Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Spiegel, Maciej

doi:10.1021/acs.jcim.2c00104

Cited by 57 publications

(38 citation statements)

References 266 publications

(692 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1) direct scavenging of free radicals, also known as primary antioxidation, which essentially consists of a reaction between a powerful free radical and an antioxidant with the formation of a new less active radical, and reaction can proceed until the formation of a neutral specie ( Milenković et al, 2020 ). This reaction can occur through different mechanisms such as transferring a hydrogen atom or an electron or both from the antioxidant to the free radical (HAT and SET), or sequential proton-loss electron transfer (SPLET), or by bonding the radical to the structure of the antioxidant (RAF) ( Galano et al, 2016b ; Spiegel, 2022 ):

…”

Section: Introductionmentioning

confidence: 99%

Computational investigation on the antioxidant activities and on the Mpro SARS-CoV-2 non-covalent inhibition of isorhamnetin

et al. 2023

Self Cite

View full text Add to dashboard Cite

In the present work, we report a computational study on some important chemical properties of the flavonoid isorhamnetin, used in traditional medicine in many countries. In the course of the study we determined the acid-base equilibria in aqueous solution, the possible reaction pathways with the •OOH radical and the corresponding kinetic constants, the complexing capacity of copper ions, and the reduction of these complexes by reducing agents such as superoxide and ascorbic anion by using density functional level of theory Density Functional Theory. Finally, the non-covalent inhibition ability of the SARS-CoV-2 main protease enzyme by isorhamnetin was examined by molecular dynamics (MD) and docking investigation.

show abstract

…”

Section: Introductionmentioning

confidence: 99%

Computational investigation on the antioxidant activities and on the Mpro SARS-CoV-2 non-covalent inhibition of isorhamnetin

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…Higher HOMO energy is associated with a stronger electron donor molecule, while LUMO energy reflects the ability to accept the electron. In molecules with antioxidant properties, the distribution of HOMO electron density may qualitatively indicate the active site of free radical scavenging, because the reaction of H-abstraction is associated with the transfer of electrons [ 63 ].…”

Section: Discussionmentioning

confidence: 99%

An Evaluation of the Novel Biological Properties of Diterpenes Isolated from Plectranthus ornatus Codd. In Vitro and In Silico

Sitarek

Kowalczyk

Synowiec

et al. 2022

Cells

View full text Add to dashboard Cite

Plectranthus ornatus Codd, the genus Plectranthus of the Lamiaceae family, has been used as traditional medicine in Africa, India and Australia. Pharmacological studies show the use of this plant to treat digestive problems. In turn, leaves were used for their antibiotic properties in some regions of Brazil to treat skin infections. The present study examines the anti-inflammatory, antioxidant and cytotoxic effects of the halimane and labdane diterpenes (11R*,13E)-11-acetoxyhalima-5,13-dien-15-oic acid (HAL) and 1α,6β-diacetoxy-8α,13R*-epoxy-14-labden-11-one (PLEC) and the forskolin-like 1:1 mixture of 1,6-di-O-acetylforskolin and 1,6-di-O-acetyl-9-deoxyforskolin (MRC) isolated from P. ornatus on lung (A549) and leukemia (CCRF-CEM) cancer cell lines, and on normal human retinal pigment epithelial (ARPE-19) cell line in vitro. Additionally, molecular docking and computational approaches were used. ADMET properties were analysed through SwissADME and proTox-II—Prediction. The results indicate that all tested compounds significantly reduced the viability of the cancer cells and demonstrated no cytotoxic effects against the non-neoplastic cell line. The apoptosis indicators showed increased ROS levels for both the tested A549 and CCRF-CEM cancer cell lines after treatment. Furthermore, computational studies found HAL to exhibit moderate antioxidant activity. In addition, selected compounds changed mitochondrial membrane potential (MMP), and increased DNA damage and mitochondrial copy number for the CCRF-CEM cancer cell line; they also demonstrated anti-inflammatory effects on the ARPE-19 normal cell line upon lipopolysaccharide (LPS) treatment, which was associated with the modulation of IL-6, IL-8, TNF-α and GM-CSF genes expression. Docking studies gave indication about the lowest binding energy for 1,6-di-O-acetylforskolin docked into IL-6, TNF-α and GM-CSF, and 1,6-di-O-acetyl-9-deoxyforskolin docked into IL-8. The ADMET studies showed drug-likeness properties for the studied compounds. Thus, halimane and labdane diterpenes isolated from P. ornatus appear to offer biological potential; however, further research is necessary to understand their interactions and beneficial properties.

show abstract

“…The highest hydroperoxide radical scavenging activity of AVN-C and the molecular basis of which, as explored here, is in complete agreement with the experimental results. [15] In order to verify the hydroperoxide radical scavenging activity trend obtained at the B3LYP level, we have reproduced all reaction barriers employing the popular M06-2X functional known for kinetic analysis [29,53] in both gas and aqueous phase (see Table 4). In general, the Gibbs free energies of reaction calculated at the UM06-2X/6-311 + G** level are found to be higher than that computed at the UB3LYP/6-311 + G** level.…”

Section: • Ooh Scavenging By Avns Via the Hat Mechanismmentioning

confidence: 99%

Mechanistic insights on the radical scavenging activity of oat avenanthramides

Purushothaman

Janardanan

2022

J of Physical Organic Chem

View full text Add to dashboard Cite

Avenanthramides, the phenolic antioxidants exclusively found in oats (Avena sativa L.), have long been recognized for their immense health benefits owing to their antioxidant potential. Herein, hydroperoxyl radical ( • OOH) scavenging activity of oat avenanthramides is investigated in detail, using density functional theory for the first time. Three probable mechanisms: (a) hydrogen atom transfer (HAT), (b) single electron transfer followed by proton transfer, and (c) sequential proton loss electron transfer (SPLET), are considered towards evaluating the antioxidant potential of avenanthramides (A-C) in the gas phase as well as in both polar and non-polar media. Based on the computed data, HAT is found to be the thermodynamically preferred mechanism for antioxidant activity in the gas phase. In the polar medium, SPLET represents the most probable reaction pathway. Our thermodynamic and kinetic data computed at the B3LYP level predict avenanthramide C, characterized by an ortho-dihydroxy functionality on the aromatic ring, as the most potent radical scavenger among the three variants, in agreement with the available experimental reports.

show abstract

Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity

Cited by 57 publications

References 266 publications

Computational investigation on the antioxidant activities and on the Mpro SARS-CoV-2 non-covalent inhibition of isorhamnetin

Computational investigation on the antioxidant activities and on the Mpro SARS-CoV-2 non-covalent inhibition of isorhamnetin

An Evaluation of the Novel Biological Properties of Diterpenes Isolated from Plectranthus ornatus Codd. In Vitro and In Silico

Mechanistic insights on the radical scavenging activity of oat avenanthramides

Contact Info

Product

Resources

About