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1.
Food Chem ; 317: 126346, 2020 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-32070843

RESUMO

The inhibitory mechanisms of ferulic acid against α-amylase and α-glucosidase were investigated by enzyme kinetic analysis, circular dichroism (CD), Fourier-transform infrared (FT-IR) spectroscopy, fluorescence quenching and molecular docking. Results indicated that ferulic acid strongly inhibited α-amylase (IC50: 0.622 mg ml-1) and α-glucosidase (IC50: 0.866 mg ml-1) by mixed and non-competitive mechanisms, respectively. CD spectra and fluorescence intensity measurements confirmed that the secondary structure of α-amylase and α-glucosidase were changed and the microenvironments of certain amino acid residues were modulated by the binding of ferulic acid. FT-IR spectra indicated that the interaction between ferulic acid and α-amylase/α-glucosidase mainly involved in non-covalent bonds. Molecular docking further demonstrated that the interaction forces between ferulic acid and α-amylase/α-glucosidase were hydrogen bonds, with the binding energy of -5.30 to -5.10 and -5.70 kcal mol-1, respectively. This study might provide a theoretical basis for the designing of novel functional foods with ferulic acid.


Assuntos
Ácidos Cumáricos/metabolismo , Inibidores de Glicosídeo Hidrolases/metabolismo , alfa-Amilases/metabolismo , alfa-Glucosidases/metabolismo , Sítios de Ligação , Ácidos Cumáricos/química , Inibidores de Glicosídeo Hidrolases/química , Ligação de Hidrogênio , Cinética , Simulação de Acoplamento Molecular , Estrutura Secundária de Proteína , Termodinâmica , alfa-Amilases/química , alfa-Glucosidases/química
2.
Food Chem ; 312: 126085, 2020 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-31896460

RESUMO

The effects of hydroxycinnamic acids such as cinnamic acid (CNA), p-coumaric acid(CMA), caffeic acid (CFA), and chlorogenic acid (CGA) on the reduction of furan in canned-coffee model systems (CCMS) containing α-dicarbonyls [glyoxal (GO) or methylglyoxal (MGO)] were investigated. The concentration of furan in CCMS containing GO, which was 59.76 µg/L, was reduced by the addition of CFA and CGA to 48.31 µg/L and 41.38 µg/L, respectively; similarly, the furan concentration in model system containing MGO was 45.79 µg/L, and this decreased to 35.41 µg/L (by CFA) and 32.65 µg/L (by CGA), respectively. In addition, the effects of hydroxycinnamic acids on the trapping of GO and MGO were determined. CFA and CGA greatly reduced the concentration of GO to 303.51 µg/L and 267.80 µg/L, respectively (compared to 515.79 µg/L in the control), whereas that of MGO was decreased to 207.01 µg/L and 219.14 µg/L (compared to 417.14 µg/L in the control). The trapping of α-dicarbonyls such as GO and MGO by CFA and CGA could be closely related to furan reduction in CCMS.


Assuntos
Ácidos Cumáricos/química , Furanos/química , Aldeído Pirúvico/química , Ácido Clorogênico/química , Café/química , Glioxal/química
3.
Anal Bioanal Chem ; 412(6): 1431-1439, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31912183

RESUMO

Triatominae are hematophagous insects involved in the transmission of Chagas disease. Among the 19 genera of the subfamily, those with the highest epidemiological importance regarding the dissemination of Trypanosoma cruzi are Panstrongylus, Rhodnius, and Triatoma. Of these three genera, Rhodnius presents the greatest difficulties for specific identification. Thus, there is a need to overcome the difficulties in identifying phenotypes of similar species of this genus. In the present study, the MALDI-TOF MS methodology was used to identify 12 Rhodnius species, among the 21 admitted. The MALDI-TOF MS methodology allowed specific characterization through the identification of peptides and proteins, starting from four different methods of extraction: (A) acetonitrile/formic acid (ACN/AF), (B) acetonitrile/trifluoroacetic acid (ACN/TFA), (C) isopropyl/formic acid (IPA/AF), and (D) methanol/formic acid (MeOH/AF), and four types of MALDI-TOF matrices: α-cyano-4-hydroxycinnamic acid (CHCA), sinapic acid (SA), 6-aza-2-thiothymine (ATT), and 2,6-dihydroxyacetophenone (DHAP). The experiments were performed by combining the four solvents and four matrices to select the best MALDI extraction/matrix. The application of the MALDI-TOF MS technique, through the digital mass spectrometry approach combined with chemometric tools, such as partial least squares-discriminant analysis (PLS-DA), was able to discriminate 12 species of Rhodnius genus, which are difficult to identify using morphological characteristics. Thus, in view of the results obtained, the methodology described in the present article can be applied with speed and efficiency for the discrimination of Triatominae species. Graphical Abstract.


Assuntos
Proteínas de Insetos/química , Peptídeos/química , Rhodnius/classificação , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz/métodos , Acetofenonas/química , Animais , Ácidos Cumáricos/química , Formiatos/química
4.
Environ Sci Pollut Res Int ; 27(8): 7910-7921, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31889292

RESUMO

Liver injury is one of the adverse effects of methotrexate (MTX). Ferulic acid (FA) is an antioxidant phytochemical that confers hepatoprotective efficacy; however, its effect against MTX hepatotoxicity remains unexplored. This study investigated the role of FA in modulating oxidative stress, inflammation, Nrf2/HO-1 signaling, and PPARγ in MTX-administered rats. Following oral FA supplementation for 15 days, rats received a single dose of MTX at day 16 and samples were collected at day 19. MTX provoked multiple histological manifestations, including degenerative changes, steatosis, inflammatory cells infiltration and hemorrhage, and altered serum transaminases, bilirubin, and albumin. Reactive oxygen species, lipid peroxidation, and nitric oxide were increased in the liver of rats that received MTX. FA prevented all histological alterations, ameliorated liver function markers, suppressed oxidative stress, and boosted antioxidants in MTX-induced rats. FA reduced serum TNF-α and IL-1ß, and hepatic NF-κB p65, Bax, and caspase-3, whereas increased Bcl-2, Nrf2, NQO1, HO-1, and PPARγ. In conclusion, FA prevented MTX hepatotoxicity by activating Nrf2/HO-1 signaling and PPARγ, and attenuating oxidative stress, inflammation, and cell death.


Assuntos
Antioxidantes/química , Fígado/fisiopatologia , Metotrexato , Fator 2 Relacionado a NF-E2 , Animais , Ácidos Cumáricos/química , Inflamação , Metotrexato/química , Estresse Oxidativo , Ratos , Ratos Wistar , Regulação para Cima
5.
J Agric Food Chem ; 68(7): 2124-2131, 2020 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-31985223

RESUMO

Lignin acylated with acetate and/or p-coumarate is common in many herbaceous plants. Herein, the biomimetic oxidation of γ-acylated monolignols with Ag2O was studied to understand the effect of γ-acyl groups on monolignol polymerization. The oxidation of sinapyl acetate gave γ-acylated and α-acylated ß-O-4 dimers in 71 and 9.5% yields, respectively. The oxidation of sinapyl p-coumarate produced γ-acylated ß-O-4 and γ-acylated tetralin ß-ß dimers in 53 and 16% yields, respectively. Only the sinapyl alcohol moiety in sinapyl p-coumarate reacted, and the p-coumarate moiety remained unchanged, suggesting that p-coumaric acid is not incorporated into the lignin backbone in the acylated lignins. All of the γ-acylated monolignols used in this study produced the γ-acylated ß-O-4 dimers, which suggests that the γ-acylated monolignols act as lignin monomers. The relatively high yields of the ß-O-4 dimers indicate that Ag2O oxidation of the monolignols can be used as an easy method for synthesizing the ß-O-4 dimer model compounds.


Assuntos
Ácidos Cumáricos/química , Dioxanos/química , Lignina/química , Óxidos/química , Compostos de Prata/química , Acetatos/química , Biomimética , Oxirredução
6.
Phytochemistry ; 170: 112218, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31812108

RESUMO

The vast majority of previous studies dealing with antioxidant potency of (poly)phenols does not investigate the fate of phenoxyl radical obtained after single free radical scavenging. We investigated possible pathways of inactivation of ferulic acid phenoxyl radical (FAPR) using DFT method. Direct coupling with a set of 10 physiologically important free radicals, H-atom donation and dimerization were analysed by estimation of Gibbs free energy changes related to these processes. The former two processes are thermodynamically feasible to inactivate more dangerous free radicals such as hydroxyl, alkoxyl and carbon-centered radicals. Among dimerization reactions, the least energy demanding is formation of C-5-C-5 dimer of ferulic acid (FA), which has higher antiradical potency than FA itself. Obtained results reveal that FAPR, a priori considered as stable and unreactive, may contribute to the overall antioxidant activity of FA. This is a beneficial behavior, which makes FA a particularly valuable protector against oxidative stress. Hence, the contribution of phenoxyl radicals to the antioxidant activity of (poly)phenolic compounds should be taken into account, what has been scarcely considered until now.


Assuntos
Antioxidantes/farmacologia , Ácidos Cumáricos/farmacologia , Fenóis/farmacologia , Compostos Fitoquímicos/farmacologia , Antioxidantes/química , Ácidos Cumáricos/química , Teoria da Densidade Funcional , Radicais Livres/química , Radicais Livres/farmacologia , Estrutura Molecular , Estresse Oxidativo/efeitos dos fármacos , Fenóis/química , Compostos Fitoquímicos/química
7.
J Sci Food Agric ; 100(4): 1479-1485, 2020 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-31756272

RESUMO

BACKGROUND: Sweet corn cob (SCC), an agricultural by-product of the corn-processing industry, contains more than 80% insoluble bound ferulic acid (FA). Extraction of these bound phenolics can be achieved through chemical or enzymatic hydrolysis; however, the shift towards greener chemistry has raised awareness about the use of enzymatic hydrolysis. In the present study, the ability of ferulic acid esterase (FAE) and xylanase (XY) to catalyze the hydrolysis of FA from SCC was investigated. Response surface methodology (RSM), based on a five-level, four-factor central composite rotatable design (CCRD), was used to establish the optimum conditions for enzymatic hydrolysis of FA from SCC. Sweet corn cob was treated with a combination of FAE and XY at various concentrations (FAE: 0.00 to 0.04 U/g; XY: 0.00 to 18 093.5 U/g), temperatures (45 to 65 °C), and pH levels (pH 4.5 to 6.5). RESULTS: The optimum extraction conditions predicted by the model were: FAE concentration of 0.02 U/g, XY concentration of 3475.3 U/g, extraction pH of 4.5, and an extraction temperature of 45 °C. CONCLUSION: Under these conditions, the experimental yield of FA was 1.69 ± 0.02 g kg-1 of SCC, which is in agreement with the value predicted by the model. © 2019 Society of Chemical Industry.


Assuntos
Hidrolases de Éster Carboxílico/química , Ácidos Cumáricos/isolamento & purificação , Endo-1,4-beta-Xilanases/química , Química Verde/métodos , Extratos Vegetais/isolamento & purificação , Resíduos/análise , Zea mays/química , Biocatálise , Ácidos Cumáricos/química , Concentração de Íons de Hidrogênio , Hidrólise , Extratos Vegetais/química , Temperatura
8.
Food Chem ; 309: 125586, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-31670124

RESUMO

Oil-in-water (O/W) emulsions are important delivery systems of omega-3 fatty acids (n-3 FA). We investigated the effect of sinapic acid esters concentration and chain length, the electrical charge of the emulsifier and emulsion pH on the oxidative stability of n-3 FA rich O/W emulsions. Echium oil was applied as n-3 FA source. A 24 factorial design was used to simultaneously evaluate these factors. Peroxide value, malondialdehyde, 2,4-heptadienal and 2,4-decadienal were measured in the emulsions. pH and the electrical charge of the emulsifier modulated the antioxidant effectiveness of sinapic acid esters, while concentration was not relevant. The combination of positively charged emulsifier with neutral pH provided the best oxidative stability for echium oil emulsions. Our results also suggested that the increase of length chain of sinapic acid, from C4 to C12, reduced the secondary products of oxidation, when echium oil emulsions were prepared using negatively charged emulsifier under acidic conditions.


Assuntos
Ácidos Cumáricos/química , Ácidos Graxos Ômega-3/química , Antioxidantes/química , Antioxidantes/farmacologia , Ácidos Cumáricos/farmacologia , Echium/química , Emulsões , Ésteres , Oxirredução , Óleos Vegetais/química
9.
J Zhejiang Univ Sci B ; 20(11): 868-876, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31595723

RESUMO

Acrolein, known as one of the most common reactive carbonyl species, is a toxic small molecule affecting human health in daily life. This study is focused on the scavenging abilities and mechanism of ferulic acid and some other phenolic acids against acrolein. Among the 13 phenolic compounds investigated, ferulic acid was found to have the highest efficiency in scavenging acrolein under physiological conditions. Ferulic acid remained at (3.04±1.89)% and acrolein remained at (29.51±4.44)% after being incubated with each other for 24 h. The molecular mechanism of the detoxifying process was also studied. Detoxifying products, namely 2-methoxy-4-vinylphenol (product 21) and 5-(4-hydroxy-3-methoxyphenyl)pent-4-enal (product 22), were identified though nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS), after the scavenging process. Ferulic acid showed significant activity in scavenging acrolein under physiological conditions. This study indicates a new method for inhibiting damage from acrolein.


Assuntos
Acroleína/toxicidade , Ácidos Cumáricos/farmacologia , Acroleína/química , Ácidos Cumáricos/química , Glutationa/fisiologia , Hidroxibenzoatos/farmacologia , Espectroscopia de Ressonância Magnética , Relação Estrutura-Atividade
10.
J Agric Food Chem ; 67(46): 12962-12971, 2019 Nov 20.
Artigo em Inglês | MEDLINE | ID: mdl-31644281

RESUMO

Ferulate (FA) units esterified to grass arabinoxylans are involved in cross-linking cell wall polymers. In this work, this contention is strengthened by the identification of FA homo- and heterodimers esterified to methyl arabinofuranoside (MeAra) units after their release from the xylan by mild acidolysis in dioxane/methanol/HCl. Acidolysis of poorly lignified maize bran cell walls provided diferulate (DFA) isomers, including those from 8-5, 8-O-4, and 5-5 interunit bonding, esterified to one or two MeAra units. Acidolysis of lignified grass samples released crossed dimers esterified to one MeAra unit and derived from the ß-O-4 coupling of coniferyl alcohol to FA esters. The evaluation of these heterodimeric esters by LC-UV of their aglycones revealed that the parent structures occur in significant amounts in lignified cell walls (0.5-1 mg/g expressed as FA equivalents). The present results position mild acidolysis as an efficient strategy to obtain improved details regarding the FA-mediated cross-linking of grass cell walls.


Assuntos
Arabinose/química , Parede Celular/química , Ácidos Cumáricos/química , Poaceae/química , Ácidos/química , Dimerização , Ésteres/química , Hidrólise , Lignina/química , Fenóis/química , Zea mays/química
11.
J Agric Food Chem ; 67(43): 12054-12060, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31560529

RESUMO

The purpose of current research is to design and acquire novel biological macromolecule materials with enhanced functional properties. Chitosan-ferulic acid binary conjugate (CFC) was synthesized based on the carbodiimide-mediated coupling reaction, and then ß-lactoglobulin-ferulic acid-chitosan ternary conjugate (BFCC) was fabricated by laccase induction. Furthermore, the impact of laccase concentration on the formation mechanism of BFCC was investigated by the analyses of reaction group content, ultraviolet-visible (UV-vis) absorption, circular dichroism (CD), and fluorescence spectroscopy. Results showed that hetero- and homo-conjugates between CFC and ß-lactoglobulin (ß-LG) were achievable at the low concentration (≤4 U/mL) and high concentration (≥6 U/mL) of laccase, respectively. The CD spectrum indicated that the interaction with CFC made ß-LG more disorderly. Functional evaluation results revealed that the antioxidant activity and thermal stability of BFCC were improved compared with ß-LG. The knowledge obtained in the present study provided an effective method to acquire innovative biological macromolecule materials with desirable functional characteristics.


Assuntos
Quitosana/química , Ácidos Cumáricos/química , Lacase/química , Lactoglobulinas/química , Animais , Biocatálise , Bovinos , Dicroísmo Circular , Proteínas Fúngicas/química , Conformação Proteica , Trametes/enzimologia
12.
Molecules ; 24(17)2019 Sep 03.
Artigo em Inglês | MEDLINE | ID: mdl-31484471

RESUMO

The byproducts (seeds and peels) of an avocado cultivated in the south of Colombia were extracted with aqueous acetone and their antioxidant properties were measured with ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and DPPH (2,2-diphenyl-1-picrylhydrazyl) assays, and total polyphenol content was determined by Folin-Ciocalteu method. A bioguided fractionation was performed, first by SPE (solid phase extraction) on Amberlite XAD-7, and then by size exclusion chromatography on Sephadex LH-20. The polyphenolic-rich extracts and their fractions were analyzed by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS), finding the presence of organic acids, hydroxycinnamic acids, catechins, free and glycosylated flavonoids, and dimeric and trimeric procyanidins. Catechin, epicatechin, six quercetin derivatives, four dimeric procyanidins (three type B and one type A), and three trimeric procyanidins (two type B and one type A) were detected in the most active fractions of avocado peel and seeds. The most antioxidant fractions contain the higher molecular weight phenolic compounds (condensed tannins).


Assuntos
Persea/química , Polifenóis/química , Sementes/química , Espectrometria de Massas em Tandem/métodos , Catequina/química , Colômbia , Ácidos Cumáricos/química , Fenóis/química , Proantocianidinas/química
13.
Anal Bioanal Chem ; 411(27): 7147-7156, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31492999

RESUMO

Ester and amide derivatives of hydroxycinnamic acids are found in black cohosh (Actaea racemosa) and other Actaea plants. These two compound groups were evaluated for authentication of black cohosh dietary supplements. The hydroxycinnamic acid esters (HCAE) were profiled by ultra-performance liquid chromatography-photodiode array detection (UPLC-PDA). The hydroxycinnamic acid amides (HCAA) were acquired simultaneously by mass spectrometry-multiple reaction monitoring (UPLC-MRM) mode. In contrast with the traditional HCAE method using 8 compounds, profiles of HCAA using only 4 feruloyl dopamine-O-hexosides was more convenient for peak by peak comparison. Partial least square discriminant analysis (PLS-DA) was applied to both HCAE and HCAA datasets. Authenticated plant samples of five Actaea species were randomly divided into training and test sets to build and validate the two PLS-DA models. Both models provided reasonable estimates for the classification of A. racemosa and other Actaea plant samples. However, HCAA model performs better in sensitivity, specificity, and accuracy. Assessment of supplement samples provided quite different results for the solid and liquid dietary supplement samples, indicating the dosage form could affect the composition of marker compounds. Graphical abstract.


Assuntos
Actaea/química , Ácidos Cumáricos/química , Suplementos Nutricionais/análise , Amidas/análise , Cromatografia Líquida/métodos , Contaminação de Medicamentos , Ésteres/análise , Limite de Detecção , Espectrometria de Massas/métodos , Espectrofotometria Ultravioleta
14.
J Agric Food Chem ; 67(40): 11053-11065, 2019 Oct 09.
Artigo em Inglês | MEDLINE | ID: mdl-31525973

RESUMO

Oilseed rape (Brassica napus L.) is the second highest yielding oil crop worldwide. In addition to being used as an edible oil and a feed for livestock, rapeseed has high ornamental value. In this study, we identified and characterized the main floral major constituents, including phenolic acids and flavonoids components, in rapeseed accessions with different-colored petals. A total of 144 constituents were identified using ultrahigh-performance liquid chromatography-HESI-mass spectrometry (UPLC-HESI-MS/MS), 57 of which were confirmed and quantified using known standards and mainly contained phenolic acids, flavonoids, and glucosinolates compounds. Most of the epicatechin, quercetin, and isorhamnetin derivates were found in red and pink petals of B. napus, while kaempferol derivates were in yellow and pale white petals. Moreover, petal-specific compounds, including a putative hydroxycinnamic acid derivative, sinapoyl malate, 1-O-sinapoyl-ß-d-glucose, feruloyl glucose, naringenin-7-O-glucoside, cyanidin-3-glucoside, cyanidin-3,5-di-O-glucoside, petunidin-3-O-ß-glucopyranoside, isorhamnetin-3-O-glucoside, kaempferol-3-O-glucoside-7-O-glucoside, quercetin-3,4'-O-di-ß-glucopyranoside, quercetin-3-O-glucoside, and delphinidin-3-O-glucoside, might contribute to a variety of petal colors in B. napus. In addition, bound phenolics were tentatively identified and contained three abundant compounds (p-coumaric acid, ferulic acid, and 8-O-4'-diferulic acid). These results provide insight into the molecular mechanisms underlying petal color and suggest strategies for breeding rapeseed with a specific petal color in the future.


Assuntos
Brassica napus/química , Flores/química , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão/métodos , Cor , Ácidos Cumáricos/química , Flavonoides/química , Hidroxibenzoatos/química , Quempferóis/química , Espectrometria de Massas em Tandem/métodos
15.
Environ Sci Pollut Res Int ; 26(31): 31675-31684, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31482528

RESUMO

Oxidative stress is an imbalance between free radicals and antioxidants which leads to reactive oxygen species (ROS) production in cells. Reactive oxygen species contains oxygen radicals that easily react with other molecules in the biological system. For decades, lead acetate (Pb(C2H3O2)2) is used as an additive for many widely used chemical products such as insecticides, hair dyes, and cosmetics; however, contact with lead acetate may irritate skin, eyes, and mucous membranes.In the present study, the antioxidant and anti-inflammatory effect of using ferulic acid to inhibit lead acetate-induced toxicity in rats is investigated. Lead acetate was orally given at a dose of 20 mg/kg body weight for 10 days, either alone or with ferulic acid at dose 25 mg/kg. Serum luteinizing hormone (LH), total testosterone, and follicle-stimulating hormone (FSH) levels were measured. Also, reactive oxygen species (ROS), lipid peroxidation (LPO), total antioxidant capacity (TAC), and catalase (CAT) activities were determined. In addition, histopathological changes of testes and kidney were examined. Results showed that administration of lead acetate induced oxidative stress through attenuation of luteinizing hormone, total testosterone, and follicle-stimulating hormone levels in serum. Moreover, the kidney and testes of lead acetate-treated animals exhibited elevation of ROS level, lipid peroxide levels, as well as lysosomal enzyme activity such acid phosphatase and N-acetyl-ß-glucosminidase. DNA fragmentation and histological changes were also observed in lead acetate-treated group. In contrast, ferulic acid treatment reduced the deleterious effects induced by lead acetate in both testes and kidney tissues. These results illustrated that ferulic acid has a protective action against toxicity caused by lead acetate in rats. In conclusions, ferulic acid may have future therapeutic relevance in the prevention of lead acetate-induced testicular and renal toxicity in rats.


Assuntos
Antioxidantes/metabolismo , Ácidos Cumáricos/análise , Dano ao DNA/efeitos dos fármacos , Radicais Livres/metabolismo , Rim/efeitos dos fármacos , Chumbo/metabolismo , Peroxidação de Lipídeos/efeitos dos fármacos , Hormônio Luteinizante/sangue , Estresse Oxidativo/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Testículo/efeitos dos fármacos , Animais , Ácidos Cumáricos/química , Radicais Livres/química , Hormônio Luteinizante/química , Masculino , Ratos , Ratos Wistar , Espécies Reativas de Oxigênio/química
16.
Food Chem ; 301: 125254, 2019 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-31398672

RESUMO

Researches based on metal complexes of plant-derived phenolic acids have attracted much attention due to their beneficial applications in the development of functional food products, dietary supplements and pharmacology. Binding of phenolic acids with serum proteins greatly influences their pharmacological properties. In this context, interactions of a naturally occurring phenolic acid, sinapic acid (SA) and its Cu2+ complex with a model transport protein, bovine serum albumin (BSA), have been explored by means of different spectroscopic and theoretical tools. Spectroscopic studies revealed that the interaction of SA and its Cu2+ complex with BSA occurred through quenching of intrinsic fluorescence of BSA. Site-specific experimental and docking studies were performed to predict the binding site. The geometies of bound Cu2+ and interacting residues of protein were predicted from a solution dynamics study. Interestingly, the complexation of SA with Cu2+ enhanced the antioxidant activity of SA.


Assuntos
Cobre/química , Ácidos Cumáricos/química , Ácidos Cumáricos/metabolismo , Simulação de Acoplamento Molecular , Compostos Organometálicos/química , Compostos Organometálicos/metabolismo , Soroalbumina Bovina/metabolismo , Animais , Sítios de Ligação , Bovinos , Ligação Proteica , Conformação Proteica , Soroalbumina Bovina/química , Espectrometria de Fluorescência , Termodinâmica
17.
Mol Cell Biochem ; 462(1-2): 25-31, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31440879

RESUMO

Resveratrol, a phytoalexin present in grapes and other edible foods, has been reported to have beneficial effects against various diseases including cancer. We previously reported that resveratrol and its derivative, caffeic acid-adducted resveratrol, selectively inhibit the three-dimensional (3D) proliferation of a human colorectal cancer cell line, HCT116 with activating KRAS mutation. Herein, we demonstrated that a novel compound, ferulic acid-bound resveratrol, also represses the 3D proliferation of HCT116 cells. We observed that resveratrol conjugated to two ferulic acids represses the 3D proliferation of HCT116 cells more strongly than resveratrol and resveratrol conjugated to one ferulic acid. Resveratrol conjugated to two ferulic acids also inhibited the 3D proliferation of MCF7 human breast cancer cells. We further uncovered that the resveratrol derivative increases the mRNA level of the tumor suppressor p15, a CDK inhibitor that functions as a brake of cell proliferation in HCT116 cells. These results imply that the resveratrol derivative represses 3D proliferation via increasing p15 expression in HCT116 cells.


Assuntos
Neoplasias Colorretais/genética , Neoplasias Colorretais/patologia , Ácidos Cumáricos/farmacologia , Inibidor de Quinase Dependente de Ciclina p15/genética , Genes Supressores de Tumor , Resveratrol/farmacologia , Proliferação de Células/efeitos dos fármacos , Ácidos Cumáricos/química , Inibidor de Quinase Dependente de Ciclina p15/metabolismo , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células HCT116 , Humanos , Concentração Inibidora 50 , Células MCF-7 , RNA Mensageiro/genética , RNA Mensageiro/metabolismo , Resveratrol/química
18.
Int J Nanomedicine ; 14: 4589-4599, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31296988

RESUMO

Purpose: Ferulic acid (FA) is a poorly water-soluble natural antioxidant with anticancer activity. This poor solubility limits the application of FA in the food and pharmaceutical industry. Cyclodextrin nanosponges (CD-NSs) are a novel group of cross-linked CD derivatives which can be used to enhance the solubility of low-soluble bioactive compounds. Methods: In this study, FA was encapsulated into the NSs in the proportion of 1:4 (FA:NS). Diphenyl carbonate was used as a cross-linker in different proportions with ß-CD. Characterization of obtained NSs was performed using scanning electron microscopy, X-ray diffraction (XRD), differential scanning calorimetry (DSC), and Fourier transform infrared (FTIR) analysis. Results: Our results revealed that the solubility of encapsulated FA was increased up to fifteenfold compared with pure FA in the proportion of 1:4 (CD:cross-linker). The results of FTIR, XRD, and DSC confirmed the interaction of FA with NSs. The cytotoxicity of encapsulated FA against MCF7 and 4T1 breast cancer cell lines was investigated using different concentrations of FA in 24, 48, and 72 hrs. The cytotoxicity assay indicated that FA treatment reduced viability and enhanced apoptosis of cancer cells. IC50 value of encapsulated FA (250 ppm) was decreased by threefold when compared with pure FA (750 ppm). Conclusion: In general, CD-NS was found to be a suitable delivery system for poorly soluble bioactives such as FA.


Assuntos
Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Ciclodextrinas/química , Nanoestruturas/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/patologia , Varredura Diferencial de Calorimetria , Linhagem Celular Tumoral , Liberação Controlada de Fármacos , Feminino , Humanos , Microscopia Eletrônica de Varredura , Solubilidade , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Difração de Raios X
19.
Eur J Med Chem ; 180: 111-120, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31301562

RESUMO

N-methyl-d-aspartate receptors (NMDAR) are critically involved in the pathogenesis of Alzheimer's disease (AD). Acting as an open-channel blocker, the anti-AD drug memantine preferentially targets NMDAR overactivation, which has been proposed to trigger neurotoxic events mediated by amyloid ß peptide (Aß) and oxidative stress. In this study, we applied a multifunctional approach by conjugating memantine to ferulic acid, which is known to protect the brain from Aß neurotoxicity and neuronal death caused by ROS. The most interesting compound (7) behaved, like memantine, as a voltage-dependent antagonist of NMDAR (IC50 = 6.9 µM). In addition, at 10 µM concentration, 7 exerted antioxidant properties both directly and indirectly through the activation of the Nrf-2 pathway in SH-SY5Y cells. At the same concentration, differently from the parent compounds memantine and ferulic acid alone, it was able to modulate Aß production, as revealed by the observed increase of the non-amyloidogenic sAPPα in H4-SW cells. These findings suggest that compound 7 may represent a promising tool for investigating NMDAR-mediated neurotoxic events involving Aß burden and oxidative damage.


Assuntos
Doença de Alzheimer/tratamento farmacológico , Peptídeos beta-Amiloides/antagonistas & inibidores , Ácidos Cumáricos/farmacologia , Memantina/farmacologia , Fármacos Neuroprotetores/farmacologia , Receptores de N-Metil-D-Aspartato/antagonistas & inibidores , Doença de Alzheimer/patologia , Peptídeos beta-Amiloides/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Ácidos Cumáricos/síntese química , Ácidos Cumáricos/química , Relação Dose-Resposta a Droga , Humanos , Memantina/síntese química , Memantina/química , Estrutura Molecular , Fármacos Neuroprotetores/síntese química , Fármacos Neuroprotetores/química , Estresse Oxidativo/efeitos dos fármacos , Receptores de N-Metil-D-Aspartato/metabolismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
20.
Int J Biol Macromol ; 138: 244-251, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31279877

RESUMO

The objective of this study was to develop zein-casein-lysine nanoparticles to modulate the intestinal permeability of ferulic acid (FA), a bioactive compound with proven antioxidant properties. The nanoparticles were obtained by a liquid-liquid dispersion method and were characterized in terms of mean size, polydispersity index, zeta potential, association efficiency (AE), in vitro drug release, x-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR). The in vitro intestinal permeability of nanoparticles was evaluated through Caco-2 and Caco-2/HT29-MTX monoculture and co-culture models, respectively. Nanoparticles presented a mean size of 199 nm and zeta potential of -26 mV. The AE of FA was 23% evaluated by high-performance liquid chromatography (HPLC). XRD showed amorphization of FA after association and FT-IR showed no changes in chemical structures of the compounds after nanoencapsulation. The cytotoxicity assays demonstrated that multicomposite nanoparticles presented a safe profile against Caco-2 and HT29-MTX cells. In the in vitro permeability assay, free FA exhibited higher permeability compared to FA-loaded nanoparticles, possibly due to prolonged FA release from nanoparticles. These new developed zein-casein-lysine nanoparticles may be used for FA sustained delivery by the oral route.


Assuntos
Caseínas/química , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Mucosa Intestinal/metabolismo , Lisina/química , Nanopartículas/química , Zeína/química , Administração Oral , Células CACO-2 , Sobrevivência Celular/efeitos dos fármacos , Ácidos Cumáricos/administração & dosagem , Portadores de Fármacos/química , Liberação Controlada de Fármacos , Humanos , Mucosa Intestinal/efeitos dos fármacos
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