Antioxidative capacities of stilbenoid Suaveolensone A and Flavonoid Suaveolensone B: A detailed analysis of structural-electronic properties and mechanisms

• Published in: Journal of molecular structure 2021-01, Vol.1224, p.129025, Article 129025
• Main Authors: Son, Ninh The, Thuy, Phan Thi, Van Trang, Nguyen
• Format: Article
• Language: English
• Subjects: Antioxidative; Density functional theory; Flavonoid; Stilbenoid
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.129025

•Antioxidant activities of studied compounds are followed HAT mechanism in gas and SPLET mechanism in liquids.•Antioxidative actions are due to OH bond breaking.•Polyphenol type of flavonoid is better than stilbenoid in antioxidative treatment. Searching for bioactive compounds from natural products to antioxidative drugs, polyphenols type stilbenoids and flavonoids are recognized as useful candidates. The current study aims to elucidate the promising antioxidative capacity of two previously undescribed compounds silbenoid suaveolensone A (1) and flavonoid suaveolensone B (2), which mainly based upon DFT computational method. The antioxidant actions of both two studied compounds 1-2 is due to OH bond disruption, and followed by HAT mechanism in gas, but SPLET model in solvents acetone, methanol, and water. Structural and electronic analyses point out the role of aromatic phenyl units in antioxidative reactions. They respond for the more delocalization of electrons, thereby facilitating antiradical reactions. From the kinetic reaction of HOO• radicals attack OH groups, flavanonol 2 is better than stilbenoid 1 in antioxidative treatment, in which the lower Gibbs activation energies ΔG# of 9.8 - 12.9 kcal/mol and the higher rate constants K of 8.266 × 106 - 2.946 × 108 L/mol.s of compound 2 compared to those of compound 1 (the ΔG# values of 11.2 - 25.3 kcal/mol and the K values of 1.946 × 101 - 6.297 × 107 L/mol.s) [Display omitted]