Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

Fourteen triazole benzoic acid hybrids were previously characterized. This work aimed to screen their in vitro antioxidant activity using different assays, i.e., DPPH (1,1-diphenyl-1-picrylhydrazyl), reducing the power capability, FRAP (ferric reducing antioxidants power) and ABTS (2,2′-azino-bis(3-ethylben zothiazoline-6-sulfonate) radical scavenging. The 14 compounds showed antioxidant properties in relation to standard BHA (butylated hydroxylanisole) and Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid). Higher antioxidant activity was observed by the parent (1) at a concentration of 100 µg/mL (89.95 ± 0.34 and 88.59 ± 0.13%) when tested by DPPH and ABTS methods in relation to BHA at 100 µg/mL (95.02 ± 0.74 and 96.18 ± 0.33%). The parent (2) demonstrated remarkable scavenging activity when tested by ABTS (62.00 ± 0.24%), however, 3 was less active (29.98 ± 0.13%). Compounds 5, 6, 9, and 11 exhibited good scavenging activity compared to 1. DFT studies were performed using the B3LYP/6-311++g (2d,2p) level of theory to evaluate different antioxidant descriptors for the targets. Three antioxidant mechanisms, i.e., hydrogen atom transfer (HAT), sequential electron transfer proton transfer (SETPT) and sequential proton loss electron transfer (SPLET) were suggested to describe the antioxidant properties of 1–14. Out of the 14 triazole benzoic acid hybrids, 5, 9, 6, and 11 showed some good theoretical results, which were in agreement with some experimental outcomes. Based on the computed (PA and ETE) and (BDE and IP) values in (SPLET) and (HAT and SETPT) mechanisms, respectively, compound 9 emerged has having good antioxidant activity.

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Green One-Pot Synthesis of Coumarin-Hydroxybenzohydrazide Hybrids and Their Antioxidant Potency

Antioxidants ◽

10.3390/antiox10071106 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1106

Author(s):

Marko R. Antonijević ◽

Dušica M. Simijonović ◽

Edina H. Avdović ◽

Andrija Ćirić ◽

Zorica D. Petrović ◽

...

Keyword(s):

Antioxidant Activity ◽

Electron Transfer ◽

Density Functional ◽

Electron Transfer Reaction ◽

Hydrogen Atom Transfer ◽

Special Importance ◽

Theory Approach ◽

One Pot ◽

Antioxidant Potency

Compounds from the plant world that possess antioxidant abilities are of special importance for the food and pharmaceutical industry. Coumarins are a large, widely distributed group of natural compounds, usually found in plants, often with good antioxidant capacity. The coumarin-hydroxybenzohydrazide derivatives were synthesized using a green, one-pot protocol. This procedure includes the use of an environmentally benign mixture (vinegar and ethanol) as a catalyst and solvent, as well as very easy isolation of the desired products. The obtained compounds were structurally characterized by IR and NMR spectroscopy. The purity of all compounds was determined by HPLC and by elemental microanalysis. In addition, these compounds were evaluated for their in vitro antioxidant activity. Mechanisms of antioxidative activity were theoretically investigated by the density functional theory approach and the calculated values of various thermodynamic parameters, such as bond dissociation enthalpy, proton affinity, frontier molecular orbitals, and ionization potential. In silico calculations indicated that hydrogen atom transfer and sequential proton loss–electron transfer reaction mechanisms are probable, in non-polar and polar solvents respectively. Additionally, it was found that the single-electron transfer followed by proton transfer was not an operative mechanism in either solvent. The conducted tests indicate the excellent antioxidant activity, as well as the low potential toxicity, of the investigated compounds, which makes them good candidates for potential use in food chemistry.

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Determination of in vitro antioxidant activity of the leaves extracts of Ehretia pubescens

International Journal of Research in Pharmaceutical Sciences ◽

10.26452/ijrps.v11i4.3308 ◽

2020 ◽

Vol 11 (4) ◽

pp. 6262-6267

Author(s):

Krishnamoorthy Meenakumari ◽

Giridharan Bupesh ◽

Mayur Mausoom Phukan

Keyword(s):

Antioxidant Activity ◽

Ethyl Acetate ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Reducing Power ◽

Biological Properties ◽

Scavenging Activity ◽

Reducing Power Assay

The foods from plants were known to ensure against degenerative diseases and maturing because of their antioxidant activitycredited to their high content. Information on antioxidant activity of Indian medicinal plant is abundant. To the best of our knowledge, biological properties have not been accounted in the literature for this species of . As a point, this is the first results to assess the anti-oxidant activity of the plant which belongs to the family . The antioxidant activity of Methanol, , Ethyl acetate and Aqueous extracts of E. was determined using the DPPH free radical scavenging activity, ABTS radical scavenging activity and reducing power assay. The DPPH scavenging activity showed higher activity observed in extract (63%) of E. than (54%), (44%) and aqueous (30%). the ABTS assay inhibition in extract (58%) than (43%), (38%) and aqueous (32%) extracts. The reducing power assay of different extracts was increased in extract (54%) than (40%), (34%) and aqueous (28%) extracts. Overall, the and ethyl acetate extract had higher antioxidant properties than other extract. However, in this study, extracts exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions.

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Synthesis, Characterization, and Biological Evaluation of Some New Functionalized Terphenyl Derivatives

International Journal of Medicinal Chemistry ◽

10.1155/2012/530392 ◽

2012 ◽

Vol 2012 ◽

pp. 1-13 ◽

Cited By ~ 4

Author(s):

Seranthimata Samshuddin ◽

Badiadka Narayana ◽

Balladka Kunhanna Sarojini ◽

Divya N. Shetty ◽

Nalilu Suchetha Kumari

Keyword(s):

Antimicrobial Activity ◽

Antioxidant Activity ◽

Spectral Data ◽

Antioxidant Properties ◽

Biological Evaluation ◽

Mass Spectral Data ◽

Mass Spectral ◽

H Nmr

New functionalized terphenyl derivatives incorporating various heterocyclic rings are prepared by using 4,4′′-difluoro-5′-hydroxy-1,1′:3′,1′′-terphenyl-4′-carbohydrazide as a key intermediate derived from 4,4′-difluoro chalcone, a versatile synthone. All the derivatives are characterized by 1H NMR, IR, and mass spectral data. All the synthesized products are screened for their in vitro antimicrobial and antioxidant properties. The majority of the tested compounds exhibited significant antioxidant activity and some of them showed good antimicrobial activity.

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IN VITRO ANTIOXIDANT ACTIVITY OF PHYLLODIUM PULCHELLUM L. DESV - AN THREATENED MEDICINAL PLANT

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2017.v10i10.19919 ◽

2017 ◽

Vol 10 (10) ◽

pp. 282

Author(s):

Gopal Murugan Velmurugan ◽

Subramaniam Parvathi Anand

Keyword(s):

Antioxidant Activity ◽

Leaf Extract ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Reducing Power ◽

Scavenging Activity ◽

Threatened Medicinal Plant ◽

In Vitro Antioxidant Activity

Objectives: In this study, we determined the in vitro antioxidant capacity of Phyllodium pulchellum of aqueous, ethanol, and chloroform leaf extracts.Methods: In this context, the in vitro antioxidant activity was demonstrated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azinobis(3- ethylbenzothiazolone-6-sulfonic acid) (ABTS+) radical scavenging assay, the total antioxidant activity of phosphomolybdenum assay and hydroxyl radical scavenging activity in different leaf extracts of P. pulchellum. The antioxidant activity of the extracts was compared to standard ascorbic acid.Results: All the four methods of antioxidant showed good reducing power and reducing capacity with increasing concentration again taking the ethanol leaf extract to the top position. Remarkable of antioxidant activity was observed in ethanol leaf extract on the hydrogen peroxide scavenging activity with the lowest inhibitory concentration 50 values of (155.40 μg/ml) followed by DPPH (432.90 μg/ml) and ABTS+ (524.40 μg/ml).Conclusion: These results suggest that the leaf of P. pulchellum could be a valuable source of new antioxidant properties, from the above results it seen that this plant exhibits pharmaceutical activity.

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Structure-antioxidant Activity Relationships of Dendrocandin Analogues Determined Using Density Functional Theory

10.21203/rs.3.rs-1181760/v1 ◽

2021 ◽

Author(s):

Ning Zhang ◽

Yilong Wu ◽

Miao Qiao ◽

Wenjuan Yuan ◽

Xingyu Li ◽

...

Keyword(s):

Density Functional Theory ◽

Antioxidant Activity ◽

Electron Transfer ◽

Molecular Orbital ◽

Density Functional ◽

Antioxidant Properties ◽

Hydrogen Atom Transfer ◽

Antioxidant Compounds ◽

Functional Theory ◽

Chemical Structures

Abstract Quantum-chemical calculations based on the density functional theory (DFT) at the B3LYP/6–311++G(2d,2p)//B3LYP/6–31G(d,p) level were employed to study the relationship between the antioxidant properties and chemical structures of six dendrocandin (DDCD) analogues in the gas phase and two solvents (methanol and water). The hydrogen atom transfer (HAT), electron-transfer-proton-transfer (ET-PT), and sequential proton-loss-electron-transfer (SPLET) mechanisms are explored. The highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), reactivity indices (η, μ, ω, ω+, and ω–), and molecular electrostatic potentials (MEPs) were also evaluated. The results suggest that the D ring plays an important role in mediating the antioxidant activity of DDCDs. For all the studied compounds, indicating that HAT was identified as the most favorable mechanism, whereas the SPLET mechanism was the most thermodynamically favorable pathway in polar solvents. The results of our study should aid in the development of new or modified antioxidant compounds.

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Radical Scavenging Activity of Puerarin: A Theoretical Study

Antioxidants ◽

10.3390/antiox8120590 ◽

2019 ◽

Vol 8 (12) ◽

pp. 590 ◽

Cited By ~ 5

Author(s):

Huakang Zhou ◽

Xiangzhou Li ◽

Yaxuan Shang ◽

Kai Chen

Keyword(s):

Electron Transfer ◽

Density Functional ◽

Theoretical Study ◽

Wide Spectrum ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Hydrogen Atom Transfer ◽

Scavenging Activity ◽

Dissociation Enthalpy

Puerarin is a C-glycoside of daidzein, one of the major bioactive ingredients isolated from the root of Pueraria lobata, 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.

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Synthesis and antioxidant activity of derivatives of 8Н -[1,2,4]triazolo[4,3-в][1,2,4]triazin-7-ones

Pharmacology and Drug Toxicology ◽

10.33250/13.05.344 ◽

2020 ◽

Vol 13 (5) ◽

Author(s):

Y. N. Novodvorskyi ◽

O. Y. Bahlai ◽

I. V. Komarov ◽

A. M. Demchenko

Keyword(s):

Antioxidant Activity ◽

Benzene Ring ◽

Antioxidant Properties ◽

Pharmacological Action ◽

Hydroxyl Group ◽

Tert Butyl ◽

Antioxidant Agents ◽

Heterocyclic Aldehydes ◽

Derivatives Of

Oxidative stress is usually connected with many severe diseases, such as atherosclerosis, hypertension, Alzheimer’s disease etc. Therefore, the search for new antioxidants is a very important pharmacological task. The aim of the study – to synthesize new derivatives of 8-(41-hydroxy-3R-benzylidenamino)-6-tertbutyl-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazine-7-ones and to evaluate their antioxidant properties in screening test in vitro as compared with ionol and ascorbic acid. By interaction of equimolar amounts of 8-amino-6-tert-butyl-8H-[1,2,4]triazolo[4,3-b][1,2,4]triazin7-one with the corresponding aromatic and heterocyclic aldehydes in ethanol, a series of Schiff bases with the key fragment 8H-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-one were synthesized. The structure and purity of all the substances obtained were confirmed by 1H NMR spectroscopy. Screening of compound’s antioxidant activity (AOA) was studied in vitro by their ability to inhibit lipoperoxide formation, induced by FeSO4 in yolk lipoproteins emulsion. It is shown, that, depending on the structure, the test substances exhibit both antioxidant and prooxidant properties. The regularities of the chemical structure – pharmacological action are established. It is shown that the introduction of electron-withdrawing substituents (F, Cl, Br and COOMe) into the benzene ring leads to a decrease in the antioxidant properties as to the base molecule 6-tert-butyl-8(benzylideneamino)-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-оne 8 а without substitutes. The most active were derivatives of 8-(benzylideneamino)-6-~{tert}-butyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin7-ones, which had a hydroxyl group and an additional oxyalkyl fragment in the third position of the benzene ring (8 l, 8 o). The data obtained substantiate the feasibility of further studying the most active derivatives of 6-tertbutyl-8-(benzylideneamino)-8Н-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-оnes as potential antioxidant agents.

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Synthesis of some novel 3- (4-ethoxyphenyl) -5- (4-substituted) -4,5-dihydro-1H-pyrazole derivatives as potent antioxidant agents

International Journal of Research in Pharmaceutical Sciences ◽

10.26452/ijrps.v11i2.2035 ◽

2020 ◽

Vol 11 (2) ◽

pp. 1571-1577

Author(s):

Lakshminarayanan B ◽

Kannappan N ◽

Subburaju T ◽

Kalaichelvan V K

Keyword(s):

Hydrogen Peroxide ◽

Antioxidant Activity ◽

Ascorbic Acid ◽

Free Radical ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Assay Method ◽

Antioxidant Agents ◽

Ic50 Value

Pyrazolines are the most useful heterocyclic moiety in Pharmaceutical and Chemical fields and as the most potential molecules for the design of new chemical entities. Nitrogen-containing heterocyclic compounds, pyrazolines and their derivatives showed a variety of pharmacological activities, including antioxidant properties. In the present study, eleven novel ethoxylated pyrazoline derivatives were synthesized by condensing chalcones with electron releasingethoxy group at one end and different electron-donating, electron-withdrawing groups in another end with hydrazine hydrate andalcohol. The compounds synthesized were structural elucidated by their spectroscopic studies. All the compounds synthesized were evaluated for their in vitro antioxidant potential by 2,2’-diphenyl-1-picrylhydrazyl (DPPH)and hydrogen peroxide free radical scavenging assay methods.Some of these molecules possess moderate to good antioxidant activitywhen compared to standard ascorbic acid. The compound with methoxy group (EH2) exhibits potent antioxidant activity with IC50 value of 9.02 and 9.44µg/ml in DPPH and hydrogen peroxide assay method respectively and the compound with hydroxy group (EH9) also showed potent antioxidant activity with IC50 value of 12.41 and 14.56µg/ml in DPPH and hydrogen peroxide free radical scavengingassay method respectively when compared to standard. The compounds containing electron-donating substituents were found to be good antioxidantswhen compared to standard ascorbic acid.

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Evaluation of the Antioxidant Activity of Cis/Trans-N-Phenyl-1,4,4a,5,8,8a-Hexahydro-3,1-Benzoxazin-2-Imines

Antioxidants ◽

10.3390/antiox8060197 ◽

2019 ◽

Vol 8 (6) ◽

pp. 197 ◽

Cited By ~ 3

Author(s):

Guadalupe Firpo ◽

María L. Ramírez ◽

Martín S. Faillace ◽

Maria dos R. Mendes de Brito ◽

Ana P. S. Correia Lima e Silva ◽

...

Keyword(s):

Antioxidant Activity ◽

Electron Transfer ◽

Hydroxyl Radicals ◽

Ex Vivo ◽

Antioxidant Properties ◽

Comprehensive Analysis ◽

Biologically Active ◽

Acetyl Cholinesterase ◽

In Vitro Antioxidant Activity

The growing interest in the chemistry of unsaturated ring-fused 1,3-heterocycles, in this particular case 1,3-oxazines, arise in part from their versatile pharmacological applications. In the present article, the evaluation of the in vitro and ex vivo antioxidant activity of two cyclohexene-fused oxazines is discussed. The in vitro antioxidant activity was evaluated by trapping the ABTS and hydroxyl radicals as well as the inhibition of the enzyme acetyl-cholinesterase and hemolysis of erythrocytes by 2,2’-Azobis(2-amidinopropane) dihydrochloride (AAPH). The results suggest that both unsaturated 1,3-oxazines are auspicious sources of biologically active compounds with good antioxidant properties. In addition, a comprehensive analysis of the interaction between these heterocycles with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals, as well as the measurements of redox potential, provided evidence for a mechanism of antioxidant activity that takes place through electron transfer (ET) processes.

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Micropropagation of Alocasia longiloba Miq and Comparative Antioxidant Properties of Ethanolic Extracts of the Field-Grown Plant, In Vitro Propagated and In Vitro-Derived Callus

Plants ◽

10.3390/plants9070816 ◽

2020 ◽

Vol 9 (7) ◽

pp. 816

Author(s):

Ferid Abdulhafiz ◽

Arifullah Mohammed ◽

Fatimah Kayat ◽

Suhana Zakaria ◽

Zulhazman Hamzah ◽

...

Keyword(s):

Antioxidant Activity ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Peat Moss ◽

Scavenging Activity ◽

Tetrazolium Chloride ◽

In Vitro Plant ◽

Grown Plant

In this study, an efficient micropropagation protocol was developed for A. longiloba and the antioxidant properties of field-grown plant, in vitro-derived greenhouse-grown plant and in vitro-derived callus extracts were compared. The A. longiloba seeds tested using tetrazolium chloride salt exhibited 89% viability. Due to poor germination capacity of A. longiloba seeds, the seeds were treated with gibberellic acid (GA3) or sulfuric acid (H2SO4). The maximum seed germination of 87% was observed at 30% H2SO4 treatment after 19.00 d, whereas GA3 treatment showed maximum germination of 53% after 22 d. In vitro shoot multiplication was carried out using various types of cytokinins alone or in combination with auxin. Among them, 6-benzyl amino purine (BAP) single treatment was found to be the best hormone. The highest shoot-length (7.26 cm) and maximum number of shoots per explant (18) were recorded at 3-mg L−1 BAP. For in vitro rooting, indole-3-acetic acid at 0.5-mg L−1 was found to be the optimum concentration. Callus was induced using various types of auxins alone or in combinations with cytokinins. The highest percentage of callus of 91 and fresh weight of 6 g was obtained with 3-mg L−1 IAA. The plantlets produced in the current study were subjected to acclimatization. The combination of topsoil and peat moss at 1:2 ratio was found to be the best soil media. In this study, in vitro-derived callus extract showed the highest phenolic content (538 mg GAE), followed by extracts of field-grown plant parts, i.e., fruit and petiole (504 and 300 mg GAE) while in vitro plant extract showed the lowest (98 mg GAE). Meanwhile, the highest flavonoids was recorded in petiole extract. Comparative antioxidant activity study shows, in vitro-derived callus exhibited better DPPH-radical-scavenging activity (IC50: 0.113-mg mL−1) whereas the extracts of petiole, fruit and in vitro plant showed 0.126-, 0.137- and 0.173-mg mL−1, respectively. At the same time, the fruit extract showed better (IC50: 0.088-mg mL−1) ABTS radical scavenging activity than all extracts tested. In conclusion, the in vitro-derived callus extract could be favored for high TPC and better DPPH scavenging activity. Hence, the present study was conducted to establish an efficient micropropagation protocol and to compare the antioxidant activity of the field-grown plant, in vitro plant and in vitro derived callus extracts of A. longiloba.

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