Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

On the Scavenging Ability of Scutellarein against the OOH Radical in Water and Lipid-like Environments: A Theoretical Study.

ABSTRACT: The antioxidant capability of scutellarein, a flavonoid extracted from different plants of the Scutellaria family, was computationally predicted by considering its reaction with the OOH radical in both lipid-like and water environments. The pKa and equilibrium behavior in the aqueous phase were also calculated. Different reaction mechanisms involving the most populated species were considered. The work was performed by using the density functional level of theory. The individual, total, and fraction-corrected total rate constants were obtained. The results show that scutellarein has scavenging power against the hydroperoxyl radical similar to that of Trolox, which is generally used as a reference antioxidant.

SUBMITTER: Spiegel M

PROVIDER: S-EPMC8868326 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

On the Scavenging Ability of Scutellarein against the OOH Radical in Water and Lipid-like Environments: A Theoretical Study.

Spiegel Maciej M Marino Tiziana T Prejanò Mario M Russo Nino N

Antioxidants (Basel, Switzerland) 20220125 2

The antioxidant capability of scutellarein, a flavonoid extracted from different plants of the Scutellaria family, was computationally predicted by considering its reaction with the OOH radical in both lipid-like and water environments. The pKa and equilibrium behavior in the aqueous phase were also calculated. Different reaction mechanisms involving the most populated species were considered. The work was performed by using the density functional level of theory. The individual, total, and frac ...[more]

PMID: 35204107

Similar Datasets

Radical Scavenging Activity of Puerarin: A Theoretical Study.

Project description:Puerarin is a C-glycoside of daidzein, one of the major bioactive ingredients isolated from the root of Puerarialobata, which has a wide spectrum of pharmacological effects. Although puerarin is well-known for its effective antioxidant activity, there is seldom a systematic theoretical study on its radical scavenging activity. Herein, the free radical scavenging ability of puerarin was investigated systematically by density functional theory (DFT) calculations. The reaction activity was compared with daidzein as well. Three reaction pathways: hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) were discussed and compared by thermodynamic parameters such as bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE). The reaction kinetics of puerarin with special radicals •OH and •OOH were also studied. The results obtained may be of great significance for better understanding the relationship between the antioxidant properties and structural design of puerarin, as well as other antioxidants.

| S-EPMC6943502 | biostudies-literature

The radical scavenging activity of moracins: theoretical insights.

Project description:Moracins are natural products that have been isolated from different plants such as Artocarpus heterophyllus, Cassia fistula, Morus alba, and Morus mesozygia. Studies showed that moracins may have various advantageous physiological effects such as anticancer, anti-inflammatory, anticholinesterase and particularly antioxidant activities. Most of these bioactivities have not been studied systematically. In this study, the radical scavenging of a typical moracin (moracin M, MM) against HO˙ and HOO˙ radicals was evaluated by thermodynamic and kinetic calculations in the gas phase as well as in water and pentyl ethanoate solvents. It was found that the overall rate constants for the HO˙ radical scavenging in the gas phase and the physiological environments are in the range of 1011 to 1010 M-1 s-1, respectively. For the HOO˙ + MM reaction the rate constants are 4.10 × 107 and 3.80 × 104 M-1 s-1 in the polar and lipid media, respectively. It is important to notice that the single electron transfer pathway of the anion state (MM-O6'-) dominated the HOO˙ radical scavenging in the aqueous solution, whereas in lipid medium the neutral MM exerted its activity by the formal hydrogen transfer mechanism. The HOO˙ radical scavenging of MM is comparable to that of Trolox in lipid medium, whereas it is 315.4 times more active in the polar environment.

| S-EPMC9057055 | biostudies-literature

Radical Scavenging Activity of Natural Anthraquinones: a Theoretical Insight.

Project description:Anthraquinones (ANQs) isolated from Paederia plants are known to have antidiarrheal, antitussive, anthelmintic, analgesic, anti-inflammatory, antihyperlipidemic, antihyperglycaemic, and antimicrobial activities. The antioxidant properties were also noted but not confirmed thus far. In this study, the superoxide and hydroperoxide radical scavenging activities of six ANQs were evaluated using a computational approach. The results suggest that the ANQs exhibit low HOO• antiradical activity in all environments, including the gas phase (k < 102 M-1 s-1). In contrast, the ANQs might exert excellent O2 •- radical scavenging activity, particularly in aqueous solution. The rate constants of the superoxide anion scavenging in water (at pH = 7.4) range from 3.42 × 106 to 3.70 × 108 M-1 s-1. Compared with typical antioxidants such as ascorbic acid and quercetin, the superoxide anion scavenging activity of ANQs is significantly higher. Thus, the ANQs are promising O2 •- radical scavengers in polar media.

| S-EPMC8158809 | biostudies-literature

Novel tyrosinase inhibitory peptide with free radical scavenging ability.

Project description:Tyrosinase is a key enzyme involved in melanin synthesis. Therefore, various tyrosinase inhibitors have been screened by researchers in recent years. In the present study, we discovered a novel tyrosinase inhibitor, a peptide ECGYF (named EF-5), with free radical scavenging ability. The effect of tyrosinase inhibition by EF-5 was stronger than that of arbutin and glutathione, when analyzed both in vitro (IC50: 0.46 mM) and in vivo. The UV-Vis absorption and circular dichroism spectroscopies indicated that EF-5 interacted with tyrosinase in a different way as that of glutathione. The results of molecular docking showed that the binding between EF-5 and tyrosinase was determined majorly by hydrogen bonds and hydrophobic interactions. EF-5 had also retained its ability to scavenge both hydroxyl and superoxide radicals in vitro and was found to be nontoxic to cells, as revealed by the MTT assay. These features suggested that the EF-5 peptide may serve as a safe and effective alternative as a tyrosinase inhibitor.

| S-EPMC6746264 | biostudies-literature

A theoretical study of the radical scavenging activity of natural stilbenes.

Project description:Oxidative stress is implicated in aging and aging-related diseases, including cancer. Prevention-focused health management approaches emphasize the importance of dietary antioxidants, which naturally draws attention to the antioxidant capacity of natural products. Several groups of plant-derived antioxidant compounds have been identified and their radical scavenging activity confirmed and measured; it has proven challenging, however, to link the experimentally determined activity quantitatively to a molecular mechanism of action. Based on our success with a computational approach, in this study, the methylperoxyl radical scavenging activity of 12 natural stilbenes was evaluated based on kinetic and thermodynamic calculations. The results suggest that for stilbenes hydrogen atom transfer (HAT) is a main mechanism for the ROO˙ radical scavenging in the gas. Assessing the role of substitutes on the antioxidant properties of stilbenes revealed that the presence of O-H groups in ring B can increase the antioxidant activity due to a decrease in the bond dissociation energy (BDE) of the O4'-H, while the replacement of a H atom in the O-H groups by a methyl group reduces the radical scavenging capacity. Among the studied compounds, astringin is a promising antioxidant with the low BDE(O-H) value (73.4 kcal mol-1) and the high rate constants (3.36 × 106, 4.11 × 103 and 9.31 × 108 M-1 s-1 in the gas phase, pentyl ethanoate and water, respectively) that suggest higher activity than trans-resveratrol.

| S-EPMC9076562 | biostudies-literature

The radical scavenging activity of glycozolidol in physiological environments: a quantum chemical study.

Project description:Glycozolidol was isolated from the root of Glycosmis pentaphylla (6-hydroxy-2-methoxy-3-methylcarbazole, GLD). This molecule attracted considerable interest due to its beneficial biological activities that likely stem from its antioxidant activity; yet, the radical scavenging action of GLD has not been investigated thus far. In this study, DFT calculations were used to estimate the radical scavenging activity of GLD against a variety of biologically significant radical species in physiological environments. The findings demonstrated that GLD exerts significant antiradical activity in water at pH = 7.40 and in pentyl ethanoate (as a model of lipidic media) with k overall = 8.23 × 106 and 3.53 × 104 M-1 s-1, respectively. In aqueous solution, the sequential proton-loss electron transfer mechanism made the highest contribution to the activity, whereas in nonpolar solvents the formal hydrogen transfer mechanism dominated the activity. GLD is predicted to have strong antiradical activity against CH3O˙, CH3OO˙, CCl3OO˙, NO2, SO4˙-, DPPH and ABTS+˙ k app ≈ 109 M-1 s-1 and k f ≈ 106 M-1 s-1. The results suggest that GLD is a good radical scavenger in physiological environments.

| S-EPMC9671143 | biostudies-literature

Ligand-to-Metal Ratio Governs Radical-Scavenging Ability of Malate-Stabilised Ceria Nanoparticles.

Project description:Cerium dioxide sols stabilised with L-malic acid were shown to exhibit significant antioxidant activity towards alkyl peroxyl radicals in the range of ligand:CeO2 molar ratios of 0.2-1 (0.2:1, 0.4:1, 0.5:1, 0.6:1, 0.8:1 and 1:1). The antioxidant activity of cerium dioxide nanoparticles greatly depended on L-malic acid content and increased by 8 times when the ligand:CeO2 molar ratio increased from 0.2:1 to 0.4:1. An estimate of the ligand:CeO2 molar ratio required to ensure complete surface coverage of CeO2 nanoparticles with malate anions resulted in a value of 0.2. Aggregation degree of CeO2 nanoparticles depends on the ligand:CeO2 molar ratio. In the range of ligand:CeO2 molar ratios 0.2-0.4, the size of aggregates decreased by an order of magnitude. The antioxidant capacity of 1 mM malate-stabilised cerium dioxide (0.2:1) relative to sodium ascorbate was 0.012 ± 0.001 mM. The antioxidant activity of cerium dioxide stabilised with L-malic acid at a ligand:CeO2 molar ratio of 0.2:1 was 80 times less than the antioxidant activity of sodium ascorbate. Cerium dioxide nanoparticles stabilised with L-malic acid did not demonstrate a cytotoxic effect against human mesenchymal stem cells, in a wide range of concentrations (10-3-10-5 M), and their proliferation was stimulated after 72 h of cultivation. The results obtained show new possibilities for the design of biocompatible ceria-based nanomaterials with tunable pro- and antioxidant properties; these materials can further be assessed in view of their potential for treating oxidative stress-related disorders.

| S-EPMC11643014 | biostudies-literature

Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin.

Project description:Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.

| S-EPMC7999741 | biostudies-literature

Direct free radical scavenging effects of water-soluble HMG-CoA reductase inhibitors.

Project description:3-Hydroxy-3-methylglutaryl coenzyme A reductase inhibitors, statins, are widely used for preventing cardiovascular and cerebrovascular diseases by controlling blood cholesterol level. Additionally, previous studies revealed the scavenging effects of statins on free radicals. We assessed direct scavenging activities of two water-soluble statins, fluvastatin and pravastatin, on multiple free radicals using electron spin resonance spectrometry with spin trapping method. We estimated reaction rate constants (k fv for fluvastatin, and k pv for pravastatin). Superoxide anion was scavenged by fluvastatin and pravastatin with k fv and k pv of 4.82 M-1s-1 and 49.0 M-1s-1, respectively. Scavenging effects of fluvastatin and pravastatin on hydroxyl radical were comparable; both k fv and k pv were >109 M-1s-1. Fluvastatin also eliminated tert-butyl peroxyl radical with relative k fv of 2.63 to that of CYPMPO, whereas pravastatin did not affect tert-butyl peroxyl radical. Nitric oxide was scavenged by fluvastatin and pravastatin with k fv and k pv of 68.6 M-1s-1 and 701 M-1s-1, respectively. Both fluvastatin and pravastatin had scavenging effects on superoxide anion, hydroxyl radical and nitric oxide radical. On the other hand, tert-butyl peroxyl radical was scavenged only by fluvastatin, suggesting that fluvastatin might have more potential effect than pravastatin to prevent atherosclerosis and ischemia/reperfusion injury via inhibiting oxidation of lipids.

| S-EPMC6348410 | biostudies-literature

Antioxidant Properties of Embelin in Cell Culture. Electrochemistry and Theoretical Mechanism of Scavenging. Potential Scavenging of Superoxide Radical through the Cell Membrane.

Project description:Embelin, a plant natural product found in Lysimachia punctata (Primulaceae), and Embelia ribes Burm (Myrsinaceae) fruit, possesses interesting biological and pharmacological properties. It is a unique chemical species as it includes both quinone and hydroquinone functional groups plus a long hydrophobic tail. By using hydrodynamic voltammetry, which generates the superoxide radical in situ, we show an unusual scavenging capability by embelin. Embelin as a scavenger of superoxide is stronger than the common food additive antioxidant 2,6-bis(1,1-dimethylethyl)-4-20 methylphenol, (butylated hydroxytoluene, BHT). In fact, embelin is even able to completely abolish the superoxide radical in the voltaic cell. Computational results indicate that two different types of embelin scavenging actions may be involved, initially through π-π interaction and followed by proton capture in the cell. A related mechanism describes embelin's ability to circumvent superoxide leaking by transforming the anion radical into molecular oxygen. In order to confirm its antioxidant properties, its biological activity was tested in a study carried out in THP-1 human leukemic monocytes and BV-2 mice microglia. A 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, proliferation curves and antioxidant activity by the use of a fluorescent probe showed good antioxidant properties at 24 h. This suggests that embelin's long alkyl C10 tail may be useful for cell membrane insertion which stimulates the antioxidant defense system, and cytoprotection in microglia. In conclusion, embelin could be an interesting pharmacological tool able to decrease the damage associated with metabolic and neurodegenerative diseases.

| S-EPMC7278612 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data