Computational Insights into the Radical Scavenging Activity and Xanthine Oxidase Inhibition of the Five Anthocyanins Derived from Grape Skin

• Main Authors: Xiao-Qin Lu (Author), Jindong Li (Author), Bin Wang (Author), Shu Qin (Author)
• Format: Book
• Published: MDPI AG, 2024-09-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

Anthocyanins, typical polyphenol compounds in grape skin, have attracted increasing interest due to their health-promoting properties. In this body of work, five representative anthocyanins (Cy-3-<i>O</i>-glc, Dp-3-<i>O</i>-glc, Pn-3-<i>O</i>-glc, Mv-3-<i>O</i>-glc, and Pt-3-<i>O</i>-glc) were studied using the density functional theory (DFT) to elucidate structure-radical scavenging activity in the relationship and the reaction path underlying the radical-trapping process. Based on thermodynamic parameters involved in HAT, SET-PT, and SPLET mechanisms, along with the structural attributes, it was found that the C4' hydroxyl group mainly contributes to the radical scavenging activities of the investigated compounds. Pt-3-<i>O</i>-glc exhibits a good antioxidant capacity among the five compounds. The preferred radical scavenging mechanisms vary in different phases. For the Pt-3-<i>O</i>-glc compound, the calculations indicate the thermodynamically favoured product is benzodioxole, rather than <i>o</i>-quinone, displaying considerably reduced energy in double HAT mechanisms. Additionally, the thermodynamic and kinetic calculations indicate that the reaction of ^•OH into the 4'-OH site of Pt-3-<i>O</i>-glc has a lower energy barrier (7.6 kcal/mol), a higher rate constant (5.72 × 10⁹ M⁻¹ s⁻¹), and exhibits potent ^•OH radical scavenging properties. Molecular docking results have shown the strong affinity of the studied anthocyanins with the pro-oxidant enzyme xanthine oxidase, displaying their significant role in inhibiting ROS formation.

Item Description

10.3390/antiox13091117
2076-3921