Influence of spontaneous and inoculated fermentation of açai on simulated digestion, antioxidant capacity and cytotoxic activity
Amanda Laís Alves Almeida NascimentoMariane Sampaio da Silveira de SouzaLarissa Lorrane Rodrigues BorgesMonique Renon EllerFrederico Augusto Ribeiro de BarrosAdriana Corrêa MendonçaLuciana AzevedoMariana Araújo Vieira do CarmoAmanda dos Santos LimaLaura da Silva CruzGabriel Abranches Dias CastroSérgio Antônio FernandesPaulo César Stringheta
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A series of Trolox amide derivatives were synthesized by modifying the carboxyl groups of Trolox. Thirty target compounds were obtained and characterized through nuclear magnetic resonance and mass spectrometry. Trolox derivatives were employed to explore the potential structure-antioxidant activity relationships. The antioxidant activities of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), ferric reducing antioxidant power (FRAP) and hydroxyl radical assays. DPPH scavenging activity test results illustrated that compounds exhibited scavenging activities similar to L-ascorbic acid and Trolox, with compounds 14a, 18a, 24a and 26a in particular exhibiting higher scavenging activities than L-ascorbic acid. The results demonstrated that compounds displayed ABTS scavenging activities similar to L-ascorbic acid and Trolox, with compounds 26a and 29a in particular having potency twofold higher. FRAP assay results indicated that compounds 11a, 19a, 25a, 29a and 30a had activity similar to Trolox. The results revealed that compounds 6a and 19a had similarly high hydroxyl radical-scavenging activities as Trolox. The results of α-glucosidase experiments uncovered that compounds 10a, 25a, 28a and 29a had excellent inhibitory activity, which was similar to that of acarbose and different from Trolox. The results of acetylcholinesterase and butyrylcholinesterase experiments demonstrated that some compounds had weak anticholinesterase activities. 26a and 29a are important Trolox derivatives with better biological activity profiles and deserve further study.
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The peroxidation of human erythrocytes induced by peroxyl radical initiator and its inhibition by several gallate esters (e.g., propyl, methyl, ethyl) and Trolox (a more polar analogue of vitamin E) have been studied. The antioxidant activity was determined on erythrocytes against hemolysis generated by a thermal activator, 2,2prime-azobis-(2-amidinopropane)dihydrogenchloride. It was found that propyl gallate and its two analogues were more effective than Trolox in preventing cell lysis. However, the combination of gallate esters and Trolox produced a protective effect exceeding the arithmetic sum of their individual contributions. These perceived synergisms occur at more than one level of Trolox at a given level of a gallate ester.Key words: Trolox, gallates, synergism, peroxyl radicals.
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Comprehensive research is required to achieve the optimization of the antioxidant protection through baby foods, in particular, the commercially available fruit-based baby foods. This study investigated the physicochemical properties, ascorbic acid (AA), total carotenoids (TC), total phenolic content (TPC), trolox equivalent antioxidant capacity (TEAC) and oxygen radical absorbance capacity (ORAC) of 23 different commercially available fruit-based baby foods. The main contribution to the total antioxidant capacity (trolox equivalent antioxidant capacity and oxygen radical absorbance capacity) was provided by ascorbic acid, followed by phenolic compounds, in accordance with a mathematical equation obtained from the data: TEAC = 245.906 + 7.727 × (AA) + 1.988 × (TPC) − 0.008 × (TC) and ORAC = 318.662 + 2.775 × (AA) − 0.531 × (TPC) − 0.073 × (TC). Moreover, a positive correlation ( r = 0.346, p < 0.05) was found for oxygen radical absorbance capacity and trolox equivalent antioxidant capacity methods. Baby foods with different kind of fruits used as ingredients showed higher antioxidant capacity. Among the commercial baby foods analysed in this work, that treated by gentle steam cooking process had high levels of bioactive compounds and antioxidant capacity.
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AbstractTrolox C (Trolox), a water-soluble analogue of vitamin E lacking the phytyl chain, was investigated with respect to its effect on the oxidation of low-density lipoprotein (LDL). Trolox was added at different time points of LDL oxidation induced by Cu2+ and aqueous peroxyl radicals. In the case of Cu2+ -induced LDL oxidation, the effect of Trolox changed from antioxidant to prooxidant when added at later time points during oxidation; this transition occurred whenever α-tocopherol was just consumed in oxidizing LDL. Thus, in the case of Cu2+-dependent LDL oxidation, the presence of lipophilic antioxidants in the LDL particle is likely to be a prerequisite for the antioxidant activity of Trolox.When oxidation was induced by peroxyl radicals, as a model of metal-independent oxidation, the effect of Trolox was always antioxidant, suggesting the importance of Cu2+/Cu+ redox-cycling in the prooxidant mechanism of Trolox. Our data suggest that, in the absence of significant amounts of lipophilic antioxidants, LDL becomes highly susceptible to oxidation induced by transition metals in the presence of aqueous reductants.Keywords: Low-density lipoproteinlipid peroxidationantioxidantsTroloxprooxidant effect
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The antioxidant and membranoprotective properties of trolox have been studied in vitro. It is established that trolox possesses antioxidant properties, inhibiting ascorbate-dependent lipid peroxidation of liver homogenates and Fe(2+)-induced lipid chemiluminescence of egg-yolk lipids. In addition, trolox exhibits a broad spectrum of antiradical activity and interacts with stable free 2,2-diphenyl-1-picrylhydrazyl radical so as to reduce the generation of luminol radicals and reactive oxygen species and to bind peroxy radicals. Trolox also possessed membranoprotective properties, being capable of reducing the oxidative hemolysis of erythrocytes.
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In this paper the antioxidant activity of Trolox derivatives were investigated by density function theory and polarization continuum model as solvent model in order to propose the novel derivatives with higher antioxidant activity from a theoretical viewpoint. The effects of various ortho and meta substituents on the reaction enthalpies of antioxidant mechanisms of Trolox were investigated. Also the effect of reducing the number of atoms in the heterocyclic ring and effect of replacing the oxygen heteroatom of Trolox with other heteroatoms on the antioxidant activity of Trolox were evaluated. Results show that the NH2, OH and NHMe substituents in meta and ortho positions decrease the BDE and IP values and also increase the antioxidant activity of Trolox from the theoretical viewpoint. The derivatives e, c and d with NH, S and Se instead of O have higher antioxidant activity from the theoretical viewpoint. Obtained results show that reducing the number of atom in the heterocyclic ring (derivatives a and b) decrease the BDE and IP values and also increase the antioxidant activity of Trolox from the theoretical viewpoint. The linear dependencies between BDE of OH bond and IP values of studied Trolox derivatives and corresponding EHOMO and R(O-H) values can be useful to propose novel derivatives with higher antioxidant activity from the theoretical viewpoint.
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