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1.
Food Res Int ; 190: 114546, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38945559

RESUMEN

The thermal treatment carried out in the processing of apple products is very likely to induce Maillard reaction to produce furfurals, which have raised toxicological concerns. This study aimed to elucidate the formation of furfural compounds in apple products treated with pasteurization and high pressure processing (HPP). The method for simultaneous determination of five furfural compounds including 5-hydroxymethyl-2-furfural (5-HMF), furfural (F), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF), 2-acetylfuran (FMC), and 5-Methyl-2-furfural (MF) using high performance liquid chromatography equipped with diode array detector (HPLC-DAD) was successfully developed and validated. All five furfurals exhibited an increasing trend after the pasteurization treatment of apple clear juice, cloudy juice, and puree. 5-HMF, F, FMC, and MF were increased significantly during the precooking of apple puree. Whereas there was no significant change in the furfurals formation after apple products treated with high pressure processing (HPP) with 300 MPa and 15 min. Based on the variation of the fructose, glucose and sucrose detected in apple products after thermal treatment, it revealed that the saccharides and thermal treatment have great effect on the furfural compounds formation. The commercial fruit juice samples with different treatments and fruit puree samples treated with pasteurization were also analyzed. Five furfurals were detected more frequently in the fruit juice samples treated with pasteurization or ultra-high temperature instantaneous sterilization (UHT) than those treated with HPP. 5-HMF and FMC were detected in all fruit puree samples treated with pasteurization, followed by F, MF, and HDMF with the detection rate of 79.31 %, 72.41 %, and 51.72 %. The results could provide a reference for risk assessment of furfural compounds and dietary guidance of fruit products for human, especially for infants and young children. Moreover, moderate HPP treatment with 300 MPa and 15 min would be a worthwhile alternative processing technology in the fruit juice and puree production to reduce the formation of furfural compounds.


Asunto(s)
Manipulación de Alimentos , Jugos de Frutas y Vegetales , Furaldehído , Malus , Pasteurización , Presión , Malus/química , Furaldehído/análisis , Furaldehído/análogos & derivados , Cromatografía Líquida de Alta Presión , Jugos de Frutas y Vegetales/análisis , Manipulación de Alimentos/métodos , Reacción de Maillard , Frutas/química , Furanos/análisis
2.
Food Res Int ; 190: 114600, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38945570

RESUMEN

Browning commonly appeared in apple processing, which varied in different apple varieties. Present work investigated the metabolomics of four varieties apple of Yataka, Gala, Sansa, and Fuji, which possessed different browning characteristics and related enzymes. Sansa as browning insensitive apple variety, exhibited the least chroma change with the lowest PPO activity and the highest SOD activity among the four apple varieties. Browning inhibition pretreatment increased the activity of SOD and PAL and decreased PPO and POD activity. In addition, metabolomic variances among the four apple varieties (FC), their browning pulp (BR) and browning inhibition pulp (CM) were compared. And the key metabolites were in-depth analyzed to match the relevant KEGG pathways and speculated metabolic networks. There were 487, 644, and 494 significant differential metabolites detected in FC, BR and CM, which were consisted of lipids, benzenoids, phenylpropanoids, organheterocyclic compounds, organic acids, nucleosides, accounting for 23 %, 11 %, 15 %, 16 %, 11 % of the total metabolites. The differential metabolites were matched with 39, 49, and 36 KEGG pathways in FC, BR, and CM, respectively, in which other secondary metabolites biosynthesis metabolism was the most significant in FC, lipid metabolism was the most significant in BR and CM, and energy metabolism was markedly annotated in CM. Notably, Sansa displayed the highest number of differential metabolites in both its BR (484) and CM (342). The BR of Sansa was characterized by flavonoid biosynthesis, while the other three apple varieties were associated with α-linolenic acid metabolism. Furthermore, in browning sensitive apple varieties, the flavonoid and phenylpropanoid biosynthesis pathway was significantly activated by browning inhibition pretreatment. Phenolic compounds, lipids, sugars, organic acids, nucleotides, and adenosine were regulated differently in the four apple varieties, potentially serving as key regulatory sites. Overall, this work provides novel insight for browning prevention in different apple varieties.


Asunto(s)
Frutas , Malus , Metabolómica , Malus/metabolismo , Malus/clasificación , Frutas/metabolismo , Frutas/química , Manipulación de Alimentos/métodos , Reacción de Maillard
3.
Food Res Int ; 190: 114608, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38945618

RESUMEN

In dairy products, the added sodium hyaluronate may form complexes with proteins, thereby affecting product properties. In the present study, the interaction between whey protein isolate (WPI)/ whey protein hydrolysate (WPH) and sodium hyaluronate (SH) was characterized under thermal treatment at different temperatures (25 ℃, 65 ℃, 90 ℃ and 121 ℃) after studying effects of protein/SH ratio and pH on complex formation. The addition of SH reduced the particle size of WPI/WPH and increased potential value in the system, with greater variation with increasing treatment temperature. The structural properties of complexes were studied. The binding with SH decreased the contents of free amino group and free thiol group, as well as the fluorescence intensity and surface hydrophobicity. FTIR results and browning intensity measurement demonstrated the formation of Maillard reaction products. Moreover, the attachment of SH improved the thermal stability of WPI/WPH and decreased their antigenicity.


Asunto(s)
Calor , Ácido Hialurónico , Hidrolisados de Proteína , Proteína de Suero de Leche , Proteína de Suero de Leche/química , Ácido Hialurónico/química , Hidrolisados de Proteína/química , Concentración de Iones de Hidrógeno , Reacción de Maillard , Interacciones Hidrofóbicas e Hidrofílicas , Tamaño de la Partícula , Espectroscopía Infrarroja por Transformada de Fourier , Manipulación de Alimentos/métodos
4.
J Agric Food Chem ; 72(25): 14284-14293, 2024 Jun 26.
Artículo en Inglés | MEDLINE | ID: mdl-38869215

RESUMEN

Several compounds with taste-modulating properties have been investigated, improving the taste impression without having a pronounced intrinsic taste. The best-known representatives of umami taste-modulating compounds are ribonucleotides and their derivatives. Especially the thio derivatives showed high taste-modulating potential in structure-activity relationship investigations. Therefore, this study focuses on the formation of guanosine 5'-monophosphate derivatives consisting of Maillard-type generated compounds like the aroma-active thiols (2-methyl-3-furanthiol, 3-mercapto-2-pentanone, 2-furfurylthiol) and formaldehyde to gain insights into the potential of combinations of taste and aroma-active compounds. One literature-known (N2-(furfurylthiomethyl)-guanosine 5'-monophosphate) and three new derivatives (N2-(2-methyl-1-furylthiomethyl)-guanosine 5'-monophosphate, N2-((5-hydroxymethyl)-2-methyl-1-furylthiomethyl)-guanosine 5'-monophosphate, N2-((2-pentanon-1-yl)thiomethyl)-guanosine 5'-monophosphate) were successfully produced using green natural deep eutectic solvents and isolated, and their structures were completely elucidated. Besides the intrinsic taste properties, the kokumi and umami taste-modulating effects of the four derivatives were evaluated via psychophysical investigations, ranging from 19 to 22 µmol/L.


Asunto(s)
Aromatizantes , Guanosina Monofosfato , Reacción de Maillard , Gusto , Guanosina Monofosfato/química , Humanos , Aromatizantes/química , Masculino , Femenino , Estructura Molecular , Adulto , Adulto Joven
5.
Carbohydr Polym ; 340: 122293, 2024 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-38858005

RESUMEN

A few protein- and polysaccharide-based particles have shown promising potential as stabilizers in multi-phase food systems. By incorporating polymer-based particles and modifying the wettability of colloidal systems, it is possible to create particle-stabilized emulsions with excellent stability. A Pickering emulsifier (AGMs) with better emulsifying properties was obtained by the Maillard reaction between acid-hydrolysed agar and gelatin. Laser confocal microscopy imaging revealed that AGMs particles can be used as solid emulsifiers to produce a typical O/W Pickering emulsion, with AGMs adsorbing onto the droplet surface to form a dense interfacial layer. Cryo-scanning electron microscopy analysis showed that AGMs self-assembled into a three-dimensional network structure, which prevented droplets aggregation through strong spatial site resistance, contributing to emulsion stabilization. These emulsions exhibited stability within a pH range of 1 to 11, NaCl concentrations not exceeding 300 mM, and at temperatures below 80 °C. The most stable emulsion oil-water ratio was 6:4 at a particle concentration of 0.75 % (w/v). AGMs-stabilized Pickering emulsion was utilized to create a semi-solid mayonnaise as a replacement for hydrogenated oil. Rheological analysis demonstrated that low-fat mayonnaise stabilized with AGMs exhibited similar rheological behavior to traditional mayonnaise, offering new avenues for the application of Pickering emulsions in the food industry.


Asunto(s)
Agar , Emulsionantes , Emulsiones , Gelatina , Reacción de Maillard , Gelatina/química , Agar/química , Emulsiones/química , Emulsionantes/química , Reología , Concentración de Iones de Hidrógeno , Tamaño de la Partícula , Temperatura
6.
Food Res Int ; 188: 114454, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38823832

RESUMEN

The Amadori rearrangement products are an important flavor precursor in the Maillard reaction. Its thermal decomposition products usually contribute good flavors in foods. Therefore, investigating the thermal breakdown of Amadori products is significant for understanding the flavor forming mechanism in the Maillard reaction. In this study, volatiles from thermal decomposition of Amadori products in cysteine and glucose Maillard reaction was investigated by a thermal desorption cryo-trapping system combined with gas chromatography-mass spectrometry (GC-MS). A total of 60 volatiles were detected and identified. Meanwhile, the forming mechanism of 2-methylthiophene, a major decomposition product, was also investigated by using density functional theory. Seventeen reactions, 12 transition states, energy barrier and rate constant of each reaction were finally obtained. Results reveal that it is more likely for Amadori products of cysteine and glucose to undergo decomposition under neutral or weakly alkaline conditions.


Asunto(s)
Cisteína , Cromatografía de Gases y Espectrometría de Masas , Glucosa , Reacción de Maillard , Compuestos Orgánicos Volátiles , Cisteína/química , Glucosa/química , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/análisis , Teoría Funcional de la Densidad , Calor
7.
J Food Sci ; 89(6): 3745-3758, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38752387

RESUMEN

α-Dicarbonyls and advanced glycation end products (AGEs) are the heat-induced potential toxicants commonly found in thermally processed foods due to the Maillard reaction. Research has shown that both α-dicarbonyls and AGEs can cause oxidative stress and inflammation and have a positive link with several chronic diseases, such as diabetes. This study found that commonly consumed berry fruits exhibited excellent methylglyoxal (MGO)-trapping and antiglycative activities, positively associated with their total phenolic and flavonoid contents. Blackcurrant exhibited the strongest MGO-trapping and antiglycative activities among the tested berry fruits. In addition, we demonstrated that fortification with blackcurrant significantly reduced α-dicarbonyls and AGEs formation in the chocolate cookies and marinated ground pork. Delphinidin and cyanidin glycosides were identified as the primary bioactive compounds of blackcurrant that trapped MGO to form the corresponding mono- and di-MGO adducts. This study suggested that blackcurrant anthocyanins might serve as a novel additive to reduce the consumption of dietary reactive carbonyl species and AGEs from both animal- and plant-derived processed foods. PRACTICAL APPLICATION: The levels of α-dicarbonyls and advanced glycation end products in ground pork and cookies were significantly reduced when fortified with blackcurrant. The blackcurrant anthocyanins might be a novel agent inhibiting α-dicarbonyls and dietary advanced glycation end products formation in thermally processed foods.


Asunto(s)
Antocianinas , Frutas , Productos Finales de Glicación Avanzada , Piruvaldehído , Ribes , Antocianinas/análisis , Antocianinas/química , Antocianinas/farmacología , Productos Finales de Glicación Avanzada/análisis , Frutas/química , Animales , Porcinos , Ribes/química , Reacción de Maillard , Productos de la Carne/análisis , Manipulación de Alimentos/métodos
8.
Food Funct ; 15(12): 6347-6358, 2024 Jun 17.
Artículo en Inglés | MEDLINE | ID: mdl-38768294

RESUMEN

Age-related macular degeneration (AMD) is a prominent cause of vision loss among the elderly, and the treatment options for dry AMD (dAMD) are severely limited. Lutein has a favorable effect on the treatment of dAMD. Algae oil, rich in docosahexaenoic acid (DHA), is considered an effective intervention for eye diseases. In this study, casein-mannose conjugates were prepared to form algal oil-in-water Pickering emulsions by ultrasound-assisted Maillard reaction. As the ultrasound time increased from 0 to 25 min, the droplet size decreased to 648.2 ± 21.18 nm, which substantially improved the stability of the Pickering emulsions. The retention of lutein in the Pickering emulsions under ultrasonic treatment for 20 min was significantly improved under different conditions. The simulated gastrointestinal digestion revealed that ultrasound-assisted Pickering emulsions are an effective method for improving the bioaccessibility of lutein (19.76%-53.34%). In vivo studies elucidated that the lutein-loaded Pickering emulsions could effectively alleviate retinal thinning induced by sodium iodate (NaIO3) in mice with dAMD. Mechanistically, lutein-loaded Pickering emulsions significantly reduced oxidative stress by decreasing the MDA level, increasing the SOD production, and reducing the retinal ROS production. These findings explored the protective effects of lutein-loaded Pickering emulsions on dAMD and offered promising prospects for the nutritional intervention of dAMD.


Asunto(s)
Emulsiones , Luteína , Degeneración Macular , Reacción de Maillard , Animales , Emulsiones/química , Luteína/farmacología , Luteína/química , Luteína/administración & dosificación , Ratones , Masculino , Estrés Oxidativo/efectos de los fármacos , Ratones Endogámicos C57BL , Humanos , Modelos Animales de Enfermedad
9.
Food Chem ; 454: 139758, 2024 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-38805927

RESUMEN

Hot air drying (HAD) is an extensive method used on oysters and it causes the most intuitive change, a color change. However, the mechanism of color change remains unclear. This study showed that oysters underwent browning during the HAD process. The colorimetric parameter L* decreased while a* and b* increased, all of which were well described by the first-order color kinetic model. Mechanistically, the HDA process induced the oxidative browning of phenols and the generation of Maillard reaction products (5-hydroxymethylfurfural and hydrophilic pyrrole). Meanwhile, the HAD process caused lipid oxidation, leading to the reduction of phosphatidylethanolamine and the generation of reactive carbonyl compounds (aldehydes and α-dicarbonyl compounds). Moreover, the accumulation of hydrophobic pyrroles, a lipid-induced Maillard-like reaction product, was observed. These results suggest that, in addition to phenolic oxidation, sugar- and amino acid-mediated non-enzymatic browning reactions, lipid-mediated Maillard-like reactions play important roles in oyster darkening during the HAD process.


Asunto(s)
Color , Calor , Reacción de Maillard , Ostreidae , Animales , Ostreidae/química , Mariscos/análisis , Oxidación-Reducción , Cinética , Fenoles/química , Manipulación de Alimentos , Desecación/métodos
10.
Food Chem ; 452: 139282, 2024 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-38723562

RESUMEN

Acrylamide (AA) is a neoformed compound in heated foods, mainly produced between asparagine (Asn) and glucose (Glc) during the Maillard reaction. Galacturonic acid (GalA), the major component of pectin, exhibits high activity in AA formation. This study investigated the pathway for AA formation between GalA and Asn. Three possible pathways were proposed: 1) The carbonyl group of GalA directly interacts with Asn to produce AA; 2) GalA undergoes an oxidative cleavage reaction to release α-dicarbonyl compounds, which subsequently leads to AA production; 3) 5-formyl-2-furancarboxylic acid, the thermal degradation product of GalA, reacts with Asn to generate AA. Structural analysis revealed that the COOH group in GalA accelerated intramolecular protonation and electron transfer processes, thereby increasing the formation of AA precursors such as decarboxylated Schiff base and α-dicarbonyl compounds, promoting AA formation. This study provides a theoretical basis and new insights into the formation and control of AA.


Asunto(s)
Acrilamida , Ácidos Hexurónicos , Acrilamida/química , Ácidos Hexurónicos/química , Reacción de Maillard , Asparagina/química , Calor , Pectinas/química , Estructura Molecular
11.
Food Res Int ; 183: 114175, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38760120

RESUMEN

Lactose hydrolysed concentrated milk was prepared using ß-galactosidase enzyme (4.76U/mL) with a reaction period of 12 h at 4 °C. Addition of polysaccharides (5 % maltodextrin/ß-cyclodextrin) to concentrated milk either before or after lactose hydrolysis did not result in significant differences (p > 0.05) in degree of hydrolysis (% DH) of lactose and residual lactose content (%). Three different inlet temperatures (165 °C, 175 °C and 185 °C) were used for the preparation of powders which were later characterised based on physico-chemical and maillard browning characteristics. Moisture content, solubility and available lysine content of the powders decreased significantly, whereas, browning parameters i.e., browning index, 5-hydroxymethylfurfural, furosine content increased significantly (p < 0.05) with an increase in inlet air temperature. The powder was finally prepared with 5 % polysaccharide and an inlet air temperature of 185 °C which reduced maillard browning. Protein-polysaccharide interactions were identified using Fourier Transform infrared spectroscopy, fluorescence spectroscopy and determination of free amino groups in the powder samples. Maltodextrin and ß-cyclodextrin containing powder samples exhibited lower free amino groups and higher degree of graft value as compared to control sample which indicated protein-polysaccharide interactions. Results obtained from Fourier Transform infrared spectroscopy also confirmed strong protein-polysaccharide interactions, moreover a significant decrease in fluorescence intensity was also observed in the powder samples. These interactions between the proteins and polysaccharides reduced the maillard browning in powders.


Asunto(s)
Furaldehído , Lactosa , Reacción de Maillard , Leche , Polisacáridos , Polvos , Lactosa/química , Polisacáridos/química , Leche/química , Animales , Espectroscopía Infrarroja por Transformada de Fourier , Furaldehído/análogos & derivados , Furaldehído/química , beta-Galactosidasa/metabolismo , beta-Ciclodextrinas/química , Hidrólisis , Secado por Pulverización , Temperatura , Lisina/química , Lisina/análogos & derivados , Solubilidad , Espectrometría de Fluorescencia , Proteínas de la Leche/química , Manipulación de Alimentos/métodos
12.
Food Res Int ; 183: 114183, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38760123

RESUMEN

A large number of volatile compounds are formed during the baking of foods by reactions such as caramelization and Maillard reactions. Elucidating the reaction mechanisms may be useful to predict and control food quality. Ten reaction volatile markers were extracted during baking of solid model cakes implemented with known amounts of precursors (glucose with or without leucine) and then quantified by Thermal desorption-Gas chromatography-Mass spectrometry. The kinetic data showed that the level of air convection in the oven had no significant influence on the reaction rates. In contrast, increasing baking temperatures had a nonlinear accelerating impact on the generation of newly formed volatile compounds with a bell-shaped kinetic curve found for most of the markers at 200 °C. The presence of leucine triggered the activation of the Maillard and Strecker routes with a specific and very rapid formation of 3-Methylbutanal and pyrazines. A dynamic model was developed, combining evaporation flow rate and kinetic formation and consumption of reaction markers. It can be used to describe, for two furanic compounds of different volatilities, the vapor concentrations in the oven from the concentrations measured in the model cakes.


Asunto(s)
Culinaria , Cromatografía de Gases y Espectrometría de Masas , Glucosa , Calor , Leucina , Reacción de Maillard , Compuestos Orgánicos Volátiles , Cinética , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/química , Culinaria/métodos , Glucosa/química , Glucosa/análisis , Leucina/química , Aldehídos/análisis , Aldehídos/química , Pirazinas/análisis , Pirazinas/química
13.
Food Res Int ; 187: 114436, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38763683

RESUMEN

Amadori compounds (ACs) are key Maillard intermediates in various foods after thermal processing, and are also important non-saponin components in red ginseng. Currently, due to the difficulty in obtaining AC standards, the determination of multiple ACs is limited and far from optimal. In this study, an ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed and validated. A green synthetic method was developed for arginyl-fructosyl-glucose (AFG), the major AC in red ginseng with potential health benefits. The UPLC-MS/MS method was then applied in identification and quantification of ACs in red ginseng samples, which showed for the first time that 12 other ACs also exist in red ginseng in addition to AFG and arginyl-fructose (total 98.88 % of all ACs). Contents of AFG and arginyl-fructose in whole red ginseng were 36.23 and 10.80 mg/g dry weight, respectively. Raw ginseng can be steamed and then dried whole to obtain whole red ginseng, or sliced before drying to obtain sliced red ginseng. Slicing before drying was found to reduce ACs content. Results of the present study will help to reveal the biological functions of red ginseng and related products associated with ACs and promote the standardization of red ginseng manufacture.


Asunto(s)
Panax , Espectrometría de Masas en Tándem , Panax/química , Espectrometría de Masas en Tándem/métodos , Cromatografía Líquida de Alta Presión/métodos , Arginina/análisis , Arginina/análogos & derivados , Reacción de Maillard , Extractos Vegetales/química , Fructosa/análisis , Fructosa/química , Cromatografía Líquida con Espectrometría de Masas
14.
J Food Sci ; 89(7): 4331-4344, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38783574

RESUMEN

Color and shape are important quality attributes in baked goods, particularly cookies. Composition and processing conditions determine and influence color development and morphological changes in these baked goods. The objective of this study was to systematically evaluate the evolution of color and shape during baking to determine useful correlations that can be implemented during the assessment and modeling of the baking process. Cookies (AACC-I standard protocol 10-53.01) were baked at 185, 205, and 225°C. Moisture content, water activity, surface temperature, characteristic dimensions (radius and thickness), and color indexes (lightness, redness, blueness, and browning index [BI]) were monitored at different locations on the cookie surface and baking times. Relationships among the tested conditions were explored using correlation analysis. The cookies' dimensions and color indexes were strongly correlated with changes in moisture content over time, and those relationships were characterized using empirical models. The temperature dependence of the kinetic parameters of the changes in lightness and BI was also described and deemed independent of the location on the cookie surface. This study provides insights into the influence of heat and mass transfer on the physical and physicochemical changes of cookies during baking. The kinetic and secondary models developed in this study can serve as important components for establishing a comprehensive approach for coupling heat transfer, mass transfer, and reaction kinetics to estimate and optimize cookie-baking processes. PRACTICAL APPLICATION: The findings from this study provide valuable information for better understanding the morphological changes and color developments during the cookie-baking process. The quantitative data and models generated in this study will allow identifying baking conditions for better quality development.


Asunto(s)
Color , Culinaria , Calor , Culinaria/métodos , Cinética , Agua , Reacción de Maillard
15.
Molecules ; 29(9)2024 Apr 26.
Artículo en Inglés | MEDLINE | ID: mdl-38731499

RESUMEN

Carbon nanodots (CDs) are commonly found in food products and have attracted significant attention from food scientists. There is a high probability of CD exposure in humans, but its impacts on health are unclear. Therefore, health effects associated with CD consumption should be investigated. In this study, we attempted to create a model system of the Maillard reaction between cystine and glucose using a simple cooking approach. The CDs (CG-CDs) were isolated from cystine-glucose-based Maillard reaction products and characterized using fluorescence spectroscopy, X-ray diffractometer (XRD), and transmission electron microscope (TEM). Furthermore, human mesenchymal stem cells (hMCs) were used as a model to unravel the CDs' cytotoxic properties. The physiochemical assessment revealed that CG-CDs emit excitation-dependent fluorescence and possess a circular shape with sizes ranging from 2 to 13 nm. CG-CDs are predominantly composed of carbon, oxygen, and sulfur. The results of the cytotoxicity evaluation indicate good biocompatibility, where no severe toxicity was observed in hMCs up to 400 µg/mL. The DPPH assay demonstrated that CDs exert potent antioxidant abilities. The qPCR analysis revealed that CDs promote the downregulation of the key regulatory genes, PPARγ, C/EBPα, SREBP-1, and HMGCR, coupled with the upregulation of anti-inflammatory genes. Our findings suggested that, along with their excellent biocompatibility, CG-CDs may offer positive health outcomes by modulating critical genes involved in lipogenesis, homeostasis, and obesity pathogenesis.


Asunto(s)
Proteína alfa Potenciadora de Unión a CCAAT , Carbono , Reacción de Maillard , Células Madre Mesenquimatosas , PPAR gamma , Proteína 1 de Unión a los Elementos Reguladores de Esteroles , Humanos , Carbono/química , PPAR gamma/genética , PPAR gamma/metabolismo , Proteína 1 de Unión a los Elementos Reguladores de Esteroles/genética , Proteína 1 de Unión a los Elementos Reguladores de Esteroles/metabolismo , Células Madre Mesenquimatosas/metabolismo , Células Madre Mesenquimatosas/efectos de los fármacos , Proteína alfa Potenciadora de Unión a CCAAT/metabolismo , Proteína alfa Potenciadora de Unión a CCAAT/genética , Puntos Cuánticos/química , Regulación hacia Abajo/efectos de los fármacos , Regulación de la Expresión Génica/efectos de los fármacos , Antioxidantes/farmacología , Antioxidantes/química , Azufre/química
16.
Carbohydr Res ; 540: 109139, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38728964

RESUMEN

The chemistry of N,N-diglycated amino acids remains unexplored due to their transient nature in the Maillard reaction. Their increased reactivity is attributed to the presence of high concentrations of open ring forms in at least one of their sugar moieties. The N,N-diglycated alanine derivatives were generated in situ via dissociation from their stable precursors the bis[N,N-diglycated alanine]iron(II) complexes, in the alanine/glucose/FeCl2 model system heated at 110 °C for 2 h. The thermal degradations of these complexes were followed in the reaction mixture, using isotope-labelled reactants, such as [13C-3] alanine and [13C-U] glucose, and ESI/qTOF/MS analysis. The N,N-diglycated amino acids exhibited a unique and characteristic chemical interaction between the neighbouring sugar moieties generating hitherto unknown heterocyclic moieties. The origin of these products was tracked by identifying ions incorporating one C-3 atom from alanine and between seven to 12 carbon atoms from the sugar moieties in the same structure. Temperature-dependent FTIR spectra of di-glycated alanine generated through ball milling provided further evidence for their reactivity.


Asunto(s)
Alanina , Alanina/química , Glicosilación , Reacción de Maillard , Glucosa/química
17.
Molecules ; 29(9)2024 May 03.
Artículo en Inglés | MEDLINE | ID: mdl-38731606

RESUMEN

The polyphenol-Maillard reaction is considered one of the important pathways in the formation of humic-like substances (HLSs). Glucose serves as a microbial energy source that drives the humification process. However, the effects of changes in glucose, particularly its concentration, on abiotic pathways remain unclear. Given that the polyphenol-Maillard reaction requires high precursor concentrations and elevated temperatures (which are not present in soil), gibbsite was used as a catalyst to overcome energetic barriers. Catechol and glycine were introduced in fixed concentrations into a phosphate-buffered solution containing gibbsite using the liquid shake-flask incubation method, while the concentration of glucose was controlled in a sterile incubation system. The supernatant fluid and HLS components were dynamically extracted over a period of 360 h for analysis, thus revealing the influence of different glucose concentrations on abiotic humification pathways. The results showed the following: (1) The addition of glucose led to a higher degree of aromatic condensation in the supernatant fluid. In contrast, the supernatant fluid without glucose (Glu0) and the control group without any Maillard precursor (CK control group) exhibited lower degrees of aromatic condensation. Although the total organic C (TOC) content in the supernatant fluid decreased in all treatments during the incubation period, the addition of Maillard precursors effectively mitigated the decreasing trend of TOC content. (2) While the C content of humic-like acid (CHLA) and the CHLA/CFLA ratio (the ratio of humic-like acid to fulvic-like acid) showed varying increases after incubation, the addition of Maillard precursors resulted in a more noticeable increase in CHLA content and the CHLA/CFLA ratio compared to the CK control group. This indicated that more FLA was converted into HLA, which exhibited a higher degree of condensation and humification, thus improving the quality of HLS. The addition of glycine and catechol without glucose or with a glucose concentration of 0.06 mol/L was particularly beneficial in enhancing the degree of HLA humification. Furthermore, the presence of glycine and catechol, as well as higher concentrations of glucose, promoted the production of N-containing compounds in HLA. (3) The presence of Maillard precursors enhanced the stretching vibration of the hydroxyl group (-OH) of HLA. After the polyphenol-Maillard reaction of glycine and catechol with glucose concentrations of 0, 0.03, 0.06, 0.12, or 0.24 mol/L, the aromatic C structure in HLA products increased, while the carboxyl group decreased. The presence of Maillard precursors facilitated the accumulation of polysaccharides in HLA with higher glucose concentrations, ultimately promoting the formation of Al-O bonds. However, the quantities of phenolic groups and phenols in HLA decreased to varying extents.


Asunto(s)
Glucosa , Sustancias Húmicas , Reacción de Maillard , Polifenoles , Sustancias Húmicas/análisis , Glucosa/química , Glucosa/metabolismo , Polifenoles/química , Catecoles/química
18.
J Agric Food Chem ; 72(19): 11153-11163, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38695891

RESUMEN

Maillard reaction (MR) plays a pivotal role in the food flavor industry, including a cascade of reactions starting with the reaction between amino compounds and reducing sugars, and thus provides various colors and flavors. A new group of volatile compounds called pyrazinones found in MR are now getting more attention. In this study, eight volatile pyrazinones were found in the asparagine MR systems, in which 3,5-dimethyl- and 3,6-dimethyl-2(1H)-pyrazinones were reported for the first time. The major formation pathways were the reactions between asparagine and α-dicarbonyls, with decarboxylation as a critical step. Besides, novel alternative pathways involving alanine amidation and successive reactions with α-dicarbonyls were explored and successfully formed eight pyrazinones. The major differences between alanine-amidated pathways and decarboxylation pathways are the amidation step and absence of the decarboxylation step. For the alanine-amidated pathways, the higher the temperature, the better the amidation effect. The optimal amidation temperature was 200 °C in this study. The reaction between the alanine amide and α-dicarbonyls after amidation can happen at low temperatures, such as 35 and 50 °C, proposing the possibility of pyrazinone formation in real food systems. Further investigations should be conducted to investigate volatile pyrazinones in various food systems as well as the biological effects and kinetic formation differences of the volatile pyrazinones.


Asunto(s)
Alanina , Asparagina , Reacción de Maillard , Pirazinas , Compuestos Orgánicos Volátiles , Pirazinas/química , Alanina/química , Asparagina/química , Compuestos Orgánicos Volátiles/química , Aromatizantes/química
19.
Food Res Int ; 186: 114333, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38729693

RESUMEN

Acrylamide is an amide formed in the Maillard reaction, with asparagine as the primary amino acid precursor. The intake of large amounts of acrylamide has induced genotoxic and carcinogenic effects in hormone-sensitive tissues of animals. The enzime asparaginase is one of the most effective methods for lowering the formation of acrylamide in foods such as potatoes. However, the reported sensory outcomes for coffee have been unsatisfactory so far. This study aimed to produce coffees with reduced levels of acrylamide by treating them with asparaginase while retaining their original sensory and bioactive profiles. Three raw samples of Coffea arabica, including two specialty coffees, and one of Coffea canephora were treated with 1000, 2000, and 3000 ASNU of the enzyme. Asparagine and bioactive compounds (chlorogenic acids-CGA, caffeine, and trigonelline) were quantified in raw and roasted beans by HPLC and LC-MS, while the determination of acrylamide and volatile organic compounds was performed in roasted beans by CG-MS. Soluble solids, titratable acidity, and pH were also determined. Professional cupping by Q-graders and consumer sensory tests were also conducted. Results were analyzed by ANOVA-Fisher, MFA, PCA and Cluster analyses, with significance levels set at p ≤ 0.05. Steam treatment alone decreased acrylamide content by 18.4%, on average, and 6.1% in medium roasted arabica and canefora coffees. Average reductions of 32.5-56.0% in acrylamide formation were observed in medium roasted arabica beans when 1000-3000 ASNU were applied. In the canefora sample, 59.4-60.7% reductions were observed. However, steam treatment primarily caused 17.1-26.7% reduction of total CGA and lactones in medium roasted arabica samples and 13.9-22.0% in canefora sample, while changes in trigonelline, caffeine, and other evaluated chemical parameters, including the volatile profiles were minimal. Increasing enzyme loads slightly elevated acidity. The only sensory changes observed by Q-graders and or consumers in treated samples were a modest increase in acidity when 3000 ASNU was used in the sample with lower acidity, loss of mild off-notes in control samples, and increased perception of sensory descriptors. The former was selected given the similarity in chemical outcomes among beans treated with 2000 and 3000 ASNU loads.


Asunto(s)
Acrilamida , Asparaginasa , Asparagina , Coffea , Café , Gusto , Acrilamida/análisis , Asparagina/análisis , Coffea/química , Café/química , Humanos , Compuestos Orgánicos Volátiles/análisis , Culinaria/métodos , Alcaloides/análisis , Ácido Clorogénico/análisis , Cafeína/análisis , Masculino , Manipulación de Alimentos/métodos , Reacción de Maillard , Calor , Cromatografía Líquida de Alta Presión , Semillas/química , Femenino
20.
Food Res Int ; 186: 114397, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38729739

RESUMEN

The formation mechanism behind the sophisticated aromas of sesame oil (SO) has not been elucidated. The interaction effects of the Maillard reaction (MR) and lipid oxidation on the aroma formation of fragrant sesame oil were investigated in model reaction systems made of l-lysine (Lys) and d-glucose (Glc) with or without fresh SO (FSO) or oxidized SO (OSO). The addition of OSO to the Lys-Glc model increased the MR browning at 294 nm and 420 nm and enhanced the DPPH radical scavenging activity greater than the addition of FSO (p < 0.05). The presence of lysine and glucose inhibited the oxidation of sesame oil, reduced the loss of γ-tocopherol, and facilitated the formation of sesamol (p < 0.05). The Maillard-lipid interaction led to the increased concentrations of some of the alkylpyrazines, alkylfurans, and MR-derived ketones and acids (p < 0.05) while reducing the concentrations of other pyrazines, lipid-derived furans, aliphatic aldehydes, ketones, alcohols, and acids (p < 0.05). The addition of FSO to the MR model enhanced the characteristic roasted, nutty, sweet, and fatty aromas in sesame oil (p < 0.05), while excessive lipid oxidation (OSO) brought about an unpleasant oxidized odor and reduced the characteristic aromas. This study helps to understand the sophisticated aroma formation mechanism in sesame oil and provides scientific instruction for precise flavor control in the production of sesame oil.


Asunto(s)
Glucosa , Lisina , Reacción de Maillard , Odorantes , Oxidación-Reducción , Aceite de Sésamo , Aceite de Sésamo/química , Glucosa/química , Odorantes/análisis , Lisina/química , Fenoles/química , Benzodioxoles
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