The hydroperoxyl radical scavenging activity of natural hydroxybenzoic acids in oil and aqueous environments: Insights into the mechanism and kinetics

Hang, Do Thi Ngoc; Hòa, Nguyễn Thị; Bich, Huynh Ngoc; Mechler, Adam; Vo, Quan V.

doi:10.1016/j.phytochem.2022.113281

Cited by 11 publications

(16 citation statements)

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“…Previous studies confirmed that the number and arrangement of –OH and –OCH 3 groups (their mutual position) affect the antioxidant activity of the phenolic acids [ 14 , 27 , 31 , 39 ], but also other parameters, such as ionization, dissociation, and the rate constants of radical scavenging, resonance, solvent solvation effects, intramolecular hydrogen bonds, bond dissociation enthalpy, etc., should also be taken in consideration as reported by Sroka [ 16 ], Hanscha at al. [ 15 ], Foti et al [ 17 ] Lucarini and Pedulli [ 18 ], Hang et al [ 21 ], and Biela et al [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

“…Sroka and Cisowski [ 16 ] in their study also reported higher activity of protocatechuic acid against DPPH free radicals in comparison to the gentisic acid. Hang et al [ 21 ] reported the influence of –OH and/or –OCH 3 groups at position 3 and/or 5 on the hydrogen transfer mechanism (characterized by bond-dissociation energy) using the hydroperoxyl radical scavenging assay. They conclude that the intramolecular hydrogen bond between the –OH group at the ortho -position and the –COOH group could be the main reason for the highest reduction of bond-dissociation energy, which indicated weaker antioxidant activity (radical scavenging activity followed the order: syringic acid > gentisic acid > gallic acid > vanillic acid > protocatechuic acid).…”

Section: Resultsmentioning

confidence: 99%

“…Scientific research indicated several factors with a possible impact on the mechanisms behind the compound’s activity. Among them, the number and position of hydroxyl groups and their methylation, the distance between phenyl and carboxylic groups, and the concentration of the compound are suggested [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

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Investigation of Antioxidant Synergisms and Antagonisms among Phenolic Acids in the Model Matrices Using FRAP and ORAC Methods

et al. 2022

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The total antioxidant potential of a sample cannot be predicted from the antioxidant activity of its compounds; thus, scientists usually explain the overall activity through their combined effects (synergistic, antagonistic, or additive). Phenolic compounds are one of the most powerful and widely investigated antioxidants, but there is a lack of information about their molecular interactions. This study aimed to investigate the individual and combined antioxidant activity of equimolar mixtures (binary, ternary, quaternary, and quinary) of 10 phenolic acids (protocatechuic, gentisic, gallic, vanillic, syringic, p-coumaric, caffeic, ferulic, sinapic, and rosmarinic acid) at different concentrations using ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC) assays. Gallic acid showed the highest antioxidant activity, determined using the FRAP assay (494–5033 µM Fe2+) and rosmarinic acid with the ORAC assay (50–92 µM Trolox Equivalents (TE)), while the lowest antioxidant potential was observed for p-coumaric acid (FRAP 24–113 µM Fe2+ and ORAC 20–33 µM TE). The synergistic effect (by FRAP) in the equimolar mixtures of hydroxybenzoic acids was confirmed for a large number of tested mixtures, especially at low concentrations. All mixtures containing gentisic acid showed a synergistic effect (28–89% difference). Using the ORAC method, only two mixtures of hydroxybenzoic acids showed an antagonistic effect, namely a mixture of gentisic + syringic acids (−24% difference) and gallic + vanillic acids (−30% difference), while all other mixtures showed a synergistic effect in a range of 26–236% difference. Among mixtures of hydroxycinnamic acids, the highest synergistic effect was observed for the mixtures of p-coumaric + ferulic acids and caffeic + sinapic acids with differences of 311% and 211%, respectively. The overall antioxidant activity of phenolic acids could be explained by the number or position of hydroxyl and/or methoxy functional groups as well as the compound concentration, but the influence of other parameters such as dissociation, intramolecular hydrogen bonds, and electron donating or withdrawing effect should not be neglected.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Investigation of Antioxidant Synergisms and Antagonisms among Phenolic Acids in the Model Matrices Using FRAP and ORAC Methods

et al. 2022

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“…Whereas the SET mechanism was investigated for dissociated state in aqueous solution, since the FHT reaction had no contribution in the HOOc antiradical activity of phenolic acids. 25,50,52 The overall reaction rate constant (k overall ) was calculated following the QM-ORSA protocol, 29,34 according to eqn (2) and ( 3), and the results were listed in Table 5 and 6. Fig.…”

Section: Computational Detailsmentioning

confidence: 99%

“…In the past few years, numerous studies were conducted on bioactivities of natural compounds using a computational approach. [20][21][22][23][24][25] From the kinetic and thermodynamic parameters, the main mechanistic pathways of radical scavenging, as well as the capacity of radical scavenging activity in different media (gas phase, polar and non-polar solvent at physiological pH) were described. 26,27 Those calculated results were useful for conrming the results of the earlier experimental studies on antioxidant activities of natural compounds.…”

Section: Introductionmentioning

confidence: 99%