Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani.
The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described.
Pedras
M S
MS
Department of Chemistry, University of Saskatchewan, Saskatoon SK, Canada. pedras@sask.usask.ca
Khan
A Q
AQ
D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000737:chemistry / Q000378:metabolism*; D012232:Rhizoctonia / Q000254:growth & development / Q000378:metabolism*; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles / Q000737:chemistry / Q000378:metabolism*; D014774:Virulence; D000094162:Phytoalexins
D007211:Indoles; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles; C102405:camalexin; D000094162:Phytoalexins