Chemically synthesized glycosides of hydroxylated flavylium ions as suitable models of anthocyanins: Binding to iron ions and human serum albumin, antioxidant activity in model gastric conditions

Abstract

Polyhydroxylated flavylium ions, such as 3′,4′,7-trihydroxyflavylium chloride (P1) and its more water-soluble 7-O-β-D-glucopyranoside (P2), are readily accessible by chemical synthesis and suitable models of natural anthocyanins in terms of color and species distribution in aqueous solution. Owing to their catechol B-ring, they rapidly bind FeIII, weakly interact with FeII and promote its autoxidation to FeIII. Both pigments inhibit heme-induced lipid peroxidation in mildly acidic conditions (a model of postprandial oxidative stress in the stomach), the colorless (chalcone) forms being more potent than the colored forms. Finally, P1 and P2 are moderate ligands of human serum albumin (HSA), their likely carrier in the blood circulation, with chalcones having a higher affinity for HSA than the corresponding colored forms.