Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory.
Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory.
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DOI：
10.1021/acsomega.0c04318
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发表时间：
2020-10-06
期刊：
影响因子：
4.1
通讯作者：
Li J
中科院分区：
文献类型：
--
作者：
Liu Y;Liu C;Li J
维生素C（VC）是一种重要的抗氧化剂，但由于其化学性质不稳定，其应用受到限制。因此，各种VC衍生物已出现在实际抗氧化剂应用中。为了探讨维生素C及其衍生物的抗氧化活性与其化学结构之间的关系，采用密度泛函理论（DFT）方法对维生素C及其衍生物清除自由基的反应机理进行了计算.在B3 LYP-D3（BJ）/6- 31 G * 水平上进行了结构优化。在PWPB 95-D3（BJ）/def 2-QZVPP水平进行单点计算（SPE）。为了估计溶剂对抗氧化剂性质的影响，使用SMD（基于密度的溶剂化模型）方法。结果表明，在优化维生素C化学结构的过程中，其衍生物在水溶剂中的抗氧化能力略有下降。在计算过程中还发现，在抗氧化机理的选择上，这些化合物更倾向于氢原子转移（HAT）机理，而从化学结构上看，内酯环的双键对其自由基清除活性至关重要。总的来说，需要继续优化VC的结构，以获得抗氧化性更好、更有实用价值的衍生物。
Vitamin C (VC) is an essential antioxidant, but its application is limited because of its unstable chemical properties. Hence, a variety of VC derivatives have emerged in practical antioxidant applications. To explore the relationship between the antioxidant properties and the chemical structures of vitamin C and its derivatives, density functional theory (DFT) was used in this work to calculate the reaction enthalpies of the mechanisms related to radical scavenging activity. The structures were optimized at the B3LYP-D3(BJ)/6-31G* level of theory. Single point calculations (SPE) were performed at the PWPB95-D3 (BJ)/def2-QZVPP level. To estimate the solvent effect on antioxidant properties, the SMD (solvation model based on density) method was used. The results showed that in the process of optimizing the chemical structure of vitamin C, the antioxidant capacity of its derivatives decreased slightly in aqueous solvents. In the calculation process, it is also found that in the choice of antioxidant mechanism, these compounds are more inclined to the hydrogen atom transfer (HAT) mechanism, and from the chemical structure point of view, the double bond of the lactone ring is essential for its free radical scavenging activity. In general, it is necessary to continue to optimize the structure of VC to obtain derivatives with better oxidation resistance and more practical value.
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