期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 20, 期 13, 页码 3991-3996出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2012.05.020
关键词
Antifungal; Brassicaceae; Biotransformation; Brussalexin A; Crucifer; Detoxification; Dihydroerucalexin; Erucalexin; Leptosphaeria maculans; Phoma lingam; Phytoalexin; Rapalexin A
资金
- Natural Sciences and Engineering Research Council of Canada
- Canada Research Chairs program, Canada Foundation for Innovation
- Saskatchewan Government
- University of Saskatchewan
The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl) carbamodithioate, an analogue of brussalexin A, was also investigated. Rapalexin A was resistant to metabolism and was the most inhibitory of all compounds tested, suggesting that increasing concentrations of rapalexin A in Brassica species would improve their disease resistance to L. maculans. By contrast, erucalexin was quickly detoxified by reduction to yield 3-dihydroerucalexins. The relative configurations of the diastereomeric mixture of dihydroerucalexins were established by 1D H-1 nuclear Overhauser enhancement spectroscopy (NOE). Brussalexin A was chemically unstable decomposing mainly to indolyl-3-methanol, a product with anti-cancer properties. For this reason, brussalexin A might be of interest to use as a prodrug. (C) 2012 Elsevier Ltd. All rights reserved.
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