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Antifungal activity of resveratrol against Botrytis cinerea is improved using 2-furyl derivatives.


ABSTRACT: The antifungal effect of three furyl compounds closely related to resveratrol, (E)-3,4,5-trimethoxy-?-(2-furyl)-styrene (1), (E)-4-methoxy-?-(2-furyl)-styrene (2) and (E)-3,5-dimethoxy-?-(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.

SUBMITTER: Caruso F 

PROVIDER: S-EPMC3191159 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Antifungal activity of resveratrol against Botrytis cinerea is improved using 2-furyl derivatives.

Caruso Francesco F   Mendoza Leonora L   Castro Paulo P   Cotoras Milena M   Aguirre Maria M   Matsuhiro Betty B   Isaacs Mauricio M   Rossi Miriam M   Viglianti Angela A   Antonioletti Roberto R  

PloS one 20111011 10


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. Th  ...[more]

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