Antioxidant properties of 3-hydroxycoumarin derivatives.
A series of hydroxylated 3-hydroxycoumarins was synthesised by the reaction of 3-aryl-2-hydroxypropenoic derivatives with boron tribromide. They were evaluated for their ability to scavenge the 2,2-diphenyl-1-picrylhydrazyl radical, the superoxide anion radical, the hydroxyl radical and the peroxynitrite anion and to inhibit copper-induced human LDL peroxidation. The physicochemical results were in accordance to establish the compounds hydroxylated on C-6 and C-7 positions as the most active of the series with antioxidant potencies comparable to those of quercetin and vitamin C. These compounds form o- and p-quinonoid derivatives upon radical scavenging and may serve as new lead compounds for pharmacological investigations.
Laboratoire de Chimie Organique et Macromoléculaire, UMR CNRS 8009, Bâtiment C3, Université de Lille 1, 59655 Villeneuve d'Ascq Cedex, France. fabrice.bailly@univ.lille1.fr
Fabrice
F
Bailly
Cédric
C
Maurin
Elisabeth
E
Teissier
Hervé
H
Vezin
Philippe
P
Cotelle
D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D003374:Coumarins / Q000737:chemistry* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects / Q000502:physiology
D000975:Antioxidants; D003374:Coumarins; D016166:Free Radical Scavengers