DFT studies on antioxidant mechanisms, electronic properties, spectroscopic (FT-IR and UV) and NBO analysis of C-glycosyl flavone, an isoorientin

Deepha, V.; Praveena, R.; Sadasivam, K.

doi:10.1016/j.molstruc.2014.10.078

Cited by 23 publications

(7 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Analyzing antioxidant protection in terms of the intrinsic reactivity of the antioxidant species is, by far, the theoretical approach most frequently found in the literature . There are several reactivity indexes that have been used for that purpose.…”

Section: The Computational Approachmentioning

confidence: 99%

Computational strategies for predicting free radical scavengers' protection against oxidative stress: Where are we and what might follow?

Galano

Álvarez-Idaboy

2018

Int J of Quantum Chemistry

213

247

View full text Add to dashboard Cite

Oxidative stress, which is frequently induced by an overproduction of free radicals (FR), poses a high risk to human health. Thus, finding efficient strategies for scavenging FR is a research area of current interest. Among many other aspects, this involves identifying chemical compounds capable of offering antioxidant protection (AOP) and quantifying such protection. This review summarizes different computational approaches that can contribute to gain a deeper knowledge on this subject. Several reaction mechanisms that may contribute to AOP are discussed, as well as some key factors influencing their relative importance including the chemical nature of the reacting FR, the polarity of the environment and the pH in aqueous solution. Kinetics‐based analyses to characterize antioxidants, through their FR scavenging activity, are presented. Trends in such activity, from the data currently available in the literature are provided. Some key aspects, regarding AOP, that still deserves further investigation, are discussed.

show abstract

Section: The Computational Approachmentioning

confidence: 99%

Computational strategies for predicting free radical scavengers' protection against oxidative stress: Where are we and what might follow?

Galano

Álvarez-Idaboy

2018

Int J of Quantum Chemistry

213

247

View full text Add to dashboard Cite

show abstract

“…There are several mechanisms for free-radical scavenging action of phenolic antioxidants, and it has been reported that phenolic O–H bond dissociation enthalpy (BDE), adiabatic ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron-transfer enthalpy (ETE) are important factors can determine thermodynamically preferred free-radical scavenging pathways . Theoretical approaches, particularly, density functional theory (DFT), have been successfully applied in the aid to calculate these physicochemical descriptors related to different radical scavenging activity mechanisms ,− and also to find structure–activity relationships (SARs) for phenolic antioxidants. − However, to the best of our knowledge, there is no reported theoretical study regarding the antioxidant activities of SHQA and SCM or their derivatives so far.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory Studies on the Antioxidant Mechanism and Electronic Properties of Some Bioactive Marine Meroterpenoids: Sargahydroquionic Acid and Sargachromanol

Farrokhnia

2020

ACS Omega

View full text Add to dashboard Cite

Certain meroterpenoids isolated from brown alga of the genus Sargassum are known to be antioxidant agents. Herein, density functional theory has been performed to analyze the preferred antioxidant mechanism of the two reactive antioxidant compounds derived from the Sargassum genus, that is, Sargahydroquinoic acid and Sargachromanol and some of their derivatives. Their global reactivity descriptors have been calculated to reveal their reactivity as an antioxidant. Molecule 1 is the most reactive antioxidant according to calculated descriptors. The results of molecule 1 are comparable to that of Trolox, suggesting their similar activity. The calculated descriptors are closely matched with experimental pieces of evidence. It has been found that hydrogen atom transfer (HAT) is more favored in gas media. Also, the effect of solvent polarity on the antioxidant activity has been explored for molecule 1 . The results disclose that the polarity of the solvent increases the contribution of two other mechanisms, that is, single-electron transfer, followed by proton transfer and sequential proton loss electron transfer.

show abstract

“…The capacity to scavenge free radicals (R

) through a hydrogen atom transfer (H

) from phenolic hydroxyl groups to the free radical, either in one step or in two steps, was mainly approached through three mechanisms (i) HAT, a direct Hydrogen Atom Transfer between the antioxidant and the active radical (Equation ( 1 )), (ii) SPLET (Sequential Proton Loss Electron Transfer): deprotonation of the antioxidant which resulting anion, followed by an electron transfer to the active radical, the final step is protonation of the anion of the active radical (Equation ( 2 )) and (iii) SET-PT (Single Electron Transfer Proton Transfer): an electron is transferred from the antioxidant to the active radical, yielding a cation-radical and an anion, followed by proton transfer from the cation-radical to the anion (Equation ( 3 )). These mechanisms may occur parallel but with different rates [ 11 , 29 , 32 , 33 , 34 , 35 ].

…”

Section: Methodsmentioning

confidence: 99%

Mechanism of Antioxidant Activity of Betanin, Betanidin and Respective C15-Epimers via Shape Theory, Molecular Dynamics, Density Functional Theory and Infrared Spectroscopy

et al. 2022

View full text Add to dashboard Cite

Betanin and betanidin are compounds with extensive interest; they are effectively free radical scavengers. The present work aims to elucidate the differences between the mechanism of the antioxidant activity of betanin, betanidin, and their respective C15-epimers. Shape Theory establishes comparisons between the molecules’ geometries and determines parallelisms with the descriptors BDE, PA, ETE IP, PDE, and infrared spectra (IR) obtained from the molecule simulations. Furthermore, the molecules were optimized using the B3LYP/6-31+G(d,p) protocol. Finally, the molecular docking technique analyzes the antioxidant activity of the compounds in the complex with the therapeutic target xanthine oxidase (XO), based on a new proposal for the geometrical arrangement of the ligand atoms in the framework of Shape Theory. The results obtained indicate that the SPLET mechanism is the most favorable in all the molecules studied and that the first group that loses the hydrogen atom in the four molecules is the C17COOH, presenting less PA the isobetanidin. Furthermore, regarding the molecular docking, the interactions of these compounds with the target were favorable, standing out to a greater extent the interactions of isobetanidin with XO, which were analyzed after applying molecular dynamics.

show abstract

DFT studies on antioxidant mechanisms, electronic properties, spectroscopic (FT-IR and UV) and NBO analysis of C-glycosyl flavone, an isoorientin

Cited by 23 publications

References 38 publications

Computational strategies for predicting free radical scavengers' protection against oxidative stress: Where are we and what might follow?

Computational strategies for predicting free radical scavengers' protection against oxidative stress: Where are we and what might follow?

Density Functional Theory Studies on the Antioxidant Mechanism and Electronic Properties of Some Bioactive Marine Meroterpenoids: Sargahydroquionic Acid and Sargachromanol

Mechanism of Antioxidant Activity of Betanin, Betanidin and Respective C15-Epimers via Shape Theory, Molecular Dynamics, Density Functional Theory and Infrared Spectroscopy

Contact Info

Product

Resources

About