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1.
Vitam Horm ; 125: 31-46, 2024.
Article in English | MEDLINE | ID: mdl-38997168

ABSTRACT

Post-translational modification of proteins by Maillard reaction, known as glycation, is thought to be the root cause of different complications, particularly in diabetes mellitus and age-related disorders. Methylglyoxal (MG), a reactive α-oxoaldehyde, increases in diabetic condition and reacts with the proteins to form advanced glycation end products (AGEs) following a Maillard-like reaction. In a time-dependent reaction study of MG with the heme protein myoglobin (Mb), MG was found to induce significant structural alterations of the heme protein, such as heme loss, changes in tryptophan fluorescence, and decrease of α-helicity with increased ß-sheet content. These changes were found to occur gradually with increasing period of incubation. Incubation of Mb with MG induced the formation of several AGE adducts, including, carboxyethyllysine at Lys-16, carboxymethyllysine at Lys-87, carboxyethyllysine or pyrraline-carboxymethyllysine at Lys-133, carboxyethyllysine at Lys-42 and hydroimidazolone or argpyrimidine at Arg-31 and Arg-139. MG induced amyloid-like aggregation of Mb was detected at a longer period of incubation. MG-derived AGEs, therefore, appear to have an important role as the precursors of protein aggregation, which, in turn, may be associated with pathophysiological complications.


Subject(s)
Glycation End Products, Advanced , Myoglobin , Protein Aggregates , Pyruvaldehyde , Animals , Humans , Glycation End Products, Advanced/metabolism , Glycosylation , Maillard Reaction , Myoglobin/metabolism , Myoglobin/chemistry , Protein Processing, Post-Translational , Pyruvaldehyde/metabolism
2.
Nutrients ; 16(13)2024 Jun 26.
Article in English | MEDLINE | ID: mdl-38999779

ABSTRACT

Changing eating habits and an increase in consumption of thermally processed products have increased the risk of the harmful impact of chemical substances in food on consumer health. A 2002 report by the Swedish National Food Administration and scientists at Stockholm University on the formation of acrylamide in food products during frying, baking and grilling contributed to an increase in scientific interest in the subject. Acrylamide is a product of Maillard's reaction, which is a non-enzymatic chemical reaction between reducing sugars and amino acids that takes place during thermal processing. The research conducted over the past 20 years has shown that consumption of acrylamide-containing products leads to disorders in human and animal organisms. The gastrointestinal tract is a complex regulatory system that determines the transport, grinding, and mixing of food, secretion of digestive juices, blood flow, growth and differentiation of tissues, and their protection. As the main route of acrylamide absorption from food, it is directly exposed to the harmful effects of acrylamide and its metabolite-glycidamide. Despite numerous studies on the effect of acrylamide on the digestive tract, no comprehensive analysis of the impact of this compound on the morphology, innervation, and secretory functions of the digestive system has been made so far. Acrylamide present in food products modifies the intestine morphology and the activity of intestinal enzymes, disrupts enteric nervous system function, affects the gut microbiome, and increases apoptosis, leading to gastrointestinal tract dysfunction. It has also been demonstrated that it interacts with other substances in food in the intestines, which increases its toxicity. This paper summarises the current knowledge of the impact of acrylamide on the gastrointestinal tract, including the enteric nervous system, and refers to strategies aimed at reducing its toxic effect.


Subject(s)
Acrylamide , Dietary Exposure , Gastrointestinal Tract , Humans , Acrylamide/toxicity , Acrylamide/adverse effects , Gastrointestinal Tract/drug effects , Gastrointestinal Tract/metabolism , Dietary Exposure/adverse effects , Animals , Gastrointestinal Microbiome/drug effects , Food Contamination , Gastrointestinal Diseases/chemically induced , Maillard Reaction , Epoxy Compounds
3.
Nat Commun ; 15(1): 5450, 2024 Jul 09.
Article in English | MEDLINE | ID: mdl-38982039

ABSTRACT

Cultured meat is emerging as a new type of food that can provide animal protein in a sustainable way. Many previous studies employed various types of scaffolds to develop cultured meat with similar properties to slaughtered meat. However, important properties such as flavor were not discussed, even though they determine the quality of food. Flavor characteristics vary dramatically depending on the amount and types of amino acids and sugars that produce volatile compounds through the Maillard reaction upon cooking. In this study, a flavor-switchable scaffold is developed to release meaty flavor compounds only upon cooking temperature mimicking the Maillard reaction of slaughtered meat. By introducing a switchable flavor compound (SFC) into a gelatin-based hydrogel, we fabricate a functional scaffold that can enhance the aromatic properties of cultured meat. The temperature-responsive SFC stably remains in the scaffold during the cell culture period and can be released at the cooking temperature. Surprisingly, cultured meat fabricated with this flavor-switchable scaffold exhibits a flavor pattern similar to that of beef. This research suggests a strategy to develop cultured meat with enhanced sensorial characteristics by developing a functional scaffold which can mimic the natural cooking flavors of conventional meat.


Subject(s)
Cooking , Flavoring Agents , Maillard Reaction , Meat , Animals , Meat/analysis , Flavoring Agents/chemistry , Taste , Cattle , Hydrogels/chemistry , Humans , Tissue Scaffolds/chemistry , Temperature , Gelatin/chemistry , In Vitro Meat
4.
Food Res Int ; 191: 114591, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39059892

ABSTRACT

Controlling the Maillard reaction may affect the generation of 2-acetyl-1-pyrroline, the key aroma compound in rice. In this study, the kinetics of 2-acetyl-1-pyrroline accumulation in the glucose/proline model system was comprehensively investigated and extra methylglyoxal or glyoxal was added to enhance 2-acetyl-1-pyrroline concentrations during rice cooking. Using the multi-response kinetic modeling to derive kinetic parameters, the formation of glyoxal, as the reactive intermediate, was rate-determining for the overall generation rate of 2-acetyl-1-pyrroline. Besides, although 2-acetyl-1-pyrroline generation was easier to occur with lower activation energy, much higher depletion rates of 2-acetyl-1-pyrrroline at 120 °C and 140 °C led to maximal 2-acetyl-1-pyrroline accumulation at the lower temperature of 100 °C. Furthermore, the inclusion of 0.05 µmol/kg additional methylglyoxal in cooked rice significantly enhanced 2-acetyl-1-pyrroline generation. The work suggested that the development of rice products with superior flavor quality may be achieved by the slight accumulation of intermediates prior to thermal processing.


Subject(s)
Cooking , Glyoxal , Maillard Reaction , Oryza , Pyrroles , Pyruvaldehyde , Oryza/chemistry , Pyrroles/chemistry , Kinetics , Pyruvaldehyde/chemistry , Glyoxal/chemistry , Taste , Hot Temperature , Glucose/chemistry , Proline
5.
Food Res Int ; 191: 114648, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39059902

ABSTRACT

In the present study, different oligosaccharides (fructooligosaccharide (FOS), galactooligosaccharide (GOS), isomaltooligosaccharide (IMO), and xylooligosaccharide (XOS)) were modified on casein (CN) via Maillard reaction. The CN-oligosaccharide conjugates were evaluated for modifications to functional groups, fluorescence intensity, water- and oil-holding properties, emulsion foaming properties, as well as general emulsion properties and stability. The results demonstrated that the covalent combination of CN and oligosaccharides augmented the spatial repulsion and altered the hydrophobic milieu of proteins, which resulted in a diminution in water-holding capacity, an augmentation in oil-holding capacity, and an enhancement in the emulsification properties of proteins. Among them, CN-XOS exhibited the most pronounced changes, with the emulsification activity index and emulsion stability index increasing by approximately 72% and 84.3%, respectively. Furthermore, CN-XOS emulsions have smaller droplet sizes and higher absolute potential values than CN emulsions. Additionally, CN-XOS emulsions demonstrate remarkable stability when ion concentration and pH are varied. These findings indicate that oligosaccharides modified via Maillard reaction can be used as good natural emulsifiers. This provides a theoretical basis for using oligosaccharides to modify proteins and act as natural emulsifiers.


Subject(s)
Caseins , Emulsifying Agents , Emulsions , Maillard Reaction , Oligosaccharides , Oligosaccharides/chemistry , Caseins/chemistry , Emulsifying Agents/chemistry , Emulsions/chemistry , Hydrogen-Ion Concentration , Particle Size , Hydrophobic and Hydrophilic Interactions , Water/chemistry
6.
J Agric Food Chem ; 72(28): 15933-15947, 2024 Jul 17.
Article in English | MEDLINE | ID: mdl-38968025

ABSTRACT

Hydroxycinnamic acids, known for their health benefits and widespread presence in plant-based food, undergo complex transformations during high-temperature processing. Recent studies revealed a high browning potential of hydroxycinnamic acids and reactive Maillard reaction intermediates, but the role of phenolic compounds in the early stage of these reactions is not unambiguously understood. Therefore, we investigated the influence of caffeic acid and ferulic acid on the nonenzymatic browning of arabinose, galactose, and/or alanine, focusing on the implications on the formation of relevant early-stage Maillard intermediates and phenol-deriving products. Contrary to previous assumptions, hydroxycinnamic acids were found to promote nonenzymatic browning instead of solely trapping reactive intermediates. This was reflected by an intense browning, which was attributed to the formation of heterogeneous phenol-containing Maillard products. Although, caffeic acid is more reactive than ferulic acid, the formation of reactive furan derivatives and of heterogeneous phenol-containing colorants was promoted in the presence of both hydroxycinnamic acids.


Subject(s)
Arabinose , Coumaric Acids , Galactose , Maillard Reaction , Coumaric Acids/chemistry , Galactose/chemistry , Arabinose/chemistry , Hot Temperature
7.
Compr Rev Food Sci Food Saf ; 23(4): e13389, 2024 Jul.
Article in English | MEDLINE | ID: mdl-39031671

ABSTRACT

Volatile sulfur compounds (VSCs) significantly influence food flavor and garner considerable attention in flavor research due to their low sensory thresholds, diverse odor attributes, and high reactivity. Extensive research studies have explored VSC formation through thermal processes such as the Maillard reaction, thermal pyrolysis, oxidation, and enzymatic reactions. However, understanding of the specific reaction mechanisms and processes remains limited. This is due to the dispersed nature of existing studies, the undefined intermediates involved, and the complexity of the matrices and processing conditions. Given these limitations, the authors have shifted their focus from foods to sulfides. The structure, source, and chemical characteristics of common precursors (sulfur-containing amino acids and derivatives, thiamine, thioglucoside, and lentinic acid) and their corresponding reactive intermediates (hydrogen sulfide, thiol, alkyl sulfide, alkyl sulfenic acid, and thial) are provided, and the degradation mechanisms, reaction rules, and matrix conditions are summarized based on their chemical characteristics. Additionally, the VSC formation processes in several typical foods during processing are elucidated, adhering to these identified rules. This article provides a comprehensive overview of VSCs, from precursors and intermediates to end products, and is crucial for understanding the mechanisms behind VSC formation and managing the flavor qualities of processed foods.


Subject(s)
Food Handling , Hot Temperature , Odorants , Sulfur Compounds , Sulfur Compounds/chemistry , Odorants/analysis , Food Handling/methods , Volatile Organic Compounds/chemistry , Taste , Maillard Reaction , Food Analysis
8.
Vitam Horm ; 125: 149-182, 2024.
Article in English | MEDLINE | ID: mdl-38997163

ABSTRACT

The century old Maillard reactions continue to draw the interest of researchers in the fields of Food Science and Technology, and Health and Medical Sciences. This chapter seeks to simplify and update this highly complicated, multifaceted topic. The simple nucleophilic attack of an amine onto a carbonyl group gives rise to a series of parallel and subsequent reactions, occurring simultaneously, resulting into a vast array of low and high mass compounds. Recent research has focused on: (1) the formation and transformation of α-dicarbonyl compounds, highly reactive intermediates which are essential in the development of the desired color and flavor of foods, but also lead to the production of the detrimental advanced glycation end products (AGEs); (2) elucidation of the structures of melanoidins in different foods and their beneficial effects on human health; and (3) harmful effects of AGEs on human health. Considering that MRs have both positive and negative consequences, their control to accentuate the former and to mitigate the latter, is also being conscientiously investigated with the use of modern techniques and technology.


Subject(s)
Glycation End Products, Advanced , Maillard Reaction , Humans , Glycation End Products, Advanced/metabolism , Glycation End Products, Advanced/chemistry , Polymers/chemistry , Animals
9.
Vitam Horm ; 125: 367-399, 2024.
Article in English | MEDLINE | ID: mdl-38997170

ABSTRACT

Oxidative damage refers to the harm caused to biological systems by reactive oxygen species such as free radicals. This damage can contribute to a range of diseases and aging processes in organisms. Moreover, oxidative deterioration of lipids is a serious problem because it reduces the shelf life of food products, degrades their nutritional value, and produces reaction products that could be toxic. Antioxidants are effective compounds for preventing lipid oxidation, and synthetic antioxidants are frequently added to foods due to their high effectiveness and low cost. However, the safety of these antioxidants is a subject that is being discussed in the public more and more. Synthetic antioxidants have been found to have potential negative effects on health due to their ability to accumulate in tissues and disrupt natural antioxidant systems. During thermal processing and storage, foods containing reducing sugars and amino compounds frequently produce Maillard reaction products (MRPs). Through the chelation of metal ions, scavenging of reactive oxygen species, destruction of hydrogen peroxide, and suppression of radical chain reaction, MRPs exhibit excellent antioxidant properties in a variety of food products and biological systems. Also, the capacity of MRPs to chelate metals makes them as a potential inhibitor of the enzymatic browning in fruits and vegetables. In this book chapter, the methods used for the evaluation of antioxidant activity of MRPs are provided. Moreover, the antioxidant and antibrowning activities of MRPs in food and biological systems is discussed. MRPs can generally be isolated and used as commercial preparations of natural antioxidants.


Subject(s)
Antioxidants , Maillard Reaction , Antioxidants/pharmacology , Antioxidants/chemistry , Humans , Animals , Reactive Oxygen Species/metabolism
10.
J Agric Food Chem ; 72(28): 16010-16017, 2024 Jul 17.
Article in English | MEDLINE | ID: mdl-38965162

ABSTRACT

Maillard reaction products (MRPs) of xylose with phenylalanine and xylose with proline exhibit high antibacterial activity. However, the active antibacterial compounds in MRPs have not yet been identified or isolated. This study aimed to isolate the active compounds in the two antibacterial MRPs. The organic layer of the MRP solution was separated and purified using silica gel chromatography and high-performance liquid chromatography. The chemical structures of the isolated compounds were determined by mass spectrometry and nuclear magnetic resonance spectroscopy. The compounds inhibited the growth of Bacillus cereus and Salmonella Typhimurium at 25 °C for 7 days at a concentration of 0.25 mM. Furthermore, the isolated compounds inhibited the growth of naturally occurring microflora of lettuce and chicken thighs at 25 °C for 2 days at a concentration of 0.5-1.0 mM. The antibacterial compounds found in MRPs demonstrated a wide range of effectiveness and indicated their potential as alternative preservatives.


Subject(s)
Anti-Bacterial Agents , Chickens , Maillard Reaction , Phenylalanine , Proline , Salmonella typhimurium , Xylose , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Proline/chemistry , Phenylalanine/chemistry , Xylose/chemistry , Salmonella typhimurium/drug effects , Animals , Bacillus cereus/drug effects , Bacillus cereus/growth & development , Chromatography, High Pressure Liquid
11.
J Agric Food Chem ; 72(30): 16930-16940, 2024 Jul 31.
Article in English | MEDLINE | ID: mdl-39038222

ABSTRACT

Lysine (Lys) is capable of forming a di-substituted Amadori rearrangement product (ARP) with xylose (Xyl), designated as diXyl-α,ε-Lys-ARP. DiXyl-α,ε-Lys-ARP degradation was characterized by two steps: Initially, Xyl-α- and Xyl-ε-Lys-ARP were formed through elimination or hydrolysis at specific Nα/Nε positions of the corresponding enol and imine intermediates, which were then further degraded to dicarbonyl compounds and regenerated Lys. Xyl-α- or Xyl-ε-Lys-ARP had a reactive free amino group (ε-NH2 or α-NH2), both of which were still highly reactive and able to undergo further reactions with Xyl. Therefore, the diXyl-α,ε-Lys-ARP/Xyl model system was established to explore the impact of extra-added Xyl on diXyl-α,ε-Lys-ARP degradation behavior. Extra-added Xyl remarkably affected the degradation pathway of diXyl-α,ε-Lys-ARP by capturing the Xyl-α- and Xyl-ε-Lys-ARP to regenerate diXyl-α,ε-Lys-ARP. This interaction between Xyl and mono-substituted Lys-ARPs promoted the shift of chemical equilibrium toward the degradation of diXyl-α,ε-Lys-ARP, thereby accelerating its degradation rate. This degradation was markedly facilitated by the elevated temperature and pH values. Interestingly, the yield of Xyl-α- and Xyl-ε-Lys-ARP was particularly dependent on the pH during diXyl-α,ε-Lys-ARP degradation. Xyl-ε-Lys-ARP was the dominant product at pH 5.5-7.5 while Xyl-α-Lys-ARP possessed a relatively higher content under weak alkaline conditions, which was related to the reactivities of the Nα/Nε positions under various reaction conditions.


Subject(s)
Lysine , Maillard Reaction , Xylose , Xylose/chemistry , Lysine/chemistry , Hydrolysis , Kinetics , Hot Temperature
12.
Carbohydr Polym ; 340: 122293, 2024 Sep 15.
Article in English | MEDLINE | ID: mdl-38858005

ABSTRACT

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.


Subject(s)
Agar , Emulsifying Agents , Emulsions , Gelatin , Maillard Reaction , Gelatin/chemistry , Agar/chemistry , Emulsions/chemistry , Emulsifying Agents/chemistry , Rheology , Hydrogen-Ion Concentration , Particle Size , Temperature
13.
Food Res Int ; 190: 114546, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38945559

ABSTRACT

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.


Subject(s)
Food Handling , Fruit and Vegetable Juices , Furaldehyde , Malus , Pasteurization , Pressure , Malus/chemistry , Furaldehyde/analysis , Furaldehyde/analogs & derivatives , Chromatography, High Pressure Liquid , Fruit and Vegetable Juices/analysis , Food Handling/methods , Maillard Reaction , Fruit/chemistry , Furans/analysis
14.
Food Res Int ; 190: 114600, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38945570

ABSTRACT

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.


Subject(s)
Fruit , Malus , Metabolomics , Malus/metabolism , Malus/classification , Fruit/metabolism , Fruit/chemistry , Food Handling/methods , Maillard Reaction
15.
Food Res Int ; 190: 114608, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38945618

ABSTRACT

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.


Subject(s)
Hot Temperature , Hyaluronic Acid , Protein Hydrolysates , Whey Proteins , Whey Proteins/chemistry , Hyaluronic Acid/chemistry , Protein Hydrolysates/chemistry , Hydrogen-Ion Concentration , Maillard Reaction , Hydrophobic and Hydrophilic Interactions , Particle Size , Spectroscopy, Fourier Transform Infrared , Food Handling/methods
16.
J Agric Food Chem ; 72(25): 14284-14293, 2024 Jun 26.
Article in English | MEDLINE | ID: mdl-38869215

ABSTRACT

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.


Subject(s)
Flavoring Agents , Guanosine Monophosphate , Maillard Reaction , Taste , Guanosine Monophosphate/chemistry , Humans , Flavoring Agents/chemistry , Male , Female , Molecular Structure , Adult , Young Adult
17.
Food Res Int ; 188: 114454, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38823832

ABSTRACT

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.


Subject(s)
Cysteine , Gas Chromatography-Mass Spectrometry , Glucose , Maillard Reaction , Volatile Organic Compounds , Cysteine/chemistry , Glucose/chemistry , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/analysis , Density Functional Theory , Hot Temperature
18.
Food Chem ; 455: 139760, 2024 Oct 15.
Article in English | MEDLINE | ID: mdl-38824734

ABSTRACT

In this study, six types of amino acids (Ala, Phe, Glu, Gly, Ser, and Lys) were combined with glucose to produce Maillard reaction products (MRPs) named G-Ala, G-Phe, G-Glu, G-Gly, G-Ser and G-Lys. The effect of MRPs on bread staling was evaluated through texture and sensory analyses during storage. Furthermore, the study comprehensively analyzed the anti-staling mechanisms of MRPs by examining moisture content, starches, and gluten network changes. The results indicated that G-Gly and G-Glu delayed bread staling, with G-Gly showing the most significant effect. Compared with control, the staling rate and starch crystallinity of G-Gly bread decreased by 24.07% and 7.70%, respectively. Moreover, G-Gly increased the moisture content (3.48%), weakly bound water mobility (0.77%), and α-helix content (1.00%) of bread. Component identification and partial least squares regression further confirmed the aldonic acid, heterocyclic acids and heterocyclic ketones in MRPs inhibit water evaporation, gluten network loosening, and starch degradation, thereby delaying bread staling.


Subject(s)
Bread , Glucose , Glutens , Maillard Reaction , Starch , Water , Bread/analysis , Starch/chemistry , Glutens/chemistry , Glucose/chemistry , Water/chemistry , Amino Acids/chemistry , Humans , Triticum/chemistry , Food Handling , Taste
19.
Food Chem ; 455: 139890, 2024 Oct 15.
Article in English | MEDLINE | ID: mdl-38838623

ABSTRACT

The composition of melanoidins in dried apple that affects quality remains unclear. The composition and structure of melanoidins in dried apple slices by hot air drying (HAAM), instant controlled pressure drop drying (DICAM), and vacuum freeze-drying (FDAM) were investigated. It showed that the melanoidins were highly heterogeneous mixtures with a light-yellow color and blue-green fluorescence, belonging to polysaccharide-type melanoidins. Specifically, HAAM had a large molecular weight (929.5 g/mol) and wide molecular weight distribution, with more double-bond conjugated systems. DICAM (610.9 g/mol), possessing the strongest fluorescence intensity, was mainly composed of compounds with fewer π-conjugated structures and more electron-donating groups. As a control, the low level of Maillard reaction in FDAM resulted in the formation of the smallest molecular weight (458.6 g/mol) with weak fluorescence intensity. Moreover, 10 compounds were tentatively identified in apple melanoidins. This study provides the foundation for the future functional preparation of apple melanoidins.


Subject(s)
Fruit , Malus , Molecular Weight , Polymers , Malus/chemistry , Fruit/chemistry , Polymers/chemistry , Desiccation , Maillard Reaction , Food Handling
20.
Food Chem ; 456: 139996, 2024 Oct 30.
Article in English | MEDLINE | ID: mdl-38925008

ABSTRACT

This study was aimed to evaluate the potential of high-humidity hot air impingement cooking (HHAIC) on Penaeus vannamei, focusing on its drying characteristics, microstructure, water distribution, enzyme activity, astaxanthin content, antioxidant capacity, color, and Maillard reaction. Results demonstrated that a 3 min HHAIC significantly improved the shrimp's color and optimized astaxanthin content with a notable increase in scavenging capacity based on an in-vitro as antioxidation activity evaluation. Compared to the untreated samples, HHAIC could significantly inactivate polyphenol oxidase by 95.76%. Also, it suppressed the Maillard reaction by decreasing 5-hydroxymethylfurfural content and shortened the drying time by 40%. In addition, the low-field nuclear magnetic resonance and microstructure analysis showed alterations in the shrimp muscle fiber structure and water distribution. This study indicated that HHAIC could elevate quality, enhance appearance, and reduce the processing time of dried shrimp, presenting valuable implications for industry progress.


Subject(s)
Color , Cooking , Hot Temperature , Maillard Reaction , Penaeidae , Animals , Penaeidae/chemistry , Penaeidae/enzymology , Catechol Oxidase/chemistry , Catechol Oxidase/metabolism , Desiccation , Shellfish/analysis , Antioxidants/chemistry , Xanthophylls/chemistry
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