Free radical scavenging potency of phloretic acid: thermodynamics of 2H+/2e processes (CROSBI ID 638815)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija
Podaci o odgovornosti
Amić, Ana ; Lučić, Bono ; Stepanić, Višnja ; Marković, Zoran ; Marković, Svetlana ; Dimitrić Marković, Jasmina ; Amić, Dragan
engleski
Free radical scavenging potency of phloretic acid: thermodynamics of 2H+/2e processes
Phloretic acid (3-(4’-hydroxyphenyl)propanoic acid) is one of the most abundant colon metabolites of various classes of polyphenols (e.g., polymeric proanthocyanidins, tea catechins, and ellagitannins). Its concentration in fecal water may reach value of 210mol/L [1], which could be high enough to exert at least in situ antioxidant activity [2]. Thermodynamics of 2H+/2e free radical scavenging mechanisms of phloretic acid was studied by DFT method using Gaussian 09 package [3]. Geometry optimizations and frequency calculations were carried out using the M06-2X/6-311++G(d, p) level of theory, in conjunction with the SMD continuum solvation model. For the first time direct involvement of carboxylic group in free radical scavenging mechanisms was investigated considering double hydrogen atom transfer (HAT), double single electron transferproton transfer (SET-PT) and double sequential proton loss electron transfer (SPLET) processes producing dienone lactone [4]. Obtained results indicate that phloretic acid possesses potential for inactivating free radicals of different characteristics (HO•, HOO•, CH3O•, CH3OO•, CH2=CH–O–O•, PhO•, Cl3COO• etc.) by direct scavenging via double HAT and double SPLET mechanisms. In this way, because phloretic acid is produced in highM concentrations and it is usually better absorbed than its precursor molecules, it may contribute to health benefits associated with regular intake of polyphenol-rich diet. References: [1] B. Halliwell, J. Rafter, A. Jenner, Am. J. Clin. Nutr. 81 (2005) 268S−276S. [2] M. Galleano, S.V. Verstraeten, P.I. Oteiza, C.G. Fraga, Arch. Biochem. Biophys. 501 (2010) 23−30. [3] M.J. Frisch, G.W. Trucks, H.B. Schlegel et al., Gaussian 09, Wallingford, CT, 2009. [4] H. Iwasaki, L.A. Cohen, B. Witkop, J. Am. Chem. Soc. 85 (1963) 3701-3702.
phloretic acid; free radical scavenging; DFT
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Podaci o prilogu
25-25.
2016.
objavljeno
Podaci o matičnoj publikaciji
The 28th International Course and Conference on the Interfaces among Mathematics, Chemistry and Computer Sciences (Math/Chem/Comp 2016) : abstracts
Vančik, Hrvoj ; Cioslowski, Jerzy
Podaci o skupu
International Course and Conference on the Interfaces among Mathematics, Chemistry and Computer Sciences (28 ; 2016)
predavanje
20.06.2016-25.06.2016
Dubrovnik, Hrvatska