Inhibitory effect of a quercetin metabolite, quercetin 3-O-beta-D-glucuronide, on lipid peroxidation in liposomal membranes.
To study the antioxidant activity of quercetin 3-O-beta-D-glucuronide (Q3GA), which is one of the quercetin metabolites in the blood after intake of quercetin-rich food, the inhibitory effect of Q3GA on lipid peroxidation was estimated using phosphatidylcholine large unilamellar vesicles (PC LUV) as a biomembrane model. Iron ion, an aqueous peroxyl radical generator, a peroxynitrite generator, or lipoxygenase was used as the inducer of lipid peroxidation. In all cases, Q3GA inhibited lipid peroxidation significantly, although its inhibitory effect was lower than that of quercetin aglycon. The ultrafiltration of PC LUV containing Q3GA revealed that Q3GA has low but significant affinity with the membranes of phospholipid bilayers. It is therefore likely that Q3GA acts as an efficient antioxidant in membranous lipid peroxidation through its localization in the phospholipid bilayer. This conjugated quercetin metabolite seems to retain the ability to protect cellular and subcellular membranes from peroxidative attack by reactive oxygen species and peroxidative enzymes.
Shirai
M
M
Department of Nutrition, School of Medicine, The University of Tokushima, Tokushima 770-8503, Japan.
Moon
J H
JH
Tsushida
T
T
Terao
J
J
D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism; D007501:Iron / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008081:Liposomes; D008567:Membranes, Artificial; D011794:Quercetin / Q000031:analogs & derivatives / Q000378:metabolism* / Q000494:pharmacology*; D014462:Ultrafiltration
D008081:Liposomes; D008567:Membranes, Artificial; C443401:quercetin 3-O-glucuronide; D011794:Quercetin; D007501:Iron; D001093:Arachidonate 15-Lipoxygenase