Kinetic characteristics of the reaction of resveratrol with peroxyl radicals and natural thiols in aqueous medium

Zinatullina, K. M.; Khrameeva, N. P.; Касаикина, О. Т.; Shapiro, B. I.; Кузьмин, В. А.

doi:10.1007/s11172-017-1995-1

Cited by 10 publications

(4 citation statements)

References 42 publications

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“…We validate our work on reaction kinetics based on the trans-resveratrol case. Our predictions of ‡ G 0 are comparable with a theoretical work reported by Iuga et al [24] (see Table 2), which computed the rate constants at room temperature with the basis of transition-state theory, whose results are comparable with the experimental results by Zinatullina et al [42]. Consequently, our densityfunctional calculations on Eq.…”

Section: The Standard Gibbs Energy Of Activationsupporting

confidence: 91%

Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C

et al. 2021

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Melinjo seed extract contains melinjo resveratrol compounds that has antioxidant activity. The radical-scavenging sites required for the antioxidant activity, however, is yet to be located. We report a computational study that aims to locate scavenging sites of the simplest resveratrol dimer, gnetin C. We consider the reaction of gnetin C and hydroperoxyl radical energetically with the basis of density-functional calculations, to be compared with the reaction of the resveratrol monomer, trans-resveratrol, and hydroperoxyl radical. The results show that OH group at the para position is the most reactive scavenging site for both molecules. Besides the OH group, gnetin C also provides two CH groups in the furan ring that are favorable as scavenging sites. Therefore, furan ring plays an important role in the scavenging activity, which is contrary to the experimental speculation that propose resorcinol ring. Our study shows the prospect of density-functional calculation for studying the radical-scavenging reaction.

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Section: The Standard Gibbs Energy Of Activationsupporting

confidence: 91%

Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C

et al. 2021

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“…• fro m AAPH k inh = 1.1•10 5 L mol -1 s -1 . 13 Reaction of acetylcysteine and glutathione with H 2 O 2 . Reactions of thiols with hydroperoxides in living beings proceed in the presence of glutathione peroxidase enzymes, but with H 2 O 2 thiols can react directly.…”

Section: Resultsmentioning

confidence: 99%

“…Peroxyl radicals were generated with azo initiator, 2,2´-azobis(2-methyl propionamidine) dihydrochloride (AAPH, Fluka) similar to the method previously described. 11, 13 Deionized water (Direct-Q UV Millipore, 18 mΩ cm, pH 7) was used as the reaction medium. The initial solutions of ASH and GSH wer e prepared in deionized water, RVT in DMSO, then they were added into the reaction mixture with an electronic pipette.…”

Section: Methodsmentioning

confidence: 99%

N-Acetylcysteine is an effective analog of glutathione in reactions with reactive oxygen species

et al. 2021

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The kinetic characteristics of the interaction of N-acetylcysteine (ASH) with reactive oxygen species (ROS), peroxyl radicals and hydrogen peroxide were determined. It was found that in terms of activity ASH in these reactions is similar to glutathione GSH, the main endogenous bioantioxidant. The kinetics of heat release in the interaction of GSH and ASH with H 2 O 2 was studied for the fi rst time by isothermal calorimetry. It is shown that the kinetic curves of heat release and changes in specifi c heat release rates practically coincide for both thiols taken in the stoichiometric ratio in the known reaction 2 TSH + H 2 O 2  TSST + 2 H 2 O.This indicates the relative autonomy of the S-H and S-S bonds in thiols and disulfi des, which are not aff ected by other groups in the molecule. At pH<7, ASH, like GSH, interacts with H 2 O 2 to form thiyl radicals, which initiate thiol-ene reactions with unsaturated phenol resveratrol. Under the same conditions, ASH ensures nearly the same radical initiation rates as GSH, and thiyl radicals from ASH are close in activity to GS • in chain propagation reactions.

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“…The stabilization of the color could be due to the reduction of the oxidation of the lutein caused by singlet oxygen quenching (Boon et al., ). Resveratrol is able to incorporate and stabilize electrons in their phenolic rings, thereby inhibiting the oxidation chain reactions caused by free radicals (Zinatullina, Khrameeva, Kasaikina, Shapiro, & Kuzmin, ). It is well known that lipid oxidation reactions occur at the oil‐water interface in emulsions and nanoemulsions (McClements & Decker, ).…”

Section: Resultsmentioning

confidence: 99%

Encapsulation of Lutein in Nanoemulsions Stabilized by Resveratrol and Maillard Conjugates

Steiner

Shukla

McClements

et al. 2019

Journal of Food Science

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Lutein is incorporated into foods as a natural yellow pigment and nutraceutical. The introduction of lutein into many foods and beverages, however, is problematic because of its strong hydrophobicity and poor chemical stability. In this research, lutein‐loaded nanoemulsions were prepared to overcome this problem. Casein‐dextran Maillard conjugates or physical complexes were utilized as emulsifiers, while either medium chain triglycerides (MCT) or grape seed oil (GSO) were used as carrier oils. The impact of resveratrol addition on nanoemulsion stability was also examined. The influence of storage temperature, pH, and CaCl2 concentration on the chemical and physical stability of the nanoemulsions was measured. The casein‐dextran conjugates were highly effective at improving the physical resistance of the nanoemulsions to environmental stresses, but had a detrimental effect on their color stability. Conversely, nanoemulsions prepared from casein‐dextran physical complexes were unstable around the protein's isoelectric point (pH 4.6), as well as upon addition of CaCl2. Incorporation of resveratrol and GSO into the nanoemulsions decreased lutein degradation and color fading at all temperatures. This study shows that casein‐dextran conjugates are highly effective at improving the physical stability of lutein‐loaded nanoemulsions, while resveratrol and GSO are effective at improving their chemical stability. Practical Application Lutein can be used by the food industry to create “clean label” and functional food products. The major challenges in incorporating lutein in foods are its poor chemical stability and its high hydrophobicity, which makes it difficult to incorporate. Emulsion‐based delivery systems assembled from natural ingredients may address these challenges. In this study, the impact of Maillard conjugates fabricated from caseinate and dextran, as well as resveratrol addition, on the formation and stability of lutein‐enriched nanoemulsions was determined. The information obtained from this study will help the formulation of more effective functional foods and beverage products.

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Kinetic characteristics of the reaction of resveratrol with peroxyl radicals and natural thiols in aqueous medium

Cited by 10 publications

References 42 publications

Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C

Computational Investigation on the ∙OOH Scavenging Sites of Gnetin C

N-Acetylcysteine is an effective analog of glutathione in reactions with reactive oxygen species

Encapsulation of Lutein in Nanoemulsions Stabilized by Resveratrol and Maillard Conjugates

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