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1.
Food Chem ; 358: 129812, 2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-33940289

RESUMO

Prunus fruits are recognized to be rich sources of polyphenols with health promoting effect. In this work we evaluated the phenolic profile and bioactivity, namely antioxidant capacity, antiproliferative effect in HT29, and inhibition capacity of α-glucosidase (α-Gls), α-amylase (α-Amy) and human dipeptidyl peptidase III (hDPP III) activities, of traditional Prunus fruits grown in Serbia. Fifteen Prunus samples were investigated and compared: common European plum and three old plum subspecies ('vlaskaca', damson plum and white damson), purple-leaf cherry plum, red and white cherry plum, sweet cherry, sweet cherry-wild type, sour cherry, steppe cherry, mahaleb cherry, blackthorn, peach, and apricot. Principal Component Analysis highlighted steppe cherry and blackthorn as Prunus species with the highest bioactive potential. In silico analysis pointed out rutinoside derivatives of cyanidin and quercetin as the most potent inhibitors of α-Gls, α-Amy and hDPP III enzymes. Quercetin 3-O-rutinoside showed the highest binding energy to α-Gls (-10.6 kcal/mol).


Assuntos
Antioxidantes/análise , Frutas/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Polifenóis/análise , Prunus/química , Antocianinas/análise , Antocianinas/farmacologia , Antioxidantes/farmacologia , Proliferação de Células/efeitos dos fármacos , Simulação por Computador , Avaliação Pré-Clínica de Medicamentos/métodos , Glucosídeos/metabolismo , Glucosídeos/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Células HT29 , Humanos , Simulação de Acoplamento Molecular , Fenóis/análise , Polifenóis/farmacologia , Quercetina/análogos & derivados , Quercetina/metabolismo , Quercetina/farmacologia , alfa-Amilases/antagonistas & inibidores
2.
Int J Mol Sci ; 22(9)2021 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-33922964

RESUMO

Plant species are precursors of a wide variety of secondary metabolites that, besides being useful for themselves, can also be used by humans for their consumption and economic benefit. Pepper (Capsicum annuum L.) fruit is not only a common food and spice source, it also stands out for containing high amounts of antioxidants (such as vitamins C and A), polyphenols and capsaicinoids. Particular attention has been paid to capsaicin, whose anti-inflammatory, antiproliferative and analgesic activities have been reported in the literature. Due to the potential interest in pepper metabolites for human use, in this project, we carried out an investigation to identify new bioactive compounds of this crop. To achieve this, we applied a metabolomic approach, using an HPLC (high-performance liquid chromatography) separative technique coupled to metabolite identification by high resolution mass spectrometry (HRMS). After chromatographic analysis and data processing against metabolic databases, 12 differential bioactive compounds were identified in sweet pepper fruits, including quercetin and its derivatives, L-tryptophan, phytosphingosin, FAD, gingerglycolipid A, tetrahydropentoxylin, blumenol C glucoside, colnelenic acid and capsoside A. The abundance of these metabolites varied depending on the ripening stage of the fruits, either immature green or ripe red. We also studied the variation of these 12 metabolites upon treatment with exogenous nitric oxide (NO), a free radical gas involved in a good number of physiological processes in higher plants such as germination, growth, flowering, senescence, and fruit ripening, among others. Overall, it was found that the content of the analyzed metabolites depended on the ripening stage and on the presence of NO. The metabolic pattern followed by quercetin and its derivatives, as a consequence of the ripening stage and NO treatment, was also corroborated by transcriptomic analysis of genes involved in the synthesis of these compounds. This opens new research perspectives on the pepper fruit's bioactive compounds with nutraceutical potentiality, where biotechnological strategies can be applied for optimizing the level of these beneficial compounds.


Assuntos
Capsicum/química , Capsicum/metabolismo , Óxido Nítrico/farmacologia , Capsicum/efeitos dos fármacos , Capsicum/crescimento & desenvolvimento , Carbolinas/análise , Carbolinas/metabolismo , Cromatografia Líquida de Alta Pressão , Flavina-Adenina Dinucleotídeo/análise , Flavina-Adenina Dinucleotídeo/metabolismo , Frutas/química , Frutas/efeitos dos fármacos , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Humanos , Espectrometria de Massas/métodos , Metabolômica/métodos , Quercetina/análise , Quercetina/metabolismo , Quercetina/farmacologia , Esfingosina/análogos & derivados , Esfingosina/análise , Esfingosina/metabolismo , Triptofano/análise , Triptofano/metabolismo
3.
Molecules ; 26(5)2021 Mar 09.
Artigo em Inglês | MEDLINE | ID: mdl-33803107

RESUMO

Polyphenols, secondary metabolites of plants, exhibit different anti-cancer and cytoprotective properties such as anti-radical, anti-angiogenic, anti-inflammation, or cardioprotective. Some of these activities could be linked to modulation of miRNAs expression. MiRNAs play an important role in posttranscriptional regulation of their target genes that could be important within cell signalling or preservation of cell homeostasis, e.g., cell survival/apoptosis. We evaluated the influence of a non-toxic concentration of taxifolin and quercetin on the expression of majority human miRNAs via Affymetrix GeneChip™ miRNA 3.0 Array. For the evaluation we used two cell models corresponding to liver tissue, Hep G2 and primary human hepatocytes. The array analysis identified four miRNAs, miR-153, miR-204, miR-211, and miR-377-3p, with reduced expression after taxifolin treatment. All of these miRNAs are linked to modulation of ZEB2 expression in various models. Indeed, ZEB2 protein displayed upregulation after taxifolin treatment in a dose dependent manner. However, the modulation did not lead to epithelial mesenchymal transition. Our data show that taxifolin inhibits Akt phosphorylation, thereby diminishing ZEB2 signalling that could trigger carcinogenesis. We conclude that biological activity of taxifolin may have ambiguous or even contradictory outcomes because of non-specific effect on the cell.


Assuntos
Quercetina/análogos & derivados , Homeobox 2 de Ligação a E-box com Dedos de Zinco/metabolismo , Apoptose/efeitos dos fármacos , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Transição Epitelial-Mesenquimal/genética , Expressão Gênica/efeitos dos fármacos , Expressão Gênica/genética , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células Hep G2/metabolismo , Hepatócitos/efeitos dos fármacos , Hepatócitos/metabolismo , Humanos , MicroRNAs/efeitos dos fármacos , MicroRNAs/genética , Polifenóis/farmacologia , Cultura Primária de Células , Quercetina/metabolismo , Quercetina/farmacologia , Transdução de Sinais/genética , Transcriptoma/efeitos dos fármacos , Transcriptoma/genética , Homeobox 2 de Ligação a E-box com Dedos de Zinco/efeitos dos fármacos
4.
Int J Mol Sci ; 22(6)2021 Mar 13.
Artigo em Inglês | MEDLINE | ID: mdl-33805725

RESUMO

Monocarboxylate transporters (MCTs) are of great research interest for their role in cancer cell metabolism and their potential ability to transport pharmacologically relevant compounds across the membrane. Each member of the MCT family could potentially provide novel therapeutic approaches to various diseases. The major differences among MCTs are related to each of their specific metabolic roles, their relative substrate and inhibitor affinities, the regulation of their expression, their intracellular localization, and their tissue distribution. MCT4 is the main mediator for the efflux of L-lactate produced in the cell. Thus, MCT4 maintains the glycolytic phenotype of the cancer cell by supplying the molecular resources for tumor cell proliferation and promotes the acidification of the extracellular microenvironment from the co-transport of protons. A promising therapeutic strategy in anti-cancer drug design is the selective inhibition of MCT4 for the glycolytic suppression of solid tumors. A small number of studies indicate molecules for dual inhibition of MCT1 and MCT4; however, no selective inhibitor with high-affinity for MCT4 has been identified. In this study, we attempt to approach the structural characteristics of MCT4 through an in silico pipeline for molecular modelling and pharmacophore elucidation towards the identification of specific inhibitors as a novel anti-cancer strategy.


Assuntos
Antineoplásicos/química , Transportadores de Ácidos Monocarboxílicos/química , Proteínas Musculares/química , Floretina/química , Pirimidinonas/química , Quercetina/química , Reserpina/análogos & derivados , Tiofenos/química , Uracila/análogos & derivados , Animais , Antineoplásicos/metabolismo , Sítios de Ligação , Transporte Biológico , Desenho de Fármacos , Glicólise/fisiologia , Humanos , Ácido Láctico/química , Ácido Láctico/metabolismo , Simulação de Acoplamento Molecular , Transportadores de Ácidos Monocarboxílicos/antagonistas & inibidores , Transportadores de Ácidos Monocarboxílicos/genética , Transportadores de Ácidos Monocarboxílicos/metabolismo , Proteínas Musculares/antagonistas & inibidores , Proteínas Musculares/genética , Proteínas Musculares/metabolismo , Floretina/metabolismo , Filogenia , Ligação Proteica , Conformação Proteica em alfa-Hélice , Domínios e Motivos de Interação entre Proteínas , Isoformas de Proteínas/antagonistas & inibidores , Isoformas de Proteínas/química , Isoformas de Proteínas/genética , Isoformas de Proteínas/metabolismo , Pirimidinonas/metabolismo , Quercetina/metabolismo , Reserpina/química , Reserpina/metabolismo , Homologia Estrutural de Proteína , Especificidade por Substrato , Tiofenos/metabolismo , Uracila/química , Uracila/metabolismo
5.
Cancer Sci ; 112(5): 1772-1784, 2021 May.
Artigo em Inglês | MEDLINE | ID: mdl-33682294

RESUMO

Traditional Chinese medicine treatment of diseases has been recognized, but the material basis and mechanisms are not clear. In this study, target prediction of the antigastric cancer (GC) effect of Guiqi Baizhu (GQBZP) and the analysis of potential key compounds, key targets, and key pathways for the therapeutic effects against GC were carried out based on the method of network analysis and Kyoto Encyclopedia of Genes and Genomes enrichment. There were 33 proteins shared between GQBZP and GC, and 131 compounds of GQBZP had a high correlation with these proteins, indicating that the PI3K-AKT signaling pathway might play a key role in GC. From these studies, we selected human epidermal growth factor receptor 2 (HER2) and programmed cell death 1-ligand 1 (PD-L1) for docking; the results showed that 385 and 189 compounds had high docking scores with HER2 and PD-L1, respectively. Six compounds were selected for microscale thermophoresis (MST). Daidzein/quercetin and isorhamnetin/formononetin had the highest binding affinity for HER2 and PD-L1, with Kd values of 3.7 µmol/L and 490, 667, and 355 nmol/L, respectively. Molecular dynamics simulation studies based on the docking complex structures as the initial conformation yielded the binding free energy between daidzein/quercetin with HER2 and isorhamnetin/formononetin with PD-L1, calculated by molecular mechanics Poisson-Boltzmann surface area, of -26.55, -14.18, -19.41, and -11.86 kcal/mol, respectively, and were consistent with the MST results. In vitro experiments showed that quercetin, daidzein, and isorhamnetin had potential antiproliferative effects in MKN-45 cells. Enzyme activity assays showed that quercetin could inhibit the activity of HER2 with an IC50 of 570.07 nmol/L. Our study provides a systematic investigation to explain the material basis and molecular mechanism of traditional Chinese medicine in treating diseases.


Assuntos
Antígeno B7-H1/metabolismo , Medicamentos de Ervas Chinesas/metabolismo , Proteínas de Neoplasias/metabolismo , Receptor ErbB-2/metabolismo , Neoplasias Gástricas/metabolismo , Antígeno B7-H1/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Medicamentos de Ervas Chinesas/uso terapêutico , Humanos , Isoflavonas/metabolismo , Isoflavonas/farmacologia , Simulação de Acoplamento Molecular/métodos , Proteínas de Neoplasias/química , Fosfatidilinositol 3-Quinases/metabolismo , Estrutura Quaternária de Proteína , Estrutura Terciária de Proteína , Proteínas Proto-Oncogênicas c-akt/metabolismo , Quercetina/análogos & derivados , Quercetina/metabolismo , Quercetina/farmacologia , Receptor ErbB-2/antagonistas & inibidores , Receptor ErbB-2/química , Transdução de Sinais , Neoplasias Gástricas/tratamento farmacológico
6.
Food Chem ; 347: 129052, 2021 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-33482484

RESUMO

Hyperoside (HYP) is an important natural product that is widely distributed in fruits and whole grasses of various plants. It is also used by consumers as a healthy ingredient. This work explored the interaction mechanisms between HYP and two main soy proteins, namely, ß-conglycinin (7S) and glycinin (11S), using computational simulation and multi-spectroscopic technology. In this study, the docking and dynamic simulation showed that HYP was stable in the hydrophobic pockets of the proteins. The conformation and microenvironment of 7S/11S also changed after binding to HYP. The binding of HYP to 7S/11S was a state quenching with a good affinity at 4 °C. This result was determined from the binding constant values of (1.995 ± 0.170) × 107 M-1 and (2.951 ± 0.109) × 107 M-1, respectively. The 7S/11S-HYP complex delineated here will provide a novel idea to construct an embedding and delivery system in improving the benefits of HYP for the development of high value-added food products.


Assuntos
Antígenos de Plantas/metabolismo , Globulinas/química , Globulinas/metabolismo , Quercetina/análogos & derivados , Proteínas de Armazenamento de Sementes/metabolismo , Proteínas de Soja/química , Proteínas de Soja/metabolismo , Soja/metabolismo , Antígenos de Plantas/química , Sítios de Ligação , Interações Hidrofóbicas e Hidrofílicas , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Quercetina/química , Quercetina/metabolismo , Proteínas de Armazenamento de Sementes/química , Soja/química , Termodinâmica
7.
Food Chem ; 337: 127959, 2021 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-32916535

RESUMO

The main objective of this study was to compare bioactive compounds and other important quality parameters of fresh and fermented caper buds and berries. Fresh samples were fermented using dry-salted and brined techniques. The higher phenolic content was determined in the fresh (1843.71 mg/100 g DW) and fermented buds (1198.54-1539.49 mg/100 g DW) rather than the berries (29.72-40.75 mg/100 g DW). Quercetin-3-O-rutinoside, kaempferol-3-O-rutinoside, and quercetin-O-galloly-O-hexoside were the principal phenolic components in fresh and fermented buds while quercetin-3-O-rutinoside in fresh and fermented berries. The amounts of isorhamnetin, quercetin, and kaempferol increased in fermented buds and berries compared to fresh samples. Similarly, antioxidant capacity of buds was found to be markedly higher than berries. As for sugar compounds, it was found that fructose in buds (1.56-3.23 g/100 g DW) and glucose in berries (1.96-6.38 g/100 g DW) had the highest amount. When total phenolics and antioxidant properties were evaluated, it was observed that they were better preserved in the dry-salted samples than the brined samples.


Assuntos
Capparis/química , Fermentação , Flavonoides/análise , Frutas/química , Fenóis/análise , Antioxidantes , Cromatografia Líquida , Flavonoides/metabolismo , Glucosídeos/análise , Glucosídeos/metabolismo , Quempferóis/análise , Quempferóis/metabolismo , Fenóis/metabolismo , Compostos Fitoquímicos/análise , Quercetina/análogos & derivados , Quercetina/análise , Quercetina/metabolismo , Espectrometria de Massas em Tandem
8.
Food Chem ; 334: 127508, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-32711265

RESUMO

Quercetin, a potential polyphenolic which possesses several biological effects. The influenza virus polymerase basic 2 (PB2) subunit of RNA polymerase responsible for replication, degree of virus conservation and active target site for designing specific antivirals. The quercetin derivatives downloaded from PubChem were screened using PyRX software configured with Vina Wizard, targeted on cap-binding site of the PB2 of influenza viral RNA polymerase. Among the PubChem library (total 97,585,747 compounds), 410 quercetin derivatives were screened using molecular docking (affinity: <-9.0 kcal) for their drug-likeness and in vitro cytopathic effect by Sulforhodamine B (SRB) assay. Among all quercetin derivatives, quercetin 3'-glucuronide (Q3G) showed strongest binding affinity towards cap-binding site of the PB2 subunit with -9.6 kcal of binding affinity and 0.00054 mM of Ki value, while quercetin 3'-glucuronide (Q7G) was presented highest anti-influenza activity with 2.10 ± 0.05 of IC50 on influenza A/PR/8/34 virus and non-cytotoxic effect as CC50 > 100 µg/mL.


Assuntos
Antivirais/farmacologia , Vírus da Influenza A/efeitos dos fármacos , Quercetina/análogos & derivados , Animais , Antivirais/química , Antivirais/metabolismo , Sítios de Ligação , Sobrevivência Celular/efeitos dos fármacos , RNA Polimerases Dirigidas por DNA/química , RNA Polimerases Dirigidas por DNA/metabolismo , Cães , Humanos , Vírus da Influenza A/enzimologia , Influenzavirus B/efeitos dos fármacos , Células Madin Darby de Rim Canino , Simulação de Acoplamento Molecular , Estrutura Terciária de Proteína , Subunidades Proteicas/química , Subunidades Proteicas/metabolismo , Quercetina/química , Quercetina/metabolismo , Quercetina/farmacologia , Termodinâmica
9.
J Sci Food Agric ; 101(2): 703-717, 2021 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-32710440

RESUMO

BACKGROUND: Ziziphus jujuba Miller cv. Dongzao is extremely susceptible to reddening, browning, nutritional loss, and perishability after harvest. In this study, we evaluated the mechanisms of calcium chloride and chitosan/nano-silica composite film treatments on the quality, especially in reddening, by physiological and metabolomic assays. RESULTS: The treatment delayed the decline of phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), and chalcone isomerase (CHI) activities. Meanwhile, the treated groups retarded the increases in anthocyanin and quercetin contents by inhibiting the gene expressions of flavonol synthase (ZjFLS), dihydroflavonol 4-reductase (ZjDFR), and anthocyanidin synthase (ZjANS), while promoting leucoanthocyanidin reductase (ZjLAR) expression, which leads to retardation of fruit reddening. Anthocyanins were found to be responsible for post-harvest winter jujube reddening through principal component analysis. Results from the technique for order preference by similarity to an ideal solution indicated that the treated group delayed the decline of the quality of 'Dongzao' and extended its shelf life. CONCLUSION: The treatment induced the heightening of flavonoids metabolism. They enhanced the nutritional value and the ability to resist stress by delaying the decline of PAL, CHS, and CHI activities. Meanwhile, the treated groups retarded the increase in anthocyanin and quercetin contents by inhibiting the gene expressions of ZjFLS, ZjDFR, and ZjANS and promoting ZjLAR expression, which leads to retardation of fruit reddening. Anthocyanins are responsible for post-harvest winter jujube reddening. Coating treatment effectively delayed the decline of winter jujube quality. © 2020 Society of Chemical Industry.


Assuntos
Cloreto de Cálcio/farmacologia , Conservação de Alimentos/métodos , Frutas/química , Ziziphus/efeitos dos fármacos , Antocianinas/análise , Antocianinas/metabolismo , Conservação de Alimentos/instrumentação , Frutas/efeitos dos fármacos , Frutas/enzimologia , Frutas/genética , Regulação da Expressão Gênica de Plantas , Oxirredutases/genética , Oxirredutases/metabolismo , Oxigenases/genética , Oxigenases/metabolismo , Fenilalanina Amônia-Liase/genética , Fenilalanina Amônia-Liase/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Quercetina/análise , Quercetina/metabolismo , Ziziphus/química , Ziziphus/enzimologia , Ziziphus/genética
10.
Food Chem ; 326: 126985, 2020 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-32413764

RESUMO

This study aims to investigate the effects of fermentation on the phenolic components and their bioaccessibility in extruded brown rice (EBR). The saccharified solution of EBR (SS-EBR) depicted higher phenolics when fermented by single or co-culture of Lactobacillusplantarum, Lactobacillus fermentum and Saccharomyces cerevisiae for 24 h at 37 °C. The co-culture fermented SS-EBR more significantly enhanced free, conjugated and bound phenolics and flavonoids with total increment of 93.3% and 61.3%, respectively. Fermentation changed the contents and compositions of phenolics in each fraction with more than 10-fold increase in vanillic acid and quercetin contents. Ferulic, p-cumaric and chlorogenic acids were increased by 83.5%, 52.2% and 113.4%, respectively, while kaempferol and cinnamic acid were found only in fermented SS-EBR. Fermentation also improved the oxygen radical absorption capacity (ORAC) and the bioaccessible phenolics in SS-EBR. Hence, the co-culture fermented SS-EBR, can be utilized as a functional supplement to provide more bioaccessible antioxidants.


Assuntos
Lactobacillus/crescimento & desenvolvimento , Oryza/química , Fenóis/química , Saccharomyces cerevisiae/crescimento & desenvolvimento , Antioxidantes/metabolismo , Técnicas de Cultura Celular por Lotes , Flavonoides/metabolismo , Oryza/metabolismo , Fenóis/metabolismo , Quercetina/metabolismo , Saccharomyces cerevisiae/metabolismo , Ácido Vanílico/metabolismo
11.
PLoS One ; 15(4): e0224853, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32298262

RESUMO

Diets rich in flavonoids have been related with low obesity rates, which could be related with their potential to inhibit pancreatic lipase, the main enzyme of fat assimilation. Some flavonoids can aggregate in aqueous medium suggesting that the inhibition mechanism could occur on both molecular and colloidal levels. This study investigates the interaction of two flavonoid aggregates, quercetin and epigallocatechin gallate (EGCG), with pancreatic lipase under simplified intestinal conditions. The stability and the morphology of these flavonoid aggregates were studied in four different solutions: Control (water), salt, low lipase concentration and high lipase concentration. Particles were found by optical microscopy in almost all the solutions tested, except EGCG-control. The results show that the precipitation rate decreases for quercetin and increases for EGCG in salt solution and that lipase stabilize quercetin aggregates. In addition, both flavonoids were shown to precipitate together with pancreatic lipase resulting in a sequestering of the enzyme.


Assuntos
Antioxidantes/farmacologia , Catequina/análogos & derivados , Mucosa Intestinal/metabolismo , Lipase/metabolismo , Quercetina/farmacologia , Animais , Antioxidantes/metabolismo , Catequina/metabolismo , Catequina/farmacologia , Dimerização , Inibidores Enzimáticos/metabolismo , Inibidores Enzimáticos/farmacologia , Mucosa Intestinal/efeitos dos fármacos , Mucosa Intestinal/enzimologia , Lipase/antagonistas & inibidores , Quercetina/metabolismo , Suínos
12.
Food Chem ; 319: 126562, 2020 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-32155536

RESUMO

This study investigated the effects of the addition of onion waste fractions into gluten-free (GF) bread to promote its health benefits. 5% of the control (C) GF flour blend was replaced with three waste fractions in the form of: fried onion (FO), dried onion (DO) and onion peel (OP). Antioxidant activity, content of flavonols and total polyphenols of breads increased in the following order: C < FO < DO < OP. No differences were observed in sensory analysis. We found that quercetin glycosides, dimers and trimer in OP-bread, determined according to their mass spectra, decomposed during baking and released free quercetin, which points to their thermal instability. Cross-over study revealed that consumption of OP-bread significantly increased (p < 0.05) antioxidant activity of consumers' blood compared to control bread consumption, indicating good bioavailability of flavonols. Results suggest incorporation of OP into GF bread can increase its biological value with satisfactory sensory acceptance.


Assuntos
Pão/análise , Cebolas/química , Cebolas/metabolismo , Disponibilidade Biológica , Culinária , Estudos Cross-Over , Polifenóis/química , Polifenóis/metabolismo , Quercetina/química , Quercetina/metabolismo , Rutina/química , Rutina/metabolismo
13.
J Agric Food Chem ; 68(14): 4205-4214, 2020 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-32141744

RESUMO

Polyphenol extracts derived from gastrointestinal digestates of buckwheat (Fagopyrum Mill) were studied for their intestinal transport and lipid-lowering effects in Caco-2/HepG2 coculture models. The relative amounts of all phenolic compounds throughout the digestion and intestinal absorption process were determined by UHPLC-Q-Orbitrap mass spectrometry. The digestible and easily transported phenolic compounds in buckwheat extract were identified. Herein, four main phenolic compounds and their metabolites were found on both the apical and basolateral sides of the Caco-2 cell transwell model. The transepithelial transport rates in the Caco-2 cell monolayer were scoparone (0.97) > hydroxycinnamic acid (0.40) > rutin (0.23) > quercetin (0.20). The main metabolism of hydroxycinnamic acid, quercetin, and scoparone in transepithelial transport was found to be methylation. Furthermore, results indicated that triglyceride, low-density lipoprotein cholesterol, total cholesterol, aspartate aminotransferase, and alanine aminotransferase levels in HepG2 cells on the basolateral side of coculture models can be suppressed by 53.64, 23.44, 36.49, 27.98, and 77.42% compared to the oleic acid-induced group (p < 0.05). In addition, the mRNA expression of Fabp4 relative to the control was found to be significantly upregulated (85.82 ± 10.64 to 355.18 ± 65.83%) by the easily transported buckwheat polyphenol components in HepG2 cells (p < 0.01).


Assuntos
Digestão , Fagopyrum/metabolismo , Extratos Vegetais/metabolismo , Polifenóis/metabolismo , Alanina Transaminase/metabolismo , Transporte Biológico , Células CACO-2 , Colesterol/metabolismo , LDL-Colesterol/metabolismo , Técnicas de Cocultura , Ácidos Cumáricos/metabolismo , Cumarínicos/metabolismo , Fagopyrum/química , Células Hep G2 , Humanos , Absorção Intestinal , Extratos Vegetais/química , Polifenóis/química , Quercetina/metabolismo , Rutina/metabolismo , Transaminases/metabolismo , Triglicerídeos/metabolismo
14.
Life Sci ; 253: 117584, 2020 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-32220623

RESUMO

Accumulating recent studies have demonstrated the preventive and therapeutic effects of polyphonic compounds such as quercetin in colorectal cancer. Therefore, we aimed to evaluate the underlying mechanisms for positive effects of quercetin in rats with 1,2-dimethylhydrazine (DMH)- induced colorectal cancer. For this purpose, male Wistar rats were classified as 6 groups, including group 1 without any intervention, group 2 as quercetin received rats (50 mg/kg), groups 3 as DMH received rats (20 mg/kg) group 4-6 DMH and quercetin received rats. DNA damage, DNA repair, the expression levels and activities of enzymic antioxidants, non-enzymic antioxidants, and NRF2/Keap1 signaling were evaluated in colon tissues of all groups. Our results showed significant suppression of DNA damage and induction of DNA repair in DMH + Quercetin groups, particularly in entire-period in comparison to other groups (p < .05). The expression levels and activities of enzymic and non-enzymic antioxidants were increased in DMH + Quercetin groups (p < .05). Lipid and protein peroxidation were significantly suppressed in DMH + Quercetin groups (p < .05). In addition, quercetin also modulated NRF2/Keap1 signaling and its targets, detoxifying enzymes in DMH + Quercetin groups. Our finding demonstrated that quercetin supplementation effectively reversed DMH-mediated oxidative stress and DNA damage through targeting NRF2/Keap1 signaling pathway.


Assuntos
1,2-Dimetilidrazina/metabolismo , Carcinógenos/metabolismo , Neoplasias do Colo/tratamento farmacológico , Fator 2 Relacionado a NF-E2/metabolismo , Quercetina/química , 1,2-Dimetilidrazina/toxicidade , Animais , Antioxidantes/química , Antioxidantes/metabolismo , Antioxidantes/farmacologia , Carcinógenos/química , Carcinógenos/toxicidade , Catalase/metabolismo , Dano ao DNA/efeitos dos fármacos , Proteína 1 Associada a ECH Semelhante a Kelch/metabolismo , Peroxidação de Lipídeos/efeitos dos fármacos , Lipídeos/química , Masculino , Neoplasias Experimentais , Estresse Oxidativo/efeitos dos fármacos , Quercetina/metabolismo , Quercetina/farmacologia , Ratos , Ratos Wistar , Espécies Reativas de Oxigênio , Transdução de Sinais
15.
J Photochem Photobiol B ; 204: 111819, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32062388

RESUMO

Solanum aculeatissimum Jacq. is a common plant in much of Brazil. Despite containing metabolites with a wide range of pharmacological applications, there are few tissue culture reports for this plant. The possibility of large-scale in vitro production of this material has significant biotechnological potential. Therefore, the objective of this study was to investigate the effect of light conditions on the growth of cells in suspension, observing the production and yield of biomass and bioactive compounds and the enzymatic behavior. Calli obtained from leaf segments were cultured in solid medium supplemented with 1 mg L-1 of 2,4-D, 2.5 mg L-1 kinetin, pH 5.7, in the dark. After 110 days of subculture, the calli were transferred to liquid medium. Cells were kept in the dark under agitation at 110 rpm and 25 °C and subcultured every 30 days. After 90 days of culture, 20 mL aliquots of cell suspension were added to flasks containing approximately 20 mL of medium (1:1) and cultured at different wavelengths (white, green, blue, red, and blue/red) under a photoperiod of 16 h with irradiance of 50 µmol m-2 s-1) and in the absence of light. The experiment was performed in a 6 × 6 factorial design (light condition × culture time). The cell cultures showed viability throughout the entire cycle, and chlorogenic and ferulic acids, orientin, quercitrin and, in higher amounts, quercetin, were detected in the first 7 days of culture. There was an increase in superoxide dismutase and catalase and a decrease in ascorbate peroxidase after exposure to different light conditions; for phenylalanine ammonia lyase, no differences were observed. The different light conditions were not sufficient to trigger responses in the concentrations of bioactive compounds, despite the detection of increased levels of the enzymes involved in cellular homeostasis.


Assuntos
Luz , Solanum/metabolismo , Catalase/metabolismo , Técnicas de Cultura de Células , Ácido Clorogênico/metabolismo , Condutividade Elétrica , Flavonoides/metabolismo , Glucosídeos/metabolismo , Concentração de Íons de Hidrogênio , Células Vegetais/metabolismo , Células Vegetais/efeitos da radiação , Folhas de Planta/citologia , Folhas de Planta/metabolismo , Quercetina/análogos & derivados , Quercetina/metabolismo , Solanum/citologia , Superóxido Dismutase/metabolismo
16.
Poult Sci ; 99(2): 906-913, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-32029167

RESUMO

Quercetin, the main component of flavonoids, has a wide range of biological actions. Quercetin can be made into a variety of additives for practice, because of the stable chemical structure and water-soluble derivatives. This study was intended to explore the effects of quercetin on immune function and its regulatory mechanism in Arbor Acre broiler to provide a practical basis for improving poultry immune function and figure out the optimum supplementation as functional feed additives. A total of 240 one-day-old healthy Arbor Acre broilers, similar in body weight, were randomly allotted to 4 treatments with 6 replicates, 10 broilers in each replicate and fed with diets containing quercetin at 0, 0.02, 0.04, and 0.06% for 6 wk. Blood and immune organs (spleen, thymus, and bursa) were collected from chickens at the end of the experiment. Growth performance, immune organs indexes, contents of serum immune molecules, splenic T lymphocyte proliferative responses, and expression of immune related genes were evaluated. The results showed that dietary quercetin had no significant effect (P > 0.05) on growth performance of broilers. Compared with control, 0.06% quercetin supplementation in diet significantly increased spleen index and thymus index (P < 0.05). It also increased the secretion of immune molecules including immunoglobulin A (IgA), interleukin-4 (IL-4) (P < 0.001), immunoglobulin M (IgM) (P = 0.007), complement component 4 (C4) (P = 0.001), and tumor necrosis factor-α (TNF-α) (P < 0.05). On the other hand, 0.02% quercetin supplementation significantly increased complement component 3 (C3) (P < 0.05). Additionally, both 0.04 and 0.06% quercetin supplementation significantly increased expression of TNF-α, TNF receptor associated factor-2 (TRAF-2), TNF receptor superfamily member 1B (TNFRSF1B), nuclear factor kappa-B p65 subunit (NF-κBp65), and interferon-γ (IFN-γ) mRNA (P < 0.05), and expression of NF-κB inhibitor-alpha (IκB-α) mRNA were significantly decreased (P < 0.05). Thus, quercetin improved immune function via NF-κB signaling pathway triggered by TNF-α.


Assuntos
Galinhas/imunologia , NF-kappa B/imunologia , Quercetina/metabolismo , Transdução de Sinais/imunologia , Ração Animal/análise , Animais , Dieta/veterinária , Suplementos Nutricionais/análise , Relação Dose-Resposta a Droga , Quercetina/administração & dosagem , Distribuição Aleatória
17.
Food Chem ; 317: 126415, 2020 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-32087518

RESUMO

This paper focused on improving antityrosinase ability of quercetin, cinnamic acid, and ferulic acid (named Q-CA-FA) from Asparagus by combining heating with ultrasound treatments. Fluorescence spectroscopy and UPLC-MS were used to evaluate inhibitory mechanisms. Results showed that the impacts of combining heating (150 °C for 30 min) with ultrasound (600 W for 30 min) treatments were similar to heating treatment (150 °C for 120 min) alone, and the inhibition rate could reach 98.2% in the addition of 5 mM Q-CA-FA. Fluorescence quenching indicated that treated Q-CA-FA-tyrosinase complex was more stable, but combining treatments did not change the major force between tyrosinase and polyphenols. Thermodynamic analysis illustrated that the randomness of compounds was also increased. Interestingly, 2-hydroxy-3-(3-hydroxy-4-methoxy-phenyl)-propionic acid 4-(2,3-dihydroxy-propyl)-phenyl ester was newly detected, which might be the major reason for enhancing antityrosinase ability. Taken together, these results provide a creative insight on increasing antityrosinase activity by combining heating with ultrasound treatments.


Assuntos
Monofenol Mono-Oxigenase/metabolismo , Polifenóis/metabolismo , Sonicação , Asparagus (Planta)/química , Asparagus (Planta)/metabolismo , Cromatografia Líquida de Alta Pressão , Cinamatos/análise , Cinamatos/metabolismo , Ácidos Cumáricos/análise , Ácidos Cumáricos/metabolismo , Temperatura Alta , Monofenol Mono-Oxigenase/antagonistas & inibidores , Polifenóis/análise , Quercetina/análise , Quercetina/metabolismo , Espectrometria de Fluorescência , Espectrometria de Massas em Tandem , Termodinâmica
18.
Molecules ; 25(3)2020 Jan 27.
Artigo em Inglês | MEDLINE | ID: mdl-32012739

RESUMO

The aim of this study was to analyze the binding interactions between a common antihypertensive drug (ramipril, R) and the widely distributed plant flavonoid quercetin (Q), in the presence of human serum albumin (HSA). From the observed fluorescence spectra of the (HSA + R) system we can assume that ramipril is also one of the Site 3 ligands-similar to fusidic acid-the binding of which has been proven by RTG crystallography. Our claim is supported by near-UV CD spectroscopy, microscale themophoresis and molecular modeling. The presence of R slightly inhibited the subsequent binding of Q to HSA and, on the contrary, the pre-incubation of HSA with Q caused a stronger binding of R, most likely due to allosteric interactions. At high concentrations, R is also able to displace Q from its binding site. The dissociation constant KD for the binding of R is more than hundredfold larger than for Q, which means that R is a very weak binder to HSA. The knowledge of qualitative and quantitative parameters of R, as well as the methods used in this study, are important for future research into HSA binding. This study shows the importance of implementing other methods for KD determination. Microscale thermophoresis has proved to be a novel, practical and accurate method for KD determination on HSA, especially in cases when fluorescence spectroscopy is unable to produce usable results.


Assuntos
Quercetina/metabolismo , Ramipril/metabolismo , Albumina Sérica Humana/metabolismo , Sítios de Ligação , Humanos , Ligantes , Modelos Moleculares , Simulação de Acoplamento Molecular , Ligação Proteica , Conformação Proteica , Quercetina/química , Ramipril/química , Albumina Sérica Humana/química
19.
Sci Rep ; 10(1): 949, 2020 01 22.
Artigo em Inglês | MEDLINE | ID: mdl-31969615

RESUMO

Tuberculosis (TB) is caused by Mycobacterium tuberculosis (MTB), a highly infectious disease accounting for nearly 1.5 million deaths every year and has been a major global concern. Moreover, resistance to anti-TB drugs is an arduous obstacle to effective prevention, TB care and management. Therefore, incessant attempts are being made to identify novel drug targets and newer anti-tubercular drugs to fight with this deadly pathogen. Increasing resistance, adverse effects and costly treatment by conventional therapeutic agents have been inclining the researchers to search for an alternative source of medicine. In this regard natural compounds have been exploited extensively for their therapeutic interventions targeting cellular machinery of MTB. Glutamate racemase (MurI) is an enzyme involved in peptidoglycan (PG) biosynthesis and has become an attractive target due to its moonlighting property. We screened various classes of natural compounds using computational approach for their binding to MTB-MurI. Shortlisted best docked compounds were evaluated for their functional, structural and anti-mycobacterial activity. The results showed that two flavonoids (naringenin and quercetin) exhibited best binding affinity with MTB-MurI and inhibited the racemization activity with induced structural perturbation. In addition, fluorescence and electron microscopy were employed to confirm the membrane and cell wall damages in mycobacterial cells on exposure to flavonoids. Together, these observations could provide impetus for further research in better understanding of anti-tubercular mechanisms of flavonoids and establishing them as lead molecules for TB treatment.


Assuntos
Isomerases de Aminoácido/metabolismo , Antituberculosos , Produtos Biológicos/metabolismo , Produtos Biológicos/farmacologia , Avaliação Pré-Clínica de Medicamentos/métodos , Flavanonas/farmacologia , Mycobacterium tuberculosis/efeitos dos fármacos , Mycobacterium tuberculosis/enzimologia , Quercetina/farmacologia , Produtos Biológicos/isolamento & purificação , Parede Celular/efeitos dos fármacos , Parede Celular/patologia , Flavanonas/isolamento & purificação , Flavanonas/metabolismo , Mycobacterium tuberculosis/citologia , Mycobacterium tuberculosis/metabolismo , Peptidoglicano/biossíntese , Ligação Proteica , Quercetina/isolamento & purificação , Quercetina/metabolismo
20.
Food Chem ; 314: 126166, 2020 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-31972406

RESUMO

The occurrence of the quercetin oxidation metabolite 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (BZF), whose antioxidant potency is notably higher than the antioxidant potency of quercetin, was investigated in twenty quercetin-rich plant foods. BZF was identified (HPLC-DAD-ESI-MS/MS) only in the dry outer scales of onions and shallots. Aqueous extracts of onions (OAE) and shallots (SAE) were evaluated for their antioxidant and cytoprotective properties. OAE, whose potency did not differ from SAE, protected ROS-exposed Caco2 cells against oxidative (78%) and cellular (90%) damage at a 3 µg/L concentration (corresponding to 0.03 nM of BZF). After chromatographic resolution of OAE, the BZF peak accounted fully and exclusively for its antioxidant effect. The antioxidant effects of OAE and of a pure BZF were described by two perfectly overlapping curves whose concentration-dependence was within the 3 × 10-4 to 102 nM BZF range. Such unprecedented low concentrations place BZF-containing plants on the frontier of the search for novel sources of antioxidants.


Assuntos
Antioxidantes/farmacologia , Benzofuranos/análise , Benzofuranos/farmacologia , Cebolas/química , Quercetina/metabolismo , Antioxidantes/química , Benzofuranos/metabolismo , Células CACO-2 , Cromatografia Líquida de Alta Pressão , Relação Dose-Resposta a Droga , Frutas/química , Humanos , Oxirredução , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Substâncias Protetoras/química , Substâncias Protetoras/farmacologia , Espectrometria de Massas em Tandem , Verduras/química
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