Antioxidative activity of quercetin and quercetin monoglucosides in solution and phospholipid bilayers.

The antioxidative effect of quercetin, quercetin 3-O-beta-D-glucopyranoside (Q3G), quercetin 4'-O-beta-D-glucopyranoside (Q4'G) and quercetin 7-O-beta-D-glucopyranoside (Q7G) was examined in solution and liposomal phospholipid suspension. First, their peroxyl radical-scavenging activities were investigated by measuring the inhibition of hydroperoxidation of methyl linoleate initiated by a radical initiator, 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). Quercetin exhibited the highest peroxyl radical-scavenging activity judging from the rate of hydroperoxidation during the induction period (Rinh) and the length of induction period (tinh). Although Q7G showed an induction period, its Rinh was higher and its tinh was lower than that of quercetin. Neither Q3G nor Q4'G gave a clear induction period in the curve of hydroperoxide formation. The rate of hydroperoxidation in the presence of Q3G was higher than Rinh of quercetin and the oxidative loss of Q3G was much slower than quercetin or Q7G when exposed to AMVN in solution. Q4'G exerted little inhibition compared to Q3G or Q7G. Next, the antioxidative activity of quercetin and its monoglucosides in phospholipid bilayers was examined by measuring the inhibition of lipid peroxidation in large unilamellar vesicles composed of egg yolk phosphatidylcholine (PC) and a water-soluble radical initiator. They retarded the accumulation of PC-hydroperoxides and the induction period increased in the order of Q4'G < Q3G approximately Q7G < quercetin. It is therefore concluded that quercetin acts as an antioxidant more efficiently than its monoglucosides when phospholipid bilayers are exposed to aqueous oxygen radicals.