Formation Of Α-dicarbonyl Compounds Research Articles

Investigation of the effects of sugar type on the formation of α-dicarbonyl compounds in jams under in vitro digestive system model

Investigation of the effects of sugar type on the formation of α-dicarbonyl compounds in jams under in vitro digestive system model

Formation of α-dicarbonyl compounds and glycation products in sesame (Sesamum indicum L.) seeds during roasting: a multiresponse kinetic modelling approach

Formation of α-dicarbonyl compounds and glycation products in sesame (Sesamum indicum L.) seeds during roasting: a multiresponse kinetic modelling approach

Investigations on the formation of α-dicarbonyl compounds and 5-hydroxymethylfurfural in fruit products during storage: New insights into the role of Maillard reaction

The formation of α-dicarbonyl compounds and 5-hydroxymethylfurfural was investigated under different conditions and the amino acid adducts of them were confirmed using high-resolution mass spectrometry in fruit products during storage. Changes in the concentrations of sugars, amino acids, α-dicarbonyl compounds, and 5-hydroxymethylfurfural in fruit juice concentrates and dried fruits were monitored. Among the dicarbonyls, glucosone was the dominant one in 30 °Bx of fruit juice concentrates, whereas 3-deoxyglucosone was the major in 50 and 70 °Bx of those and in all dried fruits during storage. The highest level of 3-deoxyglucosone was found as 7251 ± 896.6 mg/kg in dried date at the end of the storage. During storage, the loss of free amino acids significantly increased (p < 0.05) in the higher initial reactant concentrations in fruit juice concentrates. The confirmation of amino acid adducts of dicarbonyls and 5-hydroxymethylfurfural generally with high mass accuracy proved the contribution of Maillard reaction to non-enzymatic reactions in fruit products.

Investigations on the formation of α-dicarbonyl compounds and 5-hydroxymethylfurfural in apple juice, orange juice and peach puree under industrial processing conditions

The formation of α-dicarbonyl compounds and 5-hydroxymethylfurfural during industrial processing of apple juice, orange juice, and peach puree samples was investigated in this study. Changes in the concentrations of sugars, free amino acids, α-dicarbonyl compounds, and 5-hydroxymethylfurfural in the samples from the critical process stages such as pasteurization, enzyme treatment, concentration, were monitored. The concentrations of sugars and free amino acids showed no statistically significant change during processing. 3-deoxyglucosone was identified as the dominant dicarbonyl compound formed during orange juice and peach puree processes, while glucosone was the main one formed in apple juice samples at all sampling points. In general, total dicarbonyl compounds significantly increased (p < 0.05) in apple juice, orange juice, and peach puree samples during processing, varied between 2.04 and 28.09 mg/L, 9.16 and 31.2 mg/L, and 8.9 and 48.31 mg/kg, respectively. The concentration of 5-hydroxymethylfurfural was found to be low in apple and orange samples and not detected in peach puree samples. The presence of molecular oxygen, the temperature and the duration of the process were determined as the remarkable processing parameters that affect the formation of α-dicarbonyl compounds.

Formation and migration of α-dicarbonyl compounds during storage and reheating of a sugary food simulation system.

The thermal processing of food results in the formation of α-dicarbonyl compounds (α-DCs) such as glyoxal (GO), methylglyoxal (MGO), 2,3-butanedione (2,3-BD), and 3-deoxyglucosone (3-DG), which are precursors of potentially harmful advanced glycation end products. Some of the α-DCs found in food products might result from chemical deterioration reactions during storage and reheating. A range of sugary food simulation systems were stored at three different temperatures (4, 25, and 37 °C) and reheated using three different processing methods to investigate the formation and migration of α-DCs. During 20 days of storage, the concentration of α-DCs declined, following which the concentration remained approximately constant. Methylglyoxal was the major α-DC affected during storage, its relative content decreasing from 233.71 to 44.12 μg mL-1 in the glucose-lysine system. The concentration of α-DCs decreased with increasing temperature. Microwave reheating increased the formation of α-DC compounds. The largest increases in 3-DG concentrations were observed in the maltose-lysine systems (24.94 to 35.74 μg mL-1 ). The concentration of α-DCs only changed a little in response to reheating at 100 °C, but declined when reheated at 150 °C. The concentration of α-DCs following storage and reheating depends on the type of sugar, lysine content, temperature, and method of reheating. © 2020 Society of Chemical Industry.

Quality properties and formation of α-dicarbonyl compounds in abalone muscle (Haliotis discus) as affected by tenderization and baking processes

Abalone is one of the most valuable seafood products and the quality of ready-to-eat abalone products could be improved through tenderization treatments prior to a fully cooking process. In this study, a tenderization process (80 °C for 2 h) was applied to improve the quality properties of baked abalone muscle for the developing of ready-to-eat products. The quality properties of baked abalone (150–210 °C, 10–30 min) with and without pre-tenderization treatment prior to baking were evaluated through sensory evaluation, textural analysis and Hunter Lab colorimeter. In addition, amounts of sugars and α-dicarbonyl compounds in these products were determined via HPLC analyses. The baking condition at 180 °C for 20 min combined with pre-tenderization resulted in an optimal product. The baked abalone with pre-tenderization had better textural properties (hardness, 1031.12 ± 101.67; springiness, 0.96 ± 0.02; chewiness, 817.13 ± 113.43; shear, 2843.92 ± 35.67), sensory scores (30.1 ± 2.9) and color (25.28 ± 1.21) as compared to the baked abalone without pre-tenderization (hardness, 1990.91 ± 252.35; springiness, 0.87 ± 0.01; chewiness, 1164.43 ± 195.64; shear, 3910.79 ± 302.12; sensory score, 17.4 ± 1.0; color, 15.91 ± 0.74). The reducing sugar analysis indicated the presence of ribose and glucose in the baked abalone. In addition, the formation of α-dicarbonyl compounds (degraded from reducing sugars) including glucosone, 3-deoxyglucosone, glyoxal, methylglyoxal, and diacetyl were significantly promoted by the tenderization process in the baked abalone muscle. And the tenderization treatment led to an average of 218% increase in α-dicarbonyl compounds in the baked abalone muscle. The promotion of the formation of α-dicarbonyl compounds by the tenderization treatment contributed to the accumulation of pigments in the final baked products and led to desirable color.

Levels and formation of α-dicarbonyl compounds in beverages and the preventive effects of flavonoids.

Methylglyoxal (MGO) and glyoxal (GO), α-dicarbonyl compounds found in the Maillard reaction, progressively and irreversibly modify proteins. Beverages are an exogenous source of α-dicarbonyl compounds and may potentially increase MGO and GO levels in vivo. Using GC-FID method, we detected the MGO and GO contents of 86 beverages in Chinese supermarkets. The highest MGO and GO 587.5µg/100mL and 716.7µg/100mL respectively found in soyamilk and coffee. Herbal beverages, which contained bioactive components, had lower average levels of MGO (48.1µg/100mL) and GO (25.9µg/100mL). A box-and-whisker plot was used to display variation of the same group drinks, and comparing distributions between six different groups. It was further discovered that fat, protein and flavonoids, in addition to sweeteners, had notable effects on the formation of MGO and GO in soybean milk. The result of LC/MS indicated that quercetin could prevent the formation of MGO by trapping MGO to form the mono-MGO and di-MGO adducts during soybean milk manufacturing.

Influence of Quercetin and Its Methylglyoxal Adducts on the Formation of α-Dicarbonyl Compounds in a Lysine/Glucose Model System.

Increasing evidence has identified α-dicarbonyl compounds, the reactive intermediates generated during Maillard reaction, as the potential factors to cause protein glycation and the development of chronic diseases. Therefore, there is an urgent need to decrease the levels of reactive dicarbonyl compounds in foods. In this study, we investigated the inhibitory effect of quercetin, a major dietary flavonoid, and its major mono- and di-MGO adducts on the formation of dicarbonyl compounds, such as methylglyoxal (MGO) and glyoxal (GO), in a lysine/glucose aqueous system, a model system to reflect the Maillard reaction in food process. Our result indicated that quercetin could efficiently inhibit the formation of MGO and GO in a time-dependent manner. Further mechanistic study was conducted by monitoring the formation of quercetin oxidation and conjugation products using LC-MS/MS. Quercetin MGO adducts, quercetin quinones, and the quinones of quercetin MGO adducts were detected in the system, indicating quercetin plays a dual role in inhibiting the formation of MGO and GO by scavenging free radicals generated in the system and trapping of MGO and GO to form MGO adducts. In addition, we prepared the mono- and di-MGO quercetin adducts and investigated their antioxidant activity and trapping capacity of MGO and GO. Our results indicated that both mono- and di-MGO quercetin adducts could scavenge the DPPH radical in a dose-dependent manner with >40% DPPH scavenged by the MGO adducts at 10 μM, and the di-MGO quercetin adduct could further trap MGO to generate tri-MGO adducts. Therefore, we demonstrate for the first time that quercetin MGO adducts retain the antioxidant activity and trapping capacity of reactive dicarbonyl species.

Effects of Sodium Chloride, Potassium Chloride, and Calcium Chloride on the Formation of α-Dicarbonyl Compounds and Furfurals and the Development of Browning in Cookies during Baking.

Effects of NaCl, KCl, CaCl2, NaHCO3, and NH4HCO3 on the formation of glucosone, 1-deoxyglucosone, 3-deoxyglucosone, glyoxal, methylglyoxal, diacetyl, 5-hydroxymethyl-2-furfural, and 2-furfural and browning were investigated in cookies. The presence of 1.5% NaCl, 1% KCl, and 1% CaCl2 on flour basis had no effect on α-dicarbonyl compounds, except 1-deoxyglucosone increased in the presence of KCl and CaCl2. The increase in 5-hydroxymethyl-2-furfural formation in the presence of NaCl, KCl, and CaCl2 did not relate to 3-deoxyglucosone formation and pH changes. NaCl, KCl, and CaCl2 increased browning in cookies. Model reaction systems indicated that NaCl, KCl, and CaCl2 enhance browning by increasing furfurals in caramelization. NaCl, KCl, and CaCl2 decreased browning intensity in a heated glucose-glycine system. Use of CaCl2 in cookies may considerably increase furfurals but not α-dicarbonyl compounds. Sodium reduction can be obtained by replacement with potassium without sacrificing the desired consequences of caramelization in sugar-rich baked goods.

Formation of α-dicarbonyl compounds in cookies made from wheat, hull-less barley and colored corn and its relation with phenolic compounds, free amino acids and sugars

Cookies are baked at elevated temperatures to obtain a desirable browning and flavor development, which are provided by Maillard reaction and caramelization. The drawback here is the formation of α-dicarbonyl compounds, and they are associated with many metabolic disorders besides involving in the development of the desired flavor and browning. Cookies are one of the major sources of α-dicarbonyl compounds in diet. This study was performed to evaluate the formation of α-dicarbonyl compounds in cookies prepared from different cereal flours consisting of diverse natural phenolic compounds. Flours of white wheat, hull-less barley and yellow, dark-red, blue, dark-blue colored corns containing different amount of phenolic compounds were selected as raw materials. A negative correlation was observed between total phenolic compounds and glyoxal, methylglyoxal and diacetyl concentrations after baking. α-Dicarbonyl compound-trapping ability of phenolic compounds was attributed to this reduction during baking of cookies. On the other hand, higher amounts of 3-deoxyglucosone and 1-deoxyglucosone were observed with increasing total phenolic compounds, which was in accordance with the higher sucrose hydrolysis.

Chemical properties and reactive oxygen and nitrogen species quenching activities of dry sugar–amino acid maillard reaction mixtures exposed to baking temperatures

Maillard reaction products (MRPs) derived from 10 different, dry sugar–amino acid reaction model systems were examined for changes in color index (E), sugar loss, and formation of α-dicarbonyl compounds; the changes were correlated with relative activities to quench both reactive oxygen (ROS) and reactive nitrogen (RNS) species. Reducing sugars, xylose, ribose, fructose, glucose, and non-reducing sucrose were reacted with glycine (Xyl–Gly, Rib–Gly, Fru–Gly, Glc–Gly, and Suc–Gly), or lysine (Xyl–Lys, Rib–Lys, Fru–Lys, Glc–Lys, and Suc–Lys), respectively, at temperatures of 150°C and 180°C for time periods ranging from 5 to 60min. ROS quenching capacity was negatively correlated with color index (E) (r=−0.604, P<0.001), and positively correlated with sugar loss (r=0.567, P<0.001). MRPs also exhibited activity to quench RNS as assessed by nitric oxide (NO) inhibition in differentiated Caco-2 cells that were induced with interferon-γ (IFN-γ) and phorbol ester (PMA) cocktail. We also showed a correlation between RNS and color index, sugar loss, and ROS quenching activities for MR mixtures that were heated for a short time (e.g. 10min) at 150°C. MRP quenching of ROS was largely influenced by sugar type, whereas, RNS quenching was dependent more so on the interaction between reactants and reaction conditions used to generate MRPs.

Investigation of Reactive α-Dicarbonyl Compounds Generated from the Maillard Reactions of l-Methionine with Reducing Sugars via Their Stable Quinoxaline Derivatives

The formation of alpha-dicarbonyl compounds was investigated in methionine-catalyzed (Maillard reaction) thermal degradation of d-glucose, maltose, and dextrin 10 at three different pH values (3, 5, and 8). The alpha-dicarbonyl compounds were trapped as quinoxalines and could be quantified by HPLC and GC-MS. Formation of 1,4-dideoxypentodiulose from hexoses and disaccharides was evidenced for the first time. The use of l-methionine as the amino compound for the formation of 1,4-dideoxypentodiulose in model systems is explained. Furthermore, it could be shown that methionine has great effect on the formation of specific alpha-dicarbonyl compounds. At various pH values and also by application of mono-, di-, and oligosaccharides in all model reactions, 3-deoxyhexosulose and 1,4-dideoxypentodiulose were generated preferentially.

Inhibitory effects of guava ( Psidium guajava L.) leaf extracts and its active compounds on the glycation process of protein

Hyperglycaemia causes increased protein glycation and the formation of early glycation products and advanced glycation end products (AGEs) which are major factors responsible for the complications of diabetes. This study investigated the ability of guava leaf and compounds to inhibit glycation process in an albumin/glucose model system and compared the potency of these extracts with Polyphenon 60 which is a commercial polyphenol product extracted from green tea and with the standard antiglycation agent, aminoguanidine. The results showed that the inhibitory effects of guava leaf extracts on the formation of α-dicarbonyl compounds were over 95% at 50 μg/ml. Phenolic compounds present, namely gallic acid, catechin and quercetin exhibited over 80% inhibitory effects, but ferulic acid showed no activity. The guava leaf extracts also showed strong inhibitory effects on the production of Amadori products and AGEs from albumin in the presence of glucose. The phenolic compounds also showed strong inhibitory effects on the glycation of albumin, especially quercetin exhibited over 95% inhibitory effects at 100 μg/ml. According to the results obtained, guava leaf extracts are potent antiglycation agents, which can be of great value in the preventive glycation-associated complications in diabetes.

Formation of α-Dicarbonyl Compounds in Beer during Storage of Pilsner

With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.

Degradation of oligosaccharides in nonenzymatic browning by formation of alpha-dicarbonyl compounds via a "peeling off" mechanism.

The formation of alpha-dicarbonyl-containing substances and Amadori rearrangement products was studied in the glycine-catalyzed (Maillard reaction) and uncatalyzed thermal degradation of glucose, maltose, and maltotriose using o-phenylenediamine as trapping agent. Various degradation products, especially alpha-dicarbonyl compounds, are formed from carbohydrates with differing degrees of polymerization during nonenzymatic browning. The different Amadori rearrangement products, isomerization products, and alpha-dicarbonyls produced by the used carbohydrates were quantified throughout the observed reaction time, and the relevance of the different degradation pathways is discussed. In the Maillard reaction (MR) the amino-catalyzed rearrangement with subsequent elimination of water predominated, giving rise to hexosuloses with alpha-dicarbonyl structure, whereas under caramelization conditions more sugar fragments with an alpha-dicarbonyl moiety were formed. For the MR of oligosaccharides a mechanism is proposed in which 1,4-dideoxyosone is formed as the predominating alpha-dicarbonyl in the quasi-water-free thermolysis of di- and trisaccharides in the presence of glycine.