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Antifungal Activity of Resveratrol against Botrytis cinerea Is Improved Using 2-Furyl Derivatives

2011; Public Library of Science; Volume: 6; Issue: 10 Linguagem: Inglês

10.1371/journal.pone.0025421

1932-6203

Francesco Caruso, Leonora Mendoza, Paulo de Tarso Oliveira e Castro, Milena Cotoras, Marı́a J. Aguirre, Betty Matsuhiro, Maurício Isaacs, Miriam Rossi, Angela Viglianti, Roberto Antonioletti,

Forest Insect Ecology and Management

The antifungal effect of three furyl compounds closely related to resveratrol, (E)-3,4,5-trimethoxy-β-(2-furyl)-styrene (1), (E)-4-methoxy-β-(2-furyl)-styrene (2) and (E)-3,5-dimethoxy-β-(2-furyl)-styrene (3) against Botrytis cinerea was analyzed. The inhibitory effect, at 100 µg ml(-1) of compounds 1, 2, 3 and resveratrol on conidia germination, was determined to be about 70%, while at the same concentration pterostilbene (a dimethoxyl derivative of resveratrol) produced complete inhibition. The title compounds were more fungitoxic towards in vitro mycelial growth than resveratrol and pterostilbene. Compound 3 was the most active and a potential explanation of this feature is given using density functional theory (DFT) calculations on the demethoxylation/demethylation process. Compound 3 was further evaluated for its effects on laccase production, oxygen consumption and membrane integrity of B. cinerea. An increase of the laccase activity was observed in the presence of compound 3 and, using Sytox Green nucleic acid stain, it was demonstrated that this compound altered B. cinerea membrane. Finally, compound 3 partially affected conidia respiration.