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1.
Molecules ; 29(3)2024 Jan 27.
Artículo en Inglés | MEDLINE | ID: mdl-38338357

RESUMEN

With a growing focus on green chemistry, the extraction of natural products with natural deep eutectic solvents (NADES), which are eutectic mixtures of hydrogen bond donors and acceptors, has become an ever-expanding field of research. However, the use of NADES for the extraction of spilanthol from Acmella oleracea (L.) R.K.Jansen has not yet been investigated. Therefore, in this study, 20 choline chloride-based NADES, and for comparison, ethanol, were used as green extraction agents for spilanthol from Acmella oleracea flower heads. The effects of time, water addition, and temperature on NADES extractions were investigated and analysed by HPLC-DAD quantification. Additionally, UHPLC-DAD-ESI-MSn results for dichloromethane extracts, as well as the isolation of spilanthol and other main constituents as reference compounds, are reported. The best green extraction results were achieved by choline chloride (ChCl) with 1,2-propanediol (P, 1:2 molar ratio, +20% water) at 244.58 µg/mL, comparable to yields with ethanol (245.93 µg/mL). Methylurea (MeU, 1:2, +20% water) also showed promising results as a hydrogen bond donor in combination with choline chloride (208.12 µg/mL). In further experiments with NADES ChCl/P (1:2) and ChCl/MeU (1:2), extraction time had the least effect on spilanthol extraction with NADES, while yield decreased with water addition over 20% and increased with extraction temperature up to 80 °C. NADES are promising extraction agents for the extraction of spilanthol, and these findings could lead to applicable extracts for medicinal purposes, due to their non-toxic constituents.


Asunto(s)
Asteraceae , Disolventes Eutécticos Profundos , Alcamidas Poliinsaturadas , Solventes/química , Extractos Vegetales/química , Agua/química , Etanol , Colina/química
2.
Sci Rep ; 14(1): 148, 2024 01 02.
Artículo en Inglés | MEDLINE | ID: mdl-38167968

RESUMEN

Deep eutectic solvents in the extraction of plant metabolites have found many advantages, such as low toxicity, biodegradability, low cost and ease of preparation over the conventional methods. This work aims to compare natural deep eutectic solvents in extraction and optimization of oleoresin from Ferula gummosa and determining its chemical and structure properties. Box-Behnken design was applied to optimize the extraction of oleoresin from Ferula gummosa using eutectic solvents. The variables of extraction were extraction time, temperature, and ratio of eutectic solvents. Six mixtures of eutectic solvents including choline chloride/urea, acetic acid, lactic acid, formic acid, formamide and glycerol at ratios of 2:1 and 3:1 were evaluated. The highest yields were obtained for choline chloride/formic acid, choline chloride/formamide. The quadratic regression equation was set up as a predictive model with an R2 value of 0.85. The optimum condition was 6 h, 40 °C, and ratio 12.5% (w/v). No significant difference was found between the predicted and experimental yield. The main components of the oleoresin were ß-pinene (40.27%), cylcofenchen (11.93%) and α-pinene (7.53%) as characterized by gas chromatography-mass spectrometry. The chemical structure study by spectroscopy showed that no solvents remained in the oleoresin. Therefore, F. gummosa oleoresin can be explored as a novel promising natural pharmaceutical ingredient extracted with eutectic solvents.


Asunto(s)
Disolventes Eutécticos Profundos , Ferula , Solventes/química , Extractos Vegetales/química , Colina/química , Formamidas
3.
Phytochem Anal ; 35(1): 53-63, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37545032

RESUMEN

INTRODUCTION: Deep eutectic solvents (DESs) are promising extractants with tuneable properties. However, there is a lack of reports about the influence of the nature of the original DES on obtaining the metabolomic profile of a plant. OBJECTIVE: The aim of this study is to investigate the possibility of obtaining Iris sibirica L. chromatographical profiles with DESs based on various hydrogen bond donors and acceptors as extraction solvents. METHODOLOGY: DESs were prepared by mixing choline chloride or tetrabutylammonium bromide with various hydrogen bond donors and investigated for the extraction of bioactive substances from biotechnological raw materials of I. sibirica L. The obtained extracts were analysed by HPLC with diode array detector (DAD) and Q-MS. RESULTS: Chromatographic profiles for I. sibirica L. extracts by eight choline chloride DESs and six tetrabutylammonium DESs have been obtained. It has been found that selective recovery of bioactive substances can be achieved by varying the composition of DESs. Eleven phenolic compounds were identified in I. sibirica L. using HPLC-MS. Phase separation was observed with acetonitrile for four DESs. New flavonoid derivatives have been found in DES extracts compared with methanol extracts. CONCLUSION: The results showed the possibility of DES usage for extraction without water addition. Selectivity of DESs varies depending on the chemical composition of hydrogen bond donors and acceptors. Choline chloride is a more suitable hydrogen bond acceptor for the flavonoid extraction. Choline chloride-lactic acid (1:1) DES has demonstrated a metabolic profile that was the closest to the methanol one and enhanced the extraction up to 2.6-fold.


Asunto(s)
Disolventes Eutécticos Profundos , Género Iris , Metanol , Solventes/química , Flavonoides , Extractos Vegetales/química , Colina/química , Fitoquímicos
4.
Ultrason Sonochem ; 98: 106514, 2023 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-37421845

RESUMEN

The aim of this study is to develop an environmentally friendly and effective method for the extraction of nutritious date sugar using natural deep eutectic solvents (NADES) and ultrasound-assisted extraction (USAE). The careful design of a suitable NADES-USAE system was systematically supported by COSMO-RS screening, response surface method (RSM) and artificial neural network (ANN). Initially, 26 natural hydrogen bond donors (HBDs) were carefully screened for sugar affinity using COSMO-RS. The best performing HBDs were then used for the synthesis of 5 NADES using choline chloride (ChCl) as HBA. Among the synthesized NADES, the mixture of ChCl, citric acid (CA) and water (1:1:1 with 20 wt% water) resulted in the highest sugar yield of 78.30 ± 3.91 g/100 g, which is superior to conventional solvents such as water (29.92 ± 1.50 g/100 g). Further enhancements using RSM and ANN led to an even higher sugar recovery of 87.81 ± 2.61 g/100 g, at conditions of 30 °C, 45 min, and a solvent to DFP ratio of 40 mL/g. The method NADES-USAE was then compared with conventional hot water extraction (CHWE) (61.36 ± 3.06) and showed 43.1% higher sugar yield. The developed process not only improves the recovery of the nutritious date sugar but also preserves the heat-sensitive bioactive compounds in dates, making it an attractive alternative to CHWE for industrial utilization. Overall, this study shows a promising approach for the extraction of nutritive sugars from dates using environmentally friendly solvents and advanced technology. It also highlights the potential of this approach for valorizing underutilized fruits and preserving their bioactive compounds.


Asunto(s)
Disolventes Eutécticos Profundos , Azúcares , Ultrasonido , Extractos Vegetales/química , Solventes/química , Agua/química , Colina/química
5.
Food Chem ; 419: 136073, 2023 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-37030208

RESUMEN

The main by-product from olive oil extraction (alperujo) was extracted with hot water, citric acid, natural deep eutectic solvent (choline chloride: citric acid), and only choline chloride. The purified extracts were composed of macromolecular complexes constituting polyphenols associated with pectin. The extracts were structurally characterized by FT-IR and solid-NMR spectroscopy and an in vitro test revealed distinct antioxidant and antiproliferative activity, depending on the extracting agents. The choline chloride-extracted complex contained the highest amount of polyphenols among the examined agents, which exhibited a strong antioxidant activity and significant antiproliferative capacity. However, the complex extracted by hot water showed the highest antiproliferative capacity in vitro against the colon carcinoma Caco-2 cell line. In this finding, choline chloride could be used as a novel, green and promising alternative to the conventional extracting agent for the production of complexes that combine the antioxidant activity of phenolic compounds and the physiological effects of pectic polysaccharides.


Asunto(s)
Olea , Polifenoles , Humanos , Pectinas/farmacología , Extractos Vegetales/farmacología , Extractos Vegetales/química , Colina/química , Antioxidantes/química , Células CACO-2 , Espectroscopía Infrarroja por Transformada de Fourier , Solventes/química , Agua/química , Ácido Cítrico
6.
Environ Sci Pollut Res Int ; 30(55): 116878-116905, 2023 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-36917382

RESUMEN

Natural based deep eutectic solvent (NADES) is a promising green solvent to replace the conventional soil washing solvent due to the environmental benign properties such as low toxicity, high biodegradability, high polarity or hydrophilicity, and low cost of fabrication process. The application of NADES is intensively studied in the extraction of organic compounds or natural products from vegetations or organic matters. Conversely, the use of the solvent in removing heavy metals from soil is severely lacking. This review focuses on the potential application of NADES as a soil washing agent to remove heavy metal contaminants. Hydrophilicity is an important feature of a NADES to be used as a soil washing solvent. In this context, choline chloride is often used as hydrogen bond acceptor (HBA) whereby choline chloride based NADESs showed excellent performance in the extraction of various solutes in the past studies. The nature of NADES along with its chemistry, preparation and designing methods as well as potential applications were comprehensively reviewed. Subsequently, related studies on choline chloride-based NADES in heavy metal polluted soil remediation were also reviewed. Potential applications in removing other soil contaminants as well as the limitations of NADES were discussed based on the current advancements of soil washing and future research directions were also proposed.


Asunto(s)
Disolventes Eutécticos Profundos , Metales Pesados , Solventes/química , Extractos Vegetales/química , Colina/química
7.
Molecules ; 27(19)2022 Oct 06.
Artículo en Inglés | MEDLINE | ID: mdl-36235183

RESUMEN

Avocado peels are the main agro-industrial residue generated during the avocado processing, being a rich source of bioactive compounds like phenolic compounds. The growing demand for more sustainable processes requires the development of new and effective methods for extracting bioactive compounds from industrial waste. Deep eutectic solvents (DESs) are a new sustainable alternative to toxic organic solvents due to their non-toxicity and biocompatibility. In this study, five selected DESs were applied for the extraction of bioactive phenolic compounds from avocado peels. The extraction efficiency was evaluated by measuring the total phenolics and flavonoids content. The best extraction results were obtained with choline chloride-acetic acid and -lactic acid (92.03 ± 2.11 mg GAE/g DAP in TPC and 186.01 ± 3.27 mg RE/g DAP); however, all tested DESs show better extraction efficiency than ethanol. All the obtained NADES extracts have high antioxidant activity (FRAP: 72.5-121.1 mg TE/g; TAC: 90.0-126.1 mg AAE/g). The synthesized DESs and avocado peels DES extracts had activity against all tested bacteria (Staphylococcus aureus, Streptococcus dysgalactiae, Escherichia coli and Pseudomonas putida), and the extracts prepared with choline chloride-acetic acid and -lactic acid have the highest antibacterial activity against all microorganisms. These results, coupled with the non-toxic, biodegradable, low-cost, and environmentally friendly characteristics of DESs, provide strong evidence that DESs represent an effective alternative to organic solvents for the recovery of phenolic bioactive compounds from agro-industrial wastes.


Asunto(s)
Productos Biológicos , Persea , Antibacterianos , Antioxidantes/farmacología , Colina/química , Disolventes Eutécticos Profundos , Etanol , Flavonoides/química , Flavonoides/farmacología , Residuos Industriales , Ácido Láctico , Fenoles , Extractos Vegetales/química , Extractos Vegetales/farmacología , Solventes/química
8.
Int J Mol Sci ; 23(13)2022 Jun 30.
Artículo en Inglés | MEDLINE | ID: mdl-35806268

RESUMEN

Membrane-bound catechol-O-methyltransferase (MBCOMT), present in the brain and involved in the main pathway of the catechol neurotransmitter deactivation, is linked to several types of human dementia, which are relevant pharmacological targets for new potent and nontoxic inhibitors that have been developed, particularly for Parkinson's disease treatment. However, the inexistence of an MBCOMT 3D-structure presents a blockage in new drugs' design and clinical studies due to its instability. The enzyme has a clear tendency to lose its biological activity in a short period of time. To avoid the enzyme sequestering into a non-native state during the downstream processing, a multi-component buffer plays a major role, with the addition of additives such as cysteine, glycerol, and trehalose showing promising results towards minimizing hMBCOMT damage and enhancing its stability. In addition, ionic liquids, due to their virtually unlimited choices for cation/anion paring, are potential protein stabilizers for the process and storage buffers. Screening experiments were designed to evaluate the effect of distinct cation/anion ILs interaction in hMBCOMT enzymatic activity. The ionic liquids: choline glutamate [Ch][Glu], choline dihydrogen phosphate ([Ch][DHP]), choline chloride ([Ch]Cl), 1- dodecyl-3-methylimidazolium chloride ([C12mim]Cl), and 1-butyl-3-methylimidazolium chloride ([C4mim]Cl) were supplemented to hMBCOMT lysates in a concentration from 5 to 500 mM. A major potential stabilizing effect was obtained using [Ch][DHP] (10 and 50 mM). From the DoE 146% of hMBCOMT activity recovery was obtained with [Ch][DHP] optimal conditions (7.5 mM) at -80 °C during 32.4 h. These results are of crucial importance for further drug development once the enzyme can be stabilized for longer periods of time.


Asunto(s)
Catecol O-Metiltransferasa , Líquidos Iónicos , Aniones , Catecol O-Metiltransferasa/química , Colina/química , Estabilidad de Enzimas , Humanos , Líquidos Iónicos/química
9.
Electrophoresis ; 43(18-19): 1832-1840, 2022 10.
Artículo en Inglés | MEDLINE | ID: mdl-35512275

RESUMEN

In recent years, attention has been turned finding new sources of phenolic compounds, antioxidant molecules, main by-products from the agri-food chain like barley malt rootlets (BMRs). Traditionally, phenolic compounds are extracted from food matrices using different procedures, for example, solid-liquid, liquid-liquid, or solid-phase extraction techniques employing organic solvents. With the advent of green chemistry, attention has been paid to the search for green, nontoxic, inexpensive, and nonflammable solvents and the natural deep eutectic solvents (NADESs) respect these characteristics. The aim of this project was to develop and optimize an environmentally friendly, inexpensive, and rapid extraction method for phenolic compounds from BMRs using natural DESs as extractive solvents. Several natural DESs were tested as extractive solvents and, among them, the best results in terms of total phenolic content were obtained using a choline chloride-malic acid (1:2 molar ratio)-based mixture. Box-Behnken experimental design guaranteed the extraction of 9.51 ± 0.83 gallic acid equivalent/g of BMRs, under the following optimal extraction conditions: 1:21 solid-to-liquid ratio, 80°C as extraction temperature, 43 min as the time of extraction, and 29% as a percentage of added water in the NADESs. Phenolic acids and flavonoids were detected in the BMRs extract through HPLC-PDA/MS analysis.


Asunto(s)
Productos Biológicos , Hordeum , Antioxidantes , Colina/química , Disolventes Eutécticos Profundos , Flavonoides/química , Ácido Gálico , Fenoles , Extractos Vegetales/química , Solventes/química , Agua/química
10.
J Phys Chem B ; 126(4): 890-905, 2022 02 03.
Artículo en Inglés | MEDLINE | ID: mdl-35076242

RESUMEN

The dynamics of the organic components of the deep eutectic solvent (DES) glyceline are analyzed using an array of complementary nuclear magnetic resonance (NMR) methods. Fast-field cycling 1H relaxometry, pulsed field gradient diffusion, nuclear overhauser effect spectroscopy (NOESY), 13C NMR relaxation, and pressure-dependent NMR experiments are deployed to sample a range of frequencies and modes of motion of the glycerol and choline components of the DES. Generally, translational and rotational diffusion of glycerol are more rapid than those of choline while short-range rotational motions observed from 13C relaxation indicate slow local motion of glycerol at low choline chloride (ChCl) content. The rates of glycerol and choline local motions become more similar at higher ChCl. This result taken together with pressure-dependent NMR studies show that the addition of ChCl makes it easier to disrupt glycerol packing. Finally, a relatively slow hydroxyl H-exchange process between glycerol and choline protons is deduced from the data. Consistent with this, NOESY results indicate relatively little direct H-bonding between glycerol and choline. These results suggest that the glycerol H-bonding network is disrupted as choline is added, but primarily in regions where there is intimate mixing of the two components. Thus, the local dynamics of most of the glycerol resembles that of pure glycerol until substantial choline chloride is present.


Asunto(s)
Colina , Glicerol , Colina/química , Difusión , Glicerol/química , Espectroscopía de Resonancia Magnética , Solventes/química
11.
J Oleo Sci ; 70(7): 1007-1012, 2021 Jul 01.
Artículo en Inglés | MEDLINE | ID: mdl-34121031

RESUMEN

In this study, cation-exchange resin was used to prepare an esterified antioxidant, sinapate ethyl ester (SE), using ethanolic extracts from rapeseed. A concentration of sinapic acid using the cation-exchange resin in 80% ethanol (aq) and subsequent interesterification of the extract in ethanol using the same resin afforded a product with a purity of 64 wt% and 100% of SE yield. Moreover, after purification using preparative thin-layer chromatography, almost 100 wt% purity was obtained. In an auto-oxidation test, purified SE conferred a much higher antioxidative effect on the bulk oil, emphasising the effectiveness of the protocol using cation-exchange resin for the purification.


Asunto(s)
Brassica napus/química , Resinas de Intercambio de Catión/química , Ésteres/química , Depuradores de Radicales Libres/química , Extractos Vegetales/química , Adsorción , Catálisis , Colina/análogos & derivados , Colina/química , Colina/aislamiento & purificación , Ácidos Cumáricos/química , Ácidos Cumáricos/aislamiento & purificación , Esterificación , Ésteres/síntesis química , Depuradores de Radicales Libres/síntesis química
12.
Food Chem ; 362: 130226, 2021 Nov 15.
Artículo en Inglés | MEDLINE | ID: mdl-34118512

RESUMEN

The focus of this study was to evaluate whether six choline chloride-based natural deep eutectic solvents (NADES) could serve as solvents for the extraction of bioactives from the leaves of Mentha piperita. NADES extracted significantly higher amounts of phenols from peppermint than 70% ethanol and may be useful in the extraction of targeted major compounds from peppermint, like rosmarinic acid, at a similar level as 70% ethanol. The microdilution method for in vitro antibacterial activity showed that all NADES exhibit bacterial growth inhibition at a lower concentration than 70% ethanol, especially NADESs containing organic acids. The majority of NADES extracts neutralize DPPH radical at a lower concentration than conventional solvent and showed similar ability to reduce Fe3+ to Fe2+ ions in FRAP assay. NADES can be useful in the isolation of phenolic compounds from plant sources and should be considered as novel, sustainable, and low-cost solvents with a variety of applications.


Asunto(s)
Antibacterianos/farmacología , Antioxidantes/farmacología , Mentha piperita/química , Fenoles/análisis , Extractos Vegetales/farmacología , Antibacterianos/química , Antioxidantes/química , Colina/química , Etanol/química , Recuperación de Fluorescencia tras Fotoblanqueo , Pruebas de Sensibilidad Microbiana , Fenoles/química , Extractos Vegetales/química , Hojas de la Planta/química , Solventes/química
13.
Molecules ; 26(7)2021 Apr 05.
Artículo en Inglés | MEDLINE | ID: mdl-33916390

RESUMEN

In the present study, a simple and environmentally friendly extraction method based on natural deep eutectic solvents (NADESs) was established to extract four bioactive steroidal saponins from Dioscoreae Nipponicae Rhizoma (DNR). A total of twenty-one types of choline chloride, betaine, and L-proline based NADESs were tailored, and the NADES composed of 1:1 molar ratio of choline chloride and malonic acid showed the best extraction efficiency for the four steroidal saponins compared with other NADESs. Then, the extraction parameters for extraction of steroidal saponins by selected tailor-made NADES were optimized using response surface methodology and the optimal extraction conditions are extraction time, 23.5 min; liquid-solid ratio, 57.5 mL/g; and water content, 54%. The microstructure of the DNR powder before and after ultrasonic extraction by conventional solvents (water and methanol) and the selected NADES were observed using field emission scanning electron microscope. In addition, the four steroidal saponins were recovered from NADESs by D101 macroporous resin with a satisfactory recovery yield between 67.27% and 79.90%. The present research demonstrates that NADESs are a suitable green media for the extraction of the bioactive steroidal saponins from DNR, and have a great potential as possible alternatives to organic solvents for efficiently extracting bioactive compounds from natural products.


Asunto(s)
Dioscorea/química , Extracción Líquido-Líquido/métodos , Fitoquímicos/aislamiento & purificación , Saponinas/aislamiento & purificación , Colina/química , Análisis Factorial , Tecnología Química Verde , Malonatos/química , Estructura Molecular , Fitoquímicos/química , Extractos Vegetales/química , Rizoma/química
14.
Molecules ; 26(5)2021 Mar 01.
Artículo en Inglés | MEDLINE | ID: mdl-33804392

RESUMEN

Deep eutectic solvents (DESs) are green organic solvents that have broad prospects in the extraction of effective components of traditional Chinese medicine. This work employed the quantitative analysis of multi-components by a single marker (QAMS) method to quantitatively determine the six effective components of glycyrrhizic acid, liquiritin, isoliquiritin apioside, liquiritigenin, isoliquiritin, and glycyrrhetinic acid in Glycyrrhiza uralensis, which was used for comprehensive evaluation of the optimal extraction process by DESs. First, Choline Chloride: Lactic Acid (ChCl-LA, molar ratio 1:1) was selected as the most suitable DES by comparing the extraction yields of different DESs. Second, the extraction protocol was investigated by extraction time, extraction temperature, liquid-to-material ratio, molar ratio, and ultrasonic power. The Box-Behnken design (BBD) combined with response surface methodology (RSM) was used to investigate the optimal DES conditions. The result showed that the best DES system was 1.3-butanediol/choline chloride (ChCl) with the molar ratio of 4:1. The optimal extraction process of licorice was 20 mL/g, the water content was 30%, and the extraction time was 41 min. The comprehensive impact factor (z) was 0.92. At the same time, it was found that the microstructure of the residue extracted by the eutectic solvent was more severely damaged than the residue after the traditional solvent extraction through observation under an electron microscope. The DES has the characteristics of high efficiency and rapidity as an extraction solution.


Asunto(s)
Butileno Glicoles/química , Colina/química , Flavonoides/análisis , Flavonoides/aislamiento & purificación , Glycyrrhiza uralensis/química , Extractos Vegetales/química , Cromatografía Líquida de Alta Presión
15.
Photochem Photobiol Sci ; 20(2): 245-254, 2021 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-33721249

RESUMEN

BACKGROUND: Photo-thermal therapy (PTT) has been at the center of attention as a new method for cancer treatment in recent years. It is important to predict the response to treatment in the PTT procedure. Using magnetic resonance spectroscopy (MRS) can be considered a novel technique in evaluating changes in metabolites resulted from PTT. METHODS: In the present project, we conducted an in vivo study to assess the efficacy of 1H-MRS as a noninvasive technique to evaluate the response to treatment in the early hours following PTT. The BALB/c mice subcutaneously bearing tumor cells (CT26 cell line) were scanned by 1H-MRS before and after PTT. Iron oxide-gold core-shell (Fe3O4@Au) as PTT agent was injected into intra-peritoneal at first and then irradiated by NIR laser. Single-voxel Point RESolved Spectroscopy (PRESS) sequence (TE = 144) was used, and metabolites alternations were evaluated by the non-parametric Wilcoxon test. Besides, Nanoparticle (NP) relaxometry was conducted for negative contrast agents' potentials. RESULTS: MRS choline (Cho) peak dramatically reduced 24 h post-PTT (p = 0.01) and lipid peak as a marker for necrosis of tumor elevated (p = 0.01) just in group 3 (NPs injection + laser irradiation) 24 h after the procedure. CONCLUSION: 1H-MRS showed its potential as a method in detecting the changes in metabolites and revealing the outcome accurately. Response to photo-thermal therapy evaluation was achievable only one day after PTT and proved by a 10-day follow-up of the tumor size. Iron oxide-gold core-shell can also be used as a negative contrast agent in MRI images during therapy.


Asunto(s)
Compuestos Férricos/química , Oro/química , Nanopartículas/química , Fototerapia/métodos , Espectroscopía de Protones por Resonancia Magnética , Animales , Línea Celular Tumoral , Colina/química , Colina/metabolismo , Rayos Infrarrojos , Imagen por Resonancia Magnética , Masculino , Ratones , Ratones Endogámicos BALB C , Nanopartículas/uso terapéutico , Neoplasias/diagnóstico por imagen , Neoplasias/patología , Neoplasias/terapia , Trasplante Homólogo
16.
J Chromatogr A ; 1641: 461998, 2021 Mar 29.
Artículo en Inglés | MEDLINE | ID: mdl-33611114

RESUMEN

In the present experiment, a green and highly efficient extraction method for flavonoids established on deep eutectic solvents (DESs) was investigated by using the response surface methodology. The DES-based high-speed countercurrent chromatography (HSCCC) solvent systems were developed for the separation of high purity compounds from the DES extract of Malus hupehensis for the first time. Under the optimal conditions (liquid-to-solid ratio of 26.3 mL/g, water content of 25.5%, and extraction temperature of 77.5°C), the yield of flavonoids was 15.3 ± 0.1%, which was superior to that of the methanol extraction method. In accordance with the physical property of DES-based HSCCC solvent systems and K values of target compounds, DES-based HSCCC solvent systems composed of choline chloride/glucose-water-ethyl acetate (ChCl/Glu-H2O-EAC, 1:1:2, v/v) was selected for the HSCCC separation. Thus, five flavonoids (two novel compounds 1-2, 6´´-O-coumaroyl-2´-O-glucopyranosylphloretin and 3´´´-methoxy-6´´-O-feruloy-2´-O-glucopyranosylphloretin; three know compounds 3-5, namely, avicularin, phloridzin, and sieboldin) were efficiently separated from Malus hupehensis. DESs are the environment friendly and highly efficient solvents as the components of extraction solvent and HSCCC solvent system, and can be re-utilized many times. However, ethyl acetate can be soluble with a few hydrogen bond donors, such as urea, carboxylic acid and polyol, through the shake flask test. It is the great difficulty for the efficient and rapid separation of target compounds from the DESs extract because of the DESs residual in the HSCCC fractions. ChCl and Glu are the great choices of DESs without this problem. In addition, K values increased with the increase of the molar ratio of ChCl/Glu and the content of water, which could effectively guide us to choose the suitable DES-based HSCCC solvent system. The twice HSCCC separation results indicated that DES was the valuable and green solvent for the HSCCC separation of pure compounds from the extract for the first time, and showed the recycle superiority of DES-based HSCCC solvent system.


Asunto(s)
Distribución en Contracorriente/métodos , Flavonoides/aislamiento & purificación , Malus/química , Solventes/química , Colina/química , Cromatografía Líquida de Alta Presión , Estudios de Factibilidad , Flavonoides/análisis , Flavonoides/química , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Agua/química
17.
Molecules ; 27(1)2021 Dec 27.
Artículo en Inglés | MEDLINE | ID: mdl-35011365

RESUMEN

Borage flower (Echium amoenum), an annual herb native to the Mediterranean region, is an excellent source of anthocyanins and is widely used in various forms due to its biological activities. In the present study, a choline chloride and glycerol (CHGLY)-based natural deep eutectic solvent (NADES) was applied in order to extract the anthocyanins from borage flowers. The traditional solvents, including water, methanol, and ethanol, were used to evaluate the efficiency of CHGLY. The results showed that CHGLY was highly efficient compared to the traditional solvents, providing the highest amounts of the total anthocyanin content (TAC), total phenolic content (TPC), total flavonoid content (TFC), individual anthocyanins, and antioxidant activity (DPPH radical scavenging (DPPH) and ferric-reducing antioxidant power (FRAP) assays). The most dominant anthocyanin found in studied borage was cyanidin-3-glucoside, followed by cyanin chloride, cyanidin-3-rutinoside, and pelargonidin-3-glucoside. The bioavailability % was 71.86 ± 0.47%, 77.29 ± 0.57%, 80.22 ± 0.65%, and 90.95 ± 1.01% for cyanidin-3-glucoside, cyanidin-3-rutinoside, by pelargonidin-3-glucoside and cyanin chloride, respectively. However, cyanidin-3-glucoside was the anthocyanin compound showing the highest stability (99.11 ± 1.66%) in the gastrointestinal environment. These results suggested that choline chloride and glycerol-based NADES is not only an efficient, eco-friendly solvent for the extraction of anthocyanins but can also be used to increase the bioavailability of anthocyanins.


Asunto(s)
Antocianinas/química , Borago/química , Extractos Vegetales/química , Antocianinas/análisis , Cloruros/química , Colina/química , Disolventes Eutécticos Profundos/química , Flores/química , Glicerol/química , Hidrólisis , Oxidación-Reducción
18.
Int J Biol Macromol ; 163: 1276-1282, 2020 Nov 15.
Artículo en Inglés | MEDLINE | ID: mdl-32673725

RESUMEN

The potential of Averrhoa bilimbi pectin (ABP) as a source of biopolymer for edible film (EF) production was explored, and deep eutectic solvent (DES) (1% w/w) containing choline chloride-citric acid monohydrate at a molar ratio of 1:1 was used as the plasticizer. The EF-ABP3:1, which was produced from ABP with large branch size, showed a higher value of melting temperature (175.30 °C), tensile stress (7.32 MPa) and modulus (33.64 MPa). The EF-ABP3:1 also showed better barrier properties by obtaining the lowest water vapor transmission rates (1.10-1.18 mg/m2.s) and moisture absorption values (2.61-32.13%) depending on the relative humidity compared to other EF-ABPs (1.39-1.83 mg/m2.s and 3.48-51.50%, respectively) that have linear structure with smaller branch size. From these results, it was suggested that the galacturonic acid content, molecular weight, degree of esterification and pectin structure of ABP significantly influenced the properties of EFs. The interaction of highly branched pectin chains was stronger than the linear chains, thus reduced the effect of plasticizer and produced a mechanically stronger EF with better barrier properties. Hence, it was suggested that these EFs could be used as alternative degradable packaging/coating materials.


Asunto(s)
Averrhoa/química , Pectinas/química , Biopolímeros/química , Colina/química , Ácido Cítrico/química , Películas Comestibles , Embalaje de Alimentos/métodos , Humedad , Peso Molecular , Plastificantes/química , Solubilidad/efectos de los fármacos , Solventes/química , Vapor , Temperatura , Resistencia a la Tracción/efectos de los fármacos
19.
Int J Mol Sci ; 21(14)2020 Jul 17.
Artículo en Inglés | MEDLINE | ID: mdl-32708987

RESUMEN

Curcumin (CUR) has shown remarkable efficacy in the treatment of skin diseases, but its effective transdermal delivery is still a major challenge and stimulates interest in the design of novel systems for CUR dispersion, preservation, and delivery facilitation to the deeper layers of the skin. The present work aimed to investigate the potential of a nanohydrogel, formed by a micellar choline-calix[4]arene amphiphile (CALIX) and CUR, in the treatment of skin diseases through an imiquimod (IMQ)-induced psoriasis model. Psoriasis plaques are associated with aberrant keratinization, abnormal distribution of tight junctions (TJs) proteins, and enhanced expression of inflammatory markers. The nanohydrogel restored the normal distribution of TJs proteins ZO1 and occludin and reduced the expression of TNF-α and inducible nitric oxide synthetase (iNOS) compared to the untreated IMQ group. The novelty lies in the calix[4]arene-based nanohydrogel as a potential new soft material for the topical skin delivery of CUR. The nanohydrogel, due to its physicochemical and mechanical properties, enhances the drug water-solubility, preserves CUR from rapid degradation, and eases the local skin administration and penetration.


Asunto(s)
Antiinflamatorios no Esteroideos/administración & dosificación , Calixarenos/química , Colina/química , Curcumina/administración & dosificación , Portadores de Fármacos/química , Fenoles/química , Psoriasis/tratamiento farmacológico , Administración Cutánea , Animales , Antiinflamatorios no Esteroideos/uso terapéutico , Curcumina/uso terapéutico , Modelos Animales de Enfermedad , Hidrogeles/química , Masculino , Ratones , Ratones Endogámicos BALB C , Psoriasis/patología
20.
Artículo en Inglés | MEDLINE | ID: mdl-32298197

RESUMEN

A fast, cheap and green analytical method was developed for the determination and extraction of curcumin in tea, honey, and spices using deep eutectic solvent-assisted emulsification liquid-liquid micro-extraction (DES-ELLME) coupled to UV-VIS spectrophotometry. Quantitative extraction of curcumin from the sample was obtained by the DES, which was prepared by mixing choline chloride and maltose in a 1:3 molar ratio. Response surface design was used for the optimisation of significant experimental parameters including sample pH, amount of extraction solvent, amount of emulsifier solvent and vortex time. The optimum conditions obtained were pH 4.25, 762.5 µL of DES, 107.5 mL of tetrahydrofuran and 3.4 min vortex time, while keeping centrifugation speed fixed at 4000 rpm, 5 min. Under the extraction conditions obtained, analytical features such as calibration equation, limit of detection, enrichment factor, and linearity were Abs = 6.5 × 10-4 [Curcumin, ng mL-1]-1.2 × 10-5, 0.1 ng mL-1, 114 and 0.4-120 ng mL-1, respectively. Moreover, the repeatability and reproducibility of the DES-ELLME method, expressed as relative standard deviation (RSDs%), varied in the ranges of 1.4-3.0% and 2.0-4.3%, respectively. Finally, the proposed method was successfully applied to the extraction and determination of curcumin from prepared samples. The relative mean recovery ranged from 92.3% to 104.4%.


Asunto(s)
Curcumina/análisis , Contaminación de Alimentos/análisis , Miel/análisis , Microextracción en Fase Líquida , Especias/análisis , Té/química , Cloruros/química , Colina/química , Análisis de los Alimentos , Maltosa/química , Solventes/química , Propiedades de Superficie
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