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The role of guaiacyl moiety and carboxyl group in radical scavenging by dihydroferulic acid

Thermodynamics of 2H+/2e- radical scavenging mechanisms of dihydroferulic acid, a naturally occurring plant compound and colon catabolite of (poly)phenols, was studied by DFT method using SMD/M06–2X/6–311++G(d, p) level of theory with the Gaussian 09 program package [1]. Until recently, radical inactivation by (poly)phenolic compounds has been investigated by considering involvement of only phenolic –OH group(s) via 1H+/1e- mechanisms. Here, we studied the role of guaiacyl moiety (reaction path a [2]) and carboxyl group (reaction path b [3]) (Figure 1) in radical scavenging by dihydroferulic acid via double hydrogen atom transfer (dHAT), double electron transfer- proton transfer (dETPT) and double sequential proton loss electron transfer (dSPLET) mechanisms in polar and non-polar solvents [4]. Obtained results indicate that dihydroferulic acid possesses potential for inactivating radicals of different characteristics (HO•, HOO•, CH3O•, CH3OO•, PhO•, Cl3COO• etc.) what can be ascribed to 2H+/2e- mechanisms such as dHAT and dSPLET, rather than to a single 1H+/1e- processes. We found that reaction path a is less energy demanding than reaction path b. References [1] M.J. Frisch, G.W. Trucks et al., Gaussian 09. Revision A.02. Gaussian, Inc., Wallingford CT, 2009. [2] D. Kozlowski, P. Trouillas, C. Calliste, P. Marsal, R. Lazzaroni and J.-L. Duroux, J. Phys. Chem. A 111 (2007) 1138–1145. [3] H. Iwasaki, L.A. Cohen and B. Witkop, J. Am. Chem. Soc. 85 (1963) 3701–3702. [4] A. Amić, B. Lučić, V. Stepanić, Z. Marković, S. Marković, J.M. Dimitrić Marković and D. Amić, Food Chem. 218 (2017) 144–151. Acknowledgment This work has been supported by The Foundation of the Croatian Academy of Sciences and Arts, under the project No. 10-102/244-1-2016. – “Investigations of the antioxidant mechanisms of polyphenols and their metabolites.”

radical scavenging ; dihydroferulic acid ; DFT ; dHAT ; dET-PT ; dSPLET

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