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1.
Molecules ; 26(12)2021 Jun 20.
Artigo em Inglês | MEDLINE | ID: mdl-34203057

RESUMO

A biosensing membrane base on ferulic acid and glucose oxidase is synthesized onto a carbon paste electrode by electropolymerization via cyclic voltammetry in aqueous media at neutral pH at a single step. The developed biosensors exhibit a linear response from 0.082 to 34 mM glucose concentration, with a coefficient of determination R2 equal to 0.997. The biosensors display a sensitivity of 1.1 µAmM-1 cm-2, a detection limit of 0.025 mM, and 0.082 mM as glucose quantification limit. The studies reveal stable, repeatable, and reproducible biosensors response. The results indicate that the novel poly-ferulic acid membrane synthesized by electropolymerization is a promising method for glucose oxidase immobilization towards the development of glucose biosensors. The developed glucose biosensors exhibit a broader linear glucose response than other polymer-based glucose biosensors.


Assuntos
Técnicas Biossensoriais/métodos , Carbono/química , Ácidos Cumáricos/química , Técnicas Eletroquímicas/métodos , Glucose Oxidase/metabolismo , Glucose/análise , Polímeros/química , Técnicas Biossensoriais/normas , Eletrodos , Enzimas Imobilizadas , Glucose Oxidase/química , Limite de Detecção
2.
Molecules ; 26(9)2021 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-34068636

RESUMO

The polyphenols curcumin (CU) and ferulic acid (FA) are able to inhibit the aggregation of amyloid-ß (Aß) peptide with different strengths. CU is a strong inhibitor while FA is a weaker one. In the present study, we examine the effects of CU and FA on the folding process of an Aß monomer by 1 µs molecular dynamics (MD) simulations. We found that both inhibitors increase the helical propensity and decrease the non-helical propensity of Aß peptide. They prevent the formation of a dense bulk core and shorten the average lifetime of intramolecular hydrogen bonds in Aß. CU makes more and longer-lived hydrogen bonds, hydrophobic, π-π, and cation-π interactions with Aß peptide than FA does, which is in a good agreement with the observed stronger inhibitory activity of CU on Aß aggregation.


Assuntos
Peptídeos beta-Amiloides/química , Ácidos Cumáricos/farmacologia , Curcumina/farmacologia , Dobramento de Proteína , Ácidos Cumáricos/química , Curcumina/química , Ligação de Hidrogênio , Ligantes , Modelos Moleculares , Dobramento de Proteína/efeitos dos fármacos , Estabilidade Proteica/efeitos dos fármacos , Estrutura Secundária de Proteína , Solventes , Eletricidade Estática
3.
Int J Mol Sci ; 22(9)2021 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-34062799

RESUMO

In recent years, researchers have focused on developing simple and efficient methods based on electrochemical biosensors to determine hydroxycinnamic acids from various real samples (wine, beer, propolis, tea, and coffee). Enzymatic biosensors represent a promising, low-cost technology for the direct monitoring of these biologically important compounds, which implies a fast response and simple sample processing procedures. The present review aims at highlighting the structural features of this class of compounds and the importance of hydroxycinnamic acids for the human body, as well as presenting a series of enzymatic biosensors commonly used to quantify these phenolic compounds. Enzyme immobilization techniques on support electrodes are very important for their stability and for obtaining adequate results. The following sections of this review will briefly describe some of the laccase (Lac) and tyrosinase (Tyr) biosensors used for determining the main hydroxycinnamic acids of interest in the food or cosmetics industry. Considering relevant studies in the field, the fact has been noticed that there is a greater number of studies on laccase-based biosensors as compared to those based on tyrosinase for the detection of hydroxycinnamic acids. Significant progress has been made in relation to using the synergy of nanomaterials and nanocomposites for more stable and efficient enzyme immobilization. These nanomaterials are mainly carbon- and/or polymer-based nanostructures and metallic nanoparticles which provide a suitable environment for maintaining the biocatalytic activity of the enzyme and for increasing the rate of electron transport.


Assuntos
Técnicas Biossensoriais , Ácidos Cumáricos/isolamento & purificação , Lacase/isolamento & purificação , Monofenol Mono-Oxigenase/isolamento & purificação , Carbono/química , Ácidos Cumáricos/química , Técnicas Eletroquímicas , Enzimas Imobilizadas/química , Humanos , Lacase/química , Nanopartículas Metálicas/química , Monofenol Mono-Oxigenase/química
4.
Molecules ; 26(11)2021 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-34072250

RESUMO

In order to extract antioxidant phenolic compounds from spent grain (SG) two extraction methods were studied: the ultrasound-assisted method (US) and the Ultra-Turrax method (high stirring rate) (UT). Liquid to solid ratios, solvent concentration, time, and temperature/stirring rate were optimized. Spent grain extracts were analyzed for their total phenol content (TPC) (0.62 to 1.76 mg GAE/g SG DW for Ultra-Turrax pretreatment, and 0.57 to 2.11 mg GAE/g SG DW for ultrasound-assisted pretreatment), total flavonoid content (TFC) (0.6 to 1.67 mg QE/g SG DW for UT, and 0.5 to 1.63 mg QE/g SG DW for US), and antioxidant activity was measured using 2,2-diphenyl-2-picrylhydrazyl (DPPH) free radical (25.88% to 79.58% for UT, and 27.49% to 78.30% for UT). TPC was greater at a high stirring rate and high exposure time up to a certain extent for the Ultra-Turrax method, and at a high temperature for the ultrasound-assisted method. P-coumaric acid (20.4 ± 1.72 mg/100 SG DW for UT, and 14.0 ± 1.14 mg/100 SG DW for US) accounted for the majority of the phenolic found compounds, followed by rosmarinic (6.5 ± 0.96 mg/100 SG DW for UT, and 4.0 ± 0.76 mg/100 SG DW for US), chlorogenic (5.4 ± 1.1 mg/100 SG DW for UT, and non-detectable for US), and vanillic acids (3.1 ± 0.8 mg/100 SG DW for UT, and 10.0 ± 1.03 mg/100 SG DW for US) were found in lower quantities. Protocatechuic (0.7 ± 0.05 mg/100 SG DW for UT, and non-detectable for US), 4-hydroxy benzoic (1.1 ± 0.06 mg/100 SG DW for UT, and non-detectable for US), and caffeic acids (0.7 ± 0.03 mg/100 SG DW for UT, and non-detectable for US) were present in very small amounts. Ultrasound-assisted and Ultra-Turrax pretreatments were demonstrated to be efficient methods to recover these value-added compounds.


Assuntos
Bebidas Alcoólicas/análise , Tecnologia de Alimentos/métodos , Fenol/química , Antioxidantes/química , Compostos de Bifenilo/química , Ácidos Cafeicos/química , Cromatografia Líquida de Alta Pressão , Ácidos Cumáricos/química , Flavonoides/química , Radicais Livres , Hidroxibenzoatos , Picratos/química , Extratos Vegetais/química , Análise de Regressão , Solventes/química , Espectrofotometria , Espectroscopia de Infravermelho com Transformada de Fourier , Temperatura , Ultrassom
5.
Molecules ; 26(10)2021 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-34069043

RESUMO

Cherries are rich in bioactive phenolic compounds and are often fermented into cherry wines. The degradation of anthocyanins during storage will cause color deterioration. The study aimed to utilize sinapic acid and grape tannins in cherry wine to maintain a high fraction in the colored forms of anthocyanins, in order to maximize the color intensity, the latter being associated with good product quality. The effects on the anthocyanin profile and on color parameters of copigments, utilizing spectral measurement combined with UPLC-MS quantitative analysis, have been evaluated in sweet cherry wines. The copigmentation effect of sinapic acid and grape tannin was accompanied by the bathochromic shift and the hyperchromic effect, which lead to an increase in color intensity (lower L*, higher a* and b*). During the aging process, sinapic and grape tannin increased the content of pyranoanthocyanins in cherry wine, especially the addition of sinapic acid makes the cherry wine generate 10-syringyl-pyranocyanidin-3-rutinoside. These results demonstrate that sinapic acid is suitable for adding before alcohol fermentation, while grape tannins can be added before aging.


Assuntos
Antocianinas/análise , Ácidos Cumáricos/análise , Prunus avium/química , Taninos/análise , Vinho/análise , Antocianinas/química , Cor , Ácidos Cumáricos/química , Pigmentação , Análise de Componente Principal , Proantocianidinas/análise , Proantocianidinas/química , Espectrofotometria Ultravioleta , Taninos/química
6.
Int J Mol Sci ; 22(10)2021 May 12.
Artigo em Inglês | MEDLINE | ID: mdl-34065957

RESUMO

The presented research concerns the triple activity of trans-cinnamic (tCA), ferulic (FA) and syringic acids (SA). They act as thyroid peroxidase (TPO) activators, lipoxygenase (LOX) inhibitors and show antiradical activity. All compounds showed a dose-dependent TPO activatory effect, thus the AC50 value (the concentration resulting in 50% activation) was determined. The tested compounds can be ranked as follows: tCA > FA > SA with AC50 = 0.10, 0.39, 0.69 mM, respectively. Strong synergism was found between FA and SA. The activatory effects of all tested compounds may result from interaction with the TPO allosteric site. It was proposed that conformational change resulting from activator binding to TPO allosteric pocket results from the flexibility of a nearby loop formed by residues Val352-Tyr363. All compounds act as uncompetitive LOX inhibitors. The most effective were tCA and SA, whereas the weakest was FA (IC50 = 0.009 mM and IC50 0.027 mM, respectively). In all cases, an interaction between the inhibitors carboxylic groups and side-chain atoms of Arg102 and Arg139 in an allosteric pocket of LOX was suggested. FA/tCA and FA/SA acted synergistically, whereas tCA/SA demonstrated antagonism. The highest antiradical activity was found in the case of SA (IC50 = 0.22 mM). FA/tCA and tCA/SA acted synergistically, whereas antagonism was found for the SA/FA mixture.


Assuntos
Autoantígenos/metabolismo , Ativadores de Enzimas/farmacologia , Iodeto Peroxidase/metabolismo , Proteínas de Ligação ao Ferro/metabolismo , Inibidores de Lipoxigenase/farmacologia , Compostos Fitoquímicos/farmacologia , Proteína-Lisina 6-Oxidase/metabolismo , Autoantígenos/química , Cinamatos/química , Cinamatos/farmacologia , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Relação Dose-Resposta a Droga , Ativadores de Enzimas/química , Ácido Gálico/análogos & derivados , Ácido Gálico/química , Ácido Gálico/farmacologia , Humanos , Concentração Inibidora 50 , Iodeto Peroxidase/química , Proteínas de Ligação ao Ferro/química , Inibidores de Lipoxigenase/química , Modelos Moleculares , Compostos Fitoquímicos/química , Proteína-Lisina 6-Oxidase/química , Relação Estrutura-Atividade
7.
Food Chem ; 358: 129872, 2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-33965743

RESUMO

Chemical profiles, distribution, and antioxidant activity of bound phenolics from brown rice were investigated. Four new dehydrodiferulic acid dimers (DFA) along with eighteen known phenolics were isolated from brown rice bound phenolic extracts and their structures were determined by multiple spectroscopic methods. Among them, ferulic acid and 8-5' DFA were the most abundant monomeric and dimeric bound phenolics in brown rice, rice bran and polished rice. In whole brown rice, polished rice contributed more than 50% of three phenolic monomers and six phenolic dimers, while rice bran contributed more than half of the other thirteen phenolics including eight monomers, four dimers, and one trimer. All the isolated compounds exhibited oxygen radical absorbance capacity. Thomasidioic acid, caffeic acid, methyl caffeate, and 8-5' DC DFA displayed potent peroxyl radical scavenging capacity, and the last three compounds also showed moderate cellular antioxidant activity.


Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Oryza/química , Fenóis/química , Grãos Integrais/química , Ácidos Cumáricos/análise , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Peróxidos/química , Fenóis/análise , Fenóis/farmacologia , Extratos Vegetais/química
8.
Molecules ; 26(6)2021 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-33804141

RESUMO

In this work, a green extraction technique, subcritical water extraction (SBWE), was employed to extract active pharmaceutical ingredients (APIs) from an important Chinese medicinal herb, Salvia miltiorrhiza (danshen), at various temperatures. The APIs included tanshinone I, tanshinone IIA, protocatechualdehyde, caffeic acid, and ferulic acid. Traditional herbal decoction (THD) of Salvia miltiorrhiza was also carried out for comparison purposes. Reproduction assay of herbal extracts obtained by both SBWE and THD were then conducted on Caenorhabditis elegans so that SBWE conditions could be optimized for the purpose of developing efficacious herbal medicine from Salvia miltiorrhiza. The extraction efficiency was mostly enhanced with increasing extraction temperature. The quantity of tanshinone I in the herbal extract obtained by SBWE at 150 °C was 370-fold higher than that achieved by THD extraction. Reproduction evaluation revealed that the worm reproduction rate decreased and the reproduction inhibition rate increased with elevated SBWE temperatures. Most importantly, the reproduction inhibition rate of the SBWE herbal extracts obtained at all four temperatures investigated was higher than that of traditional herbal decoction extracts. The results of this work show that there are several benefits of subcritical water extraction of medicinal herbs over other existing herbal medicine preparation techniques. Compared to THD, the thousand-year-old and yet still popular herbal preparation method used in herbal medicine, subcritical water extraction is conducted in a closed system where no loss of volatile active pharmaceutical ingredients occurs, although analyte degradation may happen at higher temperatures. Temperature optimization in SBWE makes it possible to be more efficient in extracting APIs from medicinal herbs than the THD method. Compared to other industrial processes of producing herbal medicine, subcritical water extraction eliminates toxic organic solvents. Thus, subcritical water extraction is not only environmentally friendly but also produces safer herbal medicine for patients.


Assuntos
Extratos Vegetais/química , Salvia miltiorrhiza/química , Água/química , Abietanos/química , Benzaldeídos/química , Ácidos Cafeicos/química , Catecóis/química , Ácidos Cumáricos/química , Medicamentos de Ervas Chinesas/química , Temperatura Alta , Plantas Medicinais/química
9.
Food Chem ; 355: 129587, 2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-33857721

RESUMO

The efficiency of laccase-catalyzed protein cross-linking can be impacted by substrate protein structure and competing reactions. In this study, chemical grafting of ferulic acid (FA) on protein surface was applied to modulate the cross-linking of two inflexible globular proteins, lysozyme (LZM) and ovalbumin (OVA). The extent of FA-grafting was positively correlated with protein cross-linking extent, and determined the molecular weight profile and structures of the cross-linked product. While laccase-catalyzed reactions (with or without free FA mediator) did not lead to evident cross-linking of the native proteins, oligomeric (up to 16.4%), polymeric (up to 30.6%) FA-LZMs and oligomeric FA-OVA (5.1-31.1%) were obtained upon the enzymatic treatments. The cross-linking on the grafted FA sites occurred mainly through the formation of 8-5'-noncyclic-dehydro-diferulic linkages. The effects of investigated cross-linking approach on the emulsifying, foaming properties and the immunoglobulin E (IgE) binding capacity of LZM and OVA were also evaluated in relation to the structural properties of cross-linked proteins.


Assuntos
Imunoglobulina E/imunologia , Lacase/metabolismo , Muramidase/imunologia , Ovalbumina/imunologia , Fenóis/química , Reações Antígeno-Anticorpo , Biocatálise , Ácidos Cumáricos/química , Reagentes para Ligações Cruzadas/química , Humanos , Peso Molecular , Muramidase/química , Ovalbumina/química , Oxirredução
10.
Molecules ; 26(9)2021 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-33922767

RESUMO

When dealing with simple phenols such as caffeic acid (CA) and ferulic acid (FA), found in a variety of plants, it is very important to have control over the most important factors that accelerate their degradation reactions. This is the first report in which the stabilities of these two compounds have been systematically tested by exposure to various different factors. Forced degradation studies were performed on pure standards (trans-CA and trans-FA), dissolved in different solvents and exposed to different oxidative, photolytic and thermal stress conditions. Additionally, a rapid, sensitive, and selective stability-indicating gas chromatographic-mass spectrometric method was developed and validated for determination of trans-CA and trans-FA in the presence of their degradation products. Cis-CA and cis-FA were confirmed as the only degradation products in all the experiments performed. All the compounds were perfectly separated by gas chromatography (GC) and identified using mass spectrometry (MS), a method that additionally elucidated their structures. In general, more protic solvents, higher temperatures, UV radiation and longer storage times led to more significant degradation (isomerization) of both trans-isomers. The most progressive isomerization of both compounds (up to 43%) was observed when the polar solutions were exposed to daylight at room temperature for 1 month. The method was validated for linearity, precision as repeatability, limit of detection (LOD) and limit of quantitation (LOQ). The method was confirmed as linear over tested concentration ranges from 1-100 mg L-1 (r2s were above 0.999). The LOD and LOQ for trans-FA were 0.15 mg L-1 and 0.50 mg L-1, respectively. The LOD and LOQ for trans-CA were 0.23 mg L-1 and 0.77 mg L-1, respectively.


Assuntos
Ácidos Cafeicos/química , Ácidos Cumáricos/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Cromatografia Líquida de Alta Pressão
11.
Biomed Res Int ; 2021: 6624347, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33880371

RESUMO

Distichochlamys benenica is a native black ginger that grows in Vietnam. In point of fact, there is limitation of available information in the literature making mention of the chemical constituents and bioactive properties of this plant. This study is aimed at isolating trans-o-coumaric acid (1), trans-cinnamic acid (2), and borneol (3) from the rhizomes of D. benenica Q.B.Nguyen & Skornick and evaluate the anti-inflammatory and antimicrobial activities of 1-3 using the carrageenan paw edema model and the dilution broth method, respectively. This revealed that 1 was as effective as diclofenac in reducing the intensity of the edema development. The in silico research showed that the activity of 1 might be derived from inhibiting COX-2 by generating h-bonds at the positions of Arg 120, Tyr 355, and Arg 513 residues. The antimicrobial activities against Gram-positive strains (Staphylococcus aureus and Bacillus subtilis) were comparable, with the minimum inhibitory concentrations ranging from 1.52 to 3.37 mM. This is the first study of the bioactivity of compounds isolated from D. benenica Q.B.Nguyen & Skornick. Our results suggest that 1 may be a nature-derived compound which demonstrates the anti-inflammatory properties and inhibit the proliferation of several Gram-positive bacteria.


Assuntos
Anti-Infecciosos/farmacologia , Anti-Inflamatórios/farmacologia , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Zingiberaceae/química , Animais , Anti-Infecciosos/química , Anti-Inflamatórios/química , Anti-Inflamatórios/uso terapêutico , Bactérias/efeitos dos fármacos , Sítios de Ligação , Carragenina , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacologia , Ácidos Cumáricos/uso terapêutico , Ciclo-Oxigenase 2/metabolismo , Diclofenaco/administração & dosagem , Diclofenaco/farmacologia , Diclofenaco/uso terapêutico , Edema/tratamento farmacológico , Edema/patologia , Camundongos , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/uso terapêutico
12.
Molecules ; 26(4)2021 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-33669666

RESUMO

Preliminary bioassay-guided fractionation was performed to identify cytotoxic compounds from Hechtia glomerata, a plant that is used in Mexican ethnomedicine. Organic and aqueous extracts were prepared from H. glomerata's leaves and evaluated against two cancer cell lines. The CHCl3/MeOH (1:1) active extract was fractionated, and the resulting fractions were assayed against prostate adenocarcinoma PC3 and breast adenocarcinoma MCF7 cell lines. Active fraction 4 was further analyzed by high-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry analysis to identify its active constituents. Among the compounds that were responsible for the cytotoxic effects of this fraction were flavonoids, phenolic acids, and aromatic compounds, of which p-coumaric acid (p-CA) and its derivatives were abundant. To understand the mechanisms that underlie p-CA cytotoxicity, a microarray assay was performed on PC3 cells that were treated or not with this compound. The results showed that mitogen-activated protein kinases (MAPKs) that regulate many cancer-related pathways were targeted by p-CA, which could be related to the reported effects of reactive oxygen species (ROS). A molecular docking study of p-CA showed that this phenolic acid targeted these protein active sites (MAPK8 and Serine/Threonine protein kinase 3) at the same binding site as their inhibitors. Thus, we hypothesize that p-CA produces ROS, directly affects the MAPK signaling pathway, and consequently causes apoptosis, among other effects. Additionally, p-CA could be used as a platform for the design of new MAPK inhibitors and re-sensitizing agents for resistant cancers.


Assuntos
Bromeliaceae/química , Ácidos Cumáricos/farmacologia , Proteínas Quinases Ativadas por Mitógeno/antagonistas & inibidores , Extratos Vegetais/química , Inibidores de Proteínas Quinases/farmacologia , Bioensaio , Morte Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Ácidos Cumáricos/química , Regulação para Baixo/efeitos dos fármacos , Regulação para Baixo/genética , Humanos , Células MCF-7 , Proteínas Quinases Ativadas por Mitógeno/química , Proteínas Quinases Ativadas por Mitógeno/metabolismo , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Células PC-3 , Fenóis/farmacologia , Regulação para Cima/efeitos dos fármacos , Regulação para Cima/genética
13.
Molecules ; 26(4)2021 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-33669973

RESUMO

Phenolic acids represent about one-third of the dietary phenols and are widespread in vegetable and fruits. Several plants belonging to both vegetables and medical herbs have been studied for their hydroxycinnamic acid content. Among them, Echinacea purpurea is preferentially used for caffeic acid-derivatives extraction. The wine industry is a source of by-products that are rich in phenolic compounds. This work demonstrates that unripe grape juice (verjuice) presents a simple high-pressure liquid chromatography (HPLC) profile for hydroxycinnamic acids (HCAs), with a great separation of the caffeic-derived acids and a low content of other phenolic compounds when compared to E. purpurea and other grape by-products. Here it is shown how this allows the recovery of pure hydroxycinnamic acids by a simple and fast method, fast protein liquid chromatography (FPLC). In addition, verjuice can be easily obtained by pressing grape berries and filtering, thus avoiding any extraction step as required for other vegetable sources. Overall, the proposed protocol could strongly reduce the engagement of solvent in industrial phenolic extraction.


Assuntos
Ácidos Cumáricos/química , Fenóis/isolamento & purificação , Vitis/química , Cromatografia Líquida de Alta Pressão , Sucos de Frutas e Vegetais/análise , Estrutura Molecular , Fenóis/química
14.
Int J Biol Macromol ; 177: 463-473, 2021 Apr 30.
Artigo em Inglês | MEDLINE | ID: mdl-33609580

RESUMO

Here we report the preparation of biomimetic fibrin/chitosan/keratin hybrid scaffolds with a synergistic combination of ferulic acid loaded silica microspheres for antimicrobial wound dressing applications. The infrared and X-ray powder diffraction studies confirm the homogenous nature of the prepared hybrid scaffolds without any major interactions between the constituents. The developed hybrid scaffolds show good thermal, porosity, compression and water uptake properties. Scanning electron microscopic analysis shows that the as-synthesized ferulic acid loaded silica microspheres exhibit an average size of 35 ± 10 µm and also exposes the smooth surface with interconnected porosity in the prepared hybrid scaffolds. The incorporated ferulic acid loaded silica microspheres hybrid scaffolds show effective antimicrobial activity against the common wound pathogens. In vitro NIH3T3 fibroblast cell culture and drug release studies reveal that the prepared hybrid scaffolds have enhanced cell proliferation and adhesion with a prolonged drug release for about 72 h. In vitro wound healing and actin cytoskeleton analysis reveal that the incorporated ferulic acid loaded silica microspheres in fibrin/chitosan/keratin hybrid scaffolds facilitates cell growth and migration to damaged area through cell-cell interactions. These results suggest that the prepared hybrid scaffolds with ferulic acid loaded silica microspheres have great potential for soft tissue engineering applications particularly for the treatment of chronic and infected wounds.


Assuntos
Anti-Infecciosos/química , Bandagens , Ácidos Cumáricos/química , Escherichia coli/crescimento & desenvolvimento , Microesferas , Staphylococcus aureus/crescimento & desenvolvimento , Animais , Camundongos , Células NIH 3T3
15.
Food Chem ; 349: 129166, 2021 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-33550019

RESUMO

Grafting copolymerization of phenolic acids onto polysaccharides is an important strategy to improve their biological activities. In this study, ferulic acid (FA)-grafted carboxylic curdlan conjugates, namely, Cur-8-g-FA, Cur-24-g-FA, and Cur-48-g-FA, were synthesized by free radical-induced grafting. Results showed that FA was covalently grafted onto carboxylic curdlans via ester bonds. The grafting ratios of Cur-8-g-FA, Cur-24-g-FA, and Cur-48-g-FA were 223.03 ± 12.63, 115.63 ± 5.96, and 152.30 ± 4.57 mg FA/g, respectively, which were related with the carboxylate contents, molecular weights, and chain conformations of carboxylic curdlans. Compared with carboxylic curdlans, the FA-grafted carboxylic curdlan conjugates had lower thermal stability, molecular weight, and rheological property and looser surface morphology but had more prominent antioxidant benefits in vitro, which were proportional to their grafting ratios. Moreover, good storage stability against chemical degradation was exhibited by the ß-carotene in Pickering emulsions stabilized by Cur-8-g-FA with a high grafting ratio and molecular weight.


Assuntos
Antioxidantes/química , Ácidos Carboxílicos/química , Ácidos Cumáricos/química , beta Caroteno/química , beta-Glucanas/química , Emulsões/química , Radicais Livres/química , Hidroxibenzoatos , Peso Molecular
16.
Food Chem Toxicol ; 149: 111978, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33428987

RESUMO

Phenolic acids can improve obesity-related and metabolic syndrome-related conditions including non-alcoholic fatty liver disease (NAFLD). In this study, the effects of ferulic acid (FA) on the metabolic changes related to NAFLD were investigated in oleic acid (OA)-treated HepG2 cells and C57BL/6 mice fed a high fat diet (HFD). In vitro, FA (25 and 50 µg/mL) treatment significantly reduced cellular lipid accumulation with no obvious cytotoxicity, in-part mediated by the suppression of ERK1/2, JNK1/2/3, and HGMB1 expression. However, in vivo administration of FA (20 mg/kg bw·day) for 17 weeks led to no obvious effects on body weight and liver weight gain, blood lipid profiles, or histological abnormalities in obese C57BL/6 mice induced by HFD. Taken together, the positive effects of FA on the reduction of hepatic triglyceride accumulation were therefore demonstrated in cellular model, while its hepatic protective effects might need to be further explored in rodent models and clinical trials.


Assuntos
Ácidos Cumáricos/farmacologia , Dieta Hiperlipídica/efeitos adversos , Fígado/efeitos dos fármacos , Hepatopatia Gordurosa não Alcoólica/induzido quimicamente , Triglicerídeos/metabolismo , Animais , Sobrevivência Celular , Ácidos Cumáricos/química , Células Hep G2 , Humanos , Fígado/patologia , Camundongos , Camundongos Endogâmicos C57BL , Estrutura Molecular
17.
Life Sci ; 270: 119128, 2021 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-33508299

RESUMO

Nanotechnology-based approaches have enabled overcoming the challenging issues such as the rapid clearance, poor solubility, and non-specific action or cellular uptake of drugs. In this study, we have evaluated the therapeutic effects of the phenolic compound, ferulic acid (FA), in the acute pancreatitis (AP) as this phenolic compound has demonstrated promising effects against the oxidative stress and inflammatory reactions. In order to overcome the poor solubility and bioavailability of FA, it was entrapped into the nanoparticles (NPs) based on the silk fibroin (SF) as a biomimetic substance. Neutrophil membrane-coated SF-NPs with appropriate capacity of FA loading and physicochemical characteristics, released FA in a controlled fashion, selectively delivered FA into the inflammatory pancreas lesion, and demonstrated protective effects against the detrimental aspects of the disease. The prepared nanoformulation by improving the pharmacological profile of FA and targeted delivery could be of therapeutic importance against the AP via suppressing the inflammation and oxidative stress.


Assuntos
Ácidos Cumáricos/farmacologia , Neutrófilos/química , Pancreatite/tratamento farmacológico , Animais , Disponibilidade Biológica , Ácidos Cumáricos/química , Ácidos Cumáricos/metabolismo , Sistemas de Liberação de Medicamentos , Fibroínas/química , Fibroínas/metabolismo , Fibroínas/farmacologia , Masculino , Nanopartículas/química , Neutrófilos/metabolismo , Pancreatite/metabolismo , Tamanho da Partícula , Ratos , Ratos Wistar
18.
Carbohydr Polym ; 256: 117428, 2021 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-33483017

RESUMO

For investigation of antioxidant capacity relationship, four cinnamic acids (CNAs), including cinnamic (CA), ferulic (FA), p-coumaric (p-CA) and sinapic (SA) acids, were selected to modify porous starch (PS) with different degrees of substitution by esterification, respectively. The ester linkage of CNAs modified PS was confirmed by 1H NMR, 13C solid-state NMR and FT-IR. The porous structure was maintained after esterification. Three in vitro antioxidant assays were applied to measure antioxidant capacities. The order of antioxidant capacity was SA@PS > FA@PS > p-CA@PS > CA@PS, due to the presence of phenolic hydroxyl groups with hydrogen donating abilities. Besides electron-donating group on ortho or para positions the benzene ring further enhances the hydrogen donating ability and the stability of hydroxyl radical. This study not only investigated the antioxidant mechanism of CNA modified starch derivatives but probed the way for synthesis of biodegradable antioxidant materials for the food industries.


Assuntos
Antioxidantes/química , Cinamatos/química , Ácidos Cumáricos/química , Amido/química , Compostos de Bifenilo , Isótopos de Carbono , Cristalização , Elétrons , Ésteres , Indústria Alimentícia , Tecnologia de Alimentos , Sequestradores de Radicais Livres/química , Radicais Livres , Hidrogênio/química , Radical Hidroxila , Espectroscopia de Ressonância Magnética , Microscopia Eletrônica de Varredura , Fenol/química , Picratos , Porosidade , Solanum tuberosum , Solubilidade , Espectroscopia de Infravermelho com Transformada de Fourier
19.
Biomed Chromatogr ; 35(2): e4984, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33025603

RESUMO

Rosmarinic acid (RA), an ester compound of caffeic acid (CA) and 3,4-dihydroxyphenyllacic acid, is widely distributed in the herbs of the Lamiaceae family and has shown a wide spectrum of pharmacological properties. CA and FA (ferulic acid) are two bioactive metabolites in vivo after oral administration of RA; however, a rapid and robust analytical approach that can enable the quantitative assay of RA and two bioactive metabolites is still lacking. A liquid chromatography/tandem mass spectrometry method was established that was capable of the quantitative determination of RA, CA and FA by negative-mode multiple reaction monitoring within 7 min using a Zorbax SB-C18 column and an isocratic elution. This assay method was validated as linear over the investigated ranges with correlation coefficients (r) > 0.9950. The intra- and inter-day precision was <10.65%, and the accuracies (relative error, %) <-6.41%. The validated approach was applied to a pharmacokinetics study of RA and its two metabolites in rats after oral and intravenous administration. RA was rapidly metabolized in both administration modes, whilst the metabolites CA and FA were only detectable by oral administration. The absolute availability of RA was calculated to be 4.13%.


Assuntos
Ácidos Cafeicos/sangue , Cromatografia Líquida/métodos , Cinamatos/sangue , Ácidos Cumáricos/sangue , Depsídeos/sangue , Espectrometria de Massas em Tandem/métodos , Animais , Ácidos Cafeicos/química , Ácidos Cafeicos/farmacocinética , Cinamatos/química , Cinamatos/farmacocinética , Ácidos Cumáricos/química , Ácidos Cumáricos/farmacocinética , Depsídeos/química , Depsídeos/farmacocinética , Modelos Lineares , Masculino , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
20.
J Sci Food Agric ; 101(5): 1979-1988, 2021 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-32918287

RESUMO

BACKGROUND: Glutenin macropolymer (GMP), glutenin and gliadin proteins are important indicators of the baking quality of dough. This study investigated the impacts of wheat bran and a mixture of ferulic acid (FA) and dietary fiber (DF) on the constitution of gluten proteins. Addition of wheat bran (100 and 150 g kg-1 ) into gluten decreased the gliadin/glutenin ratio, while the addition of different amounts of FA + DF (C1 group: 20 g kg-1 FA and 60 g kg-1 DF; C2 group: 30 g kg-1 FA and 90 g kg-1 DF) had the opposite effect. RESULTS: The GMP contents of wheat bran groups (B1 group: 100 g kg-1 ; B2 group: 150 g kg-1 ) were similar to that of the control group, and disulfide bond contents were increased. However, both GMP and disulfide bond contents of FA + DF groups significantly decreased. The GMP gel properties and microstructures were destroyed after addition of wheat bran and FA + DF. The wheat bran and FA + DF additives induced different effects on the thermal properties and secondary structures of glutenin, gliadin and GMP. CONCLUSIONS: The results suggest that the interaction mechanism of bran fractions and gluten proteins is not only related to the physicochemical properties of the additives, but also to interactions between the additives and the components of gluten protein. © 2020 Society of Chemical Industry.


Assuntos
Ácidos Cumáricos/química , Fibras na Dieta/análise , Farinha/análise , Gliadina/química , Glutens/química , Triticum/química , Pão/análise
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