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Thermodynamics of 2H+/2e- Free Radical Scavenging Mechanisms of 3-(4-Hydroxy-3- methoxyphenyl)propanoic Acid

The thermodynamic preference of different free radical scavenging mechanisms of 3-(4-hydroxy- 3-methoxyphenyl) propanoic acid (HMPPA), a colon catabolite of dietary (poly)phenols, was studied using density functional theory. The role of guaiacyl moiety and carboxyl group of HMPPA in double (2H+/2e-) processes of inactivation of free radicals was theoretically investigated in polar and nonpolar media using Gaussian 09 software package. Obtained results indicate that HMPPA possesses potential for inactivating free radicals of different characteristics (HO•, HOO•, CH3O•, CH3OO•, PhO•, Cl3COO• etc.) via double hydrogen atom transfer (dHAT) and double sequential proton loss electron transfer (dSPLET) mechanisms. Concentration of HMPPA in serum may reach very low micromolar values and may contribute to health benefits associated with regular intake of polyphenol-rich diet by direct scavenging of reactive oxygen species.

guaiacyl moiety, carboxyl group, HAT, ET-PT, SPLET

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