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Trans-p-coumaric and trans-sinapinic acids are cinnamic acid`s derivatives which show strong antioxidant properties. In this work full optimization of both chemical structures and their radical, cation radical and anionic forms in vacuum and water medium has been performed, and antioxidant descriptors: Bond Dissociation Enthalpy, Adiabatic Ionization Potential, Proton Dissociation Enthalpy, Proton Affinity, Electron Transfer Enthalpy, Gas Phase Acidity , Free Gibbs Energy have been calculated. The Highest Occupied and Lowest Unoccupied Molecular Orbital energies have been employed to determine groups in compounds studied with the highest electron density. All calculations were performed using Gaussian 03W software package at the DFT level of theory (B3LYP hybrid functional) together with 6-311+G(2d,2p) basis set. Strong antioxidant properties of both investigated compounds were determined in this study. Based on the results it may be suggested that trans-p-coumaric and transsinapinic acids react according to the Hydrogen Atom Transfer mechanism in vacuum and according to Single-Electron Transfer followed by the Proton Transfer mechanism in water medium. Moreover, in both compounds studied the O-H bond is a preferred place of free radical attack.

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Abstract:The structure-activity relationship analysis has been performed for trans-and cis-hydroxycinnamic acids, to determine their theoretical antioxidant pharmacophore. Based on the detailed conformational studies, the most stable rotamers have been selected. We have analyzed the descriptors of four antioxidant mechanisms important in free radical scavenging: hydrogen atom transfer, sequential proton loss electron transfer, single electron transfer -proton transfer and transition metal chelation, based on the B3LYP/6-311++G(2d,2p) calculations in vacuum and polar media. The results explain the activity difference between cinnamic acid and its derivatives. The descending order of antioxidant potential is as follows:The results have shown that transisomers indicate higher reactivity than cis-and may be considered as good antioxidants. It has been determined that the highest antioxidant ability is related to the hydroxyl group in para position, supported by planar structure and stability of radical forms. π-Type delocalization of unpaired electron on aromatic ring, double bond and para O-atom is the key to radical stabilization. The ortho-dihydroxy substitution in benzene ring positively influences the ability to neutralize free radicals and makes caffeic acid the antioxidant pharmacophore of hydroxycinnamic acids.

BackgroundThe aim of this study was to analyse the effect of pomegranate juice (POM) supplementation on the levels of selected pro-inflammatory cytokines, hepcidin and markers of iron metabolism in well-trained rowers.MethodThe double-blind placebo-controlled study included 19 members of the Polish Rowing Team. The athletes were randomised into the supplemented group (n = 10), receiving 50 ml of standardised POM daily for two months, or the placebo group (n = 9). The subjects performed a 2000 m test on the rowing ergometer at the start of the project (baseline) and end of follow-up period. Blood samples from the antecubital vein were obtained three times during each trial: prior to the exercise, one minute after the test, and following a 24 h recovery.ResultsThe study documented the beneficial effect of supplementation with pomegranate fruit juice on TAC (P < 0.002). During the resting period, TAC level in the supplemented group was significantly higher than in the placebo group (x ± SD, 2.49 ± 0.39 vs. 1.88 ± 0.45, P < 0.05). The ergometric test conducted at baseline demonstrated a significant post-exercise increase in the concentrations of soluble transferrin receptors (P < 0.04), iron (P < 0.002) and IL-6 (P < 0.02), and to a significant post-exercise decrease in TAC. A significant increase in IL-6 concentration was also observed 24 h post-exercise. The exercise test conducted at the end of the follow-up period resulted in a significant decrease in TBIC and a significant increase in UIBC (P < 0.001), observed in both groups, both immediately post-exercise and after the resting period.ConclusionSupplementation with POM contributed to a significant strengthening of plasma antioxidant potential in the group of well-trained rowers, but had no effect on iron metabolism markers.