Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

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.

Wood and roots of major grapevine cultivars and rootstocks: A comparative analysis of stilbenes by UHPLC‐DAD‐MS/MS and NMR

“…This would explain the strong decrease in E ‐ɛ‐viniferin in the roots and the increase in vitisin B (Table ). In addition, the oxidation of stilbenes has already been reported in studies on the dimerization of monomers under the action of fungal‐derived enzymes . Furthermore, the time factor could also play a role in these differing degrees of polymerization.…”

“…In addition, the oxidation of stilbenes has already been reported in studies on the dimerization of monomers under the action of fungalderived enzymes. 38,39 Furthermore, the time factor could also play a role in these differing degrees of polymerization. Indeed, grapevine canes that are pruned each year do not undergo much stress, whereas wood and roots that are several decades old would accumulate stilbenes over time.…”

Comparative Study of Secreted Proteins, Enzymatic Activities of Wood Degradation and Stilbene Metabolization in Grapevine Botryosphaeria Dieback Fungi

“…Beneveneti et al also reported the oligomerization of phenolic compounds by purified laccases of Trametes versicolor , which is a white rot fungus [ 62 ], notably the transformation of trans -resveratrol into trans -δ-viniferin. Recently, using the secretome of B. cinerea, Gindro et al have demonstrated the dimerization of trans -resveratrol into several compounds such as leachianol F/G, restrytisol B, trans / cis -δ-viniferin, and 3 β- (3′,5′-dihydroxyohenyl )-2 α -(4″-hydroxyphenyl)dihydrobenzofuran-5-carbaldehyde [ 63 ].…”

Biotransformation of 4-Chromanone, 4-Flavanone, and their Analogs by Fungi

“…In contrast, grapes infected with this fungus can be used to produce concentrated sweet wine [14][15][16]. In addition, a recent study used the protein secretome of B. cinerea for biotransformation reactions, such as that of resveratrol [17]. Here we report the biotransformation of 4-chromanone and its analogs as a follow-up to our study using acetophenones [10] 2.…”

“…Although we used two types of phytopathogenic fungi, other studies have reported using B. cinerea and Colletotrichum spp. (species) [11][12][13]. B. cinerea can adversely affect agricultural crops as a plant pathogen.…”