Improving the antioxidant activity of natural antioxidant honokiol by introducing the amino group

Exploring and synthesizing the compounds with stronger antioxidant activity have always been the goal of researchers. Herein, the substitution effects of the amino (NH₂-) group with the excellent electron-donating ability in different positions on the antioxidant activity of Honokiol (Hon) were systematically explored by using the quantum chemistry calculation based on the density functional theory method. The three possible antioxidant mechanisms of Hon and its four NH₂-substituted derivatives (Hon1-Hon4), containing the hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET), were explored in depth considering the gas and solvent phases. In addition, the frontier molecular orbital energies, natural bond orbital (NBO) charge population, and global descriptive parameters were used to study their antioxidant activity. The results indicate that compared with the original molecule Hon, the NH₂ substituents would have the stronger antioxidant activity. Moreover, the radical scavenging process of Hon and its derivatives has a disposition to the HAT and SPLET mechanisms in the gas and solvent phases, respectively. Meaningfully, owing to the lowest bond dissociation enthalpy and proton affinity values, Hon4 would show the most prominent antioxidant activity by comparison with the other compounds. In conclusion, this work will provide the purposeful reference for designing and synthesizing the antioxidants with more outstanding performance.