Determination of hydrogen peroxide scavenging activity of cinnamic and benzoic acids employing a highly sensitive peroxyoxalate chemiluminescence-based assay: Structure–activity relationships (original) (raw)
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Journal of agricultural …, 1999
The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2′-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids.
Antioxidant Activities of Cinnamic and Benzoic Acid Derivaties
2005
Antioxidant and antiradical activities of cinnamic and benzoic acid derivatives, using different methods, were investigated. The total antioxidant effect was evaluated using method with linoleic acid-water emulsion. The ability to scavenge free radicals was checked using 2,2-azinobis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS) or 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The reducing power of the studied compounds solutions was also evaluated. It was stated, that the applied measuring method strongly influenced the obtained result, because in the system with ABTS free radicals, the highest antioxidant activities possessed vanillic, sinapic and protocatechuic acid, whereas the most effective DPPH radical scavengers were methyl ferulate, methyl syringate, syringaldehyde and vanillic acid. In another method, linoleic acid peroxidation was effectively inhibited by the caffeic, sinapic and syringic acid. The highest reducing powers possessed protocatechuic acid, caffeic, sinapic a...
Evaluation of Antioxidant Activity of Cinnamic Acid and Some of its Derivatives
European Chemical Bulletin
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Antioxidant and Hypolipidemic Activities of Cinnamic Acid Derivatives
Molecules
Oxidative stress and hyperlipidemia are important factors for the initiation and progression of various cell degenerative pathological conditions, including cardiovascular and neurological diseases. A series of cinnamic acid-derived acids, such as ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, p-coumaric acid, and (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylic acid, were esterified or amidated with various moieties, bearing different biological activities, and evaluated. The antioxidant and radical scavenging abilities of the compounds via inhibition of rat hepatic microsomal membrane lipid peroxidation, as well as their interaction with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH), were assessed. Further, their hypolipidemic activity in vivo was tested. The majority of the obtained compounds demonstrated considerable radical scavenging and antioxidant action, with a parallel decrease in Triton-induced hyperlipidemia in rats. The (E)-3-(3,5-di-tert-butyl-4-hydr...
Journal of Student Research, 2020
Reactive oxygen species (ROS), such as hydrogen peroxide (H2O2), are highly reactive and can inhibit the normal function of cells. Due to the damage ROS can cause, much interest has been generated around the effects of antioxidant supplements, which could potentially prevent or slow down ROS in the body. In this study, a variety of antioxidants were evaluated for their ability to inactivate H2O2 in a peroxidase-catalyzed reaction. Six of the fourteen antioxidants were significantly effective at inactivating H2O2 compared to the control. This study should be used to further understand how antioxidant supplements could be beneficial in the human diet.
Antioxidant properties of benzoic acid derivatives against Superoxide radical
Free Radicals and Antioxidants, 2012
Reactive species play a dual deleterious and beneficial antioxidant role. Overproduction of reactive species can cause damage of cell structures, including lipids and membranes, proteins and DNA. Hydroxybenzoic acid belongs to a group of phenolic compounds. Hydroxybenzoic acids itself and its derivatives showed antioxidant properties against different type of free radicals and can prevent or decrease overproduction of reactive species. Methods: In this study we tested antioxidant properties of 14 different benzoic acid derivatives against superoxide radical. The antioxidant properties of tested compound were determined by Beauchamp and Fridovich methods (1971). We studied kinetics and relationship between structure and antioxidant activity of the compounds. Results: The monohydroxybenzoic derivatives showed the best antioxidant properties. The results showed different antioxidant properties of hydroxybenzoic acid derivatives in 5, 10, 15 and 20 minutes of the reaction. Very important is the position of -OH group to carboxylate group. The compounds with hydroxyl group in ortho and para position to the carboxylate group showed the best antioxidant properties. Derivatives with blocked -OH group showed very low antioxidant properties in comparison with derivatives with blocked -COOH group. Conclusion: The structure and position of hydroxyl group is very important for antioxidant acitivy.
Journal of Chemistry, 2022
A series of seventeen cinnamic acid hybrids (4a i-c i) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from diferent substituted cinnamic acid and ethyl chloroformate. 1 H NMR, 13 C NMR, IR, and HRMS were used for the confrmation of the structures of the synthesized hybrids. Moreover, the antioxidant profles of amides were estimated as per fve diferent in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS⁺), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, cafeic acid (CafA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. Te results revealed that the most prominent antioxidant activity was demonstrated by compound 4b 2 , with excellent CUPRAC, FRAP, scavenging ABTS + _ potential, and inhibition of Fe/asc-induced LP, followed by 4c 6 > 4a 6 > CafA > 4c 5 and 4a 5 > 4a 7. Overall, the results suggest that the hybrids (4b 2 , 4c 6 , and 4a 6) consisting of a cafeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (cafeic acid), especially against LP. Tus, these promising antioxidants could have benefcial efects in various pathological conditions, where oxidative stress is implicated.
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Open Chemistry, 2015
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: caffeic > sinapinic ~ ferulic > p-coumaric > o-coumaric > m-coumaric ~ phenol. 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 ...