Theoretical Study on Methylated Resveratrol Analogues towards the Antioxidant Activity and Mechanisms: Understanding the Structure–Activity Relationship

• Published in: Russian Journal of Physical Chemistry A Vol. 97; no. 6; pp. 1121 - 1127
• Main Author: Pei, Ling
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.06.2023; Springer Nature B.V
• Subjects: Antioxidants; Chemical Kinetics and Catalysis; Chemistry; Chemistry and Materials Science; Density functional theory; Electron transfer; Physical Chemistry; Protons; Reaction mechanisms; Single electrons; Solvents; Vapor phases; SPLET; HAT; SET-PT; resveratrol analogues; antioxidant activity and mechanism; density functional theory
• ISSN: 0036-0244; 1531-863X
• DOI: 10.1134/S0036024423060171

Theoretically, the antioxidant properties of substances are usually evaluated by three working mechanisms, including H-atom transfer (HAT), single-electron transfer-proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET). In this paper, the antioxidant activity of resveratrol and methyl derivatives (1-4,4-methylresveratrol) in the gas phase and solvents were investigated by using density functional theory (DFT). Results show that 4'-OH is still the most crutical active site of resveratrol and its derivatives. The increased number of methyl groups can enhance the antioxidant activity of resveratrol. It was also found that in the gas phase and non-polar solvents, HAT was the dominant reaction mechanism. In polar solvents, SPLET is the dominant reaction mechanism.