Issue 13, 2006

Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation

Abstract

The strongly antifungal phytoalexins brassilexin and sinalexin were metabolized by the stem rot fungus Sclerotinia sclerotiorum to glucosyl derivatives, whereas the phytoalexins brassicanal A, spirobrassinin and 1-methoxyspirobrassinin, displaying lower antifungal activity, were transformed via non-glucosylating pathways. Significantly, these transformations led to metabolites displaying no detectable antifungal activity. The chemical characterization of all new metabolites as well as the chemistry of these processes and a facile chemical synthesis of 1-β-D-glucopyranosylbrassilexin are reported. Overall, our results indicate that phytoalexins, strongly antifungal against S. sclerotiorum, are detoxified via glucosylation, which in turn suggests that S. sclerotiorum has acquired efficient glucosyltransferase(s) that can disarm some of the most active plant chemical defenses. Consequently, we suggest that these glucosylation reactions are potential metabolic targets to control S. sclerotiorum.

Graphical abstract: Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation

Supplementary files

Article information

Article type
Paper
Submitted
28 Mar 2006
Accepted
04 May 2006
First published
30 May 2006

Org. Biomol. Chem., 2006,4, 2581-2590

Metabolism of crucifer phytoalexins in Sclerotinia sclerotiorum: detoxification of strongly antifungal compounds involves glucosylation

M. S. C. Pedras and M. Hossain, Org. Biomol. Chem., 2006, 4, 2581 DOI: 10.1039/B604400J

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