Theoretical studies on the antioxidant activity of viniferifuran

Shang, Yaxuan; Zhou, Huakang; Li, Xiangzhou; Zhou, Jun; Chen, Kai

doi:10.1039/c9nj02735a

Cited by 58 publications

(35 citation statements)

References 44 publications

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“…As antioxidant mostly functioned as electron donor to provide electron to radical, the phenyl ring C should play a more important role in radical scavenging reactions. The HOMO-LUMO gaps were close, 6.5 eV and 6.4 eV for puerarin and daidzein, respectively, which were similar to that of another natural antioxidant, resveratrol, 6.3 eV [32].…”

Section: Frontier Molecular Orbital Analysissupporting

confidence: 54%

Radical Scavenging Activity of Puerarin: A Theoretical Study

Zhou

Shang

et al. 2019

Antioxidants

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Puerarin is a C-glycoside of daidzein, one of the major bioactive ingredients isolated from the root of Pueraria lobata, which has a wide spectrum of pharmacological effects. Although puerarin is well-known for its effective antioxidant activity, there is seldom a systematic theoretical study on its radical scavenging activity. Herein, the free radical scavenging ability of puerarin was investigated systematically by density functional theory (DFT) calculations. The reaction activity was compared with daidzein as well. Three reaction pathways: hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were discussed and compared by thermodynamic parameters such as bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE). The reaction kinetics of puerarin with special radicals •OH and •OOH were also studied. The results obtained may be of great significance for better understanding the relationship between the antioxidant properties and structural design of puerarin, as well as other antioxidants.

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Section: Frontier Molecular Orbital Analysissupporting

confidence: 54%

Radical Scavenging Activity of Puerarin: A Theoretical Study

Zhou

Shang

et al. 2019

Antioxidants

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“…PA values of TQ are lower in water than in gas phase which is in good consistent with previous literature [31]. lower in gas than in water which is also in agreement with literature [43]. The ETEs are in the range of 32-56 kcal/mole in gas whereas in the range of 74-106 kcal/mole in water.…”

Section: Proton Affinity and Electron Transfer Enthalpy: Splet Mechanismsupporting

confidence: 92%

“…The electron-donating ability is related to an extended electronic delocalization over the entire molecule. A molecule having a high degree of π-delocalization is more active [43]. From the above discussion it can be said that, TQ is less likely to pose SETPT formalism of antioxidant behavior.…”

Section: Ionization Potential and Proton Dissociation Enthalpy: Setpt Mechanismmentioning

confidence: 90%

Theoretical investigations on the antioxidant potential of a non-phenolic compound thymoquinone: a DFT approach

2021

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Thymoquinone (TQ) is a natural compound occurred in black cumin (Nigella sativa L.), which possesses potent antioxidant activity without having any phenolic hydroxyl group believed to be responsible for antioxidant activity of a molecule. In the present study, computational calculation based on Density Functional Theory (DFT) have been executed to assess systematically the worth of antioxidant behavior of this compound. Geometrical characteristics, HOMO-LUMO and MEP surface have been studied. Thermochemical parameters correlated to the leading antioxidant mechanisms such as HAT, SETPT and SPLET have been studied in gas and water media. In addition, the changes of thermochemical parameters such as ∆G and ∆H have been computed for HA from TQ to hydroxyl radical in gas and water phases to investigate its free radical scavenging potency. The low and comparable values of BDE, PDE, IP, PA and ETE suggest the antioxidant activity. The ∆G and ∆H also convey apposite thermodynamic evidence in favor of antiradical capability of TQ. The attack of the free radical takes place preferentially at 3CH position of the molecule.

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“…As per table 1, the lowest BDE value was predicted for O4′−H at 77.5 kcal mol −1 . This value is lower than that of natural antioxidants such as viniferifuran (82.7 kcal mol −1 ) [43], resveratrol (83.9 kcal mol −1 ) [43], puerarin (87.3 kcal mol −1 ) [44] and vanillic acid (85.2 kcal mol −1 ) [45]. The lowest PA and IE values are about 4.14 and 2.25 times higher than the BDE value.…”

Section: Resultsmentioning

confidence: 93%

“…Open Sci. 8: 210626 [43], puerarin (87.3 kcal mol −1 ) [44] and vanillic acid (85.2 kcal mol −1 ) [45]. The lowest PA and IE values are about 4.14 and 2.25 times higher than the BDE value.…”

Section: Thermodynamic Evaluationmentioning

confidence: 95%

The hydroperoxyl radical scavenging activity of sulfuretin: insights from theory

et al. 2021

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Sulfuretin (SFR), which is isolated from Rhus verniciflua , Toxicodendron vernicifluum, Dahlia, Bidens tripartite and Dipterx lacunifera , is one of the most important natural flavonoids. This compound is known to have numerous biological activities; among these, the antioxidant activity has not been thoroughly studied yet. In this study, the hydroperoxyl scavenging activity of SFR was examined by using density functional theory calculations. SFR is predicted to be an excellent HOO • scavenger in water at pH = 7.40 with k overall = 4.75 × 10 7 M −1 s −1 , principally due to an increase in the activity of the anionic form following the single-electron transfer mechanism. Consistently, the activity of the neutral form is more prominent in the non-polar environment with k overall = 1.79 × 10 4 M −1 s −1 following the formal hydrogen transfer mechanism. Thus, it is predicted that SFR exhibits better HOO • antiradical activity than typical antioxidants such as resveratrol, ascorbic acid or Trolox in the lipid medium. The hydroperoxyl radical scavenging of SFR in the aqueous solution is approximately 530 times faster than that of Trolox and similar to ascorbic acid or resveratrol. This suggests that SFR is a promising radical scavenger in physiological environments.

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Theoretical studies on the antioxidant activity of viniferifuran

Abstract: DFT studies reveal the thermodynamics and kinetics of radical scavenging reactions of a resveratrol dimer derivative – viniferifuran.

Cited by 58 publications

References 44 publications

Radical Scavenging Activity of Puerarin: A Theoretical Study

Radical Scavenging Activity of Puerarin: A Theoretical Study

Theoretical investigations on the antioxidant potential of a non-phenolic compound thymoquinone: a DFT approach

The hydroperoxyl radical scavenging activity of sulfuretin: insights from theory

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