7-O-Galloyltricetifavan: a promising natural radical scavenger

Le Trung Hieu; Tran Thi Van Thi; Nguyen Thi Hoa; Adam Mechler; Quan V Vo

doi:10.1098/rsos.211906

7-O-Galloyltricetifavan: a promising natural radical scavenger

R Soc Open Sci. 2022 Jun 22;9(6):211906. doi: 10.1098/rsos.211906. eCollection 2022 Jun.

Authors

Le Trung Hieu¹, Tran Thi Van Thi¹, Nguyen Thi Hoa², Adam Mechler³, Quan V Vo²

Affiliations

¹ University of Sciences, Hue University, Thua Thien Hue 530000, Vietnam.
² The University of Danang - University of Technology and Education, Danang 550000, Vietnam.
³ Department of Chemistry and Physics, La Trobe University, Victoria 3086, Australia.

Abstract

7-O-Galloyltricetifavan (7OGT), a natural flavonoid, is isolated from the leaves of Pithecellobium clypearia. The compound exhibits a variety of biological activities. This study details the evaluation of the HOO^• antiradical activity of 7OGT by quantum chemistry calculations. The HOO^• trapping activity of 7OGT in the gas phase (reference state) was discovered to follow the formal hydrogen transfer mechanism with a rate constant of k = 4.58 × 10⁸ M^-1 s^-1. In physiological environments, 7OGT is predicted to be an excellent HOO^• radical scavenger with k _overall = 2.65 × 10⁸ and 1.40 × 10⁴ M^-1 s^-1 in water and pentyl ethanoate solvents, respectively. The HOO^• antiradical activity of 7OGT in water at physiological pH is approximately 2000 times that of Trolox and substantially higher than that of other well-known natural antioxidants such as trans-resveratrol or ascorbic acid. Thus, 7OGT is an excellent natural antioxidant in polar environments.

Keywords: antioxidant; antiradical activity; density functional theory; flavonoid; kinetics.

Associated data

Dryad/10.5061/dryad.jh9w0vtcq