A Deep Insight in the Antioxidant Property of Carnosic Acid: From Computational Study to Experimental Analysis
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Materials
2.2. Determination of the Antioxidant Activity
2.3. The Exploration of CA Activity for Free Radicals Scavenge
2.4. Mechanism of α-Carbon Dehydrogenation of OA
2.5. Determination of Induction Period (IP)
2.6. Assessment of the Oxidation Kinetics
2.7. ESR Spectroscopy Measurements
2.8. Statistical Analysis
3. Results
3.1. Mechanism of CA for Free Radicals Scavenge
3.1.1. Geometric Configuration and Parameters of CA
3.1.2. Charge Distribution of CA Natural Bond Orbital (NBO)
3.1.3. BDE of the Phenolic Hydroxyl in CA
3.1.4. The Distribution Pattern of Molecular Orbitals of CA
3.2. Mechanism of the Hydrogen Extraction Reaction of α-C-H in OA
3.2.1. Geometric Configuration and Parameters of OA
3.2.2. BDE of the α-C-H in OA
3.3. The Discussion of CA against the Oxidation of OA
3.3.1. Theoretical Analysis of OA against CA Oxidation
3.3.2. Assessment of Thermal Stability
3.3.3. The Analysis of OA Stability by DSC
3.3.4. Free Radicals Scavenging Activity and ESR Analysis of OA Stability
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Free Radicals | Energy (kJ/mol) | BDE (kJ/mol) |
---|---|---|
CA | −2,836,114.23 | — |
CA-(15)O | −2,834,498.68 | 303.27 |
CA-(18)O | −2,834,506.32 | 295.63 |
H | −1312.28 | — |
Molecules | 1# α-C(8)-H | 2# α-C(11)-H |
---|---|---|
OA (Es, hartree) | −856.390 | −856.390 |
α-H (Ehr, hartree) | −0.498 | −0.498 |
OA radicals (Esr, hartree) | −855.757199 | −855.757275 |
α-C-H (BDE, kJ/mol) | 353.92 | 353.72 |
ln (k) = ln (A) − Ea/RT (3) | ln (k/T) = ln (kB/h) + ΔS/R − ΔH/RT (4) | |||||
---|---|---|---|---|---|---|
Ea (kJ/mol) | R2 | ln (kB/h) | ΔH (kJ/mol) | ΔS (J/molK) | R2 | |
OA | 50.59 | 0.9585 | 21.46 | 47.37 | −103.95 | 0.9528 |
TBHQ + OA | 57.32 | 0.9876 | 21.46 | 54.11 | −87.66 | 0.9860 |
CA + OA | 66.29 | 0.9792 | 21.46 | 63.09 | −65.36 | 0.9770 |
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Wei, J.; Liang, Q.; Guo, Y.; Zhang, W.; Wu, L. A Deep Insight in the Antioxidant Property of Carnosic Acid: From Computational Study to Experimental Analysis. Foods 2021, 10, 2279. https://doi.org/10.3390/foods10102279
Wei J, Liang Q, Guo Y, Zhang W, Wu L. A Deep Insight in the Antioxidant Property of Carnosic Acid: From Computational Study to Experimental Analysis. Foods. 2021; 10(10):2279. https://doi.org/10.3390/foods10102279
Chicago/Turabian StyleWei, Jing, Qian Liang, Yuxin Guo, Weimin Zhang, and Long Wu. 2021. "A Deep Insight in the Antioxidant Property of Carnosic Acid: From Computational Study to Experimental Analysis" Foods 10, no. 10: 2279. https://doi.org/10.3390/foods10102279