Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

Gindro, Katia; Schnee, Sylvain; Righi, Davide; Marcourt, Laurence; Nejad Ebrahimi, Samad; Codina, Josep Massana; Voinesco, Francine; Michellod, Emilie; Wolfender, Jean-Luc; Queiroz, Emerson Ferreira

doi:10.1021/acs.jnatprod.6b00760

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Title		Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea
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 show all authors [1 - 10]
Published in		Journal of Natural Products. 2017, vol. 80, no. 4, p. 887-898
Abstract		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.
Keywords		Antifungal Agents/chemistry/pharmacology — Biotransformation — Botrytis/chemistry — Fungal Proteins/chemistry — Molecular Structure — Nuclear Magnetic Resonance — Biomolecular — Oomycetes/chemistry — Plant Diseases/microbiology — Stilbenes/chemistry/metabolism/pharmacology — Vitis/chemistry
Identifiers		DOI: 10.1021/acs.jnatprod.6b00760 PMID: 28332842
Full text		Article (Published version) (565 Kb) - Limited access to UNIGE
Structures		Faculté des sciences / Section des sciences pharmaceutiques
Research group		Phytochimie et produits naturels bioactifs
Citation (ISO format)		GINDRO, Katia et al. Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea. In: Journal of Natural Products, 2017, vol. 80, n° 4, p. 887-898. doi: 10.1021/acs.jnatprod.6b00760 https://archive-ouverte.unige.ch/unige:112406