Antioxidant of Trans-Resveratrol: A Comparison between OH and CH Groups Based on Thermodynamic Views

Abstract

Trans-resveratrol establishes the planarity in its structure which makes it an interesting compound in both experimental and theoretical examinations. The current study, using the density functional method (DFT), attempts to compare the antioxidative capacities between hydroxyl (OH) and aromatic methine (CH) groups of this molecule. Becke’s exchange-correlation B3LYP functional together with 6-311++G(d, p) basis set was used to reveal the effects of structural geometry and electronic feature on the antioxidative results of OH and CH groups. The antioxidative action of trans-resveratrol has followed the HAT mechanism in gas, but the SPLET pathway in liquids. OH bond breaking is easier than CH bond disruption. 4-OH bond breaking induces the lowest BDE values of 74.4–77.9 kcal/mol in gas, acetone, methanol, and water, as well as the lowest PA values of 37.2–46.2 kcal/mol in acetone, methanol, and water. From the kinetic view, 4-OH is also an active center to capture laboratory radical DPPH, ROS radicals HOO• and CH3O•, and RNS radical •NO2.

A Potential Valorization Strategy of Wine Industry by-Products and Their Application in Cosmetics—Case Study: Grape Pomace and Grapeseed

“…This result can be explained by the GP constitution since it is composed not only of seeds but also of skins. Red grapes' skin is rich in trans-resveratrol, and this PC has a high antioxidant capacity, therefore this can be the main cause for the increase in antioxidant capacity in GP extract [47][48][49]. The obtained results prove that both GS extract and GP extract display high antioxidant capacity, since the value of IC50 for both samples is between 50 and 100 μgextract•mLDPPH −1 , which validates the possibility of using them as antioxidant agents from natural sources [50].…”

Synthesis and characterization of innovative resveratrol nanobelt-like particles and assessment of their bioactivity, antioxidative and antibacterial properties

“…Resveratrol is known for its antioxidative activity, mainly based on the breakage of the OH bond. 37 Results of the DPPH assay confirming the antioxidative potential of ResNPs are presented in Table 1. Although both commercial resveratrol and ResNPs showed lower scavenging activity than vitamin C, the difference at higher concentrations was not pronounced.…”