Activity Of Maillard Reaction Products Research Articles

Preparation of chitosan-glucosamine derivatives (Maillard reaction products) by gamma Co-60 irradiation method and investigation of antibacterial activity

The mixture solutions of glucosamine and chitosan with different molecular weights (123.5; 40.7 and 6.1 kDa) were irradiated by Co-60 gamma ray at dose of 50 kGy to prepare chitosanglucosamine Maillard reaction products (MRPs). The formation of MRPs was determined by measuring UV absorbance (at 284) nm and browning (at 420 nm). The reaction efficiency was calculated based on the ratio of reacted glucosamine and total added glucosamine. The antibacterial activity of chitosan-glucosamine MRPs against Escherichia coli was also investigated. The obtained results showed that the chitosan-glucosamine MRPs exhibited strong antibacterial activity, in which chitosan-glucosamine MRPs prepared from 123.5 kDa chitosan could reduce up to 4 log CFU/ml in comparison with the control (45 × 106 CFU/ml). Therefore, the chitosan-glucosamine MRPs prepared by the Co-60 gamma irradiation method can be potentially applied as a natural preservative for food, cosmetics and substituted for banned chemical preservatives.

Antioxidant activities of chicken bone peptide fractions and their Maillard reaction products: Effects of different molecular weight distributions

ABSTRACTChicken bone protein hydrolysate (CBPH) and its peptide fractions (CBPH-I, molecular weight < 3 kDa; CBPH-II, molecular weight 3–10 kDa) were heated with galactose in aqueous solution at 100°C for 90 min. Antioxidant activities of CBPH, CBPH-I, CBPH-II, and their derived Maillard reaction products (MRPs) were evaluated. CBPH, peptide fractions, and their MRP exerted strong DPPH radical scavenging activity and reducing power, but low scavenging activity toward the hydroxyl radicals. All the tested antioxidant activities of CBPH and its peptide fractions were significantly increased after the Maillard reaction with galactose. The increment in the antioxidant activity of CBPH-II MRP was higher than that of CBPH-I MRP, although more glycation was found in CBPH-I MRP. The results indicated that the improvement of the antioxidant activity of peptide fraction via the Maillard reaction should be closely related to its molecular size.

Antioxidant and chelating capacity of Maillard reaction products in amino acid-sugar model systems: applications for food processing.

Maillard reaction products (MRP) have gained increasing interest owing to their both positive and negative effects on human health. Aqueous amino acid-sugar model systems were studied in order to evaluate the antioxidant and chelating activity of MRP under conditions similar to those of food processing. Amino acids (cysteine, glycine, isoleucine and lysine) combined with different sugars (fructose or glucose) were heated to 100 and 130 °C for 30, 60 and 90 min. Antioxidant capacity was evaluated via ABTS and DPPH free radical scavenging assays, in addition to Fe2+ and Cu2+ ion chelating capacity. In the ABTS assay, the cysteine-fructose model system presented the highest antioxidant activity at 7.05 µmol mL-1 (130 °C, 60 min), expressed in Trolox equivalents. In the DPPH assay, the cysteine-glucose system presented the highest antioxidant activity at 3.79 µmol mL-1 (100 °C, 90 min). The maximum rate of chelation of Fe2+ and Cu2+ was 96.31 and 59.44% respectively in the lysine-fructose and cysteine-glucose systems (100 °C, 30 min). The model systems presented antioxidant and chelating activity under the analyzed temperatures and heating times, which are similar to the processing conditions of some foods. © 2017 Society of Chemical Industry.

Production of Antioxidative Maillard Reaction Products from Gelatin Hydrolysate of Unicorn Leatherjacket Skin

ABSTRACTAntioxidative activities of Maillard reaction products (MRPs) derived from gelatin hydrolysate (GH) of unicorn leatherjacket skin as affected by types of saccharides, GH to saccharide ratio, incubation temperatures, relative humidity (RH), and times were investigated. MRPs prepared using mixture of GH and galactose at 2:1 (w/w) ratio showed the highest antioxidative activity. At different incubation temperatures (50–70°C) and RHs (55–75%), optimal condition for preparing antioxidative MRPs included heating GH and galactose (2:1) powder at 70°C and 55% RH for 36 h. Electrophoresis and Fourier transform infrared spectroscopy revealed the formation of high molecular weight polymers, and the advanced glycation took place in MRPs.

Immune modulating activity of Maillard reaction products from milk proteins with lactose by nitric oxide reduction on macrophage

Caseins and whey proteins constitute most of the milk proteins. Also, lactose is the most abundant sugar in milk. The Maillard reaction makes the chemical compounds using reducing sugars and amino acids by non‐enzymatic reactions. The macrophages are participating in the initiation of inflammation, and they are activated by numerous inflammation factors, lipopolysaccharide (LPS), cytokines and other chemical factors. The activated macrophages synthesize nitric oxides for further anti‐inflammation processes. Using sodium caseinate and whey protein concentrate with lactose, we made Maillard reaction products (MRPs) as lactose‐sodium caseinate (LSC) and lactose‐whey protein concentrate (LWPC). The reaction was conducted with 120°C for 20 minutes in 0.1M sodium phosphate buffer solution, proteins (sodium caseinate or whey protein concentrate) and lactose ratio was 1:2 (w:w). As a result, the fluorescence of MRPs was increased and we confirmed by SDS‐PAGE that high molecular weight proteins were generated. Also, an intermediate in the Maillard reaction, hydroxymethylfurfural (HMF) was increased. Macrophage cells were produced more nitric oxide with sodium caseinate and whey protein concentrate, but lactose MRPs of each proteins are reduce nitric oxide level below the LPS‐induced nitric oxide level. Using RT‐PCR method, cytokine levels of IL‐1β and IL‐8 were also measured.

Antioxidant activity of Maillard reaction products (MRPs) in a lipid-rich model system

Ribose-lysine (RL), ribose-glycine (RG), fructose-lysine (FL) and fructose-glycine (FG) Maillard models (whole mixture (WM) pH 4 and 9) were heated at 60, 80, 121°C for 30, 60, 120min, and dialysed into low (LMW) and high molecular weight (HMW) fractions. Reducing power (RP), DPPH and peroxyl radical scavenging (PRS) evaluated indirect antioxidant activity (AA). Direct AA in a water-in-oil emulsion was evaluated through peroxide value (PV), p-anisidine, TBARs inhibition and oxidative stability (OS). PRS and RP increased significantly with temperature and time from FL<FG<RL<RG and LMW<WM<HMW for all pHs. MRPs showed higher PRS and RP than BHA. DPPH decreased (p<0.05) with temperature and time from LMW>WM>HMW. With DPPH, only MRPs at 121°C exhibited higher AA than BHA. MRPs exhibited low PV, p-anisidine and inhibited the formation of TBARs. BHA showed the highest OS, with p-anisidine, PV and inhibition of TBARS similar to that of MRPs.

Antioxidant balance and accumulation of advanced glycation end products after the consumption of standard diets including Maillard reaction products from silver carp peptides.

The aim of this research was to investigate the accumulation and excretion of AGEs including fluorescent compounds and N-ε-carboxymethyllysine (CML) in streptozotocin-induced diabetes C57BL/6J mice fed on a diet containing Maillard reaction products (MRPs) from a silver carp peptide-glucose model system at different heating temperatures for the first time, and analyze the relationship between their in vitro antioxidant activity based on DPPH and ORAC assays and in vivo oxidative stress. The in vitro antioxidant activity of MRPs positively correlated with their AGEs level and molecular weight distribution. However, the opposite results were found by malondialdehyde (MDA) and super oxide dismutase (SOD) assays that MRPs from a higher heating temperature could aggravate the oxidative stress of diabetic mice. CML accumulation in serum was aggravated, but changes of MRPs in diets hardly affected CML accumulation in the kidney and liver. Therefore, the high AGEs levels from a diet containing peptide MRPs have negative effects on the oxidative stress of diabetic mice.

Protective Effects of Maillard Reaction Products of Whey Protein Concentrate against Oxidative Stress through an Nrf2-Dependent Pathway in HepG2 Cells.

Whey protein concentrate (WPC), which contains α-lactalbumin and β-lactoglobulin, is utilized widely in the food industry. The Maillard reaction is a complex reaction that produces Maillard reaction products (MRPs), which are associated with the formation of antioxidant compounds. In this study, the hepatoprotection activity of MRPs of WPC against oxidative stress through the nuclear factor-E2-related factor 2 (Nrf2)-dependent antioxidant pathway in HepG2 cells was examined. Glucose-whey protein concentrate conjugate (Glc-WPC) was obtained from Maillard reaction between WPC and glucose. The fluorescence intensity of Glc-WPC increased after 7 d compared to native WPC, and resulted in loss of 48% of the free amino groups of WPC. The sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) patterns of Glc-WPC showed the presence of a high-molecular-weight portion. Treatment of HepG2 cells with Glc-WPC increased cell viability in the presence of oxidative stress, inhibited the generation of intracellular reactive oxygen species by tert-butyl hydroperoxide (t-BHP), and increased the glutathione level. Nrf2 translocation and Nrf2, reduced nicotinamide adenine dinucleotide phosphate (NAD(P)H)-quinone oxidoreductase 1 (NOQ1), heme oxygenase-1 (HO-1), glutamate-L-cysteine ligase (GCL)M and GCLC mRNA levels were increased by Glc-WPC. Also, Glc-WPC increased the phosphorylation of extracellular signal-regulated kinase (ERK) 1/2 and c-Jun N-terminal kinase (JNK). The results of this study demonstrate that Glc-WPC activates the Nrf2-dependent pathway through the phosphorylation of ERK1/2 and JNK in HepG2 cells, and induces production of antioxidant enzymes and phase II enzymes.

Chemical characteristics and enhanced hepatoprotective activities of Maillard reaction products derived from milk protein-sugar system

The objective of this study was to investigate the characteristics, antioxidative properties, and hepatoprotective effects of Maillard reaction products (MRP) from milk protein reacted with sugars. The MRP were obtained from milk protein, whey protein concentrates and sodium caseinate, using 2 types of sugars, lactose and glucose, by heating the mixture at 55°C for 7d in a sodium phosphate buffer (pH 7.4). Changes in the chemical modification of the milk protein were monitored by measuring the protein-bound carbonyls and PAGE protein profiles. The results showed that the amount of protein-bound carbonyls increased after Maillard reaction (MR). In addition, sodium dodecyl sulfate-PAGE analysis indicated a formation of high-molecular weight complexes through MR. The modification sites induced by MR of milk protein were monitored by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analysis of tryptic-digested gel spots of MRP. As a result, modification and their localization in AA sequence of MRP was identified. Also, the MRP showed higher antioxidant activities than the intact milk protein, and they reduced intracellular reactive oxygen species production and inhibited the depletion of the reduced glutathione concentrations in the HepG2 cells. In particular, glucose-sodium caseinate MRP showed the highest biological activities among all MRP. Therefore, these results suggest that the MRP from milk protein reacting with sugars possess effective antioxidant activity and have a protective ability against oxidative damage.

In vivo effects of Maillard reaction products derived from biscuits

The antioxidant activity, antihypertensive effect and prebiotic activity of Maillard reaction products (MRPs) derived from biscuits were investigated in Wistar rats. Animals were fed the following diets for 6weeks: control (AIN-93 diet); Asc-diet (AIN-93 diet with ascorbic acid in the drinking water); HT-B diet (containing high amount of MRP derived from biscuits) and LT-B diet (containing negligible amounts of biscuit MRP). Serum antioxidant activity (FRAP, ABTS), as well as lipid peroxidation (TBARS) were determined at the end of the experiment. Results showed that dietary MRP reduced the food efficiency, increased the antioxidant activity of serum, increased the ratio between lactic and total aerobic bacteria, increased water-holding capacity of faeces and reduced blood pressure, but did not reduce mineral absorption. Therefore, the biscuit MRP functional claims could be demonstrated by an in vivo study.

Lipid Peroxidation Inhibitation Activity of Maillard Reaction Products Derived from Sugar-amino Acid Model Systems

The present study aimed to evaluate the lipid peroxidation inhibitation activity of Maillard Reaction Products (MRPs) derived from sugar (glucose, fructose, lactose and maltose) and 18 amino acid model systems in soybean oil. MRPs were produced by heating at 130°C for 2 h. Of the 18 amino acids-fructose model systems studied, MRPs derived from fructose-leucine, fructose-methionine, fructose-phenylalanine and fructose-isoleucine model sytems showed high lipid peroxidation inhibitation activity and best performance was observed from fructose-phenylalanine MRPs. Interestingly, glucose-phenylalanine MRPs also exhibited high inhibitation activity and inhibitation activity of both glucose-phenylalanine and fructose-phenylalanine MRPs exceeded 87% even with concentration at 1.1 wt % after 8 days storage.

Dietary Maillard reaction products and their fermented products reduce cardiovascular risk in an animal model

This study examined the effects of Maillard reaction products (MRP) and MRP fermented by lactic acid bacteria on antioxidants and their enhancement of cardiovascular health in ICR mouse and rat models. In previous in vitro studies, the selected lactic acid bacteria were shown to significantly affect the activity of MRP. The expression of genes (e.g., superoxide dismutase, catalase, and glutathione peroxidase) related to antioxidant activity was upregulated by Maillard-reacted sodium caseinate (cMRP), and cMRP fermented by Lactobacillus fermentum H9 (F-cMRP) synergistically increased the expression of catalase and superoxide dismutase when compared with the high-cholesterol-diet group. Bleeding time, the assay for determination of antithrombotic activity, was significantly prolonged by Maillard-reacted whey protein concentration (wMRP) and wMRP fermented by Lactobacillus gasseri H10 (F-wMRP), similar to the bleeding time of the aspirin group (positive control). In addition, the acute pulmonary thromboembolism–induced mice overcame severe body paralysis or death in both the wMRP and the F-wMRP groups. In the serum-level experiment, cMRP and F-cMRP significantly reduced the serum total and low-density lipoprotein cholesterol levels and triglycerides but had only a slight effect on high-density lipoprotein cholesterol. The levels of aspartate transaminase and alanine transaminase also declined in the cMRP and F-cMRP intake groups compared with the high-cholesterol-diet group. In particular, F-cMRP showed the highest reducing effects on triglycerides, aspartate transaminase, and alanine transaminase. Moreover, the expression of cholesterol-related genes in the F-cMRP group demonstrated greater effects than for the cMRP group in the level of cholesterol 7 α-hydroxylase (CYP7A1), 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR), and low-density lipoprotein receptors compared with the high-cholesterol-diet group. The protective role of cMRP and F-cMRP in the high-cholesterol group may have been the result of an antioxidative defense mechanism that regulated cholesterol synthesis and metabolism. Therefore, F-cMRP and cMRP have the potential to play preventive and therapeutic roles in the management of cardiovascular disease.

Effect of the Reactant Ratio on the Characteristics and Antioxidant Activities of Maillard Reaction Products in a Porcine Plasma Protein Hydrolysate-Galactose Model System

The chemical characteristics and antioxidant properties of Maillard reaction products formed in the Maillard reaction in a model system at 95°C for different lengths of time (0–6 h) were investigated at three mass ratios (1:1, 1:2, and 1:3) of porcine plasma protein hydrolysate to galactose. The results revealed that the pH value and free amino group content decreased (p < 0.05), whereas the browning index, intermediate products, and browning intensity, as well as reducing power and 2,2’-amino-di(2-ethyl-benzothiazoline sulfonic acid-6)ammonium salt radical scavenging activity of the Maillard reaction products increased as the reaction time increased (p < 0.05). Moreover, when the mass ratio of porcine plasma protein hydrolysate to galactose was 1:3, the Maillard reaction progressed easily, which rendered a higher degree of glycation and antioxidant activity (p < 0.05). These results indicated that the Maillard reaction can improve the antioxidant capacity of porcine plasma protein hydrolysate.

Preventive effect of fermented Maillard reaction products from milk proteins in cardiovascular health

The aim of this study was to determine the dual effect of Maillard reaction and fermentation on the preventive cardiovascular effects of milk proteins. Maillard reaction products (MRP) were prepared from the reaction between milk proteins, such as whey protein concentrates (WPC) and sodium caseinate (SC), and lactose. The hydrolysates of MRP were obtained from fermentation by lactic acid bacteria (LAB; i.e., Lactobacillus gasseri H10, L. gasseri H11, Lactobacillus fermentum H4, and L. fermentum H9, where human-isolated strains were designated H1 to H15), which had excellent proteolytic and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities (>20%). The antioxidant activity of MRP was greater than that of intact proteins in assays of the reaction with 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt and trivalent ferric ions; moreover, the effect of MRP was synergistically improved by fermentation. The Maillard reaction dramatically increased the level of antithrombotic activity and 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitory effect of milk proteins, but did not change the level of activity for micellar cholesterol solubility. Furthermore, specific biological properties were enhanced by fermentation. Lactobacillus gasseri H11 demonstrated the greatest activity for thrombin and HMGR inhibition in Maillard-reacted WPC, by 42 and 33%, respectively, whereas hydrolysates of Maillard-reacted SC fermented by L. fermentum H9 demonstrated the highest reduction rate for micellar cholesterol solubility, at 52%. In addition, the small compounds that were likely released by fermentation of MRP were identified by size-exclusion chromatography. Therefore, MRP and hydrolysates of fermented MRP could be used to reduce cardiovascular risks.

Antioxidant activity of Maillard reaction products derived from stingray (Himantura signifier) non-protein nitrogenous fraction and sugar model systems

This study aimed to evaluate the antioxidant activity of the Maillard reaction products (MRPs) derived from stingray non-protein nitrogenous (NPN) fraction and sugar (glucose, galactose and fructose) model systems. MRPs were prepared by heating the solution containing NPN (2 g nitrogen/100 ml) and sugar (2 g/100 ml) in 0.05 M sodium hydrogen carbonate buffer, pH 12 for 120 min at 100 °C. Reducing power and capacity to scavenge hydrogen peroxide (H2O2), hydroxyl radical (OH), 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) radical (ABTS+) and 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) of all MRPs were greater than those of original NPN solution (P < 0.05). The MRPs derived from NPN–fructose tended to have the highest reducing capacity and free radical scavenging ability. However, the ferrous (Fe2+) chelating activity of all MRPs was lower than the original NPN solution (P < 0.05). Therefore, reducing power and scavenging activity toward free radicals and reactive oxygen species of NPN from stingray muscle can be improved significantly by reacting NPN with sugar particularly fructose via the Maillard reaction. However, the Maillard reaction seemed to show a negative impact on the Fe2+ chelating activity of stingray NPN.

The reduction effect of dietary flavone C- and O-glycosides on the formation of acrylamide and its correlation and prediction with the antioxidant activity of Maillard reaction products

The effect of dietary flavone C- and O-glycosides on the formation of acrylamide contaminants has been investigated in the present work.

Correction: The reduction effect of dietary flavone C- and O-glycosides on the formation of acrylamide and its correlation and prediction with the antioxidant activity of Maillard reaction products

Correction: The reduction effect of dietary flavone C- and O-glycosides on the formation of acrylamide and its correlation and prediction with the antioxidant activity of Maillard reaction products

Effect of chitosan molecular weight on the functional properties of chitosan-maltose Maillard reaction products and their application to fresh-cut Typha latifolia L.

The objective was to evaluate antimicrobial, antioxidant and copper-chelating activities of Maillard reaction products (MRP) prepared from maltose and different molecular weight chitosan, and their effects on preservation of fresh-cut Typha latifolia L. (TLL). LMRP (maltose and low molecular weight chitosan MRP) showed the highest browning and UV absorbance as well as fluorescence intensity. The DPPH radical scavenging activity, reducing power and copper-chelating activity of chitosan-maltose MRP varied depending on the chitosan molecular weight. HMRP (maltose-high molecular weight chitosan MRP) exhibited better effects on inhibiting PPO activity and discoloration, alleviating declines of total soluble solids and ascorbic acid content of fresh-cut TLL. LMRP and MMRP (maltose-medium molecular weight chitosan MRP) effectively decreased weight loss and maintained firmness of TLL, respectively. These results indicated that molecular weight of chitosan had a great impact on the functional properties of chitosan-maltose MRP and their application to be used as a preservative.

Antioxidant and antimicrobial activity of Maillard reaction products from xylan with chitosan/chitooligomer/glucosamine hydrochloride/taurine model systems

The structure, UV absorbance, browning intensity, fluorescence changes, antioxidant activity and antimicrobial assessment of Maillard reaction products (MRPs) derived from xylan with chitosan, chitooligomer, glucosamine hydrochloride and taurine model systems were evaluated. The results revealed that all MRPs had similar infrared spectra and molecular structures. MRPs from different model systems on the UV absorbance at 294nm after heated 90min and browning intensity at 420nm showed the similar law: xylan-taurine>xylan-glucosamine hydrochloride>xylan-chitooligomer>xylan-chitosan, and the order of DPPH scavenging activity of MRPs was as follows: xylan-chitosan>xylan-chitooligomer>xylan-glucosamine hydrochloride>xylan-taurine, which revealed that the properties of MRPs were closely related to molecular weight of model systems. Moreover, the highest radical scavenging activity of MRPs from xylan with chitosan/chitooligomer/glucosamine hydrochloride/taurine model systems was 65.9%, 63.7%, 46.4% and 42.5%, respectively.

Antioxidant and antiradical properties of maillard reaction products in both aqueous and ethanolic fructose-glycine oligomer solutions

The purpose of this study was to evaluate the antioxidant and antiradical properties of Maillard reaction products (MRP) in both aqueous and ethanolic fructoseglycine oligomer solutions. Antioxidant and radical scavenging activities of MRPs were investigated using different in vitro assays: the ferric ion (Fe3+) reducing ability, cupric ion (Cu2+), ferrous ion (Fe2+) chelating effects, DPPH and ABTS radical scavenging activities, and Fe3+-TPTZ reducing ability. MRPs derived from fructose-diglycine (GG) were found to be effective antioxidants in different in vitro assays. The antioxidant activity was higher in ethanolic solutions than in aqueous MRP solutions.