Evaluation of the antiradical properties of phenolic acids

Olga Koroleva, Anna Torkova, Ilya Nikolaev, Ekaterina Khrameeva, Tatyana Fedorova, Mikhail Tsentalovich, Ryszard Amarowicz

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)16351-16380
Number of pages30
JournalInternational Journal of Molecular Sciences
Volume15
Issue number9
DOIs
Publication statusPublished - 16 Sep 2014
Externally publishedYes

Keywords

  • Antioxidant descriptors
  • Antioxitant capacity
  • Phenolic acids
  • Quantum-chemical calculations

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