The effect of DNA on the kinetics of reactions of propyl gallate radicals

Zakharova, N. A.; Lashkova, D. L.; Odintsova, S. P.; Troitskaya, G. P.; Kruglyakova, K. E.

doi:10.1007/bf00925287

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“…They have shown that, at high NaOH concentration, propyl gallate is hydrolysed to gallic acid, and, in the presence of ADN, the concentration of the semiquinone radical anion is reduced. 17 It has been reported that the ester alkyl group does not influence the stability of the semiquinone radical anion. 18 Trihydroxy substitutions in the propyl gallate molecule (PG) are responsible for its antioxidant activity, the para-hydroxyl group with respect to the ester group appearing to be the most important one.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant activity of propyl gallate in aqueous and lipid media: a theoretical study

Medina

Iuga

Álvarez-Idaboy

2013

Phys. Chem. Chem. Phys.

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In this work, we have carried out a quantum chemistry and computational kinetics study on the reactivity of propyl gallate towards ˙OOH, ˙OOCH3 and ˙OOCHCH2 radicals, in aqueous and lipid media. We have considered three reaction mechanisms: hydrogen transfer (HT), radical adduct formation (RAF) and single electron transfer (SET). Rate constants and relative branching ratios for the different paths contributing to the overall reaction, at 298.15 K, are reported. Our results show that propyl gallate reacts mainly through the HT mechanism, independently of the solvent or the peroxyl radical, contrary to other phenols such as catechols and guayacols previously studied, which react mainly via the SET mechanism. In aqueous media at physiological pH, the calculated rate constants towards the ˙OOH, ˙OOCH3 and ˙OOCHCH2 radicals are 4.56 × 10(8), 1.59 × 10(6) and 4.05 × 10(8) M(-1) s(-1), while in lipid media the rate constants are 2.94 × 10(4), 7.73 × 10(3) and 9.94 × 10(5) M(-1) s(-1). Thus, a propyl gallate molecule acts as a very efficient peroxyl radical scavenger, both in aqueous and lipid media. Since the gallate moiety is a part of other naturally occurring polyphenols such as aflavine gallates and epigallocatechin gallates, the results of this study could be extrapolated to these compounds. Even if these compounds have other antioxidant structures or enhancers, the activity of the gallate moiety could be considered as a lower limit to their antioxidant activity.

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Section: Introductionmentioning

confidence: 99%