Comparison of Vitamin C and Its Derivative Antioxidant Activity: Evaluated by Using Density Functional Theory

Abstract

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.

Evaluation of the Putative Duplicity Effect of Novel Nutraceuticals Using Physico-Chemical and Biological In Vitro Models

“…The FRAP method has been used successfully on a large scale to determine the antioxidant activity of anthocyanins in various matrices, so the highest value obtained for sour cherries was that obtained using the FRAP method [ 58 ]. In the case of vitamin C, the results obtained correlate with the mechanism proposed by Liu et al [ 59 ]; higher values being given by the methods that have as HAT mechanism of action (TEAC and DPPH) and lower values for the methods, SET ones (FRAP and CUPRAC) [ 60 ]. Among the ingredients used, the antioxidant activity is given mainly by Vitamin C, pollen, and sour cherries.…”

Effects of Cold-Pressing and Hydrodistillation on the Active Non-volatile Components in Lemon Essential Oil and the Effects of the Resulting Oils on Aging-Related Oxidative Stress in Mice

“…It can replace other substances to be oxidized first, so as to protect other substances from oxidation. It is a safe antioxidant ( 15 ). Therefore, vitamin C was selected as a positive control.…”

Novel Multifunctional Ascorbic Triazole Derivatives for Amyloidogenic Pathway Inhibition, Anti-Inflammation, and Neuroprotection

“…Noticeably, the ascorbic derivatives exhibited higher percent cell viability than those in ascorbic acid and 0.5% DMSO. This implies that a structural modification of ascorbic acid might help reduce pro-oxidation activity by potentially reducing reactivity or increasing steric hindrance of the structure [ 36 , 37 ]. However, further experiments are required to assess intracellular ROS levels upon exposure to these derivatives.…”