Interference of malvidin and its mono- and di-glucosides on the membrane — Combined in vitro and computational chemistry study

Abstract

The antioxidative and antiradical properties of malvidin (Mv), malvidin 3-O-glucoside (Mv 3-glc) and malvidin 3,5-O-diglucoside (Mv 3,5-diglc) were evaluated by AAPH● and DPPH● assays, respectively. In both cases, a decrease in activity was observed in the following order Mv > Mv 3-glc > Mv 3,5-diglc. Quantum mechanics studies have confirmed this pattern, which can be explained by an underlying activity based on hydrogen atom transfer from C3-hydroxyl. Further measurements of the ability of malvidins to interact with membrane-mimicking liposomes revealed that malvidins, depending on their structure, increase packing order mainly in the hydrophilic region of the membrane bilayer. A mixed molecular dynamics and quantum mechanics protocol explained this in terms of fluctuating charge distribution among the species investigated. These findings are key in explaining elucidating the antioxidant activity of malvidins against membranes as a result of surface rearrangement and may have important implications for future pharmacological applications.

Keywords

• Anthocyanins
• Malvidins
• Lipid membrane
• Theoretical studies
• Structure-dependent relationships