A Potent Antioxidant Sesquiterpene, Abelsaginol, from Abelmoschus sagittifolius: Experimental and Theoretical Insights.

Abstract

The sesquiterpenoid compound abelsaginol (AS) was successfully isolated from Abelmoschus sagittifolius for the first time. The compound was identified using NMR and MS data. The antioxidant activity of AS was also evaluated both theoretically and experimentally. AS was found to be a weak HOO• radical scavenger in organic solvents such as pentyl ethanoate and dimethyl sulfoxide (koverall = ∼ 102 M–1 s–1), in a good agreement with the results of the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assay. However, AS exhibited good HOO• antiradical activity in water at pH 7.40 (koverall = 9.00 × 106 M–1 s–1) through the single-electron transfer mechanism of the anion state. Further calculations also demonstrated that AS could exert good to moderate activity against CH3O•, CH3OO•, CCl3OO•, NO2, and SO4•– radicals, with kf values from 4.00 × 103 to 1.52 × 107 M–1 s–1. However, AS exerted much lower activity against HO•, CCl3O•, NO, O2•–, and N3• radicals under the studied conditions. In general, the activity of AS in water at pH 7.40 is higher than that of Trolox or butylated hydroxytoluene, which are common reference antioxidants. Thus, in an aqueous physiological milieu, AS is a promising natural antioxidant.