Synthesis, antioxidant activity, and density functional theory study of catechin derivatives

Wang, Jing; Tang, Han; Hou, Bo; Zhang, Pan; Wang, Qi; Zhang, Bang-Lei; Huang, Yewei; Ya, Wang; Xiang, Zemin; Zi, Cheng-Ting; Sheng, Jun

doi:10.1039/c7ra11496f

Cited by 35 publications

(18 citation statements)

References 28 publications

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“…Measurement of spin density MEP is a very useful approach for exploring the reactivity and structure-activity relationships of compounds [45][46][47]. A previous study used the MEP to characterize the antioxidant activity of catechin derivatives [48]. To further elucidate the structure-antioxidant activity relationships of DDCDs 1-6, MEP analyses were carried out for the lowest-energy conformers to characterize the similarity and dissimilarity in the electrostatic binding characteristics of the surface of the molecules (Fig.…”

Section: Mepsmentioning

confidence: 99%

Structure–antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Zhang

Qiao

et al. 2022

Struct Chem

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Quantum-chemical calculations based on the density functional theory (DFT) at the B3LYP/6-311 + + G(2d,2p)//B3LYP/6-31G(d,p) level were employed to study the relationship between the antioxidant properties and chemical structures of six dendrocandin (DDCD) analogues in the gas phase and two solvents (methanol and water). The hydrogen atom transfer (HAT), electron-transfer-proton-transfer (ET-PT), and sequential proton-loss-electron-transfer (SPLET) mechanisms are explored. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), reactivity indices (η, μ, ω, ω + , and ω -), and molecular electrostatic potentials (MEPs) were also evaluated. The results suggest that the D ring plays an important role in mediating the antioxidant activity of DDCDs. For all the studied compounds, indicating that HAT was identified as the most favorable mechanism, whereas the SPLET mechanism was the most thermodynamically favorable pathway in polar solvents. The results of our study should aid in the development of new or modified antioxidant compounds.

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Section: Mepsmentioning

confidence: 99%

Structure–antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Zhang

Qiao

et al. 2022

Struct Chem

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“…It was previously demonstrated that DFT/B3LYP calculations are a good choice for estimation of the reaction enthalpies as they can provide a fairly accurate agreement between the calculated values and the available experimental data as well as describe reliably the structure-activity relationship for antioxidants with diverse chemical structure at reasonable computational time. [60][61][62][63][64] On the other hand, the use of at least double-zeta basis set, including polarization and diffuse functions, is recommended, 65 therefore the B3LYP//6-311++G(d,p) combination was applied in the present calculations. The results obtained at this computational level allow a useful comparison with earlier studied antioxidants.…”

Section: Computational Study Of the Radical Scavenging Activitymentioning

confidence: 99%

New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity

et al. 2021

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“…GA possesses the most robust antiradical property than Trolox, and hence, in many cases, this molecule is widely used as a reference compound for antioxidant studies. Green tea contains the highest concentration of GA-based compounds responsible for the plant's antioxidant capacity [22,23].…”

Section: Introductionmentioning

confidence: 99%

DFT Study of Structure and Radical Scavenging Activity of Natural Pigment Delphinidin and Derivatives

Pottachola¹,

Kaniyantavida²,

Karuvanthodiyil³

2022

Density Functional Theory - Recent Advances, New Perspectives and Applications

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A theoretical evaluation of the antioxidant activity of natural pigment delphinidin (1a) and derivatives 1b, 1c, 1d & 1e was performed using the DFT-B3LYP/6–311 + G (d, p) level of theory. Three potential working mechanisms, hydrogen atom transfer (HAT), stepwise electron transfer proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET), have been investigated. The physiochemical parameters, including O–H bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE), have been calculated in the gas phase and aqueous phase. The study found that the most suitable mechanism for explaining antioxidant activity is HAT in the gas phase and SPLET in the aqueous medium in this level of theory. Spin density calculation and delocalization index of studied molecules also support the radical scavenging activity. When incorporated into natural pigment delphinidin, the gallate moiety can enhance the activity and stability of the compounds.

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Synthesis, antioxidant activity, and density functional theory study of catechin derivatives

Abstract: Catechin derivatives were synthesized, and their structures were characterized by 1H-NMR, 13C-NMR, and mass spectrometry.

Cited by 35 publications

References 28 publications

Structure–antioxidant activity relationships of dendrocandin analogues determined using density functional theory

Structure–antioxidant activity relationships of dendrocandin analogues determined using density functional theory

New 1H-benzimidazole-2-yl hydrazones with combined antiparasitic and antioxidant activity

DFT Study of Structure and Radical Scavenging Activity of Natural Pigment Delphinidin and Derivatives

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