Theoretical and Experimental Studies of the Antioxidant and Antinitrosant Activity of Syringic Acid

Abstract

Syringic acid (SA) is a natural phenolic acid found in vegetables, fruits, and other plant-based foods. A range of biological activities were proposed for this compound including anticancer, antimicrobial, anti-inflammation, and anti-diabetic activities, as well as antioxidant and antinitrosant properties. In this study, the focus is on the latter two. The HO^•, HOO^•, NO, and NO₂ scavenging activities of SA were evaluated in physiological environments by kinetic and thermodynamic calculations. The computed rate constants of the HO^• radical scavenging of SA were 4.63 × 10⁹ and 9.77 × 10⁷ M^-1 s^-1 in polar and nonpolar solvents, respectively. A comparison with the experimentally determined rate constant in aqueous solution yields a <i>k</i>_calculated/<i>k</i>_experimental ratio of 0.3, thus the computed kinetic data are reasonably accurate. SA exhibited excellent HOO^• and NO₂ scavenging activity in water (<i>k</i>_overall(HOO^•) = 1.53 × 10⁸ M^-1 s^-1 and <i>k</i>_overall(NO₂) = 1.98 × 10⁸ M^-1 s^-1), whereas it did not show NO scavenging activity in any of the studied environments. In lipid medium, SA exhibited weak activity. Thus, in polar environments, the HOO^• radical scavenging of SA is 1.53 times higher than that of ascorbic acid. Consistently, SA is a promising antioxidant and antinitrosant agent in polar environments.