title: Probing the phytopathogenic stem rot fungus with phytoalexins and analogues: unprecedented glucosylation of camalexin and 6-methoxycamalexin.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Saskatchewan, 110 Science Place, SK, Saskatoon, Canada. soledade.pedras@usask.ca
authors.forename: M Soledade C
authors.initials: MS
authors.lastname: Pedras
authors.forename: Pearson W K
authors.initials: PW
authors.lastname: Ahiahonu
mesh_terms: 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
chemical_list: D000890:Anti-Infective Agents; D007211:Indoles; D015335:Molecular Probes; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; D013844:Thiazoles; C102405:camalexin; D005947:Glucose; D000094162:Phytoalexins