title: Antifungal activity of resveratrol derivatives against Candida species.
abstract: trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of 1a purified from Vitis vinifera grape canes and several analogues (1b-1j) of 1a obtained through semisynthesis using methylation and acetylation. Moreover, trans-ε-viniferin (2a), a dimer of 1a, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of 1a (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives 1d and 1e exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 μg/mL and against 11 other Candida species. Compound 1e inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 μg/mL.
authors.affiliation: EA 2106 "Biomolécules et Biotechnologie Végétales", UFR des Sciences Pharmaceutiques, Université François Rabelais de Tours , F-37200 Tours, France.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Houillé
authors.forename: Nicolas
authors.initials: N
authors.lastname: Papon
authors.forename: Leslie
authors.initials: L
authors.lastname: Boudesocque
authors.forename: Eric
authors.initials: E
authors.lastname: Bourdeaud
authors.forename: Sébastien
authors.initials: S
authors.lastname: Besseau
authors.forename: Vincent
authors.initials: V
authors.lastname: Courdavault
authors.forename: Cécile
authors.initials: C
authors.lastname: Enguehard-Gueiffier
authors.forename: Guillaume
authors.initials: G
authors.lastname: Delanoue
authors.forename: Laurence
authors.initials: L
authors.lastname: Guérin
authors.forename: Jean-Philippe
authors.initials: JP
authors.lastname: Bouchara
authors.forename: Marc
authors.initials: M
authors.lastname: Clastre
authors.forename: Nathalie
authors.initials: N
authors.lastname: Giglioli-Guivarc'h
authors.forename: Jérôme
authors.initials: J
authors.lastname: Guillard
authors.forename: Arnaud
authors.initials: A
authors.lastname: Lanoue
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology; D002175:Candida / Q000187:drug effects*; D002176:Candida albicans / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*; D027843:Vitis / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D001572:Benzofurans; D013267:Stilbenes; C091891:epsilon-viniferin; D000077185:Resveratrol