期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 21, 期 15, 页码 4541-4549出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.05.026
关键词
Antifungal; Brassicaceae; Biotransformation; Camalexin; Crucifer; Detoxification; 6-Methoxycamalexin; 1-Methylcamalexin; Alternaria brassicicola; Indole-3-thiocarboxamide; Thiazolyl-3-indole; Oxadiazolyl-3-indole; Thiadiazolyl-3-indole; Phytoalexin
资金
- Natural Sciences and Engineering Research Council of Canada
- Canada Research Chairs program
- Canada Foundation for Innovation
- Saskatchewan Government
- University of Saskatchewan
The metabolism of the phytoalexins camalexin (1), 1-methylcamalexin (10) and 6-methoxycamalexin (11) by Alternaria brassicicola and their antifungal activity is reported. This work establishes that camalexins are slowly biotransformed (ca. six days) to the corresponding indole-3-thiocarboxamides, which are further transformed to the indole-3-carboxylic acids. These metabolites are substantially less inhibitory to A. brassicicola than the parent camalexins, indicating that these enzyme-mediated transformations are detoxifications. In addition, analyses of the metabolism of synthetic isomers and bioisosteres of camalexin (1) indicate that isomers of camalexin in the thiazole ring are not metabolized. Based on these results, the potential intermediates that lead to formation of indole-3-thiocarboxamides are proposed. (C) 2013 Elsevier Ltd. All rights reserved.
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