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 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.
Agroscope, Domaine de Recherche Protection des Végétaux , Route de Duillier 50, P.O. Box 1012, 1260 Nyon, Switzerland.
Katia
K
Gindro
Agroscope, Domaine de Recherche Protection des Végétaux , Route de Duillier 50, P.O. Box 1012, 1260 Nyon, Switzerland.
Sylvain
S
Schnee
School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , CMU, 1, Rue Michel Servet, 1211 Geneva 4, Switzerland.
Davide
D
Righi
School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , CMU, 1, Rue Michel Servet, 1211 Geneva 4, Switzerland.
Laurence
L
Marcourt
Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, ShahidBeheshti University , G. C., Evin, Tehran, Iran.
Samad
S
Nejad Ebrahimi
Agroscope, Domaine de Recherche Protection des Végétaux , Route de Duillier 50, P.O. Box 1012, 1260 Nyon, Switzerland.
Josep Massana
JM
Codina
Agroscope, Domaine de Recherche Protection des Végétaux , Route de Duillier 50, P.O. Box 1012, 1260 Nyon, Switzerland.
Francine
F
Voinesco
Agroscope, Domaine de Recherche Protection des Végétaux , Route de Duillier 50, P.O. Box 1012, 1260 Nyon, Switzerland.
Emilie
E
Michellod
School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , CMU, 1, Rue Michel Servet, 1211 Geneva 4, Switzerland.
Jean-Luc
JL
Wolfender
School of Pharmaceutical Sciences, EPGL, University of Geneva, University of Lausanne , CMU, 1, Rue Michel Servet, 1211 Geneva 4, Switzerland.
Emerson Ferreira
0000-0001-9567-1664
EF
Queiroz
D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D001711:Biotransformation; D020171:Botrytis / Q000737:chemistry*; D005656:Fungal Proteins / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009868:Oomycetes / Q000737:chemistry; D010935:Plant Diseases / Q000382:microbiology; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D027843:Vitis / Q000737:chemistry
D000935:Antifungal Agents; D005656:Fungal Proteins; D013267:Stilbenes; C107773:pterostilbene; D000077185:Resveratrol