Substituent Effects on the Radical Scavenging Activity of Isoflavonoid

Zheng, Yujun; Deng, Geng; Guo, Rui; Chen, Dafu; Fu, Zhanli

doi:10.3390/ijms20020397

Cited by 18 publications

(10 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One would wonder why such unusual basis sets as Ahlrich’s or Dunning’s, or methods such as TPSSh or WB97, were chosen when Pople’s [ 53 , 54 , 55 ], particularly when combined with Minnesota’s functionals [ 26 , 56 , 57 , 58 , 59 ], are leading the way? At the time of writing this paper, we were barely able to find articles that used def2– [ 60 ] or (aug–)cc–pVXZ [ 61 , 62 , 63 ] basis sets in their studies on antioxidative activity.…”

Section: Methodsmentioning

confidence: 99%

A Statistically Supported Antioxidant Activity DFT Benchmark—The Effects of Hartree–Fock Exchange and Basis Set Selection on Accuracy and Resources Uptake

2021

View full text Add to dashboard Cite

Polyphenolic compounds are now widely studied using computational chemistry approaches, the most popular of which is Density Functional Theory. To ease this process, it is critical to identify the optimal level of theory in terms of both accuracy and resource usage—a challenge we tackle in this study. Eleven DFT functionals with varied Hartree–Fock exchange values, both global and range-separated hybrids, were combined with 14 differently augmented basis sets to calculate the reactivity indices of caffeic acid, a phenolic acid representative, and compare them to experimental data or a high-level of theory outcome. Aside from the main course, a validation of the widely used Janak’s theorem in the establishment of vertical ionization potential and vertical electron affinity was evaluated. To investigate what influences the values of the properties under consideration, linear regression models were developed and thoroughly discussed. The results were utilized to compute the scores, which let us determine the best and worst combinations and make broad suggestions on the final option. The study demonstrates that M06–2X/6–311G(d,p) is the best fit for such research, and, curiously, it is not necessarily essential to include a diffuse function to produce satisfactory results.

show abstract

Section: Methodsmentioning

confidence: 99%

A Statistically Supported Antioxidant Activity DFT Benchmark—The Effects of Hartree–Fock Exchange and Basis Set Selection on Accuracy and Resources Uptake

2021

View full text Add to dashboard Cite

show abstract

“…Consequently, antioxidant activity depends on two things: the first being the capacity/skill of compounds to lose hydrogen atoms, and the second being the stability of the formed radical [36,39,40]. Therefore, the structure of the tested compounds and electronic effects of groups/substituents in structures plays a significant role in antioxidant activity [36,37,41]. It is generally known that there are 3 types of electron effects: mesomeric (or resonance), inductive, and steric hindrance.…”

Section: Evaluation Of Antioxidant Activitymentioning

confidence: 99%

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Yakan¹

2020

Turk J Chem

View full text Add to dashboard Cite

Schiff-base-bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT-IR, 1 H NMR, 13 C NMR, and UV-Vis spectroscopic methods and elemental analysis were used to elucidate the identification of the synthesized molecules. The in vitro antioxidant activity of the synthesized compounds was analysed with the 1,1-diphenyl-2-picryl hydrazyl free-radical-trapping process. The synthesized compounds exhibited lower antioxidant activity than the standard ascorbic acid. IC 50 values of the synthesized molecules measured from 3.81 ± 0.01 to 29.05 ± 0.11 µ M. Among the synthesized compounds, compound 3 had the best antioxidant activity. Moreover, this study explained the structure-activity relationship of the synthesized molecules with different substituents in radical trapping reactions.

show abstract

“…In short, the antioxidant process of butein and (S)-butin is considered to be a single process comprising ET accompanied by PT (designated as ET plus PT). One important type of ET plus PT is the HAT (hydrogen atom transfer) mechanism [48,[52][53][54][55][56][57], which was determined using DPPH • as a probe. The DPPH • probe, however, was recently suggested to have some limitations [35].…”

Section: Resultsmentioning

confidence: 99%

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Liu

Cai

et al. 2020

Molecules

View full text Add to dashboard Cite

To elucidate the mechanism of anti-ferroptosis and examine structural optimization in natural phenolics, cellular and chemical assays were performed with 2′-hydroxy chalcone butein and dihydroflavone (S)-butin. C11-BODIPY staining and flow cytometric assays suggest that butein more effectively inhibits ferroptosis in erastin-treated bone marrow-derived mesenchymal stem cells than (S)-butin. Butein also exhibited higher antioxidant percentages than (S)-butin in five antioxidant assays: linoleic acid emulsion assay, Fe3+-reducing antioxidant power assay, Cu2+-reducing antioxidant power assay, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-trapping assay, and α,α-diphenyl-β-picrylhydrazyl radical (DPPH•)-trapping assay. Their reaction products with DPPH• were further analyzed using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS). Butein and (S)-butin produced a butein 5,5-dimer (m/z 542, 271, 253, 225, 135, and 91) and a (S)-butin 5′,5′-dimer (m/z 542, 389, 269, 253, and 151), respectively. Interestingly, butein forms a cross dimer with (S)-butin (m/z 542, 523, 433, 419, 415, 406, and 375). Therefore, we conclude that butein and (S)-butin exert anti-ferroptotic action via an antioxidant pathway (especially the hydrogen atom transfer pathway). Following this pathway, butein and (S)-butin yield both self-dimers and cross dimers. Butein displays superior antioxidant or anti-ferroptosis action to (S)-butin. This can be attributed the decrease in π-π conjugation in butein due to saturation of its α,β-double bond and loss of its 2′-hydroxy group upon biocatalytical isomerization.

show abstract

Substituent Effects on the Radical Scavenging Activity of Isoflavonoid

Cited by 18 publications

References 27 publications

A Statistically Supported Antioxidant Activity DFT Benchmark—The Effects of Hartree–Fock Exchange and Basis Set Selection on Accuracy and Resources Uptake

A Statistically Supported Antioxidant Activity DFT Benchmark—The Effects of Hartree–Fock Exchange and Basis Set Selection on Accuracy and Resources Uptake

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Contact Info

Product

Resources

About