during the infection process. Fomannoxin shows growth-inhibiting effects on callus and suspension cultures of conifer cells. By investigating the interaction of the phytotoxin with Pinus sylvestris cells a detoxification of fomannoxin was detected, presumably as a defense reaction of the plant cells. Undifferentiated green cell lines of Pinus sylvestris were used as target cells. To provide rac-fomannoxin as a substrate a simple method for the chemical synthesis was developed. It was found that the aromatic aldehyde group is reduced by the plant cells producing the non-toxic fomannoxin alcohol which was isolated and identified by spectroscopy. After longer incubation times, also fomannoxin acid-beta-glucoside could be isolated as another detoxification metabolite. For comparison this glucoside was also synthesized.

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / metabolism*
  • Antifungal Agents / toxicity
  • Basidiomycota / metabolism
  • Benzofurans / chemical synthesis
  • Benzofurans / metabolism*
  • Benzofurans / toxicity
  • Biotransformation
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cycadopsida / microbiology*
  • Isomerism
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Plant Diseases / microbiology
  • Temperature

Substances

  • Antifungal Agents
  • Benzofurans
  • fomannoxin