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.
Highlights
Anthocyanins are responsible for the colors of numerous flowers, fruits, vegetables and even cereals.Colors expressed by anthocyanins vary from red to blue depending on pH, self-association and interactions with metal ions (Al3+, Fe3+, Mg2+) and phenolic copigments, such as flavones, flavonols and hydroxycinnamic acids [1,2,3,4,5]
In a previous paper [31], we reported the chemical synthesis, structural transformations, aluminium binding and radical-scavenging (DPPH test) of 3',4',7-trihydroxyflavylium chloride (P1) and its
7-O-β-D-glucopyranoside (P2), come up as suitable models for investigating important properties of anthocyanins: binding of iron ions and serum albumin, inhibition of lipid peroxidation induced by dietary iron in model gastric conditions
Summary
Colors expressed by anthocyanins vary from red to blue depending on pH, self-association (especially, in the case of acylated anthocyanins) and interactions with metal ions (Al3+, Fe3+, Mg2+) and phenolic copigments, such as flavones, flavonols and hydroxycinnamic acids [1,2,3,4,5]. Through their coloring properties, anthocyanins strongly contribute to food quality and appeal to consumers. A large part of the health benefits of anthocyanins is expected to be mediated by their degradation products and their conjugates [16]
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