Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids
Introduction
Excessive concentrations of reactive oxygen species in the human body can be involved in a number of pathological events (Werns and Lucchesi, 1989, Auroma, 1994, Kirkinezos and Moraes, 2001, Lee and Wei, 2001). Hydrogen peroxide (H2O2), when present in excess, is one of the many compounds that can be injurious for the cells (Halliwell and Gutteridge, 1999a).
Lipid peroxidation is another process that produces many pathological events in the cells and the organism of man (Halliwell and Gutteridge, 1999b, Noguchi and Niki, 1999, Drueke et al., 2001, Spiteller, 2001). This process, causing damage to unsaturated fatty acids, tends to decrease membrane fluidity and leads to many other pathological events.
The above processes can be effectively quenched by plant phenolics (Bahorun et al., 1996, Periera da Silva et al., 2000, Czinner et al., 2001, Lodovici et al., 2001), among them phenolic acids (Croft, 1998, Morton et al., 2000), which are known to be scavengers of various oxygen species, even as toxic as the HO• radical and singlet oxygen. The efficiency of phenolic compounds as anti-radicals and antioxidants is diverse and depends on many factors, such as the number of hydroxyl groups bonded to the aromatic ring, the site of bonding and mutual position of hydroxyls in the aromatic ring. For example, Rice-Evans et al., 1996, Joyeux et al., 1995 described the advantageous effect of an o-hydroxyl substitution in the aromatic ring for the anti-radical and antioxidant activity of phenolic acids.
The aim of the present study was to examine and compare the inhibition of lipid peroxidation, scavenging of H2O2 and scavenging of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) by some water-soluble phenolic acids with different models of hydroxylation of the aromatic ring.
Section snippets
Phenolic acids
Extrasynthesis: 4-hydroxyphenylacetic acid; 3,4-dihydroxyphenylacetic acid. Fluka: 3,4-dicaffeoylquinic (isochlorogenic acid), 3-caffeoylquinic acid (chlorogenic acid), 2-hydroxybenzoic acid (salicylic acid); 3-hydroxybenzoic acid, 3,4-dihydroxycinnamic acid (caffeic acid), 3,4-dihydroxybenzoic acid (protocatechuic acid), 3,5-dihydroxybenzoic acid (α-resorcylic), 2,3-dihydroxybenzoic acid (o-pyrocatechuic), 2,4-dihydroxybenzoic acid (β-resorcylic), 2,5-dihydroxybenzoic (gentisic). Mallinckrodt
Results
The results of the investigation of the antioxidative activity of phenolic acids are shown in Table 1.
The strongest inhibition of rapeseed oil peroxidation (Pi) was observed for 3,4,5-trihydroxybenzoic acid 1,2,3-trihydroxybenzene, reaching 96 and 95% of the reaction, respectively. Also 3,4-dihydroxycinnamic, 3,4-dihydroxybenzoic, 3-caffeoylquinic and 3,4-dicaffeoylquinic acids appeared to be strong inhibitors of the peroxidation process, the reaction being inhibited by 81, 89, 93 and 86%,
Discussion
Rice-Evans et al. (1996), having shown the antioxidant activity of gallic acids to be higher than that of pyrogallol, proved an advantageous influence of carboxylate on the antioxidant activity of phenolic acids.
Our investigation confirmed the strong activity of 3,4,5-trihydroxybenzoic acid and 1,2,3-trihydroxybenzene on both lipid peroxidation, hydrogen peroxide scavenging and DPPH• scavenging tests (Table 1). However, we observed no influence of carboxylate on the antioxidant or anti-radical
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