Primary and secondary antioxidant properties of scutellarin and scutellarein in water and lipid-like environments: A theoretical investigation

Computational insights on the antioxidant, antinitrosant, and xanthine oxidase inhibitory capacities of neobavaisoflavone

“…Neo , on the other hand, was anticipated to have high HOO˙ radical scavenging activity in water with k overall = 2.46 × 10 7 M −1 s −1 . In comparison, this value is comparable to that of scutellarein ( k overall = 4.73 × 10 7 M −1 s −1 ), 61 higher than that of the typical antioxidants BHT ( k = 2.51 × 10 5 M −1 s −1 ) 59 and Trolox ( k = 1.30 × 10 5 M −1 s −1 ), 59 as well as natural antioxidants carnosic acid ( k = 4.73 × 10 6 M −1 s −1 ), 62 coumestrol ( k = 6.26 × 10 3 M −1 s −1 ), 63 and cannabidiol ( k = 9.09 × 10 6 M −1 s −1 ), 64 but lower than that of quercetin ( k overall = 8.11 × 10 9 M −1 s −1 ). 60 Thus, Neo is a potent radical scavenger in polar media.…”

“…As can be seen from Table 1, Neo exhibits moderate activity for HOO˙ scavenging in pentyl ethanoate with k overall = 2.71 × 10 1 M −1 s −1 . This value is substantially lower than that of the usual antioxidants BHT ( k overall = 1.70 × 10 4 M −1 s −1 ) 59 and Trolox ( k overall = 1.00 × 10 5 M −1 s −1 ) 59 as well as the structurally similar systems quercetin ( k overall = 4.39 × 10 3 M −1 s −1 ) 60 and scutellarein ( k overall = 1.06 × 10 3 M −1 s −1 ), 61 indicating that Neo is not an effective HOO˙ radical scavenger in lipid environments. The 14OH and 17CH groups were found to contribute almost equally to the overall rate constants, which highlights the important role of benzylic hydrogen bonds in the free radical scavenging activity.…”

Computational investigation on the antioxidant activities and on the Mpro SARS-CoV-2 non-covalent inhibition of isorhamnetin

“…In pentylethanoate, the scavenging activity of isorhamnetin against the •OOH radical is relatively low and lower than that of the other compounds tested except for scutellarin (Spiegel et al, 2022b). On the contrary, in aqueous solution, its kinetic constant takes on a very high value (4.60 × 10 9 M −1 s −1 ), comparable to that of quercetin (k = 8.11 × 10 9 M −1 s −1 ) (Castaneda-Arriaga et al, 2020) and daphnetin (1.51 × 10 7 ) (Boulebd and Khodja, 2021) and about five orders of magnitude higher than the corresponding value of Trolox (8.96 × 10 4 M −1 s −1 ) (Alberto et al, 2013), which is generally used as a comparison to determine the antioxidant power of a molecule.…”

“…Taking into account the molar fraction of the ligand at physiological pH, the apparent equilibrium constant becomes equal 4.56 × 10 10 M −1 s −1 , implying that all species present in the water solvent equilibrium must be taken into account to obtain a reliable outcomes. Comparison with other systems treated at the same level of theory reveals that the copper chelating power of isorhamnetin is lower than that of scutellarin and scutellarein, as the values of these systems are 4.77 × 10 20 and 1.29 × 10 12 , respectively ( Spiegel et al, 2022b ).…”

Computational assessment of the primary and secondary antioxidant potential of alkylresorcinols in physiological media

“…Previous research has validated the reliability of this method. 33 The number of imaginary frequencies was used to conrm both the ground (0) and transition states (1), which was also conrmed using intrinsic reaction coordinate (IRC) calculations. To simulate physiological conditions in polar and lipid environments, the solvation effect of water and pentyl ethanoate was utilized by employing the SMD solvation model.…”