Scavenging of Hydrogen Peroxide by Allyl Methyl Sulfide and Diallyl Sulfide, Two Garlic Active Compounds: A Theoretical Study

DÍAZ, MARIO G.; VEGA?HISSI, ESTEBAN G.; ANDRADA, MATIAS F.; GARRO MARTINEZ, JUAN C.

ChemistrySelect

Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Año: 2020 vol. 5 p. 3234 - 3242

2365-6549

We study potential scavenging of hydrogen peroxide by AllylMethyl Sulfide and Diallyl Sulfide, two garlic components. Theantioxidant properties of garlic are attributed to organosulfidecompounds, which react with reactive oxygen species preventingthe oxidative stress. We used the B3LYP functional forstructure analysis and M06-2X functional for the reactionsemploying gaseous, aqueous and non-polar environments. Theconformational analysis and Fukui functions allowed theselection of the initial structures and the region of nucleophilicattack by hydrogen peroxide. The scavenging reactionsanalyzed are: 1) Sulfoxidation; 2) Epoxidation; and 3) Hydrogenation.Through the intrinsic reaction coordinate, the energyprofile, the activation energies, the rate constant and itstemperature-dependence were calculated. The results predictthat reactions occur slowly and hydrogenation is not a feasibleprocess. Finally, the sulfoxidation of Allyl Methyl Sulfide andDiallyl Sulfide resulted to be more thermodynamically andkinetically favorable than epoxidation (rate constant values,10􀀀 10 s􀀀 1, in comparison with 10􀀀 18 s􀀀 1 from epoxidation),becoming the most probable pathway for hydrogen peroxidescavenging.