Synthesis, characterization and antioxidant capacity of naringenin-oxime

Türkkan, Baki; Özyürek, Mustafa; Bener, Mustafa; Güçlü, Kubilay; Apak, Reşat

doi:10.1016/j.saa.2011.09.066

Cited by 27 publications

(15 citation statements)

References 27 publications

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“…The NGN containing formulation inhibited UVB irradiation-induced production of O 2 •- and inflammatory cytokines. In vitro , NGN exhibits low O 2 •- radical scavenging ability, reaching 12% inhibition at 1 mM [ 75 ]. In this study, the authors used a non-enzymatic source of O 2 •- (phenazine methosulfate/NADH) and NBT reduction test to evaluate O 2 •- scavenging ability [ 75 ].…”

Section: Discussionmentioning

confidence: 99%

“…In vitro , NGN exhibits low O 2 •- radical scavenging ability, reaching 12% inhibition at 1 mM [ 75 ]. In this study, the authors used a non-enzymatic source of O 2 •- (phenazine methosulfate/NADH) and NBT reduction test to evaluate O 2 •- scavenging ability [ 75 ]. Therefore, this evidence [ 63 ] suggests that our observations regarding the inhibition of NBT reduction in vivo depend on the anti-inflammatory activity of NGN rather than to an O 2 •- scavenging activity.…”

Section: Discussionmentioning

confidence: 99%

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Topical Formulation Containing Naringenin: Efficacy against Ultraviolet B Irradiation-Induced Skin Inflammation and Oxidative Stress in Mice

et al. 2016

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Naringenin (NGN) exhibits anti-inflammatory and antioxidant activities, but it remains undetermined its topical actions against ultraviolet B (UVB)-induced inflammation and oxidative stress in vivo. The purpose of this study was to evaluate the physicochemical and functional antioxidant stability of NGN containing formulations, and the effects of selected NGN containing formulation on UVB irradiation-induced skin inflammation and oxidative damage in hairless mice. NGN presented ferric reducing power, ability to scavenge 2,2′-azinobis (3-ethylbenzothiazoline- 6-sulfonic acid) (ABTS) and hydroxyl radical, and inhibited iron-independent and dependent lipid peroxidation. Among the three formulations containing NGN, only the F3 kept its physicochemical and functional stability over 180 days. Topical application of F3 in mice protected from UVB-induced skin damage by inhibiting edema and cytokine production (TNF-α, IL-1β, IL-6, and IL-10). Furthermore, F3 inhibited superoxide anion and lipid hydroperoxides production and maintained ferric reducing and ABTS scavenging abilities, catalase activity, and reduced glutathione levels. In addition, F3 maintained mRNA expression of cellular antioxidants glutathione peroxidase 1, glutathione reductase and transcription factor Nrf2 (nuclear factor erythroid 2-related factor 2), and induced mRNA expression of heme oxygenase-1. In conclusion, a formulation containing NGN may be a promising approach to protecting the skin from the deleterious effects of UVB irradiation.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Topical Formulation Containing Naringenin: Efficacy against Ultraviolet B Irradiation-Induced Skin Inflammation and Oxidative Stress in Mice

et al. 2016

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“…All reagents and solvents were of analytical reagent grade. NOX ((±)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one oxime) was resynthesized as described in the literature ( Scheme 1 ) [ 30 ].…”

Section: Methodsmentioning

confidence: 99%

“…NG has lately been used as an inducing agent for the composition of alternative new derivatives. Özyürek et al [ 29 ] and Türkkan et al [ 30 ] composed, defined, and analyzed some antioxidant aspects of a novel NG derivative compound called naringenin-oxime (NOX) and reported that antioxidant features of NG dramatically enhance in its Ox form. NOX has more antigenotoxic and antioxidative potential than the main compound NG [ 31 ].…”

Section: Introductionmentioning

confidence: 99%

The Protective Effect of Naringenin-Oxime on Cisplatin-Induced Toxicity in Rats

Koyuncu

Koçyiğit

Gönel

et al. 2017

Biochemistry Research International

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The aim of this study is to examine the protective effect of naringenin-oxime (NOX) on cisplatin-induced major organ toxicity and DNA damage in rats. Thirty-five male Wistar albino rats were equally split into five groups as follows: control (i.p., 0.1 ml of saline), Cis administration (i.p., 7 mg/kg b.w.), NOX treatment (i.p., 20 mg/kg b.w., daily for ten days), Cis + NOX20, and Cis + NOX40 combination (i.p., 20 and 40 mg/kg b.w., daily for ten days). Serum and peripheral blood mononuclear leukocytes (PBMC) were obtained from blood. Malondialdehyde, glutathione, total antioxidant and oxidant status, and catalase were measured in serum, liver, and kidney, and oxidative stress index was calculated. In parallel, paraoxonase and arylesterase activities were tested in liver and serum. We used 8-OHdOG as a marker for DNA damage in serum via ELISA and in PMBC via comet assay. Treatment with Cis elevated the levels of serum biochemical parameters, oxidative stress, and DNA damage. Pretreatments of NOX restored biochemical and oxidative stress parameters in serum, renal, and liver tissues (p < 0.01) and reduced 8-OHdG level, a finding further supported by comet assay in PBMC. Observations of the present study support the fact that treatment with NOX prevents Cis-induced hepatotoxicity, nephrotoxicity, and genotoxicity by restoring antioxidant system.

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“…Significant secondary bonding interactions are also frequently observed in these derivatives, as a result of M─X σ* antibonding orbital which has the potential to act as an acceptor orbital towards another donor atom . Antimony derivatives are more valuable from the medicinal chemistry point of view and in drug designing as different oximes and their metal derivatives are found to be important and exhibit significant bioactivity in chelating therapeutic drugs, as inhibitors of enzymes and as intermediates in biosynthesis of nitrogen oxides, and have antimicrobial, anticancer, fungicidal, bactericidal and antioxidant activities. In addition, dithiocarbamate derivatives with various metals have also been extensively studied because of their biological activities and use in analytical chemistry and as medicines as antidotes and antioxidants .…”

Section: Introductionmentioning

confidence: 99%

Syntheses, characterization, antibacterial activity and molecular modelling of phenylantimony(III) heteroleptic derivatives containing substituted oximes and piperidine dithiocarbamate

Beniwal

Chhimpa

Gaur

et al. 2017

Applied Organom Chemis

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Six new heteroleptic phenylantimony(III) derivatives containing substituted oximes and dithiocarbamate moieties of the type (where R = ─C 6 H 5 , X = ─CH 3 (2a); R = ─C 6 H 4 CH 3 , X = ─CH 3 (2b); R = ─C 6 H 4 Cl, X = ─CH 3 (2c); R = ─C 6 H 4 Br, X = ─CH 3 (2d); R = ─C 6 H 4 OH, X = ─H (2e); R(X)C = (2f)) have been synthesized by the reactions of phenylantimony(III) dichloride with the sodium salt of substituted oximes and dithiocarbamate moiety in unimolar ratio with stirring in dichloromethane. All these newly synthesized derivatives have been characterized using physicochemical and elemental analyses. Structures have been proposed on the basis of infrared, 1 H NMR, 13 C NMR and LC-MS spectral studies and molecular modelling. In these derivatives the oxime behaves in an unidentate manner whereas dithiocarbamate behaves in a monofunctional anisobidentate manner. Pseudo-trigonal bipyramidal (ψ-TBP) geometry around the antimony metal centre is proposed for these phenylantimony(III) heteroleptic derivatives. The geometry of a representative complex has been optimized through molecular modelling. These newly synthesized derivatives were screened against Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) bacteria to evaluate their antibacterial potential. The structureactivity relationship for antibacterial activity among the four derivatives 2a, 2c, 2e and 2f is discussed.

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Synthesis, characterization and antioxidant capacity of naringenin-oxime

Cited by 27 publications

References 27 publications

Topical Formulation Containing Naringenin: Efficacy against Ultraviolet B Irradiation-Induced Skin Inflammation and Oxidative Stress in Mice

Topical Formulation Containing Naringenin: Efficacy against Ultraviolet B Irradiation-Induced Skin Inflammation and Oxidative Stress in Mice

The Protective Effect of Naringenin-Oxime on Cisplatin-Induced Toxicity in Rats

Syntheses, characterization, antibacterial activity and molecular modelling of phenylantimony(III) heteroleptic derivatives containing substituted oximes and piperidine dithiocarbamate

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