title: Evaluation of the antiradical properties of phenolic acids.
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.
authors.affiliation: Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia. koroleva@inbi.ras.ru.
authors.forename: Olga
authors.initials: O
authors.lastname: Koroleva
authors.affiliation: Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia. anna_torkova@mail.ru.
authors.forename: Anna
authors.initials: A
authors.lastname: Torkova
authors.affiliation: Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia. ilya_mbf@yahoo.com.
authors.forename: Ilya
authors.initials: I
authors.lastname: Nikolaev
authors.affiliation: Department of Bioengineering and Bioinformatics, Moscow State University, GSP-1, Leninskie Hills, bld 73, 119234 Moscow, Russia. khrameeva@genebee.msu.ru.
authors.forename: Ekaterina
authors.initials: E
authors.lastname: Khrameeva
authors.affiliation: Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia. fedorova_tv@mail.ru.
authors.forename: Tatyana
authors.initials: T
authors.lastname: Fedorova
authors.affiliation: Bach Institute of Biochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 33, bld 2, 119071 Moscow, Russia. snowsurfers1@gmail.com.
authors.forename: Mikhail
authors.initials: M
authors.lastname: Tsentalovich
authors.affiliation: Institute of Animal Reproduction and Food Research of the Polish Academy of Sciences, Tuwima Street 10, 10-748 Olsztyn, Poland. r.amarowicz@pan.olsztyn.pl.
authors.forename: Ryszard
authors.initials: R
authors.lastname: Amarowicz
mesh_terms: D000465:Algorithms; D000975:Antioxidants / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D062385:Hydroxybenzoates / Q000737:chemistry*; D007700:Kinetics; D010226:Parabens / Q000737:chemistry; D011422:Propionates; D011789:Quantum Theory; D012984:Software
chemical_list: D000975:Antioxidants; D003373:Coumaric Acids; D062385:Hydroxybenzoates; D010226:Parabens; D011422:Propionates; C495469:p-coumaric acid; C038193:4-hydroxybenzoic acid