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Int. J. Mol. Sci. 2014, 15(9), 16351-16380; doi:10.3390/ijms150916351

Evaluation of the Antiradical Properties of Phenolic Acids

1
Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia
2
Department of Bioengineering and Bioinformatics, Moscow State University, GSP-1, Leninskie Hills, bld 73, 119234 Moscow, Russia
3
Institute of Animal Reproduction and Food Research of the Polish Academy of Sciences, Tuwima Street 10, 10-748 Olsztyn, Poland
*
Author to whom correspondence should be addressed.
Received: 21 July 2014 / Revised: 5 September 2014 / Accepted: 9 September 2014 / Published: 16 September 2014
(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols)
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Abstract

Antioxidant capacity (AOC) against peroxyl radical and 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS) radical cation was measured for a series of p-hydroxybenzoic (HB) and p-hydroxycinnamic (HC) acids at different pH. Quantum-chemical computation was performed using Gaussian 3.0 software package to calculate the geometry and energy parameters of the same compounds. Significant correlations were revealed between AOC and a number of calculated parameters. The most significant AOC descriptors for the studied compounds against peroxyl radical were found to be HOMO energy, rigidity (η) and Mulliken charge on the carbon atom in m-position to the phenolic hydroxyl. The most significant descriptor of the antioxidant properties against the ABTS radical cation at рН 7.40 is electron transfer enthalpy from the phenolate ion. The mechanism of AOC realization has been proposed for HB and HC acids against both radicals. View Full-Text
Keywords: antioxitant capacity; antioxidant descriptors; quantum-chemical calculations; phenolic acids antioxitant capacity; antioxidant descriptors; quantum-chemical calculations; phenolic acids
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Koroleva, O.; Torkova, A.; Nikolaev, I.; Khrameeva, E.; Fedorova, T.; Tsentalovich, M.; Amarowicz, R. Evaluation of the Antiradical Properties of Phenolic Acids. Int. J. Mol. Sci. 2014, 15, 16351-16380.

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