Density functional theory study of the structure–antioxidant activity of polyphenolic deoxybenzoins

Xue, Yun-Shan; Zheng, Yun‐Wen; An, L.; Dou, Yunyan; Liu, Yi

doi:10.1016/j.foodchem.2013.11.064

Cited by 145 publications

(115 citation statements)

References 36 publications

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“…BDE is the numerical parameter related to HAT mechanism and characterizes the stability of the corresponding hydroxyl group. The lower BDE value indicates that the stability of the corresponding O–H bond is lower and the corresponding O–H bond can be easily broken 20, 26, 28, 29 . Hence, higher is the antioxidant capacity of the compound.…”

Section: Resultsmentioning

confidence: 99%

“…The more stable radical may indicate stronger antioxidative capacities of the compound. Spin density is a reliable parameter in rationalizing the stability of radical species 20, 28, 29 . The spin density distributions of flavonoid radicals in the gas phase were calculated and presented in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…2, the spin density of the C5–O5 · and C7–O7 · flavonoid radicals is high on the O-atom compared to the C4′–O4′ · , C3′–O3′ · and C3–O3 · radicals in the gas phase. This means that the formation of C3′–O3′ · , C4′–O4′ · and C3–O3 · radicals are more favorable for spin density localization than the formation of C5–O5 · and C7–O7 · flavonoid radicals 20, 28, 29 . This also means that the stabilization of the C3′–O3′ · , C4′–O4′ · and C3–O3 · radicals are higher than C5–O5 · and C7–O7 · flavonoid radicals 20, 28, 29 .…”

Section: Resultsmentioning

confidence: 99%

“…The electron donating ability of a flavonoid is related to an extended electronic delocalization over the entire molecule. A flavonoid having a high degree of π-delocalization is more active 20, 26, 28, 29 . The calculated ionization potentials (IPs) for quercetin and its derivatives in the gas phase as well as in solvent are given in Table 3.…”

Section: Resultsmentioning

confidence: 99%

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Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Zheng

Deng

Qin

et al. 2017

Sci Rep

249

151

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Among the multiple components of propolis, flavonoids contribute greatly to the antioxidant activities of propolis. Flavonoids mainly exist in the form of sugar-conjugated derivatives. Quercetin glycosides represent the predominant flavonoid fraction in propolis. In this work, density functional theory (DFT) calculations were applied to analyze the antioxidative properties of quercetin and its glucosides in the gas and in the liquid phase (ethanol, water). Three main antioxidant mechanisms, hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were used to analyze the antioxidative capacity of the investigated compounds. Solvent effects dominantly affect SET-PT and SPLET. Thus, the thermodynamically preferred mechanism can be altered. HAT and SPLET are the thermodynamically dominant mechanisms in gas and solvent phases, respectively. Therefore, in the gas phase, the sequence of the antioxidative capacity is similar with the bond dissociation enthalpy values: quercetin > quercetin-5-O-glucoside > quercetin-7-O-glucoside > quercetin-3-O-glucoside > quercetin-3′-O-glucoside > quercetin-4′-O-glucoside. While, in the solvent phases, the sequence is similar with the proton affinity values: quercetin-4′-O-glucoside > quercetin-5-O-glucoside > quercetin > quercetin-3-O-glucoside > quercetin-7-O-glucoside > quercetin-3′-O-glucoside. OH groups in B-ring and C-ring contribute mainly to the antioxidative activities of quercetin and glucosides compared with A-ring.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Zheng

Deng

Qin

et al. 2017

Sci Rep

249

151

View full text Add to dashboard Cite

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“…3,4 Most of natural antioxidants belong to the family of phenolic or polyphenolic compounds, which show their antioxidant activity via a hydrogen atom transfer (HAT) or single electron transfer (SET) mechanism. 5 Fisetin (3,3',4',7-tetrahydroxyflavone, Figure 1) is a phenolic flavonoid in various food, such as strawberry, onion and persimmon. 6 It has a wide range of pharmacological effects, such as antitumor, antiinflammation, 7 anticoagulant and dissolving thrombus.…”

Section: Introductionmentioning

confidence: 99%

Fisetin Protects DNA Against Oxidative Damage and Its Possible Mechanism

et al. 2016

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Investigation of HMG‐CoA reductase inhibitory and antioxidant effects of various hydroxycoumarin derivatives

Özalp

Danış

Yüce‐Dursun

et al. 2020

Archiv der Pharmazie

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Cardiovascular diseases are one of the primary causes of deaths worldwide, and the development of atherosclerosis is closely related to hypercholesterolemia. As the reduction of the low-density lipoprotein cholesterol level is critical for treating these diseases, the inhibition of 3-hydroxy-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase, which is essentially responsible for cholesterol biosynthesis, stands out as a key solution to lower plasma cholesterol levels. In this study, we synthesized several dihydroxycoumarins and investigated their antioxidant and in vitro HMG-CoA reductase inhibitory effects. Furthermore, we carried out in silico studies and examined the quantum-chemical properties of the coumarin derivatives. We also performed molecular docking experiments and analyzed the binding strength of each coumarin derivative. Our results revealed that compound IV displayed the highest HMG-CoA reductase inhibitory activity (IC 50 = 42.0 µM) in vitro. Cupricreducing antioxidant capacity and ferric-reducing antioxidant power assays demonstrated that coumarin derivatives exhibit potent antioxidant activities. Additionally, a close relationship was found between the lowest unoccupied molecular orbital energy levels and the antioxidant activities.

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Density functional theory study of the structure–antioxidant activity of polyphenolic deoxybenzoins

Cited by 145 publications

References 36 publications

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Fisetin Protects DNA Against Oxidative Damage and Its Possible Mechanism

Investigation of HMG‐CoA reductase inhibitory and antioxidant effects of various hydroxycoumarin derivatives

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