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.
Highlights
Trans-3,5,4′-trihydroxystilbene, which locally named transresveratrol (RSV), is an active polyphenol found in various medicinal plants, especially in berries, grapes, peanuts, and red wines [1, 2]
From the view of previous preclinical research, RSV itself is shown to possess a wide range of biological activities, which may be possibly employed for the prevention and treatment of cancers, cardiac diseases, neurodisorders, and so on [5]
All the calculated actions in this work have been performed using Gaussian 09 software package [11]. e B3LYP/6311++G(d, p) level is utilized to gain the optimized structural RSV and its cations, anions, and radicals since the calculations were taken into account in four media, including gas with the dielectric constant ε 1.00, water (ε 78.32), methanol (ε 32.60), and acetone (ε 20.72) [12]. e vibrational frequencies, at the same level of theory, have been calculated for correcting zero-point energy (ZPE), confirming that there are no imaginary frequencies in the ground states. e effects of liquids have been considered by using IEF-PCM [13, 14]
Summary
Trans-3,5,4′-trihydroxystilbene, which locally named transresveratrol (RSV), is an active polyphenol found in various medicinal plants, especially in berries, grapes, peanuts, and red wines [1, 2].
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