Biotransformation of the fungal toxin fomannoxin by conifer cell cultures.
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.
Zweimüller
M
M
Max-Planck-Institut für Biochemie, Martinsried, Germany.
Antus
S
S
Kovács
T
T
Sonnenbichler
J
J
D000935:Antifungal Agents / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D001487:Basidiomycota / Q000378:metabolism; D001572:Benzofurans / Q000138:chemical synthesis / Q000378:metabolism* / Q000633:toxicity; D001711:Biotransformation; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D032462:Cycadopsida / Q000382:microbiology*; D007536:Isomerism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010935:Plant Diseases / Q000382:microbiology; D013696:Temperature
D000935:Antifungal Agents; D001572:Benzofurans; C084141:fomannoxin