Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition
Abstract
:1. Introduction
2. Computational Details
2.1. Quantum Chemistry Calculations
2.2. Blind Docking Consensus Procedure
2.3. Molecular Docking Simulations
3. Results and Discussion
3.1. Evaluation of Radical Scavenging Mechanisms
3.1.1. Acid-Base Equilibrium at Physiological pH
3.1.2. Thermodynamic Evaluation of the Antiradical Mechanisms
3.1.3. Reaction Kinetics under Physiological Conditions
Effects of Polar Physiological Media
Effects of Lipid-Like Physiological Media
3.2. Blind Docking and Molecular Dynamics Simulations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Comp. | Mechanisms | State | ΔG≠ | κ | kapp | f a | kf b | Γ | koverall | |
---|---|---|---|---|---|---|---|---|---|---|
5-CQA | HAT | 12OH | 5-CQA– | 16.8 | 205.7 | 6.60 × 102 | 0.918 | 6.06 × 102 | 0 | 2.68 × 108 |
13OH | 17.5 | 436.8 | 8.40 × 101 | 7.71 × 101 | 0 | |||||
RAF | C8 | 19.6 | 1.4 | 2.50 × 10−2 | 2.30 × 10−2 | 0 | ||||
HAT | 12OH | 5-CQA–2 | 2.0 | 1.2 | 2.30 × 109 | 0.082 | 1.89 × 108 | 70 | ||
RAF | C8 | 14.2 | 1.0 | 2.40 × 102 | 1.97 × 101 | 0 | ||||
SET | 4.8 | 4.0 c | 9.70 × 108 | 7.95 × 107 | 30 | |||||
5-FQA | HAT | 13OH | 5-FQA– | 17.4 | 838.8 | 1.70 × 102 | 0.988 | 1.68 × 102 | 0 | 2.28 × 107 |
RAF | C8 | 17.5 | 1.4 | 1.20 × 100 | 1.19 × 100 | 0 | ||||
RAF | C8 | 5-FQA–2 | 10.8 | 1.0 | 7.80 × 104 | 0.012 | 9.36 × 102 | 0 | ||
SET | 3.7 | 1.1 c | 1.90 × 109 | 2.28 × 107 | 100 |
Comp. | Mechanisms | ΔG≠ | κ | kapp | Γ | koverall | |
---|---|---|---|---|---|---|---|
5-CQA | HAT | 12OH | 8.7 | 0.7 | 1.80 × 106 | 86 | 2.09 × 106 |
13OH | 5.7 | 0.0 | 2.90 × 105 | 14 | |||
RAF | C8 | 19.7 | 1.5 | 3.40 × 10−2 | 0 | ||
5-FQA | HAT | 13OH | 7.9 | 0.0 | 4.10 × 104 | 100 | 4.10 × 104 |
RAF | C8 | 16.0 | 1.5 | 1.60 × 101 | 0 |
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Boulebd, H.; Carmena-Bargueño, M.; Pérez-Sánchez, H. Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition. Antioxidants 2023, 12, 1669. https://doi.org/10.3390/antiox12091669
Boulebd H, Carmena-Bargueño M, Pérez-Sánchez H. Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition. Antioxidants. 2023; 12(9):1669. https://doi.org/10.3390/antiox12091669
Chicago/Turabian StyleBoulebd, Houssem, Miguel Carmena-Bargueño, and Horacio Pérez-Sánchez. 2023. "Exploring the Antioxidant Properties of Caffeoylquinic and Feruloylquinic Acids: A Computational Study on Hydroperoxyl Radical Scavenging and Xanthine Oxidase Inhibition" Antioxidants 12, no. 9: 1669. https://doi.org/10.3390/antiox12091669