Biotransformation of the fungal toxin fomannoxin by conifer cell cultures.

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.

• Authors: M Zweimüller, S Antus, T Kovács, J Sonnenbichler
• Journal: Biological chemistry (Biol Chem) Vol. 378 Issue 8 Pg. 915-21 (Aug 1997) ISSN: 1431-6730 [Print] Germany
• PMID: 9377489 (Publication Type: Journal Article)

Chemical References

• Antifungal Agents
• Benzofurans
• fomannoxin

Topics

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