Probing the phytopathogenic stem rot fungus with phytoalexins and analogues: unprecedented glucosylation of camalexin and 6-methoxycamalexin.
The remarkable metabolism of the cruciferous phytoalexins camalexin and 6-methoxycamalexin by the stem rot phytopathogen Sclerotinia sclerotiorum is reported. The biotransformations yielded camalexins glucosylated at N-1 or C-6 of the indole ring, with substantially lower antifungal activity than camalexins. A camalexin analogue with the positions N-1 and C-6 blocked was metabolized but at a much slower rate than the natural phytoalexins. The chemistry involved in the metabolism of natural camalexins and two new analogues, as well as their novel metabolites and respective antifungal activities is described.
Pedras
M Soledade C
MS
Department of Chemistry, University of Saskatchewan, 110 Science Place, SK, Saskatoon, Canada. soledade.pedras@usask.ca
Ahiahonu
Pearson W K
PW
D000890:Anti-Infective Agents / Q000378:metabolism*; D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D005947:Glucose / Q000378:metabolism; D006031:Glycosylation; D008658:Inactivation, Metabolic; D007211:Indoles / Q000378:metabolism; D015335:Molecular Probes; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000378:metabolism*; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles / Q000378:metabolism; D000094162:Phytoalexins
D000890:Anti-Infective Agents; D007211:Indoles; D015335:Molecular Probes; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles; C102405:camalexin; D005947:Glucose; D000094162:Phytoalexins