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1.
Molecules ; 26(6)2021 Mar 14.
Artículo en Inglés | MEDLINE | ID: mdl-33799441

RESUMEN

Medicago lupulina is an ancient edible plant from the Fabaceae family. In this work, two eco-friendly methods for extraction of bioactive phenolics from M. lupulina were developed using mixtures of water with two non-toxic, skin- and environmentally-friendly polyol solvents: glycerol and polypropylene glycol. Ultrasound-assisted extractions were optimized using a Box-Behnken design. The independent variables were the concentration of organic solvent in water (X1), extraction temperature (X2) and time (X3), while the response was phenolic content. The optimum conditions for extraction of polyphenols were (X1, X2, X3): (45%, 70 °C, 60 min) and (10%, 80 °C, 60 min) for glycerol and polypropylene glycol extraction, respectively. The extracts prepared at optimum conditions were rich in phenolic compounds, mainly derivatives of apigenin, kaempferol, luteolin, quercetin, caffeic and ferulic acid, as well as coumestrol. Their cosmeceutical and antidiabetic activity was tested. Both extracts demonstrated notable antioxidant, anti-lipoxygenase and anti-α-amylase activity. In addition to those activities, the glycerol extract efficiently inhibited protein coagulation, elastase and α-glucosidase activity. Glycerol present in the extract displayed enzyme-inhibiting activity in several assays and supported the action of the bioactive constituents. Thus, the optimized glycerol extract is a desirable candidate for direct incorporation in antidiabetic food supplements and cosmeceutical products.


Asunto(s)
Antioxidantes/química , Cosmecéuticos/química , Inhibidores de Glicósido Hidrolasas/química , Medicago/química , Fenoles/química , alfa-Amilasas/antagonistas & inhibidores , alfa-Glucosidasas/metabolismo , Antioxidantes/farmacología , Cosmecéuticos/farmacología , Glicerol/química , Inhibidores de Glicósido Hidrolasas/farmacología , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Fenoles/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Polímeros/química , Polifenoles/química , Glicoles de Propileno/química , Solventes/química
2.
Molecules ; 26(6)2021 Mar 16.
Artículo en Inglés | MEDLINE | ID: mdl-33809760

RESUMEN

Investigation of the methanol extract of the poroid fungus Fuscoporia torulosa resulted in the isolation of a novel triterpene, fuscoporic acid (1), together with inoscavin A and its previously undescribed Z isomer (2 and 3), 3,4-dihydroxy-benzaldehide (4), osmundacetone (5), senexdiolic acid (6), natalic acid (7), and ergosta-7,22-diene-3-one (8). The structures of fungal compounds were determined on the basis of NMR and MS spectroscopic analyses, as well as molecular modeling studies. Compounds 1, 6-8 were examined for their antibacterial properties on resistant clinical isolates, and cytotoxic activity on human colon adenocarcinoma cell lines. Compound 8 was effective against Colo 205 (IC50 11.65 ± 1.67 µM), Colo 320 (IC50 8.43 ± 1.1 µM) and MRC-5 (IC50 7.92 ± 1.42 µM) cell lines. Potentially synergistic relationship was investigated between 8 and doxorubicin, which revealed a synergism between the examined compounds with a combination index (CI) at the 50% growth inhibition dose (ED50) of 0.521 ± 0.15. Several compounds (1 and 6-8) were tested for P-glycoprotein modulatory effect in Colo 320 resistant cancer cells, but none of the compounds proved to be effective in this assay. Fungal metabolites 2-5 were evaluated for their antioxidant activity using the oxygen radical absorbance capacity (ORAC) and DPPH assays. Compounds 4 and 5 were found to have a considerable antioxidant effect with EC50 0.25 ± 0.01 (DPPH) and 12.20 ± 0.92 mmol TE/g (ORAC). The current article provides valuable information on both the chemical and pharmacological profiles of Fuscoporia torulosa, paving the way for future studies with this species.


Asunto(s)
Basidiomycota/química , Fenoles/química , Fenoles/farmacología , Triterpenos/química , Triterpenos/farmacología , Antibacterianos/química , Antibacterianos/farmacología , Antioxidantes/química , Antioxidantes/fisiología , Línea Celular Tumoral , Humanos , Metanol/química
3.
Food Chem ; 354: 129553, 2021 Aug 30.
Artículo en Inglés | MEDLINE | ID: mdl-33756316

RESUMEN

Aiming the simplification of the production of chitosan nanoparticles as an encapsulating material, the primary approach of this study was to investigate the extraction of active compounds from acerola-pulp by-products directly in chitosan solution by using tip sonication. The results have shown that chitosan solution can be used as a good solvent, mainly for total phenolic compounds (TPC) extraction (1792.7 mg/100 g of dry by-product). The extract was submitted to ionic gelation process using, as counter-ion, the sodium tripolyphosphate to form loaded nanoparticles with TPC. The suspension was applied as protective coatings on the guavas. The nanoengineered coatings provided an effective barrier that delayed the maturation and maintained the green pigmentation for longer periods along with good firmness. To the best of our knowledge, this was the first study that uses chitosan solution as extraction solvent of TPC from food byproducts in order to facilitate the encapsulation process.


Asunto(s)
Quitosano/química , Almacenamiento de Alimentos , Malpighiaceae/química , Fenoles/aislamiento & purificación , Psidium/química , Ácido Ascórbico/química , Cápsulas , Nanopartículas/química , Fenoles/química , Soluciones
4.
J Chromatogr A ; 1642: 462021, 2021 Apr 12.
Artículo en Inglés | MEDLINE | ID: mdl-33714771

RESUMEN

Although ultraviolet detector or mass spectrometer could be coupled with two-dimensional liquid chromatography (2DLC) to analyze complex constituents, full detection and identification of the compounds are difficult. Suffering from biased UV detection and insufficient MS data interpretation, a number of minor compounds are neglected though they are separated. In this study, we report a global chemical profiling strategy using comprehensive 2DLC coupled with dual-MS platforms, including Orbitrap-MS and QqQ-MS. It was exemplified by an 11-herb Chinese medicine formula Xiaoer-Feire-Kechuan (XFK). Firstly, constituents in XFK were separated on a CSH C18 × Phenyl-Hexyl 2DLC system with a practical peak capacity of 990.5 and an orthogonality of 90.3%. Secondly, untargeted mass spectral data was collected using dd-MS2 scan on an Orbitrap-MS. In total 542 peaks were detected, which was 4 times of that detected by 2DLC/UV (131 peaks). A total of 108 compounds were tentatively identified. Thirdly, targeted mass spectral data was collected for 8 characteristic substructures using neutral loss and precursor ion (NL/PRE) scan on a QqQ-MS. Extracted ion chromatogram was used to recognize minor constituents. An additional of 151 compounds were detected. Our study indicated that comprehensive 2DLC coupled with dd-MS2 and NL/PRE-MS is a powerful technique for the global profiling of multi-component systems.


Asunto(s)
Medicamentos Herbarios Chinos/análisis , Espectrometría de Masas , Cromatografía Liquida , Medicamentos Herbarios Chinos/química , Glicósidos/análisis , Glicósidos/química , Fenoles/análisis , Fenoles/química , Estándares de Referencia
5.
Molecules ; 26(5)2021 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-33671061

RESUMEN

Wild olive trees have important potential, but, to date, the oil from wild olives has not been studied significantly, especially from an analytical point of view. In Spain, the wild olive tree is called "Acebuche" and its fruit "Acebuchina". The objective of this work is to optimize the olive oil production process from the Acebuchina cultivar and characterize the oil, which could be marketed as healthy and functional food. A Box-Behnken experimental design with five central points was used, along with the Response Surface Methodology to obtain a mathematical experimental model. The oils from the Acebuchina cultivar meet the requirements for human consumption and have a good balance of fatty acids. In addition, the oils are rich in antioxidants and volatile compounds. The highest extraction yield, 12.0 g oil/100 g paste, was obtained at 90.0 min and the highest yield of phenolic compounds, 870.0 mg/kg, was achieved at 40.0 °C, and 90.0 min; but the maximum content of volatile compounds, 26.9 mg/kg, was obtained at 20 °C and 30.0 min. The oil yield is lower than that of commercial cultivars, but the contents of volatile and phenolic compounds is higher.


Asunto(s)
Antioxidantes/química , Olea/química , Aceite de Oliva/química , Extractos Vegetales/química , Antioxidantes/farmacología , Ácidos Grasos/química , Humanos , Aceite de Oliva/farmacología , Fenoles/química , Extractos Vegetales/farmacología , España , Compuestos Orgánicos Volátiles/química
6.
J Chromatogr A ; 1642: 462037, 2021 Apr 12.
Artículo en Inglés | MEDLINE | ID: mdl-33714768

RESUMEN

Two solid phase extraction resins (SPER) were prepared by impregnating solutions of two diglycolamide-functionalized calix[4]arenes in 10% isodecanol in n-dodecane into Chromosorb W, as the stationary phase. While SPER-I contained n-propyl functionalized calix[4]arene, SPER-II contained the calix[4]arene with isopentyl groups at the carboxamide nitrogen atoms. The SPERs were characterized by SEM, TGA, FTIR, etc. and were used for the batch uptake of neptunium(IV) from nitric acid feed solutions. While the uptake of Np(IV) was extremely high with SPER-I (Kd: 47,544 at 3 M nitric acid, ca. 8% extractant loading), SPER-II displayed a significantly lower extraction efficiency (Kd: 13,724 under identical conditions) as indicated by the batch uptake studies. Sorption isotherm studies were carried out which indicated good fitting to the Langmuir model suggesting uptake conforming to monolayer sorption. Fitting to the D-R isotherm model conformed to a chemisorption model. Column studies were also carried out and the elution profiles, obtained with solutions of oxalic acid and nitric acid indicated very sharp peaks suggesting that the column can be used for the separation of Np(IV) from acidic radioactive feeds.


Asunto(s)
Calixarenos/química , Glicolatos/química , Neptunio/análisis , Ácido Nítrico/química , Fenoles/química , Resinas Sintéticas/química , Extracción en Fase Sólida/métodos , Adsorción , Iones , Cinética , Ligandos , Espectroscopía Infrarroja por Transformada de Fourier , Temperatura , Termogravimetría , Factores de Tiempo
7.
Molecules ; 26(4)2021 Feb 22.
Artículo en Inglés | MEDLINE | ID: mdl-33671833

RESUMEN

Our present study was designed to investigate the role of both Trichoderma harzianum and chamomile (Matricaria chamomilla L.) flower extract in mutual reaction against growth of Pythium ultimum. In vitro, the activity of chamomile extract was found to reduce the radial growth of Pythium ultimum up to 30% compared to the control. Whereas, the radial growth reduction effect of T. harzianum against P. ultimum reached 81.6% after 120 h. Data also showed the productivity of total phenolics and total flavonoids by T. harzianum, was 12.18 and 6.33 mg QE/100 mL culture filtrate, respectively. However, these compounds were determined in chamomile flower extract at concentrations of 75.33 and 24.29 mg QE/100 mL, respectively. The fractionation of aqueous extract of chamomile flower using HPLC provided several polyphenolic compounds such as pyrogallol, myricetin, rosemarinic acid, catechol, p-coumaric acid, benzoic acid, chlorogenic acid and other minor compounds. In vivo, the potentiality of T. harzianum with chamomile flower extract against Pythium pathogen of bean was investigated. Data obtained showed a reduction in the percentage of rotted seed and infected seedling up to 28 and 8%, respectively. Whereas, the survival increased up to 64% compared to other ones. There was also a significant promotion in growth features, total chlorophyll, carotenoids, total polyphenols and flavonoids, polyphenol-oxidase and peroxidase enzymes compared to other ones. To the best of our knowledge, there are no reported studies that included the mutual association of fungus, T. harzianum with the extract taken from the chamomile flower against P. ultimum, either in vitro or in vivo. In conclusion, the application of both T. harzianum and/or M. chamomilla extracts in the control of bean Pythium pathogen showed significant results.


Asunto(s)
Manzanilla/química , Flavonoides/farmacología , Flores/química , Hypocreales/química , Fenoles/farmacología , Extractos Vegetales/farmacología , Pythium/efectos de los fármacos , Flavonoides/química , Flavonoides/aislamiento & purificación , Hypocreales/metabolismo , Fenoles/química , Fenoles/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Pythium/crecimiento & desarrollo , Pythium/patogenicidad
8.
Food Chem ; 352: 129404, 2021 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-33676122

RESUMEN

This study was designed to identify and quantify the major phenolic constituents in peeled kernel and pellicle of the walnut Juglans regia L. Data were compared across six different cultivars: 'Fernor', 'Fernette', 'Franquette', 'Sava', 'Krka' and 'Rubina'. High-performance liquid chromatography coupled with mass spectrometry was used to identify and quantify these compounds. Nineteen ellagitanins, 12 ellagic acid derivatives, 4 anthocyanins and 5 other phenols were identified in the pellicle of these walnuts, and 15 dicarboxylic acid derivatives and 1 phenol in the peeled walnut kernels. Thirteen previously unreported compounds were identified in the peeled walnut kernels, and 14 in the walnut pellicle. Hydrolysable tannins were the main phenolic compounds identified in the walnut kernels, and accounted for 31.0% to 35.1% of the total phenolics analysed. The highest intake of total phenolics content per walnut kernel can be obtained by consumption of 'Franquette' and 'Rubina', with the lowest for 'Krka'.


Asunto(s)
Cromatografía Líquida de Alta Presión , Juglans/química , Fenoles/análisis , Espectrometría de Masas en Tándem , Análisis de los Alimentos , Nueces/química , Fenoles/química
9.
Ecotoxicol Environ Saf ; 214: 112115, 2021 May.
Artículo en Inglés | MEDLINE | ID: mdl-33691242

RESUMEN

Nanoplastics (NPs) are becoming an emerging pollutant of global concern. A potential risk of NPs is that they can serve as carriers and synergistically function with other contaminants to cause diseases. A variety of diseases such as Alzheimer's disease are related to the generation of amyloid fibrils, and insulin is typically used as a model to study the fibrillation process. In this study, we examined the fibrillation of insulin promoted by polystyrene nanoplastics (PSNPs) alone and synergistically with organic contaminants (denoted as X, X = pyrene, bisphenol A, 2,2',4,4'-tetrabromodiphenyl ether, 4,4'-dihydroxydiphenylmethane, or 4-nonylphenol) having different polarities using thioflavin T fluorescence assays, dynamic light scattering, and circular dichroism spectroscopy. The presence of PSNPs and small organic contaminants decreased the lag phase time (tlag) for insulin fibrillation from 54.6 h to 35-51 h and their combination (PS-X) enhanced this process (tlag = 21-30 h). Notably, the lag phase time for insulin fibrillation with PS-nonpolar contaminants, PS-weakly polar contaminants, and PS-polar contaminants is around 20.8, 26.7, and 30.1 h, respectively, indicating the synergistic effect of PS-nonpolar contaminants or PS-weakly polar contaminants was more obvious than that of PS-polar contaminants. Moreover, molecular dynamic simulation reveal the interactions between insulin and PSs or small organic contaminants are primarily driven by van der Waals forces and hydrophobic interactions. Overall, the findings of this study underscore the potentially significant environmental impact of small organic contaminants assisting NPs in promoting insulin fibrillation.


Asunto(s)
Contaminantes Ambientales/química , Insulina/química , Microplásticos/química , Nanopartículas/química , Poliestirenos/química , Compuestos de Bencidrilo/química , Éteres Difenilos Halogenados/química , Fenoles/química , Pirenos/química
10.
Food Chem ; 352: 129377, 2021 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-33711730

RESUMEN

In this study, protein isolate (PI) and purified phenolic extract (PPE) were prepared from Cinnamomum camphora seed kernel (CCSK). The effects of covalent modification of PI by PPE at different concentrations (1, 2, 3, 4 and 5%, w/w) were investigated with respect to structural properties and antioxidant activities of protein. Fifteen bioactive compounds in PPE were tentatively identified by UPLC-ESI-MSn. With the increase of PPE concentration, the turbidity, covalent binding rate, phenolic content and color intensity of the PI-PPE complexes were gradually increased. Fourier transform infrared spectroscopy and circular dichroism spectroscopy analysis showed that the secondary and tertiary structures of the complexes were changed and became greater order than PI. Furthermore, the complexes exhibited stronger thermal stability and antioxidant activities than those of PI. These results suggested that the protein-phenolic covalent complexes obtained from CCSK may have great potential to be used in food formulations as functional ingredients.


Asunto(s)
Antioxidantes/química , Cinnamomum camphora/química , Fenoles/química , Preparaciones de Plantas/química , Semillas/química
11.
Molecules ; 26(5)2021 Feb 25.
Artículo en Inglés | MEDLINE | ID: mdl-33669139

RESUMEN

Numerous assays were developed to measure the antioxidant activity, but each has limitations and the results obtained by different methods are not always comparable. Popular examples are the DPPH and ABTS assay. Our aim was to study similarities and differences of these two assay regarding the measured antioxidant potentials of 24 phenolic compounds using the same measurement and evaluation methods. This should allow conclusions to be drawn as to whether one of the assays is more suitable for measuring specific subgroups like phenolic acids, flavonols, flavanones, dihydrochalcones or flavanols. The assays showed common trends for the mean values of most of the subgroups. Some dihydrochalcones and flavanones did not react with the DPPH radical in contrast to the ABTS radical, leading to significant differences. Therefore, to determine the antioxidant potential of dihydrochalcone or flavanone-rich extracts, the ABTS assay should be preferred. We found that the results of the flavonoids in the DPPH assay were dependent on the Bors criteria, whereas the structure-activity relationship in the ABTS assay was not clear. For the phenolic acids, the results in the ABTS assay were only high for pyrogallol structures, while the DPPH assay was mainly determined by the number of OH groups.


Asunto(s)
Antioxidantes/farmacología , Fenoles/farmacología , Antioxidantes/química , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Transporte de Electrón , Fenoles/química , Picratos/antagonistas & inhibidores , Ácidos Sulfónicos/antagonistas & inhibidores
12.
Molecules ; 26(4)2021 Feb 19.
Artículo en Inglés | MEDLINE | ID: mdl-33669650

RESUMEN

Apples are an important source of biologically active compounds. Consequently, we decided to model hard gelatin capsules with lyophilized apple powder by using different excipients and to evaluate the release kinetics of phenolic compounds. The apple slices of "Ligol" cultivar were immediately frozen in a freezer (at -35°C) with air circulation and were lyophilized with a sublimator at the pressure of 0.01 mbar (condenser temperature, -85°C). Lyophilized apple powder was used as an active substance filled into hard gelatin capsules. We conducted capsule disintegration and dissolution tests to evaluate the quality of apple lyophilizate-containing capsules of different encapsulating content. Individual phenolic compounds can be arranged in the following descending order according to the amount released from the capsules of different compositions: chlorogenic acid > rutin > avicularin > hyperoside > phloridzin > quercitrin > (-)-epicatechin > isoquercitrin. Chlorogenic acid was the compound that was released in the highest amounts from capsules of different encapsulating content: its released amounts ranged from 68.4 to 640.3 µg/mL. According to the obtained data, when hypromellose content ranged from 29% to 41% of the capsule mass, the capsules disintegrated within less than 30 min, and such amounts of hypromellose did not prolong the release of phenolic compounds. Based on the results of the dissolution test, the capsules can be classified as fast-dissolving preparations, as more than 85% of the active substances were released within 30 min.


Asunto(s)
Productos Biológicos/análisis , Cápsulas/química , Liofilización , Malus/química , Etanol/química , Gelatina/química , Glicósidos/química , Fenoles/análisis , Fenoles/química , Polvos
13.
Molecules ; 26(4)2021 Feb 19.
Artículo en Inglés | MEDLINE | ID: mdl-33669887

RESUMEN

In the last few years, a new term, "High-phenolic olive oil", has appeared in scientific literature and in the market. However, there is no available definition of that term regarding the concentration limits of the phenolic ingredients of olive oil. For this purpose, we performed a large-scale screening and statistical evaluation of 5764 olive oil samples from Greece coming from >30 varieties for an eleven-year period with precisely measured phenolic content by qNMR. Although there is a large variation among the different cultivars, the mean concentration of total phenolic content was 483 mg/kg. The maximum concentration recorded in Greece reached 4003 mg/kg. We also observed a statistically significant correlation of the phenolic content with the harvest period and we also identified varieties affording olive oils with higher phenolic content. In addition, we performed a study of phenolic content loss during usual storage and we found an average loss of 46% in 12 months. We propose that the term high-phenolic should be used for olive oils with phenolic content > 500 mg/kg that will be able to retain the health claim limit (250 mg/kg) for at least 12 months after bottling. The term exceptionally high phenolic olive oil should be used for olive oil with phenolic content > 1200 mg/kg (top 5%).


Asunto(s)
Espectroscopía de Resonancia Magnética , Aceite de Oliva/química , Fenoles/análisis , Estadística como Asunto , Aldehídos/análisis , Monoterpenos Ciclopentánicos/análisis , Grecia , Fenoles/química , Preservación Biológica
14.
Molecules ; 26(4)2021 Feb 12.
Artículo en Inglés | MEDLINE | ID: mdl-33673167

RESUMEN

The leaves of Homalomena aromatica are traditionally used in Bangladesh for the treatment of different chronic ailments. The purpose of this study was to explore in vitro antioxidant, thrombolytic activities, and in vivo neuropharmacological effects of methanolic extract of Homalomena aromatica (MEHA) leaves. Antioxidant activity of MEHA was assessed by a DPPH free radical scavenging assay and total phenolics content, total flavonoids content were also measured. The thrombolytic activity was determined by percentage of clot lysis and neuropharmacological activities by hole board, tail suspension, forced swimming and elevated plus maze tests. The results showed that the IC50 value of the extract against DPPH was 199.51 µg/mL. Quantitative analysis displayed higher contents of phenolics and flavonoids (147.71 mg gallic acid equivalent/g & 66.65 mg quercetin equivalent/g dried extract, respectively). The extract also showed a significant clot lysis (33.31%) activity. In case of anxiolytic activity, the elevate plus maze (EPM) test demonstrated an increase in time spent in open arms, and in case of hole board test, the number of head dipping was also significantly increased (p < 0.05). All the test compared with control (1% Tween in water) and standard (diazepam 1 mg/kg), significant dose (200 & 400 mg/kg) dependent anxiolytic activity was found. In antidepressant activity, there was a significant decrease in period of immobility in both test models (tail suspension and forced swimming) (p < 0.05). Moreover, 13 compounds were identified as bioactive, showed good binding affinities to xanthine oxidoreductase, tissue plasminogen activator receptor, potassium channel receptor, human serotonin receptor targets in molecular docking experiments. Furthermore, ADME/T analysis revealed their drug-likeness, likely pharmacological actions and non-toxic upon consumption. Taken together, our finding support the traditional medicinal use of this plant, which may provide a potential source for future drug discovery.


Asunto(s)
Antioxidantes/química , Araceae/química , Fibrinolíticos/química , Extractos Vegetales/química , Animales , Antidepresivos/química , Antidepresivos/farmacología , Antioxidantes/farmacología , Compuestos de Bifenilo/química , Simulación por Computador , Tiempo de Lisis del Coágulo de Fibrina , Fibrinolíticos/farmacología , Flavonoides/química , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Humanos , Ratones , Simulación del Acoplamiento Molecular , Neurofarmacología , Fenoles/química , Picratos/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Receptores de Serotonina/química , Antagonistas de la Serotonina/química , Antagonistas de la Serotonina/farmacología , Natación
15.
Molecules ; 26(5)2021 Feb 24.
Artículo en Inglés | MEDLINE | ID: mdl-33668373

RESUMEN

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure-property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.


Asunto(s)
Calixarenos/química , Complejos de Coordinación/química , Cetonas/química , Nanopartículas/química , Fenoles/química , Calixarenos/síntesis química , Complejos de Coordinación/síntesis química , Cetonas/síntesis química , Ligandos , Estructura Molecular , Tamaño de la Partícula , Fenoles/síntesis química , Propiedades de Superficie
16.
Molecules ; 26(4)2021 Feb 21.
Artículo en Inglés | MEDLINE | ID: mdl-33669973

RESUMEN

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.


Asunto(s)
Ácidos Cumáricos/química , Fenoles/aislamiento & purificación , Vitis/química , Cromatografía Líquida de Alta Presión , Jugos de Frutas y Vegetales/análisis , Estructura Molecular , Fenoles/química
17.
Molecules ; 26(4)2021 Feb 22.
Artículo en Inglés | MEDLINE | ID: mdl-33671811

RESUMEN

Marine algae are a promising source of potent bioactive agents against oxidative stress, diabetes, and inflammation. However, the possible therapeutic effects of many algal metabolites have not been exploited yet. In this regard, we explored the therapeutic potential of Enteromorpha intestinalis extracts obtained from methanol, ethanol, and hexane, in contrasting oxidative stress. The total phenolic (TPC) and flavonoids (TFC) content were quantified in all extracts, with ethanol yielding the best values (about 60 and 625 mg of gallic acid and rutin equivalents per gram of extract, respectively). Their antioxidant potential was also assessed through DPPH•, hydroxyl radical, hydrogen peroxide, and superoxide anion scavenging assays, showing a concentration-dependent activity which was greater in the extracts from protic and more polar solvents. The α-amylase and α-glucosidase activities were estimated for checking the antidiabetic capacity, with IC50 values of about 3.8 µg/mL for the methanolic extract, almost as low as those obtained with acarbose (about 2.8 and 3.3 µg/mL, respectively). The same extract also showed remarkable anti-inflammatory effect, as determined by hemolysis, protein denaturation, proteinase and lipoxygenase activity assays, with respectable IC50 values (about 11, 4, 6, and 5 µg/mL, respectively), also in comparison to commercially used drugs, such as acetylsalicylic acid.


Asunto(s)
Antiinflamatorios/farmacología , Antioxidantes/farmacología , Inhibidores Enzimáticos/farmacología , Hipoglucemiantes/farmacología , Extractos Vegetales/farmacología , Ulva/química , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Eritrocitos/efectos de los fármacos , Eritrocitos/metabolismo , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Humanos , Radical Hidroxilo/antagonistas & inhibidores , Hipoglucemiantes/química , Hipoglucemiantes/aislamiento & purificación , Lipooxigenasas/metabolismo , Masculino , Péptido Hidrolasas/metabolismo , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Superóxidos/antagonistas & inhibidores
18.
Molecules ; 26(3)2021 Jan 29.
Artículo en Inglés | MEDLINE | ID: mdl-33572779

RESUMEN

Plants have been used for thousands of years for various purposes because they have a wide variety of activities with biological significance. Mexican oregano is an aromatic plant of great importance to Mexico and north of Jalisco state as a spice with important economic value. Chromatographic identification and quantification of phenolic compounds and evaluation of their antioxidant activity were important tools to obtain a better characterization of this spice. Phytochemical analysis indicated the presence of flavonoids, triterpenes, saponins, quinones and tannins, the latter at high concentrations. Through chromatographic assays of Mexican oregano extracts, 62 compounds were identified, the major ones being quantified as: taxifolin, apigenin 7-O-glucoside, phlorizin, eriodictyol, quercetin, naringenin, hispidulin, pinocembrin, galangin and genkwanin (compound for the first time reported for this species). The results can be useful as a precedent to establish the bases of new quality characterization parameters and they have also suggested that Mexican oregano contains a wide variety of compounds with untapped importance for the development of new high value-added products.


Asunto(s)
Antioxidantes/química , Origanum/química , Fenoles/química , Flavonoides/química , Humanos , Fenoles/clasificación , Fenoles/aislamiento & purificación , Extractos Vegetales/química , Quinonas/química , Saponinas/química , Taninos/química , Triterpenos/química
19.
Molecules ; 26(3)2021 Jan 29.
Artículo en Inglés | MEDLINE | ID: mdl-33573099

RESUMEN

Wine is perhaps the most ancient and popular alcoholic beverage worldwide. Winemaking practices involve careful vineyard management alongside controlled alcoholic fermentation and potential aging of the wine in barrels. Afterwards, the wine is placed in bottles and stored or distributed in retail. Yet, it is considered that wine achieves its optimum properties after a certain storage time in the bottle. The main outcome of bottle storage is a decrease of astringency and bitterness, improvement of aroma and a lighter and more stable color. This is due to a series of complex chemical changes of its components revolving around the minimized and controlled passage of oxygen into the bottle. For this matter, antioxidants like sulfur oxide are added to avoid excessive oxidation and consequent degradation of the wine. In the same sense, bottles must be closed with appropriate stoppers and stored in adequate, stable conditions, as the wine may develop unappealing color, aromas and flavors otherwise. In this review, features of bottle aging, relevance of stoppers, involved chemical reactions and storage conditions affecting wine quality will be addressed.


Asunto(s)
Antioxidantes/química , Almacenamiento de Alimentos , Fenoles/química , Vino/análisis , Color , Fermentación , Odorantes/análisis , Oxidación-Reducción , Oxígeno/química , Gusto
20.
Molecules ; 26(4)2021 Feb 07.
Artículo en Inglés | MEDLINE | ID: mdl-33562414

RESUMEN

Major lignans of sesame sesamin and sesamolin are benzodioxol--substituted furofurans. Sesamol, sesaminol, its epimers, and episesamin are transformation products found in processed products. Synthetic routes to all lignans are known but only sesamol is synthesized industrially. Biosynthesis of furofuran lignans begins with the dimerization of coniferyl alcohol, followed by the formation of dioxoles, oxidation, and glycosylation. Most genes of the lignan pathway in sesame have been identified but the inheritance of lignan content is poorly understood. Health-promoting properties make lignans attractive components of functional food. Lignans enhance the efficiency of insecticides and possess antifeedant activity, but their biological function in plants remains hypothetical. In this work, extensive literature including historical texts is reviewed, controversial issues are critically examined, and errors perpetuated in literature are corrected. The following aspects are covered: chemical properties and transformations of lignans; analysis, purification, and total synthesis; occurrence in Seseamum indicum and related plants; biosynthesis and genetics; biological activities; health-promoting properties; and biological functions. Finally, the improvement of lignan content in sesame seeds by breeding and biotechnology and the potential of hairy roots for manufacturing lignans in vitro are outlined.


Asunto(s)
Benzodioxoles/química , Furanos/química , Lignanos/química , Fenoles/química , Sesamum/química , Benzodioxoles/síntesis química , Dioxoles/química , Lignanos/síntesis química , Oxidación-Reducción , Fenoles/síntesis química , Semillas/química , Sesamum/genética
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