Analytical and Theoretical Studies of Antioxidant Properties of Chosen Anthocyanins; A Structure-Dependent Relationships

The relationship between the structure and the antiradical and antioxidant activities of three anthocyanidins, namely peonidin, petunidin, and delphinidin, and their glucosides was investigated in this study. The ability of anthocyanins to scavenge free radicals was determined using DPPH? assay, whereas the inhibition of peroxidation in liposomes in relation to a model membrane that imitated the composition of a lipid membrane in tumor cells was specified using the fluorimetric method. To explore this issue at the atomistic level, density functional theory studies were applied. It was shown that glycosides performed better than anthocyanidins in protecting membranes against oxidation. The highest redox potential was demonstrated by anthocyanidins with the highest number of hydroxyl groups in the B ring in the order as follows: (Dp > Pt > Pn), and the same relationship was proven for their glucosides. The majority of the compounds studied here proved to be better antioxidants than ascorbic acid. They showed consistent electrodonating properties and though the f-HAT mechanism became more feasible with each consecutive deprotonation. Glycosylation did not have a direct impact on reactivity, apart from peonidin and petunidin in the study of which it was found that this process was responsible for lifting off steric hindrance between B and C rings and rendering certain pathways more feasible. Kinetic and molecular dynamics are essential to properly describe the membrane's lipid oxidation.

Automated summary

This study investigates the relationship between the structure and the antiradical and antioxidant activities of three anthocyanidins and their glucosides. The results show that the glucosides have a better protective effect against membrane oxidation compared to anthocyanidins.