Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

Autor: Samad Nejad Ebrahimi, Emilie Michellod, Jean-Luc Wolfender, Francine Voinesco, Katia Gindro, Josep Massana Codina, Davide Righi, Laurence Marcourt, Sylvain Schnee, Emerson Ferreira Queiroz
Rok vydání: 2017
Předmět:
0301 basic medicine
Pterostilbene
Antifungal Agents
Pharmaceutical Science
Resveratrol
01 natural sciences
Analytical Chemistry
chemistry.chemical_compound
Antifungal Agents/chemistry/pharmacology
Biotransformation
Drug Discovery
Stilbenes
Vitis
Botrytis cinerea
chemistry.chemical_classification
Fungal protein
ddc:615
biology
Molecular Structure
Plant Diseases/microbiology
Biochemistry
Stilbenes/chemistry/metabolism/pharmacology
Oomycetes
Plasmopara viticola
Molecular Medicine
Botrytis
Fungal Proteins/chemistry
food.ingredient
Vitis/chemistry
Stereochemistry
Nuclear Magnetic Resonance
Oomycetes/chemistry
Fungal Proteins
03 medical and health sciences
food
Botrytis/chemistry
Nuclear Magnetic Resonance
Biomolecular

Plant Diseases
Pharmacology
010405 organic chemistry
Organic Chemistry
biology.organism_classification
0104 chemical sciences
030104 developmental biology
Enzyme
Complementary and alternative medicine
chemistry
Biomolecular
Zdroj: Journal of Natural Products, Vol. 80, No 4 (2017) pp. 887-898
ISSN: 1520-6025
0163-3864
Popis: 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.
Databáze: OpenAIRE