Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies

Phenylhydrazine was reacted with synthesized acylpyrazolone derivatives 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one, to obtain two new azomethine phenylhydrazones, a study in continuation of our probe into the effects of acyl group substitutions on the physicochemical and free radical scavenging properties of acylpyrazolone Schiff bases. The keto imine tautomers of 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Empp-Ph) and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) according to single X-ray crystallography data which precipitated in good yield are reported. Furthermore they have been characterized by elemental analysis, FTIR, 13C and 1H NMR, and mass-spectroscopy techniques. Both phenylhydrazone Schiff bases crystallize in a triclinic crystal system, each with a space group of P-1 (number 2) having short intramolecular N3—H3…O1 hydrogen interaction between the first hydrazine hydrogen H3 and the pyrazolone oxygen O1. The antioxidant free radical scavenging activities of titled compounds against 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed a positive response almost as good as that of vitamin c under the same conditions, with the propyl substituted 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) having a stronger activity (calculated IC50 value of 175.66 μg/ml).

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Flavones and Their Analogues as Bioactive Compounds – An Overview

Mini-Reviews in Organic Chemistry ◽

10.2174/1570193x15666180418154510 ◽

2019 ◽

Vol 16 (4) ◽

pp. 377-391 ◽

Cited By ~ 1

Author(s):

B.S. Jayashree ◽

H. Venkatachalam ◽

Sanchari Basu Mallik

Keyword(s):

Biological Activity ◽

Free Radical ◽

Bioactive Compounds ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Cost Effective ◽

Free Radical Scavenging ◽

Polyphenolic Compounds ◽

Pharmacological Activities ◽

Poor Solubility

Flavonoids constitute a large group of polyphenolic compounds that are known to have antioxidant properties, through their free radical scavenging abilities. They possess a chromone (γ- benzopyrone) moiety, responsible for eliciting many pharmacological activities. Even though, natural flavonoids are highly potent, owing to their poor solubility, they are less used. Therefore, attempts have been made to improve their stability, solubility, efficacy and kinetics by introducing various substituents on the flavone ring. For nearly the last two decades, flavones were synthesized in our laboratory by simple, convenient and cost-effective methods, with the knowledge of both synthetic and semi-synthetic chemistry. In this direction, it was considered worthwhile to present an overview on the synthesized flavonoids. This review creates a platform for highlighting various modifications done on the flavone system along with their biological activity.

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Chemical Analysis, Toxicity Study, and Free-Radical Scavenging and Iron-Binding Assays Involving Coffee (Coffea arabica) Extracts

Molecules ◽

10.3390/molecules26144169 ◽

2021 ◽

Vol 26 (14) ◽

pp. 4169

Author(s):

Nuntouchaporn Hutachok ◽

Pimpisid Koonyosying ◽

Tanachai Pankasemsuk ◽

Pongsak Angkasith ◽

Chaiwat Chumpun ◽

...

Keyword(s):

Free Radical ◽

Mononuclear Cells ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Chemical Compositions ◽

Coffee Bean ◽

Dependent Manner ◽

Roasted Coffee ◽

Instant Coffee ◽

Radical Scavenging Properties

We aimed to analyze the chemical compositions in Arabica coffee bean extracts, assess the relevant antioxidant and iron-chelating activities in coffee extracts and instant coffee, and evaluate the toxicity in roasted coffee. Coffee beans were extracted using boiling, drip-filtered and espresso brewing methods. Certain phenolics were investigated including trigonelline, caffeic acid and their derivatives, gallic acid, epicatechin, chlorogenic acid (CGA) and their derivatives, p-coumaroylquinic acid, p-coumaroyl glucoside, the rutin and syringic acid that exist in green and roasted coffee extracts, along with dimethoxycinnamic acid, caffeoylarbutin and cymaroside that may be present in green coffee bean extracts. Different phytochemicals were also detected in all of the coffee extracts. Roasted coffee extracts and instant coffees exhibited free-radical scavenging properties in a dose-dependent manner, for which drip coffee was observed to be the most effective (p < 0.05). All coffee extracts, instant coffee varieties and CGA could effectively bind ferric ion in a concentration-dependent manner resulting in an iron-bound complex. Roasted coffee extracts were neither toxic to normal mononuclear cells nor breast cancer cells. The findings indicate that phenolics, particularly CGA, could effectively contribute to the iron-chelating and free-radical scavenging properties observed in coffee brews. Thus, coffee may possess high pharmacological value and could be utilized as a health beverage.

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Studies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of Schiff bases

Journal of Photochemistry and Photobiology B Biology ◽

10.1016/j.jphotobiol.2017.05.020 ◽

2017 ◽

Vol 172 ◽

pp. 129-138 ◽

Cited By ~ 20

Author(s):

Cleiton M. da Silva ◽

Marina M. Silva ◽

Fabiano S. Reis ◽

Ana Lúcia T.G. Ruiz ◽

João E. de Carvalho ◽

...

Keyword(s):

Free Radical ◽

Schiff Bases ◽

Cancer Cell ◽

Radical Scavenging ◽

Dna Interaction ◽

Free Radical Scavenging ◽

Calf Thymus Dna ◽

Calf Thymus

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Free radical scavenging properties and phenolic characterization of some edible plants

Food Chemistry ◽

10.1016/j.foodchem.2008.09.005 ◽

2009 ◽

Vol 114 (1) ◽

pp. 276-281 ◽

Cited By ~ 23

Author(s):

Ilkay Orhan ◽

Murat Kartal ◽

Mahmoud Abu-Asaker ◽

F. Sezer Şenol ◽

Gülderen Yilmaz ◽

...

Keyword(s):

Free Radical ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Edible Plants ◽

Radical Scavenging Properties

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Free radical scavenging properties of hetero-chitooligosaccharides using an ESR spectroscopy

Food and Chemical Toxicology ◽

10.1016/j.fct.2003.10.001 ◽

2004 ◽

Vol 42 (3) ◽

pp. 381-387 ◽

Cited By ~ 152

Author(s):

Jae-Young Je ◽

Pyo-Jam Park ◽

Se-Kwon Kim

Keyword(s):

Free Radical ◽

Esr Spectroscopy ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Radical Scavenging Properties

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Antihypertensive and free radical scavenging properties of enzymatic rapeseed protein hydrolysates

Food Chemistry ◽

10.1016/j.foodchem.2013.02.087 ◽

2013 ◽

Vol 141 (1) ◽

pp. 153-159 ◽

Cited By ~ 85

Author(s):

Rong He ◽

Adeola Alashi ◽

Sunday A. Malomo ◽

Abraham T. Girgih ◽

Dongfang Chao ◽

...

Keyword(s):

Free Radical ◽

Radical Scavenging ◽

Free Radical Scavenging ◽

Protein Hydrolysates ◽

Rapeseed Protein ◽

Rapeseed Protein Hydrolysates ◽

Radical Scavenging Properties

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EVALUATION OF ANTIOXIDANT AND FREE RADICAL SCAVENGING ACTIVITIES OF DIFFERENT SOLVENT EXTRACTS OF LEAVES OF PIPER UMBELLATUM

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2017.v10i2.15570 ◽

2017 ◽

Vol 10 (2) ◽

pp. 274

Author(s):

Sethupandian Geetha ◽

Kokkaiah Irulandi ◽

Palanichamy Mehalingam

Keyword(s):

Antioxidant Activity ◽

Free Radical ◽

Ethyl Acetate ◽

Methanol Extract ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Free Radical Scavenging ◽

Frap Assay ◽

Radical Scavenging Properties

Objective: This study was designed to determine the Total phenol, flavonoid content, antioxidant and free radical scavenging properties of different solvent extracts of Piper umbellatum. Methods: Different solvent extracts evaluated with DPPH radical scavenging activity and Reducing power activity.Results: The presence of phenol and flavonoid showed highly in the methanol extracts than ethyl acetate and acetone extracts. All the extracts have various level of antioxidant activity. Methanol solvent extract have good extraction and show significant antioxidant activity. The effect of reducing power of methanol extract revealed good antioxidant activity compare with other tested extracts.Conclusion: On the basis of the above results we concluded that methanol extract of Piper umbellatum whole plant extracts shows significant antioxidant activity than ethyl acetate and acetone extracts.Keywords: Piper umbellatum, Antioxidant, DPPH, FRAP assay, Polar, Non polar solvents

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Antioxidant and antimicrobial activities against Enterobacter cloacae of extracts of Eclipta alba Hassk.

Science and Technology Development Journal ◽

10.32508/stdj.v19i4.599 ◽

2016 ◽

Vol 19 (4) ◽

pp. 76-83

Author(s):

Trang Thi Xuan Dai ◽

Anh Thi Tu Vo

Keyword(s):

Free Radical ◽

Vitamin C ◽

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Enterobacter Cloacae ◽

Free Radical Scavenging ◽

Antioxidant Vitamin ◽

Eclipta Alba

This study was subjected to investigate antimicrobial and antioxidant properties of Eclipta alba extracts (methanol, hexane, chloroform and ethyl acetate extracts). The antioxidant property of the extract was assessed by 2,2- diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Kirby-Bauer method was used to determine the antibacterial activity against Enterobacter cloacae of the extracts. The extracts of Eclipta alba were tested against E. cloacae. The highest antibacterial potentiality was exhibited by the ethyl acetate extract of E. alba leaves, means of zones of bacterial growth inhibition are 26.3 mm at a concentration of 32 μg/mL. DPPH free radical scavenging effect of the extracts was compared with standard antioxidant vitamin C. The highest antioxidant activity was exhibited by the ethyl acetate extract of E. alba leaves. The result also showed that the DPPH scavenging activity of ethyl acetate extract from leaves of E. alba was high (EC50 = 419.38 μg/mL). However, this result was 18.99 times lower than that of vitamin C (EC50 = 22.08 μg/mL).

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