Maillard Reaction Products Research Articles

Unraveling the temporal changes of Maillard reaction products and aroma profile in coffee leaves during hot-air drying

Drying is a critical process that affects chemical compositions, aroma, and quality of tea. Our previous study demonstrated the impact of hot-air drying on the physiochemical properties of coffee leaves. Herein, we investigated changes in carbonyl compounds, volatiles, and their precursors in hot-air dried coffee leaves. The drying process increased the content of 5-hydroxymethylfurfural, glyoxal, and methylglyoxal, while decreasing the levels of free amino acids and sugars. Electronic-nose analysis highlighted an increase in alcohols, aldehydes, and ketones in hot-air dried leaves compared to their freeze-dried counterpart. Using head-space solid-phase microextraction-gas chromatography–mass spectrometry, combined with relative odor activity values, we identified that hexanal, 2-hexenal, α-ionone, and limonene significantly contributed to the grassy, floral, fruity, woody, and citrus flavors of the freeze-dried leaves. In contrast, 1-octen-3-ol and (E,E)-2,4-heptadienal play a key role for the mushroom and nutty aromas of hot-air dried leaves. Additionally, nonanal, (E,Z)− 2,6-nonadienal, and phenylacetaldehyde contributed significantly to the fatty, grassy, rose, and honey aromas of both coffee leaves. Furthermore, interactive network analysis revealed the close correlation between aromas and the levels of alcohols, aldehydes, and ketones. This study provides valuable guidance for production of coffee leaf tea with a prominent aroma while minimizing harmful carbonyl compounds.

Dry-air roasting impact on physicochemical, functional, antioxidant properties, phenolic profile and Maillard reaction products of flaxseed flour and cake flour

The study investigated and compared physicochemical, functional, antioxidant properties, phenolic profile and Maillard reaction products (MRP) of flaxseed flour (FF) and flaxseed cake flour (FCF) upon dry-air roasting (DaR) of flaxseeds at 140, 160 and 180 °C for 5 and 10 min. This information on FF and FCF is limited and has considerable gaps. The raw FF exhibited higher fat, ash, antioxidant and functional properties while lower protein than the FCF. Upon increasing DaR conditions, the ash and protein increased in FCF and decreased in FF. DaR at 180 °C for 10 min augmented water solubility index, ΔE, MRP, free rutin and syringic acid, bound epicatechin, gallic acid and syringic acid while lowered moisture, L*, b*, hue, chroma, potassium, iron, selenium, emulsion indexes, caffeic acid, flavonoids and free resveratrol in FF and FCF. In conclusion, DaR improves phenolic profile, antioxidant properties, MRP, water solubility and oil absorption capacity of FF and FCF.

Effects of slightly acidic electrolyzed water combined with ԑ-polylysine-chitooligosaccharide Maillard reaction products treatment on the quality of vacuum packaged sea bass (Lateolabrax japonicas)

In this study, a new natural preservative, ε-polylysine (ε-PL) and chitooligosaccharides (COS) Maillard reaction products (LC-MRPs), was prepared by Maillard reaction. The preservation effect of LC-MRPs combined with slightly acidic electrolyzed water (SAEW) pretreatment (SM) on vacuum-packed sea bass during refrigerated storage was evaluated. The results showed that after 16 days, SM treatment could effectively inhibit the microbial growth and prevent water migration in sea bass. In addition, the highest water holding capacity (69.79 %) and the best sensory characteristics, the lowest malonaldehyde (MDA) (58.96 nmol/g), trimethylamine (TMA) (3.35 mg/100 g), total volatile basic nitrogen (TVB-N) (16.93 mg N/100 g), myofibril fragmentation index (MFI) (92.2 %) and TCA-soluble peptides (2.16 μmol tyrosine/g meat) were related to SM group. Combined with sensory analysis, we can conclude that the combined treatment of SAEW and LC-MRPs could prolong the shelf-life of sea bass for another 11 days compared with the DW group. Results disclosed that the composite treatment of SAEW and LC-MRPs is a promising technology to improve the shelf-life of vacuum-packed sea bass during refrigerated storage.

Comparative analysis of functional components in Sakekasu (Sake lees)

Background:Sake lees (Sakekasu), a byproduct of sake production, has been recently attracting attention as a functional food. Sakekasu is rich in nutrients and contains glycerophosphocholine (GPC) and S-adenosylmethionine (SAM), which are well-known functional compounds. The content of these compounds in Sakekasu depends on a variety of factors, including fermentation conditions, especially the method and length of ripening. These differences are reflected prominently in the color of Sakekasu, which becomes darker due to the long ripening period and high drying temperature. Objective: This study aimed to clarify the contents of functional components in Sakekasu with different color tones (i.e., ripening period).Methods:Three types of Sakekasu with different color tones (white, ocher, and brawn) were collected from several breweries. The contents of multiple functional components in their extracts were determined by liquid chromatography coupled to high resolution ion-trap/time-of-flight mass spectrometry.Results: Sakekasu with white color had more abundant GPC, SAM, and fatty acids than those with darker color. However, ethyl glucoside and glyceryl glucosides did not differ significantly by color tone. Furthermore, the Maillard reaction products of sugar and dipeptide were mainly found in dark-colored Sakekasu, and their structures were annotated by tandem mass spectrometry.Conclusions:This study has clarified many functional compounds in Sakekasu in relation to color tone (i.e., ripening period) and highlighted the potential of Sakekasu with white color tone as a functional food.Keywords: Sakekasu, functional components, glycerophosphocholine, S-adenosylmethionine, tandem mass spectrometer

Determination of the Maillard reaction products in complementary rice, flour, and noodles by high performance liquid chromatography with a diode array detector

AbstractA method was established for the simultaneous determination of furosine, furanone, and four furfural compounds (5‐hydroxymethylfurfural, furfural, furyl methyl ketone, and methyl furfural) in complementary rice, flour, and noodles for infants and young children by high performance liquid chromatography with a diode array detector. The sample was extracted using oxalic acid aqueous solution as a solvent, and the protein was removed using trichloroacetic acid. Then the six Maillard reaction products were separated by an Eclipse XDB‐C18 column with a gradient elution at a flow rate of 0.6 mL/min using acetonitrile‐0.1% trifluoroacetic acid solution as the mobile phase, detected by a diode array detector and quantified by external standard method. The linear ranges of the six Maillard reaction products were 250–20000 μg/100 g with the correlation coefficients greater than 0.999, and the limits of quantification ranged from 250 to 1000 μg/100 g (S/N ≥ 10). The recoveries of the six Maillard reaction products ranged from 71.2% to 100% with a relative standard deviation of 0.9%–4.9%. The real sample analysis results showed that 5‐hydroxymethylfurfural was detected in two cookie samples, the contents of which were 335 μg/100 g and 436 μg/100 g, respectively. There are no studies on the detection of the six Maillard reaction products in rice, flour, and noodles in the previous reports. The established method provided reference for the quantification of expiration date in complementary rice, flour, and noodles for infants and young children.

Thiamine, cysteine and xylose added to the Maillard reaction of goat protein hydrolysate potentiates the formation of meat flavoring compounds

A protein hydrolysate of goat viscera added with xylose, cysteine, and thiamine under different pH was used to prepare a meat flavoring. Goat viscera hydrolysate and flavoring were subjected to analysis of physicochemical characteristics, amino acid profile, sugars, fatty acids, and volatile profile. Meat aroma characteristics were initiated in the hydrolysate, in which Strecker's pyrazines and aldehydes were identified, which also had fatty acids and amino acids available for the formation of 96 volatile compounds in the flavorings via lipid manipulation, Maillard occurrence, Strecker manipulation and interactions among these means. Maillard reaction products with intense meat aroma, such as 2-methyl-3-furanthiol, 2-furfurylthiol and, bis(2-methyl-3-furyl) disulfide were isolated only in the flavoring at pH 4. In contrast, the flavoring at pH 6 showed a higher concentration than all the other compounds, providing a lower meat characteristic, but an intense sweet, fatty and goat aroma.

Impact of cod skin peptide-ι-carrageenan conjugates prepared via the Maillard reaction on the physical and oxidative stability of Antarctic krill oil emulsions

This research aimed to construct an emulsifier by the Maillard reaction at various times using cod fish skin collagen peptide (CSCP) and ι-carrageenan (ι-car) to stabilize an Antarctic krill oil (AKO) emulsion. This emulsion was then investigated for physicochemical stability, oxidative stability, and gastrointestinal digestibility. The emulsion stability index and emulsifying activity index of Maillard reaction products (MRPs) were increased by 36.32 % and 66.30 %, respectively, at the appropriate graft degree (25.58 %) compared with the mixture of ι-car and CSCP. In vitro digestibility suggested the higher release of free fatty acids (FFAs) of 10d-MRPs-AKO-emulsion, and the highest bioavailability of AST in 10d-MRPs-AKO was found to be 28.48 %. The findings of this study showed the potential of MRPs to improve peptide function, serve as delivery vehicles for bioactive chemicals, and possibly serve as a valuable emulsifier to be used in the food industry.

Physiochemical, biological, and therapeutic uses of stingless bee honey

Stingless bee honey, also known as pot honey, is a unique product that differs from other honey (Apis) in terms of flavor, chemical composition, biological characteristics, and sourness. Raw and by-products made from this honey have substantial use for its diverse health benefits and human dietary requirements. The physiochemical properties of honey from stingless bee mainly rely on nectar sources, geographic locations, climate, bee species, and handling and storage conditions. The honey contains reducing sugars, water, minerals, and ash content, and its characteristic features include color, acidity, pH, electrical conductivity, and viscosity. Further, it contains several biological and therapeutic constituents such as flavonoids, antioxidants, antibacterial, wound-healing, antidiabetic, and anticancer properties, and the Maillard reaction product hydroxymethylfurfural. This review summarizes the literature on the physical and biological properties and therapeutic constituents' use of stingless bee honey. It also highlights the quality standards available worldwide and required modifications in establishing universal standards for promoting this honey.

Resolving fluorescence spectra of Maillard reaction products formed on bovine serum albumin using parallel factor analysis

Formation of Maillard reaction products (MRPs) is increasingly studied by the use of fluorescence spectroscopy, and most often, by measuring single excitation/emission pairs or use of unresolved spectra. However, due to the matrix complexity and potential co-formation of fluorescent oxidation products on tryptophan and tyrosine residues, this practice will often introduce errors in both identification and quantification. The present study investigates the combination of fluorescence excitation emission matrix (EEM) spectroscopy and parallel factor analysis (PARAFAC) to resolve the EEMs into its underlying fluorescent signals, allowing for better identification and quantification of MRPs. EEMs were recorded on a sample system of bovine serum albumin incubated at 40 °C for up to one week with either glucose, methylglyoxal or glyoxal added. Ten unique PARAFAC components were resolved, and assignment was attempted based on similarity with fluorescence of pure standards of MRPs and oxidation products and reported data from literature. Of the ten fluorescent PARAFAC components, tyrosine and buried and exposed tryptophan were resolved and identified, as well as the formation of specific MRPs (argpyrimidine and Nα-acetyl-Nδ-(5-methyl-4-imidazolon-2-yl)ornithine) and tryptophan oxidation products (kynurenine and dioxindolylalanine). The formation of the PARAFAC resolved protein modifications were qualitatively validated by liquid chromatography-mass spectrometry.

Antioxidant and antibrowning properties of Maillard reaction products in food and biological systems.

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.

Phytochemistry of Red Ginseng, a Steam-Processed Panax ginseng.

Asian ginseng, the root of Panax ginseng C.A.Meyer, occupies a prominent position in the list of best-selling natural products in the world. There are two major types of ginseng roots: white ginseng and red ginseng, each with numerous preparations. White ginseng is prepared by air-drying fresh Asian ginseng roots after harvest. Red ginseng is prepared by steaming roots in controlled conditions using fresh or raw Asian ginseng. Red ginseng is commonly used in Asian countries due to its unique chemical profile, different therapeutic efficacy, and increased stability. Compared with the widespread research on white ginseng, the study of red ginseng is relatively limited. In this paper, after a botanical feature description, the structures of different types of constituents in red ginseng are systematically described, including naturally occurring compounds and those resulting from the steam processing. In red ginseng phytochemical studies, the number of published reports on ginsenosides is significantly higher than that for other constituents. Up to now, 57 ginsenosides have been isolated and characterized in red ginseng. The structural transformation pathways during steaming have been summarized. In comparison with white ginseng, red ginseng also contains other constituents, including polyacetylenes, Maillard reaction products, other types of glycosides, lignans, amino acids, fatty acids, and polysaccharides, which have also been presented. Appropriate analytical methods are necessary for differentiating between unprocessed white ginseng and processed red ginseng. Specific marker compounds and chemical profiles have been used to discriminate red ginseng from white ginseng and adulterated commercial products. Additionally, a brief phytochemical profile comparison has been made between white ginseng and black ginseng, and the latter is another type of processed ginseng prepared from white or red ginseng by steaming several times. In conclusion, to ensure the safe and effective use of red ginseng, phytochemical and analytical studies of its constituents are necessary and even crucial.

Fish Gelatin-Based Film Containing Maillard Reaction Products: Properties and Its Use as Bag for Packing Chicken Skin Oil

Fish Gelatin-Based Film Containing Maillard Reaction Products: Properties and Its Use as Bag for Packing Chicken Skin Oil

Effect of brewer's spent grain melanoidins on Maillard reaction products during storage of whey protein model systems

Maillard reaction readily takes place in dairy products because of the association between thermal treatments, extended storage and the matrix composition. Along with the impairment of protein digestion, the formation of glycation and α-dicarbonyl compounds is a concern for quality attributes of whey proteins when used as ingredients. In this paper, we outline the capacity of brewer's spent grain melanoidins in reducing the accumulation of α-dicarbonyl compounds, thus controlling the formation of dietary advanced glycation end-products in accelerated shelf life at 35 °C. Results revealed that brewer's spent grain melanoidins targeted methylglyoxal and glyoxal reactivity leading to the reduction of N-ε-carboxymethyllysine and methylglyoxal-hydroimidazolone up to 27 and 60%, respectively. We here describe that the presence of melanoidins is instrumental in limiting the undesired effects of α-dicarbonyl compounds on whey proteins.

Preparation and characterization of white shrimp hydrolysate-xylooligosaccharide Maillard products and their in vivo promotive effects of zinc absorption in mice.

The Maillard reaction products, as a kind of glycosylation-based reaction, possess the metal-chelating ability. In this study, the white shrimp hydrolysate (WH) and xylooligosaccharides (XOS) were used to prepare the Maillard reaction product-zinc complex (WH-XOS-MR-Zn) with zinc ions. The Maillard reaction conditions, such as pH level, temperature, reaction time, and the ratio of XOS to WH, were selected by testing the products' zinc-chelating capacity, while the optimized conditions (zinc-chelating capacity = 64.8%, pH = 7, 110 °C, 180 min, XOS : WH = 2) were finally determined. The interactions between WH-XOS-MR and zinc were confirmed and characterized by various kinds of techniques and triggered new peaks of fluorescent signals. The addition of zinc in WH-XOS-MR induced the proportion changes of secondary structures, including the decrease of β-sheets (8.16%) and the increase of β-turns (5.9%) and random coils (2.23%). The addition of zinc changed the morphological surface appearance of WH-XOS-MR and the crystal signal was completely covered in the WH-XOS-MR-Zn complex involved in the chelation with carbonyl and amino groups. The high-dose and medium-dose of the WH-XOS-MR-Zn complex showed higher promotive effects on zinc absorption (11.89 and 11.05 umol L-1, respectively) and medium-dose recovered values of AKP (liver and serum: 7.15 and 12.53 U mL-1), SOD (liver, kidney and serum: 59.84, 7.86 and 13.61 U mL-1) and GSH-Px (203.22 U per mgprot), damage to testicular tissues, damage to the intact neuron cells in the hippocampus region (CA1: 54 to 61, CA3: 67 to 136, DG: 219-353), and intestinal inflammation compared with the zinc-deficient mice. These findings showed therapeutic benefits of Maillard products on intestinal health and cellular structures.

THE ANALYSIS OF THE SELECTED BIOACTIVE PARAMETERS OF BLACK GARLIC PREPARED IN THE SHORT FERMENTATION MODE

Background. Garlic (Allium sativum L.) is characterized by many health-promoting properties due to the presence of sulfur compounds, including allillin, S-allyllocysteine and the high content of polyphenolic compounds. In order to eliminate specific organoleptic characteristics – unfavorable from some consumers’ point of view, garlic can be subjected to a special, low-temperature heat treatment, referred to as aging. This process results in the hydrolysis of poly- and oligosaccharides (fructans) with the participation of intracellular enzymes (fermentation) and the formation of Maillard reaction products (condensation of sugars with amines). As a result, the color, consistency, taste and smell of the final product change and the so-called black garlic is obtained. The aim of the study was to compare the antioxidant properties and the level of total polyphenols, saccharide profile, the content of selected B vitamins and released amino acids of two varieties of raw and black garlic. The experiments were carried out with the use of a commercial short-term fermentation unit from TIROSS. The process was carried out at 70 °C for 192 hours. The amo unt of released amino acids was determined by the ninhydrin method, the content of polyphenols was found using the Folin-Ciocâlteu reagent,antioxidant properties were specified using DPPH free radical and the content of vitamin B and saccharide profile by HPLC. Results and conclusions. The results obtained indicate not only an increase in antioxidant activity, the sum of polyphenols and riboflavin, but also a decrease in the level of free amino acids and thiamine in the garlic obtained after the aging process. The project is in line with a global trend related to the nutrition model oriented towards a vegan diet and the search for new, health-promoting ingredients or recipes based on raw materials with already pre-confirmed attributes as ingredients of functional food.

Color characteristics and pyrolysis volatile properties of main colored fractions from the Maillard reaction models of glucose with three amino acids

The effects of hydrosoluble colored fractions generated in the Maillard reaction models on the volatiles of pyrolytic Maillard reaction products was investigated. The hydrosoluble colored fractions obtained by reaction of glucose with glycine (Gly-Glc), proline (Pro-Glc) and phenylalanine (Phe-Glc) respectively at 125 °C were separated using Sephadex LH-20 Gel column. The colored fraction with large molecular weight had a higher contribution to the overall color and more glucose residue structures in main skeleton than that with small molecular weight in the same model. Gel permeation chromatography analysis indicated that these colored fractions had continuous relative molecular weight distribution (1000–80000 Da). Pyrolysis - gas chromatography - mass spectrometry determination (pyrolysis temperature: 160∼900 °C) suggested that furans and pyrroles were the main volatiles of two Gly-Glc fractions after pyrolysis, and the key pyrolysis volatiles of Pro-Glc fraction were furans, pyrroles, pyran, indole and cyclopentenes, which gave a freshly baked bread, nutty, coffee-like and sweet caramel-like odor. Especially phenyl-containing compounds seemed typical indicators of Phe-Glc fraction pyrolysis products, exhibiting a benzene-like, tallowy, sweet, balsamic and floral odor. The hydrosoluble colored fractions produced by different Maillard reactions had different pyrolytic volatile properties and were suitable for the development of bakery food improver with different color and flavor requirements.

Isolation and characterization of lactic acid bacteria isolates that degrade Maillard reaction products from coffee

Isolation and characterization of lactic acid bacteria isolates that degrade Maillard reaction products from coffee

Microwave roasting effects on phenolic, tocopherol, fatty acid and phytosterol profiles, physiochemical, oxidative and antioxidant properties of hemp seed oil

In the current investigation, the different powers (180, 360, 540, 720, and 900 W) and durations (5 and 10 min) were used for microwave roasting (MwR) of hemp seeds. The influence on yield, oxidative stability, level of phenolic acids, flavonoids, fatty acids, tocopherols, phytosterols, radical scavenging activity (RSA) and physicochemical attributes of hemp oil (HO) upon MwR were investigated. The elevation in MwR conditions had decreased color and peroxide values while increased density, viscosity, p-anisidine value and Maillard reaction products in HO. The phenolic and flavonoid content, RSA, level of catechin, epicatechin, vitexin, myricetin, hydroxybenzoic and hydroxycinnamic acids in HO were highest upon MwR for 10 min at 720 W. The oxidative stability, oil yield, tocopherols and phytosterols exhibited an initial increase followed by decline at elevated conditions of MwR. The MwR (540 W for 5 min) proved effective in improving oil yield and stability, level of phytosterols, phenolic acids, tocopherols, and flavonoids in HO.

Improved protective and controlled releasing effect of flaxseed oil microcapsules with glycosylated casein as wall materials

The primary objective of this study was to explore the viability of employing casein-pectin conjugate (CA-CP conjugate) or casein-arabinogalactan conjugate (CA-AG conjugate) as wall materials for flaxseed oil microcapsules. Compared with casein, both the CA-CP conjugate and CA-AG conjugate exhibited elevated emulsifying and antioxidant characteristics and therefore, have potential as microencapsulation wall materials. Hence, flaxseed oil microcapsules were prepared using CA-CP conjugate or CA-AG conjugate as wall materials through spray-drying. When the mass ratio of wall material to core material was 1:1, the encapsulation efficiency (EE) of the prepared CA-CP conjugate + flaxseed oil microcapsules (CPM) and CA-AG conjugate + flaxseed oil microcapsules (AGM) reached 72.23% and 83.44%, respectively. Fourier infrared spectroscopy (FT-IR) and scanning electron microscope (SEM) results demonstrated that the microcapsules had smooth surfaces, overall spherical shapes, and successful encapsulation of flaxseed oil by the wall materials. Additionally, in vitro simulated gastrointestinal digestion and antioxidant analysis indicated that the microcapsules achieved controlled release of flaxseed oil in the gastrointestinal tract and improved its storage stability. Therefore, utilizing Maillard reaction products for the microencapsulation of flaxseed oil is a highly promising preservation method.

Flavor improving effects of cysteine in xylose–glycine–fish waste protein hydrolysates (FPHs) Maillard reaction system

A promising way to utilize fish by-products is to develop hydrolysis of fish proteins with enzymes. The obtained fish protein hydrolysates (FPHs) are rich in peptides and amino acids, but bitterness and aroma defects impede further utilization of FPHs. The present study adopted Maillard reaction to improve FPHs’ flavor and illustrated the role of cysteine in this system. We investigated the impact of cysteine (0, 0.25%, 0.5%, 0.75%, and 1%) on the browning intensity, free amino acids (FAAs), molecular weight distribution, structure of MRPs, volatile compounds changes and organoleptic characteristics of xylose–glycine–FPHs Maillard reaction systems. Results showed that the addition of cysteine lowered the browning degree of Maillard reaction products (MRPs) by inhibiting the cross-linking of small peptides and reducing the production of melanin. GC–MS and GC–IMS analysis indicated that cysteine inhibited the formation of furans and nitrogen-containing compounds and facilitated the formation of sulfur-containing compounds contributing to the meaty flavor. Sensory analysis revealed that 0.25–0.75% range of cysteine increased the meaty, caramel, umami, mouthfulness and salty notes, and caused a decrease in bitter taste of the MRPs as confirmed by GC–MS. A highly significant correlation between the organoleptic characteristics and physicochemical indicators of MRPs was found by Mantel test. These results elucidated the influence of cysteine on the formation of Maillard reaction products and will help improve the flavor profile of meat flavorings.Graphical