5-hydroxymethylfurfural and furosine

This study investigated the effect of roasting (150 °C for 30 min) and storage (12 months at 4 °C, 25 °C, and 25 °C in vacuum package), conditions of which are generally applied in the industry and markets, on the formation of Maillard reaction and sugar degradation products, namely dicarbonyl compounds, 5-hydroxymethylfurfural, N-ε-fructosyllysine, and N-ε-carboxymethyllysine in Tombul and Levant hazelnuts. Roasting increased all dicarbonyl compounds significantly ( p < 0.05). The concentration of methylglyoxal was the highest while 1-deoxyglucosone was the lowest in roasted hazelnuts. 5-Hydroxymethylfurfural and N-ε-carboxymethyllysine also increased significantly ( p < 0.05) with roasting while furosine decreased. Roasting changed the progress of the Maillard reaction from the early stage to the advanced stage. On the other hand, there were no significant changes ( p > 0.05) in the concentration of Maillard reaction and sugar degradation products independent of the storage conditions or time and hazelnut variety, except for glyoxal, diacetyl, and 1-deoxyglucosone. Therefore, neither 5-hydroxymethylfurfural nor furosine is suggested as a storage marker of the Maillard reaction and sugar degradation.

Topics: Cooking; Corylus; Food Storage; Furaldehyde; Hot Temperature; Lysine; Maillard Reaction; Nuts; Pyruvaldehyde; Sugars

The Maillard reaction products (MRPs) formed after roasting of oil-tea camellia seeds (camellia seeds) were investigated. Camellia seeds are inevitably heated during processing, but the effect of heating or roasting on the physicochemical properties of camellia seed or oil-tea camellia seed oil (camellia oil) has been seldom studied, especially with respect to the Maillard reaction.. Changes in reducing sugars, free amino acids, pH, color, browning intensity and MRP (furosine, glyoxal, methylglyoxal, 5-hydroxymethylfurfural and furural) concentrations were examined in camellia seeds during roasting at 120-160 °C for 20-120 min. Results showed that roasting leads first to a decrease and then to a considerable increase in free amino groups and, at the same time, to a reduction in moisture content and decrease in pH. The sucrose content of the seeds decreased, while that of glucose and fructose increased reciprocally during roasting. On the other hand, the observed changes concerning glyoxal were negligible. Furthermore, 5-hydroxymethylfurfural and furfural have been found at the end of the roasting process, with maximum values of 572.26 ± 1.91 mg kg. This investigation provides the initial groundwork necessary for the development and implementation of green and efficient technology that could be applied to obtain high-quality camellia oil. Future research is necessary to assess antioxidant capacity, quality and safety of oil after thermal processing of camellia seeds. © 2019 Society of Chemical Industry.

Topics: Amino Acids; Camellia; Chemical Phenomena; Food Handling; Furaldehyde; Glycation End Products, Advanced; Glyoxal; Hot Temperature; Hydrogen-Ion Concentration; Lysine; Maillard Reaction; Plant Oils; Seeds; Sugars; Water

Cooking modifies food composition due to chemical reactions. Additionally, food composition shapes the human gut microbiota. Thus, the objective of this research was to unravel the effect of different food cooking methods on the structure and functionality of the gut microbiota. Common culinary techniques were applied to five foods, which were submitted to in vitro digestion-fermentation. Furosine, 5-(hydroxymethyl)furfural, and furfural were used as Maillard reaction indicators to control the heat treatment. Short-chain fatty acids production was quantified as indicator of healthy metabolic output. Gut microbial community structure was analyzed through 16S rRNA. Both food composition and cooking methods modified the microbiota composition and released short-chain fatty acids. In general, intense cooking technologies (roasting and grilling) increased the abundance of beneficial bacteria like Ruminococcus spp. or Bifidobacterium spp. compared to milder treatments (boiling). However, for some foods (banana or bread), intense cooking decreased the levels of healthy bacteria.

Topics: Bacteria; Cooking; Edible Grain; Fabaceae; Fatty Acids, Volatile; Fermentation; Fruit; Furaldehyde; Gastrointestinal Microbiome; Hot Temperature; Humans; Lysine; Maillard Reaction; Meat; RNA, Ribosomal, 16S; Vegetables

Maillard reaction (MR) was assessed in 10 powdered whey samples. Initial stages of MR were evaluated using furosine, intermediate stages with hydroxymethylfurfural (HMF) and absorbance at 284nm, advanced stages with color parameters (CIELab color) and final stages with browning index; additionally, insolubility, pH and water activity (Aw) were measured. Principal component analysis (PCA) and cluster analysis (CA) were used to establish the heat damage of samples based on relations between variables. Three principal components were found which explained 79.0% of the total variance and they were the basis for cluster analysis where 5 clusters were formed. PCA and CA can separate samples according to their heat damage and they help in a clearer interpretation of the information from indicators which shows that samples with high lactose content exhibited the higher heat damage.

Topics: Cluster Analysis; Food, Preserved; Furaldehyde; Hot Temperature; Hydrogen-Ion Concentration; Lactose; Lysine; Maillard Reaction; Multivariate Analysis; Principal Component Analysis; Solubility; Water; Whey; Whey Proteins

The Maillard reaction indicators furosine, hydroxymethylfurfural (HMF), acrylamide and color were determined to evaluate heat effects induced during extrusion, infrared and microwave heating of soybean. In addition, the present paper aimed to study changes in the phenolic compounds, as well as in the overall antioxidant properties of different soybean products in relation to heating at 45-140 °C during the processes.. Soybean proteins were highly sensible to Maillard reaction and furosine was rapidly formed under slight heating conditions during extrusion and infrared heating. Microwave heating at lower temperatures for a longer time yielded lower acrylamide levels in the final soybean products, as a result of its partial degradation. However, during infrared heating, acrylamide formation greatly increased with decreasing moisture content. After a short time of extrusion and infrared heating at 140 °C and microwave heating at 135 °C for 5 min, concentrations of HMF increased to 11.34, 26.21 and 34.97 µg g(-1), respectively.. The heating conditions caused formation of acrylamide, HMF and furosine in high concentration. The results indicate that the complex structure of soybeans provides protection of phenolic compounds from thermal degradation, and that Maillard reaction products improved the antioxidant properties of heat-treated soybean.

Topics: Acrylamide; Antioxidants; Color; Flavonoids; Food Handling; Furaldehyde; Glycine max; Hot Temperature; Infrared Rays; Lysine; Maillard Reaction; Microwaves; Phenols; Seeds; Soybean Proteins

Protein changes in relation to solubility, Maillard reaction (MR), and protein cross-linking in whole milk powder (WMP), skim milk powder (SMP), and whey protein concentrate (WPC) stored at different relative humidities (RHs) were investigated by chemical and electrophoretic methods. WMP and SMP reached minimum solubility rapidly, while WPC showed no change in solubility. The loss of solubility corresponded with development of high-molecular-weight protein complexes observed by two-dimensional electrophoresis. The maximal MR rate occurred at 66% RH for WMP and SMP (high lactose/protein ratios) and 84% RH for WPC (low lactose/protein ratios) based on the furosine and hydroxymethylfurfural contents. However, browning was greatest at 84% RH in all powders. The minimum solubility corresponded with the casein and fat contents. The retention of solubility and minimal protein cross-linking of WPC compared to casein-containing powders suggest that the casein content and cross-linking strongly influence the decrease in the solubility of milk powder.

Topics: Animals; Caseins; Cross-Linking Reagents; Food, Preserved; Furaldehyde; Lysine; Maillard Reaction; Milk; Milk Proteins; Solubility; Whey Proteins

The effects of pelleting on the extent of the Maillard reaction (MR) and on calcium, magnesium and zinc solubility and absorption were analysed in a conventional pre-starter diet for suckling piglets. Development was tested measuring colour, absorbance (280/420 nm), fluorescence, residual free lysine, furosine, hydroxymethylfurfural (HMF) and furfural contents before and after pelleting. Fluorescence, absorbance and mineral solubility were also measured after in vitro digestion of diets. The effects on mineral absorption were tested using Caco-2 cells.. MR indexes confirmed the development of the reaction during the pelleting of this particular diet compared with the meal diet. The CIE-Lab colour parameters showed a decrease in luminosity (L*) and progress of the colour to the red zone (a*) in the pelleted diet. A 36% decrease in free lysine content was observed. Significant correlations were observed between fluorescence intensity and furosine levels, HMF and furfural. The pelleting process did not modify calcium and magnesium solubility after in vitro digestion, but soluble zinc increased. The efficiency of calcium and zinc transport across Caco-2 cell monolayers was greater in the pelleted diet.. Evidence of MR development is shown, resulting in various nutritional consequences. Optimisation of pelleting could result in a better formulation of diets for feedstuffs.

Topics: Animal Feed; Animal Husbandry; Animals; Animals, Suckling; Caco-2 Cells; Calcium; Cell Membrane Permeability; Color; Digestion; Fluorescence; Furaldehyde; Hot Temperature; Humans; Intestinal Absorption; Lysine; Magnesium; Maillard Reaction; Minerals; Nutritive Value; Solubility; Swine; Zinc

Contents of some indicators of the Maillard reaction (MR) in two diets adjusted to the adolescent requirements are compared: the A-diet, usually consumed by the adolescent population containing their preferred foods cooked by the culinary techniques more frequently chosen; and the B-diet, with the same foods, except those industrially processed and with high content of Maillard reaction products (MRP), cooked in softer processes to minimise the MR. Aliquots of a lunch-dinner (LD) and breakfast-afternoon (BA) snack pools separately from both diets were ground and lyophilised. Fluorescence associated to MRP, CIELAB colour parameters, furosine, hydroxymethylfurfural (HMF), carboxymethyllysine (CML) and sugar contents were investigated in the samples. Significant losses of lightness were manifested in A samples compared to the B ones. Fluorescence intensity was significantly higher in the LD and BA samples from the A-diet. Furosine measured in the A-diet was similar to that found in the B-diet. However, HMF content was significantly higher in the A-diet, as well as CML. Data showed significant higher levels of advanced MRP in the usual diet. Thus, MRP intake associated to alimentary pattern in the adolescence population might be studied in order to assess the health implications of the MRP consumption and its possible synergic effect with endogenous advanced glycation endproducts.

Topics: Adolescent; Adolescent Nutritional Physiological Phenomena; Chromatography, High Pressure Liquid; Color; Diet; Food Analysis; Food Handling; Food Preferences; Furaldehyde; Glycation End Products, Advanced; Humans; Lysine; Maillard Reaction; Spectrometry, Fluorescence

Breakfast cereals are significant contributors to the daily intake of food-derived acrylamide in Western countries. Acrylamide was determined by LC-MS in 60 commercial breakfast cereals marketed in Spain. Several SPE cartridges were evaluated for clarification of the aqueous extract. LOQ was 62 microg/kg . Acrylamide content ranged from < 62-803 microg/kg (average 292 microg/kg , and median 258 microg/kg , with an estimated acrylamide intake from breakfast cereals of 2.68 microg acrylamide/person/day. According to the German concept of minimization, a signal value 450 microg/kg was calculated. Relationships among acrylamide and some parameters of the studied samples such as type of cereal, its physical form (puffed and flaked) or certain ingredients in the formulation (proteins and dietary fibre content) were also investigated. Wheat-based cereals contained significantly higher levels of acrylamide, as did samples with higher fibre or protein content. In addition, puffed breakfast cereals also contained significantly higher levels of acrylamide. There was no significant correlation between acrylamide levels and contents of 5-hydroxymethylfurfural, furosine or cereal browning.

Topics: Acrylamide; Chromatography, Liquid; Edible Grain; Food Handling; Furaldehyde; Hot Temperature; Lysine; Maillard Reaction; Mass Spectrometry; Spain

During the advanced stage of the Maillard reaction (MR) in food processing and cooking, Amadori rearrangement products undergo dehydration and fission and fluorescent substances are formed. Free and total (free + linked to the protein backbone) fluorescence (FIC) due to Maillard compounds in 60 commercial breakfast cereals was evaluated. Pronase was used for efficient release of linked fluorescent Maillard compounds from the protein backbone. Results were correlated with some heat-induced markers of the extent of the MR or sugar caramelisation during cereal processing, such as hydroxymethylfurfural, furfural, glucosilisomaltol and furosine. The effect of sample composition (dietary-fibre added, protein, etc.) on levels of FIC, expressed as fluorescence intensity (FI) per milligram of sample, is discussed. FIC is significantly correlated to the protein content of the sample and fluorescent Maillard compounds are mainly linked to the protein backbone. The ratio of total-FIC to free-FIC was 10.4-fold for corn-based, wheat-based and multicereal-based breakfast cereals but significantly higher in rice-based samples. Addition of dietary fibre or honey increased the FIC values. Data support the usefulness of FIC measurement as an unspecific heat-induced marker in breakfast cereals.

Topics: Dietary Fiber; Dietary Proteins; Edible Grain; Fluorescence; Food Handling; Furaldehyde; Honey; Hot Temperature; Lysine; Maillard Reaction; Oryza; Triticum; Zea mays

In the context of the general applicability of hydroxymethylfurfural (HMF), lactulose and furosine as time-temperature integrators (TTIs) for thermal processing of milk, the influence of milk fat content was studied. Formation kinetics were analysed for milk with fat content of 4.0 +/- <0.1%. In previous experiments, it was observed that, under isothermal and non-isothermal heating conditions, formation of the three chemical compounds could be described by pseudo-zero order kinetics. Since the kinetic model was known, the experimental design could be simplified. Data were analysed by a non-linear regression procedure and results were evaluated by construction of joint confidence regions and temperature time tolerance (TTT-) diagrams. Formation kinetics of HMF and lactulose was not affected by milk fat content. Regarding furosine, significant differences were observed between kinetic parameters in whole, semi-skimmed and skimmed milk. The observed differences however were negligible in the context of process impact evaluation.

Topics: Animals; Food Handling; Furaldehyde; Hot Temperature; Kinetics; Lactulose; Lipids; Lysine; Milk; Regression Analysis

In the context of identifying intrinsic time temperature integrators (TTIs) for evaluating thermal processing of milk, the possible influence of seasonal variation in milk composition on the applicability of alkaline phosphatase (ALP), hydroxymethylfurfural (HMF), lactulose and furosine for process impact assessment was studied. Hereto inactivation and formation kinetics of these indicators were analysed in milk samples collected over a one year period. Based on previous research (isothermal and non-isothermal heating conditions) it was assumed that thermal inactivation of ALP followed first order kinetics, and formation of HMF, lactulose and furosine could be described by pseudo-zero order kinetics. This allowed the use of a simplified experimental design to obtain the kinetic parameters. Based on 90% joint confidence regions, kinetic parameter values differed significantly between different batches of milk for all four indicators. Additionally, variable ALP activities and HMF concentrations were observed in the raw milk samples. Nevertheless, the observed differences did not seem to restrict the applicability of the selected TTIs as illustrated by the construction of temperature time tolerance (TTT-) diagrams. Through these diagrams, use of the TTIs implied an uncertainty of approximately 2 degrees C between equivalent processes.

Topics: Alkaline Phosphatase; Animals; Food Handling; Furaldehyde; Hot Temperature; Kinetics; Lactulose; Lysine; Milk; Milk Proteins; Seasons; Temperature; Time Factors

Determination of changes in 2-furoylmethyl amino acids and hydroxymethylfurfural during the storage of four honey samples at 25 and 35 degrees C during 12 months was achieved to assess the potential use of both parameters, singly or in combination, as quality indicators. 2-Furoylmethyl amino acids increased during storage at both temperatures, whereas hydroxymethylfurfural only presented slight variations during storage at 25 degrees C but increased noticeably at 35 degrees C. The study of 2-furoylmethyl amino acids in 49 commercial honeys revealed that 2-furoylmethyl lysine (furosine) was present in all samples, whereas 2-furoylmethyl derivatives of arginine, GABA, and proline were only present in seven samples. Hydroxymethylfurfural can be considered as a good indicator of heat treatments applied to honey samples, whereas 2-furoylmethyl amino acids can be used as suitable markers of the storage period. The use of both parameters can be useful to detect adulteration with invert syrups, excessive heat treatments, or prolonged storage of honey samples.

Topics: Amino Acids; Food Preservation; Furaldehyde; Honey; Hot Temperature; Lysine; Quality Control; Temperature

A detailed kinetic study of hydroxymethylfurfural, lactulose and furosine formation was performed upon heating milk at temperatures between 90 degrees C and 140 degrees C. In case of prolonged heating, formation kinetics could be described by a fractional conversion model. Considering only the first phase of the model, kinetics could be simplified to a pseudo-zero order model. A first assessment of kinetic parameters was made by isothermal experiments. Data were analysed using both a 2-step linear and a 1-step non-linear regression method. Only for furosine, did the global 1-step regression approach seem to give better results than the individual 2-step regression approach. Next, the estimated parameters k(ref) and Ea were re-evaluated under non-isothermal conditions by subjecting milk to a time variable temperature profile. Given the complexity of Maillard reaction, it seemed better to estimate kinetic parameters under non-isothermal conditions when using a simplified model. Formation of hydroxymethylfurfural, lactulose and furosine was characterized by an Ea value of 90.2 kJ/mol (k(110 degrees C) = 1.2 micromol/l, min), 99.1 kJ/mol (k(110 degrees C) = 51.5 mg/l, min) and 88.7 kJ/mol (k(110 degrees C) = 16.3 mg/100 g protein, min) respectively. Additionally, 90% joint confidence regions were constructed in order to obtain an accurate representation of the statistical confidence associated with the simultaneously estimated parameters.

Topics: Animals; Cattle; Furaldehyde; Gastrointestinal Agents; Hot Temperature; Kinetics; Lactulose; Lysine; Milk; Models, Chemical; Regression Analysis; Thermodynamics

The reaction kinetics of two heat damage indices, HMF and furosine, were examined in four tomato products with different dry matter contents (10.2, 25.5, 28.6, and 34.5%) over a temperature-time range of 80-120 degrees C and 0-255 min. The reactions followed pseudo-zero order kinetics. E(a) and z-value were, respectively, 139. 9 kJ/mol and 19.2 degrees C for HMF, and 93.9 kJ/mol and 28.4 degrees C for furosine. The analyses of both indices in several samples of commercial and industrial tomato products showed very low levels of HMF (from 1 to 42 ppm) and a lack of correlation between HMF and furosine mainly because of the different evolution of the two indices during storage. The HMF level of a tomato paste sample stored at 25 degrees C decreased from 609 to 17 ppm after 98 days, while furosine increased from 458 to 550 mg/100 g of protein.

Topics: Food Preservation; Furaldehyde; Kinetics; Lysine; Solanum lycopersicum; Temperature

A specific and sensitive method for quantification of the fructose-lysine linkages present in non-enzymatically glycosylated albumin and other proteins is described. Protein is hydrolyzed for 18 h in 6 mol/l HCl at 95 degrees C to yield furosine (epsilon-N-(2-furoylmethyl)-L-lysine) known as a specific degradation product of fructose-lysine. Furosine is then separated on HPLC and quantified by its UV-absorbance against a prepared fructose-lysine standard. The method has been successfully used for the determination of glycosyl-albumin in diabetic patients starting from 100 microliter serum or less, as well as for various other proteins. Unlike the usually employed thiobarbituric acid assay the present procedure is truly specific for the detection of ketoamine linkages of glycosylated proteins.

Topics: Blood Glucose; Chemical Phenomena; Chemistry; Chromatography, High Pressure Liquid; Colorimetry; Fructose; Furaldehyde; Glycoproteins; Humans; Lysine; Serum Albumin; Serum Globulins; Transferrin