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1.
Anticancer Res ; 39(8): 4043-4053, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31366486

RESUMO

BACKGROUND/AIM: Triple-negative breast cancer (TNBC) is the most aggressive subtype, predominant in African American women. In this study, the antioxidant/anticancer activity of muscadine grape extracts and the role of their phenolic and flavonoid contents in exerting these properties were investigated in TNBC cells. MATERIALS AND METHODS: Berry extracts from muscadine genotypes were investigated for total phenolic content (TPC), total flavonoid content (TFC), antioxidant capacity, and anticancer effects using breast cancer cell lines, representing Caucasians and African Americans. RESULTS: The antioxidant activity was associated with high TPC content. Extracts showed cytotoxicity up to 78.6% in Caucasians and 90.7% in African American cells, with an association with high antioxidant capacity. There was a strong correlation between TPC and anticancer/antioxidant activities. CONCLUSION: The anticancer and antioxidant effects of muscadine grapes are attributed to the TPC of extracts, which showed a stronger positive correlation with growth inhibition of African American breast cancer cells compared to Caucasians.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Extratos Vegetais/farmacologia , Neoplasias de Mama Triplo Negativas/tratamento farmacológico , Vitis/química , Afro-Americanos/genética , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Antioxidantes/farmacologia , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Feminino , Flavonoides/química , Flavonoides/farmacologia , Frutas/química , Humanos , Células MCF-7 , Fenóis/química , Fenóis/farmacologia , Extratos Vegetais/química , Neoplasias de Mama Triplo Negativas/genética , Neoplasias de Mama Triplo Negativas/patologia
2.
J Agric Food Chem ; 67(38): 10653-10659, 2019 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-31464427

RESUMO

Quercetin, a polyphenolic compound, is widely distributed in plants and has numerous health benefits. However, its hydrophilicity can compromise its use in lipophilic systems. For this reason, quercetin was esterified with 12 different fatty acids as their acyl chlorides with varying chain lengths and degrees of unsaturation. Two monoesters (Q-3'-O-monoester and Q-3-O-monoester) and four diesters (Q-7,3'-O-diester, Q-3',4'-O-diester, Q-3,3'-O-diester, and Q-3,4'-O-diester) were the major products as was shown by HPLC-MS and 1H-NMR data. The lipophilicity of quercetin derivatives was calculated; this was found to increase with fatty acid chain length. The antioxidant potential of quercetin and its derivatives was evaluated by using DPPH radical and ABTS radical cation scavenging activity; quercetin showed the highest radical scavenging activity among all tested samples. Despite the decrease of antioxidant activity in this study, the derivatives may show better antioxidant activity in lipophilic media and display improved absorption and bioavailability in the body once consumed.


Assuntos
Antioxidantes/química , Ésteres/química , Quercetina/química , Antioxidantes/síntese química , Cromatografia Líquida de Alta Pressão , Esterificação , Ácidos Graxos/química , Espectrometria de Massas , Estrutura Molecular
3.
J Agric Food Chem ; 67(37): 10432-10447, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31466447

RESUMO

A composite nanogel was developed for cyanidin-3-O-glucoside (C3G) delivery by combining Maillard reaction and heat gelation. The starting materials utilized were ovalbumin, dextran, and pectin. C3G-loaded nanogel was spherical with a diameter of ∼185 nm, which was maintained over a wide range of pH and NaCl concentrations. The composite nanogel enhanced the chemical stability of C3G under accelerated degradation models and a simulated gastrointestinal tract. Clathrin-mediated, caveolae-mediated, and macropinocytosis-related endocytosis contributed to the higher cellular uptake of nano-C3G than that of free-C3G. The apparent permeability coefficients of C3G increased 2.16 times after nanoencapsulation. The transcytosis of the C3G-bearing nanogel occurred primarily through the clathrin-related pathway and macropinocytosis and followed the "common recycling endosomes-endoplasmic reticulum-Golgi complex-basolateral plasma membrane" route. Moreover, nano-C3G was more efficient in restoring the viability of cells and activities of endogenous antioxidant enzymes than free-C3G in oxidative models, which may be attributed to the former's high cellular absorption.


Assuntos
Antocianinas/química , Antocianinas/metabolismo , Antioxidantes/química , Antioxidantes/metabolismo , Portadores de Fármacos/química , Glucosídeos/química , Glucosídeos/metabolismo , Células CACO-2 , Composição de Medicamentos , Estabilidade de Medicamentos , Trato Gastrointestinal/metabolismo , Géis/química , Géis/metabolismo , Humanos , Concentração de Íons de Hidrogênio , Absorção Intestinal , Modelos Biológicos , Nanopartículas/química , Nanopartículas/metabolismo , Tamanho da Partícula
4.
Biomed Khim ; 65(4): 316-323, 2019 Jun.
Artigo em Russo | MEDLINE | ID: mdl-31436173

RESUMO

The superoxide-generating reaction of adrenaline autoxidation in an alkaline medium, used in vitro to identify the antioxidant properties of various compounds, simulates the complex multistep process of quinoid oxidation of catecholamines (CA) in the body. Sulfur-containing cysteine (Cys) and reduced glutathione (GSH), as well as oxidized glutathione (GSSG), have been shown to inhibit this process. The studied substances were considered as inhibitors of quinoid oxidation and are evaluated as antioxidants. The IC50 values for Cys and GSH were close to 7.5 mM. Inhibition by GSSG was weaker; represented approximately 50-70% of Cys and GSH. Other sulfur-containing compounds that differ in chemical structure, the amino acids taurine and methionine were ineffective. The interest in this model and the search for effective compounds acting on this reaction is associated with one of the mechanisms of the etiopathogenesis of Parkinson's disease (PD) discussed in the literature, which occurs when the biochemical transformations of dopamine CA and its quinoid oxidation process are violated. Cys, GSH and GSSG in the model system inhibit quinoid oxidation of adrenaline, as a result of which the formation of superoxide (O2 ·-) is also inhibited. Experiments with the superoxide-generating enzymatic reaction xanthine xanthioxidase, the chemistry of which is different and not related to formation of quinoid metabolites, showed that the studied substances did not inhibit O2 ·- formation in this model. Thus, it was established that the biologically active sulfur-containing compounds Cys, GSH and GSSG are specific inhibitors of quinoid oxidation of CA, and are likely to be able to play the role of a neuroprotector. It is proposed to use these compounds in the treatment and prevention of PD by activating their biosynthesis in the body.


Assuntos
Epinefrina/metabolismo , Compostos de Enxofre/química , Antioxidantes/química , Cisteína/química , Dissulfeto de Glutationa/química , Humanos , Fármacos Neuroprotetores/química , Oxirredução
5.
J Agric Food Chem ; 67(35): 9934-9941, 2019 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-31402655

RESUMO

A fluorescence microscopic method for characterizing size, quantity, and oxidation of lipid droplets (LDs) in HepG2 cells was developed. LDs were induced by palmitic (PA), oleic (OA), or linoleic acids (LA) and stained with two fluorescent probes for neutral lipids and lipid peroxides. Each fatty acid increased the number of LDs and oxidized LDs (oxLDs) and the degree of LD oxidation time dependently, as well as increased intracellular triglyceride hydroperoxides. LDs induced by LA without 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH) showed the most significant oxidation degree over PA and OA, especially in large LDs (area ≥ 3 µm2, oxLD/LD = 52.3 ± 21.7%). Under this condition, two food-derived antioxidants were evaluated, and both of them significantly improved the LD characteristics. Moreover, chlorogenic acid reduced the quantity of large LDs by 74.0-87.6% in a dose-dependent manner. The proposed method provides a new approach to evaluate the effect of dietary antioxidants on LD characteristics.


Assuntos
Antioxidantes/metabolismo , Hepatócitos/química , Hepatócitos/metabolismo , Gotículas Lipídicas/metabolismo , Microscopia de Fluorescência/métodos , Antioxidantes/química , Ácido Clorogênico/química , Ácido Clorogênico/metabolismo , Fluorescência , Células Hep G2 , Humanos , Gotículas Lipídicas/química , Oxirredução
6.
J Agric Food Chem ; 67(35): 9907-9915, 2019 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-31436102

RESUMO

The impact of covalent or non-covalent bound gallic acid (GA) on the formation, physicochemical properties, and digestion of ovotransferrin (OTF) nanofibrils was comprehensively studied. Thioflavin T fluorescence results revealed that bound GA could inhibit OTF nanofibrillation and that the fibril-inhibitory activity of bound GA was dose dependent. Covalent bound GA exerted stronger inhibition on OTF nanofibrillation than an equal amount of non-covalent bound GA. Atomic force microscopy revealed that covalent bound GA shortened OTF nanofibrils significantly, while non-covalent bound GA did not change the contour length of OTF fibrils remarkably. Bound GA altered diameter of OTF nanofibrils. Both covalent and non-covalent bound GA could alter the zeta potential, surface hydrophobicity, and rheological properties of OTF nanofibrils. Bound GA endowed OTF nanofibrils with a strong antioxidant activity. In vitro gastrointestinal digestion results showed that covalent bound GA elevated the fibril digestion rate better than non-covalent bound GA. Polyphenol binding provided a new approach to modulating the physicochemical properties of protein nanofibrils.


Assuntos
Conalbumina/química , Ácido Gálico/química , Nanofibras/química , Animais , Antioxidantes/química , Antioxidantes/metabolismo , Galinhas , Conalbumina/metabolismo , Digestão , Ácido Gálico/metabolismo , Interações Hidrofóbicas e Hidrofílicas , Microscopia de Força Atômica , Modelos Biológicos , Reologia
7.
Food Chem ; 298: 125026, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31260961

RESUMO

Roasted cotyledons of the Chilean hazelnut (Gevuina avellana) are appreciated as snacks. The aim of our work was to assess the fatty acid, oxylipin and phenolic composition using gas chromatography (GC) coupled to mass spectrometry (MS), ultra- high performance liquid chromatography (UHPLC) coupled to MS and HPLC coupled to diode array detector (HPLC-DAD). Additionally, various antioxidant activities were assessed. The inhibition of α-glucosidase, α-amylase, lipase, cyclooxygenases-1 and -2 (COX-1/COX-2), and lipoxygenase was determined. The main fatty acids were oleic and 7-hexadecenoic acids. Eight phytoprostanes and three phytofurans were identified and quantified. Hydroxybenzoic and hydroxycinnamic acids were the main phenolic compounds. Oils showed antioxidant activity determined by EPR, and inhibition of COX-1/COX-2. The statistical analysis showed that the roasting does not affect the composition of the samples. The occurrence of oxylipins in this species is reported for the first time. Chilean hazelnuts can be considered a source of health promoting compounds.


Assuntos
Antioxidantes/química , Corylus/química , Síndrome Metabólica/enzimologia , Oxilipinas/análise , Fenóis/análise , Chile , Ácidos Cumáricos/análise , Cromatografia Gasosa-Espectrometria de Massas , alfa-Amilases/antagonistas & inibidores , alfa-Glucosidases/metabolismo
8.
Planta Med ; 85(13): 1054-1072, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31261421

RESUMO

The Lauraceae family is predominantly found in Asia and in the rainforests of the Americas, and consists mostly of aromatic trees. Being an essential oil producer, this family is used in the food, pharmaceutical, and cosmetic industries. This work presents a systematic review of the chemical composition and bioactivity of the essential oils from the Lauraceae family. Medline, Scielo, Web of Science, Lilacs, and Scopus were employed to identify articles published between 2000 and 2018, using "Lauraceae", "essential oil", and "biological activity" as key words. From 177 studies identified, 53 met the inclusion criteria. These studies indicated a predominance of the compounds ß-caryophyllene and 1,8-cineole in Lauraceae species, and highlighted the antioxidant, antifungal, antibacterial, and anti-inflammatory activities. Essential oils extracted from this family thus have high potential for pharmacological applications.


Assuntos
Lauraceae/química , Óleos Vegetais/farmacologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Óleos Vegetais/química
9.
J Photochem Photobiol B ; 197: 111541, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31272033

RESUMO

Here, we report the novel fabrication of ZnO nanoparticles using the Costus igneus leaf extract. Gas chromatography-mass spectrometry (GC-MS) and proton nuclear magnetic resonance (1H NMR) spectroscopy to determine the bioactive components present in the plant extract. The synthesis of Ci-ZnO NPs (C. igneus- coated zinc oxide nanoparticles) was accomplished using a cost-effective and simple technique. Ci-ZnO NPs were specified using UV-visible spectroscopy, FTIR, XRD, and TEM. Ci-ZnO NPs was authenticated by UV-Vis and exhibited a peak at 365 nm. The XRD spectra proved the crystalline character of the Ci-ZnO NPs synthesized as hexagonal wurtzite. The FTIR spectrum illustrated the presence of possible functional groups present in Ci-ZnO NPs. The TEM micrograph showed evidence of the presence of a hexagonal organization with a size of 26.55 nm typical of Ci-ZnO NPs. The α-amylase and α-glucosidase inhibition assays demonstrated antidiabetic activity of Ci-ZnO NPs (74 % and 82 %, respectively), and the DPPH [2,2-diphenyl-1-picrylhydrazyl hydrate] assay demonstrated the antioxidant activity of the nanoparticles (75%) at a concentration of 100 µg/ml. The Ci-ZnO NPs exhibited promising antibacterial and biofilm inhibition activity against the pathogenic bacteria Streptococcus mutans, Lysinibacillus fusiformis, Proteus vulgaris, and Vibrio parahaemolyticus. Additionally, the Ci-ZnO NPs showed biocompatibility with mammalian RBCs with minimum hemolytic activity (0.633 % ±â€¯0.005 %) at a concentration of 200 µg/ml.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/química , Biofilmes/efeitos dos fármacos , Nanopartículas Metálicas/química , Extratos Vegetais/química , Óxido de Zinco/química , Antibacterianos/síntese química , Antibacterianos/química , Materiais Biocompatíveis/química , Materiais Biocompatíveis/farmacologia , Costus/química , Costus/metabolismo , Eritrócitos/citologia , Eritrócitos/efeitos dos fármacos , Eritrócitos/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/fisiologia , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/fisiologia , Química Verde , Hemólise/efeitos dos fármacos , Humanos , Insulina/química , Nanopartículas Metálicas/toxicidade , Testes de Sensibilidade Microbiana , Tamanho da Partícula , Extratos Vegetais/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo
10.
J Agric Food Chem ; 67(31): 8520-8526, 2019 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-31310120

RESUMO

Reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO), have received extensive attention recently as a result of their high activity and toxicity in vitro and in vivo. In the present study, propyl gallate (PG), a common food antioxidant, was found to effectively trap more ACR than butylated hydroxytoluene and butylated hydroxyanisole through the formation of mono-ACR adducts (PG-ACR) and di-ACR adducts (PG-2ACR). The two adducts were successfully purified, and their structures were elucidated on the basis of their high-resolution mass spectrometry and 1H, 13C, and two-dimensional nuclear magnetic resonance data. We further identified that PG-ACR had the ability to continue to trap GO and MGO to form PG-ACR-GO and PG-ACR-MGO, respectively, by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Furthermore, we verified that PG could inhibit the production of ACR, GO, and MGO via trapping these RCS simultaneously to form the corresponding adducts in pound cakes using LC-MS/MS.


Assuntos
Acroleína/química , Antioxidantes/química , Galato de Propila/química , Culinária , Temperatura Alta , Espectroscopia de Ressonância Magnética , Modelos Biológicos , Estrutura Molecular , Espectrometria de Massas em Tandem
11.
J Agric Food Chem ; 67(31): 8609-8616, 2019 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-31314514

RESUMO

Quercetin (QUE)-loaded nanoparticles (QCG-NPs) were fabricated by ionic gelation between chitosan (CS) and gum arabic (GA) at pH 3.5. At constant CS (0.5 mg/mL) and QUE (60 µM) concentrations, QCG-NPs (260-490 nm) were prepared uniformly with 0.8-2.2 mg/mL GA and exhibited high QUE encapsulation efficiency (94.8-98.0%) and sustained QUE release (4.42-8.89% after 8 h). Because of the electrostatic interaction between QCG-NPs and the mucin layer, in vitro mucin and cell adhesion of QUE were significantly (p < 0.05) enhanced in QCG-NPs (0.44-0.48 mg/mL and 31.7-78.5%), respectively, and the adhesiveness was significantly (p < 0.05) increased with an increase of GA. Because particle size and adhesion properties affect the surface area and retention time of QCG-NPs at the absorption site, cell permeation of QUE through simple diffusion by QCG-NPs exhibited the same tendency as the adhesion results. These data were verified in cellular antioxidant and in vivo ferric reducing abilities of plasma assays that evaluated the antioxidant activities of QUE absorbed into an intestinal cell model and rat blood, respectively. The results provide a better understanding of QCG-NP absorption and indicate that QCG-NPs with mucoadhesion properties can be an effective delivery system for improving QUE absorption.


Assuntos
Antioxidantes/química , Quitosana/química , Sistemas de Liberação de Medicamentos/métodos , Mucosa Intestinal/metabolismo , Nanopartículas/química , Quercetina/química , Quercetina/metabolismo , Animais , Antioxidantes/administração & dosagem , Antioxidantes/metabolismo , Células CACO-2 , Portadores de Fármacos/química , Sistemas de Liberação de Medicamentos/instrumentação , Humanos , Tamanho da Partícula , Quercetina/administração & dosagem , Ratos , Ratos Sprague-Dawley
12.
J Agric Food Chem ; 67(30): 8402-8410, 2019 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-31276623

RESUMO

Wines aged in oak wood barrels with various uniform tannin contents (which were classified according to their total ellagitannins contents as predicted by Near Infrared Spectroscopy on the untoasted wood) and different toasting levels (high precision toasting by radiation) were distinguished according to their overall abilities to resist against oxidation. Wine trials were carried out on two different vintages (2015, 2016) and three grape varieties (Sauvignon blanc, Sémillon, Chardonnay). Regardless of the vintage and the wine matrix, a relationship was established between wine oxidative stability (based on EPR spin trapping methodology) and oak barrel tannin potential. The extraction kinetic of ellagitannins by wines appeared linear during barrel aging and achieved its maximum at six or eight months, in a grape variety dependent manner. Oak wood barrel tannin potentials and toastings had no effect on wine glutathione and polyphenols contents. However, wines aged in new barrels with both low and medium tannin potentials, preserved at the end of aging and important number of S-N containing compounds, which was in addition to the known ellagitanins, revealed wines better antioxidant stability.


Assuntos
Antioxidantes/química , Manipulação de Alimentos/instrumentação , Quercus/química , Taninos/análise , Vinho/análise , Madeira/química , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas , Fenóis/química , Vitis/química
13.
J Agric Food Chem ; 67(33): 9187-9202, 2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31259552

RESUMO

The rationale and scope of the main issues of antioxidant measurement are presented, with basic definitions and terms in antioxidant research (such as reactive species and related antioxidative defenses, oxidative stress, and antioxidant activity and capacity) in a historical background. An overview of technical problems and expectations is given in terms of interpretation of results, precision and comparability of methods, capability of simulating physical reality, and analytical performance (sensitivity, selectivity, etc.). Current analytical methods for measuring antioxidant and antiradical activity are classified from various viewpoints. Reaction kinetics and thermodynamics of current analytical methods are discussed, describing physicochemical aspects of antioxidant action and measurement. Controversies and limitations of the widely used antioxidant assays are elaborated in detail. Emerging techniques in antioxidant testing (e.g., nanotechnology, sensors, electrochemistry, chemometry, and hyphenated methods) are broadly introduced. Finally, hints for the selection of suitable assays (i.e., preferable for a specific purpose) and future prospects are given.


Assuntos
Antioxidantes/química , Técnicas de Química Analítica/métodos , Técnicas Eletroquímicas/métodos , Nanotecnologia/métodos , Espécies Reativas de Oxigênio/química , Oxirredução
14.
J Nanobiotechnology ; 17(1): 84, 2019 Jul 10.
Artigo em Inglês | MEDLINE | ID: mdl-31291944

RESUMO

BACKGROUND: Nanoceria has recently received much attention, because of its widespread biomedical applications, including antibacterial, antioxidant and anticancer activity, drug/gene delivery systems, anti-diabetic property, and tissue engineering. MAIN BODY: Nanoceria exhibits excellent antibacterial activity against both Gram-positive and Gram-negative bacteria via the generation of reactive oxygen species (ROS). In healthy cells, it acts as an antioxidant by scavenging ROS (at physiological pH). Thus, it protects them, while in cancer cells (under low pH environment) it acts as pro-oxidant by generating ROS and kills them. Nanoceria has also been effectively used as a carrier for targeted drug and gene delivery in vitro and in vivo models. Besides, nanoceria can also act as an antidiabetic agent and confer protection towards diabetes-associated organ pathophysiology via decreasing the ROS level in diabetic subjects. Nanoceria also possesses excellent potential in the field of tissue engineering. In this review, firstly, we have discussed the different methods used for the synthesis of nanoceria as these are very important to control the size, shape and Ce3+/Ce4+ ratio of the particles upon which the physical, chemical, and biological properties depend. Secondly, we have extensively reviewed the different biomedical applications of nanoceria with probable mechanisms based on the literature reports. CONCLUSION: The outcome of this review will improve the understanding about the different synthetic procedures and biomedical applications of nanoceria, which should, in turn, lead to the design of novel clinical interventions associated with various health disorders.


Assuntos
Cério/química , Nanopartículas/química , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Cério/farmacologia , Sistemas de Liberação de Medicamentos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Humanos , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Oxirredução , Espécies Reativas de Oxigênio/metabolismo , Engenharia Tecidual/métodos
15.
J Enzyme Inhib Med Chem ; 34(1): 1368-1372, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31347930

RESUMO

To develop multifunctional aldose reductase (AKR1B1) inhibitors for anti-diabetic complications, a novel series of 2-phenoxypyrido[3,2-b]pyrazin-3(4H)-one derivatives were designed and synthesised. Most of the derivatives were found to be potent and selective against AKR1B1, and 2-(7-chloro-2-(3,5-dihydroxyphenoxy)-3-oxopyrido[3,2-b]pyrazin-4(3H)-yl) acetic acid (4k) was the most active with an IC50 value of 0.023 µM. Moreover, it was encouraging to find that some derivatives showed strong antioxidant activity, and among them, the phenolic 3,5-dihydroxyl compound 4l with 7-bromo in the core structure was proved to be the most potent, even comparable to that of the well-known antioxidant Trolox. Thus the results suggested success in the construction of potent and selective AKR1B1 inhibitors with antioxidant activity.


Assuntos
Aldeído Redutase/antagonistas & inibidores , Antioxidantes/farmacologia , Desenho de Drogas , Inibidores Enzimáticos/farmacologia , Hipoglicemiantes/farmacologia , Pirazinas/farmacologia , Antioxidantes/química , Compostos de Bifenilo/química , Inibidores Enzimáticos/química , Hipoglicemiantes/química , Simulação de Acoplamento Molecular , Estrutura Molecular , Picratos/química , Pirazinas/química , Relação Estrutura-Atividade
16.
Phys Chem Chem Phys ; 21(29): 16190-16197, 2019 Jul 24.
Artigo em Inglês | MEDLINE | ID: mdl-31298243

RESUMO

Over the past few years, the interest in Resveratrol (3,4',5,-trihydroxystilbene, RSV) has increased due to the evidence found of its antioxidant action that protects biomolecules and cells from oxidative damage. The interest has been further exacerbated by the natural presence of RSV in some fruits and derivatives, especially in red wine. In this paper we present evidence of RSV capacity in protecting a deoxynucleotide, an essential constituent of DNA, from one-electron oxidation. This article evaluates the mechanism responsible for the antioxidant action of RSV, after one-electron oxidation of 2'-deoxyguanosine 5'-monophosphate (dGMP), by kinetic analysis during steady-state irradiation and laser flash photolysis experiments. Results showed that RSV protects dGMP by recovering the nucleotide from its radical, which is formed after the reaction of dGMP with the triplet excited state of the photosensitizer. In the absence of RSV, dGMP is irremediably oxidized, and if the damage occurs in dGMP located in DNA molecules, the consequences can be as serious as mutations and subsequent carcinogenic lesions.


Assuntos
Guanina/química , Resveratrol/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Elétrons , Neoplasias/prevenção & controle , Oxirredução/efeitos dos fármacos , Resveratrol/química
17.
Chem Biodivers ; 16(8): e1900218, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31282123

RESUMO

Croatian wines made from native (Plavac mali and Teran) and non-native grape varieties (Cabernet Sauvignon and Merlot), all grown in Croatian coastal regions, were investigated. Analyses included measurements of antioxidant activities, total phenolic contents and concentrations of non-colored phenolic compounds, chosen based on their known nutraceutical properties. Plavac mali wines were distinguished by higher antioxidant activity, total phenolic content and catechin concentrations but lower flavonol concentrations. Teran wines had higher hydroxytyrosol, myricetin and resveratrol concentrations. Merlot and Cabernet Sauvignon wines had higher flavonol concentrations (except myricetin). Canonical analysis was successful in discriminating Plavac mali from Teran wines, and both varieties were separated from non-native varieties. The results indicate distinct genetic potentials of studied varieties and enable wine authentication based on the investigated bioactive compounds.


Assuntos
Fenóis/análise , Vitis/química , Vinho/análise , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Croácia , Análise Discriminante , Flavonoides/análise , Resveratrol/análise , Vitis/metabolismo
18.
Chem Biodivers ; 16(8): e1900204, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31298500

RESUMO

The purpose of this work was to determine the chemical composition and evaluate the antichemotactic, antioxidant, and antifungal activities of the essential oil obtained from the species Cryptocarya aschersoniana Mez, Cinnamomum amoenum (Ness & Mart.) Kosterm., and Schinus terebinthifolia Raddi, as well as the combination of C. aschersoniana essential oil and terbinafine against isolates of dermatophytes. Allo-aromadendrene, bicyclogermacrene, and germacrene B were identified as major compounds in essential oils. The essential oil of C. aschersoniana shown 100 % inhibitory effect on leukocyte migration at the concentration of 10 µg/mL while S. terebinthifolia oil presented 80.1 % inhibitory effect at the same concentration. Only S. terebinthifolia oil possessed free-radical-scavenging activity which indicates its antioxidant capacity. The essential oils were also tested against fungal isolates of dermatophyte species (Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis and Microsporum gypseum), resulting in MIC ranging from 125 µg/mL to over 500 µg/mL. C. aschersoniana oil combined with terbinafine resulted in an additive interaction effect. In this case, the essential oil may act as a complement to conventional therapy for the topical treatment of superficial fungal infections, mainly because it is associated with an anti-inflammatory effect.


Assuntos
Anacardiaceae/química , Antifúngicos/química , Cinnamomum/química , Cryptocarya/química , Óleos Voláteis/química , Anacardiaceae/metabolismo , Antifúngicos/farmacologia , Antioxidantes/química , Candida/efeitos dos fármacos , Movimento Celular/efeitos dos fármacos , Cinnamomum/metabolismo , Cryptocarya/metabolismo , Testes de Sensibilidade Microbiana , Microsporum/efeitos dos fármacos , Neutrófilos/citologia , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Óleos Voláteis/farmacologia , Extratos Vegetais/química , Trichophyton/efeitos dos fármacos
19.
Chem Biodivers ; 16(8): e1900183, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31361076

RESUMO

This work describes the study of the chemical composition and bioactivity of the essential oils (EOs) of the different organs (leaves, flowers, stems and roots) from Eruca vesicaria. According to the GC and GC/MS analysis, all the EOs were dominated by erucin (4-methylthiobutyl isothiocyanate) with a percentage ranging from 17.9 % (leaves) to 98.5 % (roots). The isolated EOs were evaluated for their antioxidant (DPPH, ABTS and ß-carotene/linoleic acid), antibacterial and inhibitory property against α-amylase and α-glucosidase. Most EOs exhibited an interesting α-glucosidase and α-amylase inhibitory potential. The roots essential oil was found to be the most active with IC50 values of 0.80±0.06 and 0.11±0.01 µg mL-1 , respectively. The essential oil of roots exhibited the highest antioxidant activity (DPPH, PI=92.76±0.01 %; ABTS, PI=78.87±0.19; and ß-carotene, PI=56.1±0.01 %). The isolated oils were also tested for their antibacterial activity against two Gram-positive and three Gram-negative bacteria. Moderate results have been noted by comparison with Gentamicin used as positive control.


Assuntos
Antioxidantes/química , Brassicaceae/metabolismo , Óleos Voláteis/química , Antibacterianos/química , Antibacterianos/farmacologia , Brassicaceae/química , Flores/química , Flores/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Hipoglicemiantes/química , Óleos Voláteis/metabolismo , Óleos Voláteis/farmacologia , Folhas de Planta/química , Folhas de Planta/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , alfa-Glucosidases/química , alfa-Glucosidases/metabolismo
20.
J Photochem Photobiol B ; 197: 111556, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31326842

RESUMO

Facile green synthesis of copper nanoparticles from different biological procedures has been indicated, but among all, biosynthesis of copper nanoparticles from medicinal plants is considered as the most suitable method. The use of medicinal plant material increases the therapeutical effects of copper nanoparticles. The aim of this study was green synthesis of copper nanoparticles from aqueous extract of Falcaria vulgaris leaf (CuNPs) and assessment of their cytotoxicity, antioxidant, antifungal, antibacterial, and cutaneous wound healing properties. These nanoparticles were characterized by X-ray diffraction (XRD), fourier-transform infrared spectroscopy (FT-IR), ultraviolet-visible spectroscopy (UV), transmission electron microscopy (TEM), and field emission scanning electron microscopy (FE-SEM) analysis. The synthesized CuNPs had great cell viability dose-dependently (Investigating the effect of the CuNPs on human umbilical vein endothelial cell (HUVEC) line) and indicated this method was nontoxic. Also, 2,2-diphenyl-1-picrylhydrazyl (DPPH) test was done to assess the antioxidant activities, which indicated similar antioxidant potentials for CuNPs and butylated hydroxytoluene. In part of cutaneous wound healing property of CuNPs, after creating the cutaneous wound, the rats were randomly divided into six groups: treatment with 0.2% CuNPs ointment, treatment with 0.2% CuSO4 ointment, treatment with 0.2% F. vulgaris ointment, treatment with 3% tetracycline ointment, treatment with Eucerin basal ointment, and untreated control. These groups were treated for 10 days. Treatment with CuNPs ointment remarkably increased (p ≤ .01) the wound contracture, vessel, hexosamine, hydroxyl proline, hexuronic acid, fibrocyte, and fibrocytes/fibroblast rate and substantially reduced (p ≤ .01) the wound area, total cells, neutrophil, and lymphocyte compared to other groups. In antibacterial and antifungal parts of this research, the concentration of CuNPs with minimum dilution and no turbidity was considered minimum inhibitory concentration (MIC). To determine minimum fungicidal concentration (MFC) and minimum bactericidal concentration (MBC), 60 µL MIC and three preceding chambers were cultured on Sabouraud Dextrose Agar and Muller Hinton Agar, respectively. The minimum concentration with no fungal and bacterial growth were considered MFC and MBC, respectively. CuNPs inhibited the growth of all fungi at 2-4 mg/mL concentrations and removed them at 4-8 mg/mL concentrations (p ≤ .01). In case of antibacterial effects of CuNPs, they inhibited the growth of all bacteria at 2-8 mg/mL concentrations and removed them at 4-16 mg/mL concentrations (p ≤ .01). The results of XRD, FT-IR, UV, TEM, and FE-SEM confirm that the aqueous extract of F. vulgaris leaf can be used to yield copper nanoparticles with notable amount of antioxidant, antifungal, antibacterial, and cutaneous wound healing potentials without any cytotoxicity. Further clinical trials are necessary for confirmation these therapeutical effects of CuNPs in human.


Assuntos
Apiaceae/química , Cobre/química , Nanopartículas Metálicas/química , Extratos Vegetais/química , Animais , Antibacterianos/síntese química , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Antifúngicos/farmacologia , Antioxidantes/química , Apiaceae/metabolismo , Candida/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Química Verde , Células Endoteliais da Veia Umbilical Humana , Humanos , Masculino , Nanopartículas Metálicas/toxicidade , Testes de Sensibilidade Microbiana , Folhas de Planta/química , Folhas de Planta/metabolismo , Ratos , Pele/efeitos dos fármacos , Pele/patologia , Cicatrização/efeitos dos fármacos
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