Antifungal activity of resveratrol against Botrytis cinerea is improved using 2-furyl derivatives.
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.
Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, University of Rome, Rome, Italy. caruso@vassar.edu
Francesco
F
Caruso
Leonora
L
Mendoza
Paulo
P
Castro
Milena
M
Cotoras
Maria
M
Aguirre
Betty
B
Matsuhiro
Mauricio
M
Isaacs
Miriam
M
Rossi
Angela
A
Viglianti
Roberto
R
Antonioletti
D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development; D002462:Cell Membrane / Q000187:drug effects / Q000378:metabolism; D003593:Cytoplasm / Q000187:drug effects / Q000378:metabolism; D004579:Electron Transport / Q000187:drug effects; D005663:Furans / Q000737:chemistry / Q000494:pharmacology*; D042845:Laccase / Q000096:biosynthesis; D008826:Microbial Sensitivity Tests; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D010101:Oxygen Consumption / Q000187:drug effects; D000077185:Resveratrol; D013172:Spores, Fungal / Q000187:drug effects / Q000254:growth & development; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*
D000935:Antifungal Agents; D005663:Furans; D013267:Stilbenes; D042845:Laccase; D000077185:Resveratrol