On the Scavenging Ability of Scutellarein against the OOH Radical in Water and Lipid-like Environments: A Theoretical Study

Spiegel, Maciej; Marino, Tiziana; Prejanò, Mario; Russo, Nino

doi:10.3390/antiox11020224

Cited by 20 publications

(23 citation statements)

References 35 publications

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“…Based on our previous experience 42,43 and that of other research groups, 39,40,44–46 the following redox and non-redox pathways were explored:Hydrogen atom transfer (HAT): HX + R˙ → X˙ + RHSingle electron transfer (SET): HX + R˙ → HX + ˙ + R – Radical adduct formation (RAF): HX + R˙ → [HX−R]˙…”

Section: Resultsmentioning

confidence: 99%

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Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Spiegel

Marino

Prejanò

et al. 2022

Phys. Chem. Chem. Phys.

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Section: Resultsmentioning

confidence: 99%

“…Based on our previous experience 42,43 and that of other research groups, 39,40,[44][45][46] the following redox and non-redox pathways were explored:…”

Section: Primary Antioxidant Propertiesmentioning

confidence: 99%

Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Spiegel

Marino

Prejanò

et al. 2022

Phys. Chem. Chem. Phys.

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“…The protocol was extensively adopted in previous works on the antioxidant activity of natural products. [ 29 , 36 , 37 , 38 , 39 ]…”

Section: Methodsmentioning

confidence: 99%

Structural Characterization of Peripolin and Study of Antioxidant Activity of HMG Flavonoids from Bergamot Fruit

et al. 2022

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The structural characterization of a new flavonoid from bergamot fruit (Citrus bergamia Risso) carrying the 3-hydroxy-3-methyl glutaryl (HMG) ester moiety has been accomplished, and its antioxidant ability was tested from a chemical point of view. The peculiarity of the new molecule, named peripolin, relies on the presence of the HMG chemical group linked to the sugar portion of neoeriocitrin; the structure was elucidated using both high-resolution mass spectrometry and nuclear magnetic resonance experiments performed on the purified molecule extracted from the fruit. The antioxidant ability of the new molecule was tested by classical chemical approaches, such as DPPH, ABTS and FRAP assays, and from a theoretical point of view. 1H and 13C NMR experiments and HR-ESI-MS/MS experiments show unequivocally that the HMG moiety is linked to the primary position of the glucose unit of neohesperidose, while the chemical tests and the computational results show that peripolin possesses strong antioxidant behavior, similar to that of neoeriocitrin and remarkably higher respect to the other flavonoids present in the fruit. Furthermore, the quantitative assays carried out by UPLC-MS/MS showed that its amount in the fruit is similar to that of the other main flavonoids. Furthermore, molecular dynamics simulations allowed us to investigate the possible conformations adopted by the antioxidants in the presence of water molecules. In particular, the switch of open-closed conformations of HMG-containing species was evidenced. As far as the reaction with DPPH, the calculation of ΔGrea supported the experimental outcomes regarding the peripolin and neoeriocitrin activity. In conclusion, bergamot fruit, already known for its potential to lower the level of blood cholesterol, has been proven to contain molecules such as neoeriocitrin and the newly characterized peripolin, which could have important in-vivo antioxidant characteristics.

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“…[ 34 ] For example, Spiegel et al used DFT to study the scavenging capacity of baicalein against hydrogen peroxide radicals in water and lipid environments. [ 35 ] Mazzone et al studied the primary antioxidant activity of coumarin chalcone hybrid using DFT and the conventional transition state theories. Their scavenging capacity of peroxy radicals in different polar solvents and reaction mechanisms was investigated.…”

Section: Resultsmentioning

confidence: 99%

Influence of the pK_a value on the antioxidant activity of licorice flavonoids under solvent‐mediated effects

Wang

Shen

et al. 2023

Archiv der Pharmazie

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Licorice flavonoids (LCFs) have been widely used in food care and medical treatment due to their significant antioxidant activities. However, the molecular mechanism of their antioxidant activity remains unclear. Therefore, network pharmacology, ADMET, density functional theory (DFT), molecular docking, and molecular dynamics (MD) simulation were employed to explore the molecular mechanism of the antioxidant effects of LCF. The network pharmacology and ADMET studies showed that the active molecules of kumatakenin (pK a = 6.18), licoflavonol (pK a = 6.86), and topazolin (pK a = 6.21) in LCF are key antioxidant components and have good biosafety. Molecular docking and MD simulation studies demonstrated that active molecules interacted with amino acid residues in target proteins to form stable protein-ligand complexes and exert their antioxidant effects. DFT studies showed that the antioxidant activity of LCF could be significantly modulated under the solvent-mediated effect. In addition, based on the derivation of the Henderson-Hasselbalch and van't Hoff formulas, the functional relationships between the reaction-free energy (ΔG) of LCF and the pH and pK a values were established. The results showed that active molecules with larger pK a values will be more conducive to the improvement of their antioxidant activity under solventmediated effects. In conclusion, this study found that increasing the pK a value of LCF would be an effective strategy to improve their antioxidant activity under the effect of solvent mediation. The pK a value of an LCF will be a direct standard to evaluate its solvent-mediated antioxidant activity. This study will provide theoretical guidance for the development of natural antioxidants.

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On the Scavenging Ability of Scutellarein against the OOH Radical in Water and Lipid-like Environments: A Theoretical Study

Cited by 20 publications

References 35 publications

Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Structural Characterization of Peripolin and Study of Antioxidant Activity of HMG Flavonoids from Bergamot Fruit

Influence of the pK_a value on the antioxidant activity of licorice flavonoids under solvent‐mediated effects

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On the Scavenging Ability of Scutellarein against the OOH Radical in Water and Lipid-like Environments: A Theoretical Study

Cited by 20 publications

References 35 publications

Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Antioxidant and copper-chelating power of new molecules suggested as multiple target agents against Alzheimer's disease. A theoretical comparative study

Structural Characterization of Peripolin and Study of Antioxidant Activity of HMG Flavonoids from Bergamot Fruit

Influence of the pKa value on the antioxidant activity of licorice flavonoids under solvent‐mediated effects

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Influence of the pK_a value on the antioxidant activity of licorice flavonoids under solvent‐mediated effects