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1.
Food Chem ; 443: 138427, 2024 Jun 15.
Artículo en Inglés | MEDLINE | ID: mdl-38277938

RESUMEN

The effects of ultrasound (500 W) on the interaction of porcine myofibrillar protein (MP) with furan flavor compounds at different salt concentrations (0.6 %, 1.2 % and 2.4 %) were investigated. With the increase of salt concentration, the particle size of MP decreased, and the surface hydrophobicity and active sulfhydryl content increased due to the unfolding and depolymerization of MP. At the same time, ultrasound promoted the exposure of hydrophobic binding sites and hydrogen bonding sites of MP in different salt concentration systems, thus improving the binding ability of MP with furan compounds by 2 % to 22 %, among which MP had the strongest binding capacity of 2-pentylfuran. In conclusion, ultrasound could effectively promote the unfolding of the secondary structure of MP, which was beneficial to the combination of MP and furan flavor compounds under different salt concentrations.


Asunto(s)
Cloruro de Sodio Dietético , Cloruro de Sodio , Animales , Porcinos , Unión Proteica , Interacciones Hidrofóbicas e Hidrofílicas , Proteínas Musculares/química
2.
ChemSusChem ; 17(1): e202301072, 2024 Jan 08.
Artículo en Inglés | MEDLINE | ID: mdl-37607884

RESUMEN

5-Hydroxymethylfurfural (5-HMF) is regarded as one of the most promising platform feedstocks for producing valuable chemicals, fuels, and materials. In this study, we present a controllable fluorination technique for biomass-based 5-HMF and its oxygenated derivatives. This technique allows us to synthesize mono-fluoromethyl, difluoromethyl, and acylfluoro-substituted furan compounds by adjusting experimental conditions such as different fluorine sources and mole ratio. To gain a deeper understanding the reactivity order, we conducted intermolecular and intramolecular competition experiments. The results revealed that the hydroxyl group exhibited the highest reactivity, followed by the aldehyde group. This finding provides important theoretical support and opens up the possibility of selective fluorination. The reaction offers several advantages, including mild conditions, no need for inert gas protection, and easy operation. Furthermore, the fluoro-substituted furan compounds can be further transformed for the preparation of drug analogs, offering a new route for the high-value utilization of biomass molecules.

3.
Food Chem ; 384: 132472, 2022 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-35240573

RESUMEN

This study was designed to explore the effects of different ultrasound power levels (0-600 W) on the ability of myofibrillar protein (MP) to bind furan compounds by analyzing the results of SDS-PAGE, particle size, Raman spectra, fluorescence intensity, solubility, turbidity, zeta potential, surface hydrophobicity, sulfhydryl content, solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS). As ultrasound power levels were increased from 0 to 500 W, the hydrophobic bonding sites, hydrogen-bonding sites, and electrostatic effects increased due to the unfolding and depolymerization of MP, thus enhancing the ability of MP to bind furan (flavor-enhancing) compounds. Consistent with these results, the positive effect of ultrasound resulted in ability of MP to bind furan compounds increased by 19.00 % to 33.32 %. However, after 600-W ultrasound treatment, the MP aggregated again and the bonding sites were re-embedded, which decreased the furan-binding ability.


Asunto(s)
Furanos , Microextracción en Fase Sólida , Animales , Furanos/análisis , Cromatografía de Gases y Espectrometría de Masas/métodos , Interacciones Hidrofóbicas e Hidrofílicas , Microextracción en Fase Sólida/métodos , Porcinos
4.
Microbiol Spectr ; 9(1): e0092421, 2021 09 03.
Artículo en Inglés | MEDLINE | ID: mdl-34378958

RESUMEN

Agrobacterium tumefaciens strain S33 can catabolize nicotine via a hybrid of the pyridine and pyrrolidine pathways. Most of the enzymes involved in this biochemical pathway have been identified and characterized, except for the one catalyzing the oxidation of 6-hydroxy-3-succinoyl-semialdehyde-pyridine to 6-hydroxy-3-succinoylpyridine. Based on a previous genomic and transcriptomic analysis, an open reading frame (ORF) annotated to encode aldehyde dehydrogenase (Ald) in the nicotine-degrading cluster was predicted to be responsible for this step. In this study, we heterologously expressed the enzyme and identified its function by biochemical assay and mass spectrum analysis. It was found that Ald catalyzes the NAD-specific dehydrogenation of 6-hydroxy-3-succinoyl-semialdehyde-pyridine to 6-hydroxy-3-succinoylpyridine. With the nonhydroxylated analog 3-succinoyl-semialdehyde-pyridine (SAP) as a substrate, Ald had a specific activity of 10.05 U/mg at pH 9.0 and apparent Km values of around 58.68 µM and 0.41 mM for SAP and NAD+, respectively. Induction at low temperature and purification and storage in low-salt buffers were helpful to prevent its aggregation and precipitation. Disruption of the ald gene caused a lower growth rate and biomass of strain S33 on nicotine but not on 6-hydroxy-3-succinoylpyridine. Ald has a broad range of substrates, including benzaldehyde, furfural, and acetaldehyde. Recombinant Escherichia coli cells harboring the ald gene can efficiently convert furfural to 2-furoic acid at a specific rate of 0.032 mmol min-1 g dry cells-1, extending the application of Ald in the catalysis of bio-based furan compounds. These findings provide new insights into the biochemical mechanism of the nicotine-degrading hybrid pathway and the possible application of Ald in industrial biocatalysis. IMPORTANCE Nicotine is one of the major toxic N-heterocyclic aromatic alkaloids produced in tobacco plants. Manufacturing tobacco and smoking may lead to some environmental and public health problems. Microorganisms can degrade nicotine by various biochemical pathways, but the biochemical mechanism for nicotine degradation has not been fully elucidated. In this study, we identified an aldehyde dehydrogenase responsible for the oxidation of 6-hydroxy-3-succinoyl-semialdehyde-pyridine to 6-hydroxy-3-succinoylpyridine; this was the only uncharacterized enzyme in the hybrid of the pyridine and pyrrolidine pathways in Agrobacterium tumefaciens S33. Similar to the known aldehyde dehydrogenase, the NAD-specific homodimeric enzyme presents a broad substrate range with high activity in alkaline and low-salt-containing buffers. It can catalyze not only the aldehyde from nicotine degradation but also those of benzaldehyde, furfural, and acetaldehyde. It was found that recombinant Escherichia coli cells harboring the ald gene could efficiently convert furfural to valuable 2-furoic acid, demonstrating its potential application for enzymatic catalysis.


Asunto(s)
Agrobacterium tumefaciens/enzimología , Proteínas Bacterianas/metabolismo , Nicotina/metabolismo , Oxidorreductasas/metabolismo , Agrobacterium tumefaciens/química , Agrobacterium tumefaciens/genética , Agrobacterium tumefaciens/metabolismo , Proteínas Bacterianas/química , Proteínas Bacterianas/genética , Biodegradación Ambiental , Cinética , NAD/metabolismo , Oxidorreductasas/química , Oxidorreductasas/genética , Piridinas/química , Piridinas/metabolismo , Especificidad por Sustrato , Succinatos
5.
Waste Manag ; 120: 202-208, 2021 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-33310132

RESUMEN

The application of thermal pretreatments to facilitate its anaerobic digestion has associated phenols and furans production, which are commonly identified as inhibitory compounds. Phenols and furans extraction can be done from a liquid phase produced after the thermal pretreatment. In the present study this dephenolized liquid phase (DLP) showed an increase of 42% in methane yield compared to the raw liquid phase (LP) demonstrating the inhibitor character of such compounds. The main extracted phenols and furans were: 3,4-Dihydroxyphenylglycol (DHPG), Hydroxytyrosol (HT), Tyrosol (Ty), Vanillic acid (AcV), Hydroxymethylfurfural (HMF), Vanillin (V) and Furfural (F).This study also aimed to evaluate the individual effect on methane production of these specific phenols and furans the within the mixture of several ones from LP. The evaluation of the individual compounds over the methanogenesis of a dephenolized liquid phase showed that only V was inhibitory on both methane yield and methane production rate. HMF had a significantly negative effect on methane yield, but improved the methane production rate instead. Ty, F, DHPG and HT favoured the methane yield and production rate. Additionally, it was observed that negative effect of some individual phenols and furans was counteracted by the positive effect of other compounds.


Asunto(s)
Furanos , Olea , Anaerobiosis , Metano , Fenoles , Residuos Sólidos
6.
Food Chem ; 301: 125256, 2019 Dec 15.
Artículo en Inglés | MEDLINE | ID: mdl-31362192

RESUMEN

Panela is a natural, unrefined non-centrifugal sugar obtained by intense dehydration of sugarcane juice. Acrylamide, hydroxymethylfurfural (HMF), and furfural were determined in 40 panela samples distributed as granulated and block according to the technological process. Colour, browning, moisture, water activity, pH and antioxidant capacity were also evaluated. Acrylamide ranged between 60 and 3058 µg/kg; granulated panela reporting the highest concentration (812 µg/kg) compared with block panela (540 µg/kg). The lower content in HMF and furfural, the intense dehydration, and the extensive darkening of granulated panela suggested the browning reactions were boosted due to the application of more severe thermal treatments. Principal component analysis showed a significant relationship between the panela presentation and the concentration of the analysed compounds. Benchmark values considering both types of processes would help to establish mitigation initiatives in panela products. The chromatic parameter a* could be used as an indirect index of the acrylamide content in panela.


Asunto(s)
Acrilamida/análisis , Antioxidantes/análisis , Fenómenos Químicos , Calor , Azúcares/química , Plásmidos de Bacteriocinas , Color , Furaldehído/análogos & derivados , Furaldehído/análisis , Concentración de Iones de Hidrógeno , Reacción de Maillard , Saccharum/química
7.
Food Chem ; 219: 364-372, 2017 Mar 15.
Artículo en Inglés | MEDLINE | ID: mdl-27765239

RESUMEN

Antioxidant capacity (AC), total phenolics (TPs), furan compounds (HMF and furfural F) and cytoprotective/cytotoxic effects upon Caco-2 cells (MTT, cell cycle and reactive oxygen species (ROS)) were evaluated in Colombian coffee (2 ground and 4 soluble samples). The AC (ABTS and FRAP), TPs and HMF ranged between 124-722, 95-802µmoles Trolox/g, 21-100mg gallic acid/g and 69-2900mg/kg, respectively. Pretreatment of cells for 24h with lyophilized coffee infusions at the highest dose without cytotoxic effects (500µg/mL) significantly prevented the decrease in cell viability compared to control stress with H2O2 (5mM/2h), recovering viability to values between 34% and 45% and restoring the control values without stress induction in the G1 phase of cell cycle. After exposure to stress, four extracts decreased ROS values significantly to 22.5-24.9%. The coffee samples exerted a cytoprotective effect against oxidative stress, with improvement in cell viability and a reduction of intracellular ROS.


Asunto(s)
Antioxidantes/farmacología , Supervivencia Celular/efectos de los fármacos , Café , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/farmacología , Especies Reactivas de Oxígeno/metabolismo , Células CACO-2 , Furanos/metabolismo , Humanos , Peróxido de Hidrógeno/toxicidad , Fenoles/metabolismo
8.
Food Chem ; 196: 309-23, 2016 Apr 01.
Artículo en Inglés | MEDLINE | ID: mdl-26593496

RESUMEN

The aim of this review is to describe the chemical characteristics of compounds present in honey, their stability when heated or stored for long periods of time and the parameters of identity and quality. Therefore, the chemical characteristics of these compounds were examined, such as sugars, proteins, amino acids, enzymes, organic acids, vitamins, minerals, phenolic and volatile compounds present in honey. The stability of these compounds in relation to the chemical reactions that occur by heating or prolonged storage were also discussed, with increased understanding of the behavior regarding the common processing of honey that may compromise its quality. In addition, the identity and quality standards were described, such as sugars, moisture, acidity, ash and electrical conductivity, color, 5-HMF and diastase activity, along with the minimum and maximum limits established by the Codex Alimentarius.


Asunto(s)
Miel/análisis , Fenoles/análisis , Compuestos Orgánicos Volátiles
9.
Bioresour Technol ; 180: 40-6, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-25585259

RESUMEN

Food waste collected from restaurants, convenience stores, and food-processing factories was mixed with sawdust and subjected to hydrothermal pretreatment at 180°C for 30min to prepare compost raw material. Furan compounds such as 5-HMF (5-hydroxymethyl furfural) and furfural were produced at concentration levels of approximately 8 and 0.5mg/g-ds, respectively, through hydrothermal pretreatment. The furan compounds inhibited the activity of composting microorganisms, thus delaying the start of organic matter degradation during composting. A newly identified fungus, Paecilomyces sp. FA13, which possesses the ability to degrade furan compounds, was isolated and used as an inoculum for the composting of the raw material prepared by hydrothermal pretreatment. By inoculating the FA13 into the compost raw material at 10(5)CFU/g-ds, the degradation of furan compounds was accelerated. As a result, bacterial activity, which contributed to composting, was enhanced, significantly promoting the start of vigorous degradation of organic materials.


Asunto(s)
Alimentos , Paecilomyces/metabolismo , Administración de Residuos/métodos , Furaldehído/análogos & derivados , Furaldehído/metabolismo , Furanos/metabolismo , Paecilomyces/aislamiento & purificación , Suelo , Microbiología del Suelo
10.
Bioresour Technol ; 180: 88-96, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-25590423

RESUMEN

Native cellulose, lignocellulosic materials from Brazil (carnauba palm leaves and macauba pulp and shell) and pine nut shell from Spain have been studied as substrates for the production of HMF and furfural in a conventional microwave oven. In order to promote the dissolution of native cellulose, several ionic liquids, catalysts, organic solvents and water doses have been assessed. The most suitable mixture (5mL of choline chloride/oxalic acid, 2mL of sulfolane, 2mL of water, 0.02g of TiO2 and 0.1g of substrate) has been chosen to conduct kinetic studies at different reaction times (5-60min) and various temperatures (120-200°C) and to evaluate the best conditions for HMF+furfural production according to Seaman's model. The best production yields of HMF+furfural have been attained for native cellulose, with a yield of 53.24% when an ultrasonic pretreatment was used prior to a microwave treatment with stirring.


Asunto(s)
Biotecnología/métodos , Celulosa/metabolismo , Furaldehído/análogos & derivados , Microondas , Brasil , Interpretación Estadística de Datos , Furaldehído/metabolismo , Líquidos Iónicos/química , Cinética , Lignina/metabolismo , Modelos Teóricos , Hojas de la Planta/química , España , Temperatura , Ultrasonido/métodos , Residuos , Agua
11.
Bioresour Technol ; 144: 504-12, 2013 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-23907066

RESUMEN

The effect of Kraft lignin presenting on the hydrolysis and dehydration of C5 and C6 sugars, cellulose, hemicelluloses and biomass under hot compressed water (HCW) in the presence of H3PO4 catalyst was intensively studied. The lignin strongly inhibited the acid hydrolysis of cellulose and hemicellulose to glucose and xylose, respectively. Interestingly, the admixed lignin markedly promoted the isomerization of glucose to fructose, and dehydration of fructose (except at the low catalyst loading), resulting in high 5-hydroxymethylfurfural yields. Nonetheless, lignin inhibited the hydrolysis of xylan to xylose and dehydration of xylose to furfural. Moreover, the acidity of the system significantly affects the hydrolysis/dehydration of biomass. It was revealed that the presence of lignin strongly interfered the yields of sugars and furans produced from raw corncob, while the delignified corncob provided significant improvement of product yields, confirming the observed role of lignin in the biomass conversion system via sugar platforms.


Asunto(s)
Biomasa , Celulosa/metabolismo , Desecación , Calor , Lignina/metabolismo , Lignina/farmacología , Agua/farmacología , Catálisis/efectos de los fármacos , Furaldehído/análogos & derivados , Furaldehído/metabolismo , Hidrólisis/efectos de los fármacos , Ácidos Fosfóricos/farmacología , Xilanos/metabolismo , Zea mays/química
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