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

Lugar: 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 for structure analysis and M06-2X functional for the reactions employing gaseous, aqueousand non-polar environments. The conformational analysis andFukui functions allowed the selection of the initial structuresand the region of nucleophilic attack by hydrogen peroxide.The scavenging reactions analyzed are: 1) Sulfoxidation; 2)Epoxidation; and 3) Hydrogenation. Through the intrinsicreaction coordinate, the energy profile, the activation energies,the rate constant and its temperature-dependence werecalculated.The results predict that reactions occur slowly and hydrogenationis not a feasible process. Finally, the sulfoxidation ofAllyl Methyl Sulfide and Diallyl Sulfide resulted to be morethermodynamically and kinetically favorable than epoxidation(rate constant values, 10􀀀 10 s􀀀 1, in comparison with 10􀀀 18 s􀀀 1from epoxidation), becoming the most probable pathway forhydrogen peroxide scavenging.