Theoretical study on the radical scavenging activity and mechanism of four kinds of Gnetin molecule

Shang, Yaxuan; Li, Xiangzhou; Li, Zhaoshuang; Zhou, Jun; Qu, Limin; Chen, Kai

doi:10.1016/j.foodchem.2021.131975

Cited by 15 publications

(7 citation statements)

References 36 publications

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“…The average activation Gibbs free energy (ΔG ≠ ) value for calycosin is 7.3 kcal/mol, indicating shallow barriers when the H atom transfer reacts with • OH. This result is in keeping with other findings for polyphenol [ 28 , 45 ]. A comparison of the Gibbs free energy values and barriers of the two positions of calycosin showed that 3′-OH is the more active site for radical attacks, which is consistent with the results obtained in the thermodynamical calculations.…”

Section: Resultssupporting

confidence: 93%

“…With the development of theoretical approaches, theoretical calculations have been used in multiple research fields [ 19 , 20 , 21 , 22 ]. Many investigations have demonstrated the successes of different density functional theory (DFT) methods in revealing structure–activity relationships, determining the most likely chemical reactions involved in the antioxidant activity, as well as explaining the experimental results [ 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. Compared with the experimental studies, theoretical calculations based on DFT can be considered as cogent tools in elucidating the antioxidant activity of flavonoid compounds with lower cost and shorter time requirements.…”

Section: Introductionmentioning

confidence: 99%

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Radical Scavenging Capability and Mechanism of Three Isoflavonoids Extracted from Radix Astragali: A Theoretical Study

Qin

2023

Molecules

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As a valuable traditional Chinese herbal medicine, Radix Astragali has attracted much attention due to its extensive pharmacological activities. In this study, density functional theory (DFT) was used thermodynamically and kinetically in detail to predict the antioxidant activity and reaction mechanisms involved in the free radical scavenging reactions of three representative isoflavonoids (formononetin, calycosin, and calycosin-7-glucoside) extracted from Radix Astragali. Three main mechanisms, including hydrogen atom transfer (HAT), proton transfer after electron transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were examined by calculating the thermodynamic parameters. It was found that HAT is the predominant mechanism in the gas phase, while SPLET is supported in the solvent environment. The isoflavonoids’ order of antioxidant activity was estimated as: calycosin > calycosin-7-glucoside > formononetin. For the calycosin compound, the result revealed the feasibility of double HAT mechanisms, which involve the formation of stable benzodioxazole with significantly reduced energy in the second H+/e− reaction. In addition, the potential energy profiles and kinetic calculations show that the reaction of •OH into the 3′-OH site of calycosin has a lower energy barrier (7.2 kcal/mol) and higher rate constant (4.55 × 109 M−1 s−1) compared with other reactions in the gas phase.

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Section: Resultssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Radical Scavenging Capability and Mechanism of Three Isoflavonoids Extracted from Radix Astragali: A Theoretical Study

Qin

2023

Molecules

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“…Resveratrol (3,5,4′-trihydroxy-trans-stilbene), a natural antioxidant, 167 has anti-tumor effects. 168 But its effects are controversial.…”

Section: Strategies For Designing Inhibitors Targeting Rrm2mentioning

confidence: 99%

Ribonucleotide reductase M2 (RRM2): Regulation, function and targeting strategy in human cancer

et al. 2024

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“…The free radical-capturing properties are estimated by antioxidant activities. Specifically, the development of computational methodologies enhances the opportunities for theoretical methods to be widely used in estimating the free radical-capturing property of a compound [13][14][15][16][17][18][19][20][21]. Theoretical methods, especially DFT calculations, with an equivalent or even better accuracy than the experiments, can reveal the molecular intrinsic mechanism for the free radical scavenging properties and disclose the relationship of the structure-antioxidant properties [13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Multiple Free Radical Scavenging Reactions of Pyranoanthocyanins

Du,

Chai,

Zheng

et al. 2023

Antioxidants

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The free radical trapping capacities of multiple pyranoanthocyanins in wine storage and ageing were theoretically explored by density functional theory (DFT) methods. Intramolecular hydrogen bonds were detected in all pyranoanthocyanins, and the planarity of the compounds worsened with an increasing dielectric constant in the environment. Solvents significantly influenced the reaction enthalpies; thus, the preferred thermodynamic mechanisms of the free radical scavenging reactions were modified in different phases. This study incorporates hydrogen atom transfer (HAT), proton loss (PL), electron transfer (ET) reactions, and demethylation (De) of methoxy group mechanisms. The three pyranoanthocyanins have the capacity to capture n1+1 free radicals, where n1 represents the number of methoxy groups. In the gas phase, they prefer employing the n1-De-HAT mechanism on the guaiacyl moiety of the B ring, resulting in the formation of a stable quinone or a quinone radical to scavenge free radicals. In the benzene phase, pyranoanthocyanins trap free radicals via a PL−n1−De−HAT mechanism. In the water phase, the targeted pyranoanthocyanins may dissociate in the form of carboxylate and tend to utilize the n2−PL−n1−De−ET mechanism, where n2 and n1 represent the number of phenolic groups and methoxy groups, respectively, facilitating multiple H+/e− reactions.

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Theoretical study on the radical scavenging activity and mechanism of four kinds of Gnetin molecule

Cited by 15 publications

References 36 publications

Radical Scavenging Capability and Mechanism of Three Isoflavonoids Extracted from Radix Astragali: A Theoretical Study

Radical Scavenging Capability and Mechanism of Three Isoflavonoids Extracted from Radix Astragali: A Theoretical Study

Ribonucleotide reductase M2 (RRM2): Regulation, function and targeting strategy in human cancer

Theoretical Study on the Multiple Free Radical Scavenging Reactions of Pyranoanthocyanins

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