title: Hypohalous acid-mediated halogenation of resveratrol and its role in antioxidant and antimicrobial activities.
abstract: The reactions of resveratrol with proinflammatory oxidants including hypochlorous and hypobromous acids in phosphate-buffered saline/methanol solution were carried out and eight halogenated resveratrol derivatives differing in the number and position of halogen atoms, and the configuration of double bond were obtained. Halogenation of resveratrol took place only at the aromatic A ring, and interestingly, the halogenation increased antioxidant activity of this parent molecule in the 2,2'-azobis(2-amidinopropane) hydrochloride-induced RBC haemolysis model. Additionally, antimicrobial activity of the derivatives against Gram-positive bacteria, Gram-negative bacteria and fungi were tested, and toward Candida albicans, 2-chloro-resveratrol and 2-bromo-resveratrol were more active than the unmodified form and the reference compound fluconazole.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.
authors.forename: Xiu-Zhuang
authors.initials: XZ
authors.lastname: Li
authors.forename: Xia
authors.initials: X
authors.lastname: Wei
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Zhang
authors.forename: Xiao-Ling
authors.initials: XL
authors.lastname: Jin
authors.forename: Jiang-Jiang
authors.initials: JJ
authors.lastname: Tang
authors.forename: Gui-Juan
authors.initials: GJ
authors.lastname: Fan
authors.forename: Bo
authors.initials: B
authors.lastname: Zhou
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001959:Bromates / Q000737:chemistry; D002460:Cell Line; D005658:Fungi / Q000187:drug effects; D054879:Halogenation; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D006997:Hypochlorous Acid / Q000737:chemistry; D015394:Molecular Structure; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000975:Antioxidants; D001959:Bromates; D013267:Stilbenes; D006997:Hypochlorous Acid; C027664:hypobromous acid; D000077185:Resveratrol