Impact of cruciferous phytoalexins on the detoxification of brassilexin by the blackleg fungus pathogenic to brown mustard
Department of Chemistry, 110 Science Place, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada.Natural product communications (Impact Factor: 0.91). 06/2010; 5(6):883-8.
The biotransformation of brassilexin, a potent phytoalexin produced by brown mustard (Brassica juncea L.), in the presence of various cruciferous phytoalexins was investigated. An important group of isolates of the fungal species Leptosphaeria maculans (Laird 2 and Mayfair 2), which is virulent to brown mustard, but not to canola, was used in this investigation. Brassilexin was detoxified by the fungus, but none of the phytoalexins seemed to affect substantially the rate of brassilexin detoxification; after 12 h of incubation, the amounts of brassilexin remaining in culture were as low as in controls, except in co-incubations with cyclobrassinin and sinalexin, which afforded intermediates that in solution oxidized spontaneously to brassilexin.
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ABSTRACT: Phytopathogenic fungi are able to overcome plant chemical defenses through detoxification reactions that are enzyme mediated. As a result of such detoxifications, the plant is quickly depleted of its most important antifungal metabolites and can succumb to pathogen attack. Understanding and predicting such detoxification pathways utilized by phytopathogenic fungi could lead to approaches to control plant pathogens. Towards this end, the inhibitory activities and metabolism of the cruciferous phytoalexins camalexin, brassinin, cyclobrassinin, and brassilexin by the phytopathogenic fungus Botrytis cinerea Pers. (teleomorph: Botryotinia fuckeliana) was investigated. Brassilexin was the most antifungal of the phytoalexins, followed by camalexin, cyclobrassinin and brassinin. Although B. cinerea is a species phylogenetically related to the phytopathogenic fungus Sclerotinia sclerotiorum (Lib) de Bary, contrary to S. sclerotiorum, detoxification of strongly antifungal phytoalexins occurred via either oxidative degradation or hydrolysis but not through glucosylation, suggesting that glucosyl transferases are not involved. A strongly antifungal bisindolylthiadiazole that B. cinerea could not detoxify was discovered, which resulted from spontaneous oxidative dimerization of 3-indolethiocarboxamide, a camalexin detoxification product.Phytochemistry 02/2011; 72(2-3):199-206. DOI:10.1016/j.phytochem.2010.11.018 · 2.55 Impact Factor
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ABSTRACT: A great number of structurally diverse natural products containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, and their saturated congeners, are abundant in nature. These naturally occurring metabolites often exhibit extensive and pharmacologically important biological activities. The latest progress in the isolation, biological activities, chemical synthetic studies, and biosynthetic pathways on these natural products is summarized in this review.Natural Product Reports 04/2011; 28(6):1143-91. DOI:10.1039/c0np00074d · 10.11 Impact Factor
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