Glucose-containing flavones—their synthesis and antioxidant and neuroprotective activities

Due to high reactivity, reactive oxygen species can attack biological molecules leading to cell or tissue injury. In this study, glucose moiety was attached at the C-7 position of quercetin 3-O-methyl ether (1) and luteolin (2) through glycosidic bond or ether linkage. The glucose-containing compounds showed potent DPPH and superoxide anion radical scavenging and lipid peroxidation inhibition activities and nearly equivalent protective actions to the parent aglycons against the H2O2-induced oxidative neuronal damage in primary cultured rat cortical cells. Among the compounds tested, 3b and 3c were the most potent (IC50 values = 7.33 and 5.34 μM, respectively), exhibiting nearly equivalent actions to the parent compounds 1 and 2 (IC50 = 3.50 and 3.75 μM, respectively).

Graphical abstractThe attachment of glucoside was performed at the position of C-7 of quercetin 3-methyl ether (1) and luteolin (2) through glycosidic bond or ether linkage to increase water solubility. Among the synthesized, compounds 3b and 3c showed most potent protection in neuronal cells with IC50 values of 7.33 and 5.34 μM, respectively, which are nearly equal to those of parent compounds 1 and 2 (IC50 = 3.50 and 3.75 μM, respectively).Figure optionsDownload full-size imageDownload as PowerPoint slide