Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?

Silva, Eduarda M. P.; Melo, Tânia; Sousa, Bebiana C.; Resende, Diana I. S. P.; Magalhães, Luís M.; Segundo, Marcela A.; Silva, Artur M. S.; Domingues, Rosário M.

doi:10.1016/j.ejmech.2016.05.040

Cited by 8 publications

(3 citation statements)

References 64 publications

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“…The evaluation of the ability of nitrated POPC in the inhibition of lipid peroxidation induced by hydroxyl radical generated under Fenton reaction conditions was performed as previously described by Silva and coauthors (Silva et al, ) with some modifications. Stock solutions of PLPC, 1,2‐dimyristoyl‐ sn ‐glycero‐3‐phosphocholine (DMPC), and nitrated POPC (1 mg/mL) were prepared in CHCl 3 .…”

Section: Methodsmentioning

confidence: 99%

New Insights into the Anti‐Inflammatory and Antioxidant Properties of Nitrated Phospholipids

Melo

Marques

Ferreira

et al. 2018

Lipids

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Nitro-fatty acids (NO -FA) have been widely studied with regard to their identification, structural characterization, and biological actions. NO -FA could also be present endogenously esterified to phospholipids (PL), and NO -PL were already detected in cardiac mitochondria from diabetic rats and cardiomyoblasts subjected to starvation. However, the biological actions of NO -PL have been overlooked. In this study, we evaluate the antioxidant and anti-inflammatory potential of the nitrated 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) formed in vitro by incubation with NO BF , in a well-recognized mimetic model of nitroxidative stress. Nitrated POPC showed anti-radical ability to reduce both 2,2-diphenyl-1-picrylhydrazyl radical (DPPH ) (IC = 225 ± 4 μg/mL; Trolox equivalent (TE) = 86 ± 6 μmol Trolox/g lipid) and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical cation (ABTS ) (IC = 124 ± 2 μg/mL; TE = 152 ± 9 μmol Trolox/g lipid). Also, higher lag times were achieved in oxygen radical absorbance capacity (ORAC) assay for nitrated POPC, indicating a faster reaction with oxygen-derived radicals (TE = 1.03 ± 0.22 and TE = 1.30 ± 0.16 mmol Trolox/g lipid for nonmodified and nitrated POPC, respectively). Nitrated POPC showed the ability to inhibit lipid oxidation induced by the hydroxyl radical generated under Fenton reaction conditions, monitored by electrospray ionization (ESI) mass spectrometry (MS) using phosphatidylcholine (PtdCho) liposomes as a model of cell membrane. Nitrated POPC showed anti-inflammatory potential, as assessed by the inhibition of inducible nitric oxide synthase (iNOS) expression in RAW 264.7 macrophages activated by the Toll-like receptor 4 (TLR4) agonist lipopolysaccharide (LPS) in a well-described in vitro model of inflammation. Altogether, this study provides new clues regarding the antioxidant and anti-inflammatory potential of nitrated POPC, which should be explored in depth.

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Section: Methodsmentioning

confidence: 99%

New Insights into the Anti‐Inflammatory and Antioxidant Properties of Nitrated Phospholipids

Melo

Marques

Ferreira

et al. 2018

Lipids

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“…Compound 6c (IC 50 = 0.269 µM), in turn, is approximately fourfold more potent than compound 6a, which shows that extension of conjugation (by replacing the styryl group with a phenylbutadienyl) further enhances MAO-B inhibition activity. Recently, it has been reported that compounds containing α, β, γ, δ-diunsaturated ketones, such as cinnamylidene acetophenones, display antioxidant and anti-inflammatory activities [30]. Compound 6c may thus be a candidate compound that displays multiple biological activities relevant to the treatment of Parkinson's disease including MAO-B inhibition, antioxidant and anti-inflammatory activities.…”

Section: Ic 50 Values For the Inhibition Of Maomentioning

confidence: 99%

The monoamine oxidase inhibition properties of C6- and N1-substituted 3-methyl-3,4-dihydroquinazolin-2(1H)-one derivatives

Marais

Petzer

2019

Mol Divers

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Quinazolinone compounds are of interest in medicinal chemistry since they display a wide range of biological properties. In the present study, a series of C6-and N1-substituted 3-methyl-3,4-dihydroquinazolin-2(1H)-one derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO). Some of these quinazolinones are structurally related to a series of 3,4-dihydro-2(1H)-quinolinone derivatives, which have previously been reported to act as specific inhibitors of MAO-B. The results document that, among 37 compounds synthesised, seven displayed IC 50 values < 1 µM for the inhibition of MAO-B. The most potent MAO-A inhibitor exhibits an IC 50 value of 7.43 µM while the most potent MAO-B inhibitor possesses an IC 50 value of 0.269 µM. Good-potency MAO inhibition was only observed among C6-substituted 3-methyl-3,4-dihydroquinazolin-2(1H)-one derivatives with N1-substitution yielding comparatively lowpotency inhibition. MAO-B-specific inhibitors such as some of the quinazolinone compounds investigated here may act as leads for the design of therapies for neurodegenerative disorders such as Parkinson's disease.

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“…The synthetic applications of cinnamaldehyde are vast and related to its abundance and low economic costs and have led to a collection of compounds with high chemodiversity [2]. The Cinnamylideneacetophenones derivative is α, β, γ, δ -unsaturated ketones show important bioactivities like antibacterial and antitubercular [3], antinociceptive [4], cytotoxicity in breast cancer cell [5], the antiproliferative effect [6], an antileshmanial activity [7], inhibitors of protein kinase C [8], antifungal [9], antimalarial [10] and antioxidant activity [11]. The cinnamylidene ketones have optimistic non liner optical material, in particular, in the short wavelength region [12].…”

Section: Introductionmentioning

confidence: 99%

Potassium Carbonate Assisted Synthesis Of α, β, γ, δ-Unsaturated Ketones

Kulkarni¹,

Gawade²

2020

Fr. Ukr. J. Chem.

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The Cinnamylideneacetophenones derivative is shows important medicinal properties and intermediate in organic synthesis. Several substituted α, β, γ, δ-Unsaturated Ketones were prepared in high yield and purity by direct reaction of substituted cinnamaldehyde and ketones in the presence of potassium carbonate as a base in ethanol at 50ºC. The merit of the method is short reaction times, high yield, easy work-up and purification process, inexpensive and easily available catalyst.

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Do cinnamylideneacetophenones have antioxidant properties and a protective effect toward the oxidation of phosphatidylcholines?

Cited by 8 publications

References 64 publications

New Insights into the Anti‐Inflammatory and Antioxidant Properties of Nitrated Phospholipids

New Insights into the Anti‐Inflammatory and Antioxidant Properties of Nitrated Phospholipids

The monoamine oxidase inhibition properties of C6- and N1-substituted 3-methyl-3,4-dihydroquinazolin-2(1H)-one derivatives

Potassium Carbonate Assisted Synthesis Of α, β, γ, δ-Unsaturated Ketones

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