Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

The protein secretome of Botrytis cinerea was used to perform the biotransformation of resveratrol, pterostilbene, and a mixture of both. Metabolite profiling by UHPLC-HRMS revealed the presence of compounds with unusual molecular formula, suggesting the existence of new products. To isolate these p...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-04, Vol.80 (4), p.887-898
Main Authors: Gindro, Katia, Schnee, Sylvain, Righi, Davide, Marcourt, Laurence, Nejad Ebrahimi, Samad, Codina, Josep Massana, Voinesco, Francine, Michellod, Emilie, Wolfender, Jean-Luc, Queiroz, Emerson Ferreira
Format: Article
Language:English
Subjects:
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Biotransformation
Botrytis - chemistry
Fungal Proteins - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oomycetes - chemistry
Plant Diseases - microbiology
Stilbenes - chemistry
Stilbenes - metabolism
Stilbenes - pharmacology
Vitis - chemistry
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Summary:The protein secretome of Botrytis cinerea was used to perform the biotransformation of resveratrol, pterostilbene, and a mixture of both. Metabolite profiling by UHPLC-HRMS revealed the presence of compounds with unusual molecular formula, suggesting the existence of new products. To isolate these products, the reactions were scaled-up, and 21 analogues were isolated and fully characterized by NMR and HRESIMS analyses. The reaction with pterostilbene afforded five new compounds, while the reaction with a mixture of pterostilbene and resveratrol afforded seven unusual stilbene dimers. The antifungal properties of these compounds were evaluated using in vitro bioassays against Plasmopara viticola. The cytological effects of the isolated antifungal compounds on the ultrastructure of P. viticola were also evaluated.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00760