Antioxidant properties of Maillard reaction products obtained by gamma-irradiation of whey proteins

The radiation processing of sugar–amino acid solutions results in formation of Maillard reaction products (MRPs). In the present study, the efficacy of gamma-irradiation in the formation of MRPs from whey protein powder was investigated. The formation of MRPs in whey protein suspension was studied by monitoring spectrophotometeric and chemical changes. A dose-dependent increase in UV absorbance and development of fluorescence was observed. Formation of brown pigments was established by increased A_420 nm and Hunter colour upon irradiation. These MRPs exhibited antioxidant activity as measured by 1,1-diphenyl-2-picrylhydrazyl and β-carotene bleaching assays. Reducing power and iron-chelating abilities of MRPs also increased upon irradiation. These MRPs were able to scavenge hydroxyl and superoxide anion radicals under in vitro conditions. Dose-dependent decrease in free amino groups and lactose suggested the formation of glycated proteins upon irradiation treatment. SDS–PAGE analyses indicated formation of crosslinked proteins upon irradiation.     

乳及乳制品加工中的美拉德反应

针对乳及乳制品在加工和储藏过程中由于发生美拉德反应不仅使乳制品的营养物质受到破坏，还产生对人体有害的物质，在很大程度上影响的乳制品的质量，对乳制品中美拉德反应的历程，产生的标志物及其测定方法等进行了的综述。     

Maillard反应合成蛋白质-多糖复合物及其应用

综述了利用美拉德反应制得的蛋白-多糖复合物的性能,这种复合物主要是在干燥状态下利用自发进行的美拉德反应制得的。同传统商业上使用的乳化剂相比,该复合物具有优良的乳化性能,热稳定性和抑菌性。因此,该复合物在工业上可以用作天然乳化剂,无毒抑菌剂。同时如果多糖与过敏原蛋白复合还具有减轻蛋白的致敏性的效果。     

脯氨酸与木糖反应产物抗氧化性能研究

Maillard反应产物受温度、pH、反应时间和不同的反应物摩尔比影响,而对抗氧化效果产生不同的影响,通过检测油脂的过氧化值检验Maillard反应产物的抗氧化效果。     

Improvement of functional properties of acid-precipitated soy protein by the attachment of dextran through Maillard reaction

The functional acid-precipitated soy protein (SAPP)–dextran conjugate was prepared by dry-heated storage at 60 °C under 79% relative humidity (RH) for 5 days through Maillard reaction between the ε-amino of lysine in soy proteins and the reducing-end carbonyl residue in the dextran. The covalent attachment of dextran to SAPP was confirmed by SDS-polyacrylamide gel electrophoresis and gel filtration chromatography. Functional properties of soy protein depend on the structural and aggregation characteristics of their major components (storage globulins 7S and 11S). The conjugate seemed to be predominantly formed by 7S, and the acidic subunits of 11S in soy protein. The emulsifying properties of the SAPP–dextran conjugate were about four times higher than those of SAPP. The solubility of the protein was not enhanced as a result of preheating, but rather it was not decreased when the conjugated protein was heated at 90 °C for 20 min due to the presence of the polysaccharide. The excellent emulsifying properties of SAPP–dextran conjugate were maintained even at pH 3.0 and were further improved at pH 10.0. The object of Maillard reaction is to guarantee the suitable reaction degree, and the resulting soluble conjugate can have excellent emulsifying properties.     

Functional properties of the Maillard reaction products of rice protein with sugar

The glycation of rice proteins with reducing sugars was investigated in an attempt to improve their solubility and functionality. Rice proteins isolated from a Chinese milled medium-grain rice were glycated with glucose, lactose, maltodextrin, or dextran in 2% aqueous dispersions. The sugar that provided the most improvement of the solubility, emulsification activity (EA) and emulsification stability (ES) of the Maillard reaction products was glucose. The optimum reaction conditions were at pH 11, 100 °C, and reaction time 15 min, which increased the solubility, EA and ES of rice protein from 20%, 0.46 and 11.1 to 92%, 0.64 and 18.2, respectively. Extending the reaction time beyond 15 min continued the development of latter-stage Maillard browning products without improvements in the functional properties of the Maillard reaction products. SEC–HPLC analysis with light scattering detection showed a decrease of the weight-averaged molecular weight from 500 to 100 K during the initial 15 min.     

Functional properties of Maillard reaction products of rice protein hydrolysates with mono-, oligo- and polysaccharides

The Maillard reaction was carried out under wet reaction conditions using rice protein product from limited hydrolysis to conjugate with various mono-, oligo- and polysaccharides. The Maillard reaction products (MRPs) prepared with rice protein hydrolysates at 5% degree (hydrolysed by Protease N) and dextran T20 (20 min at 100 °C) showed the greatest improvement in functionality. The solubility, emulsification activity (EA), and emulsification stability (ES) of the MRPs increased by factors of 3.5, 5.3 and 7.3 times, respectively as compared to MRPs formed with native rice proteins and dextran T20. Amino acid analysis indicated that lysine and arginine decreased significantly in the MRPs. Formation of MRPs reduced the surface hydrophobicity, which was in agreement with the change of solubility. However, further decreasing of the surface hydrophobicity resulted in lower EA and ES during the late stage of the reaction. Fluorescence analysis suggested that formation of late stage MRPs occurred after 20 min of the Maillard reaction. The molecular weight distributions showed that the functional properties of MRPs and the mechanisms of formation were affected by the peptide chain length.     

Structure and functional properties of rice protein–dextran conjugates prepared by the Maillard reaction

Dextran was grafted on to rice protein (RP) by the wet‐heating Maillard reaction, and the structure and functional properties of the rice protein–dextran conjugates (RPDCs) were investigated. The RPDCs obtained by the Maillard reaction exhibited superior functionality compared with original RP. The solubility, emulsifying activity index, emulsifying stability index, foaming activity index and foaming stability of the RPDCs increased by factors of 7.50, 1.79, 2.20, 1.69 and 2.01, respectively, compared to original RP. The molecular weight, particle size distribution, surface hydrophobicity, secondary structures, amino acid compositions and chemical bonds of RPDCs were also characterised. The structure–function relationship was preliminary discussed, and the relationship suggests that the improvements in the functional properties were closely related to structural changes.     

乳制品中的Maillard反应标示物及其应用

乳制品中的Maillard反应标示物既可作为乳制品热处理程度的指标，还可用于不同热处理乳制品的鉴别。介绍了在评价乳制品热处理程度以及区分不同乳制品中常用的几种Maillard反应标示物。这些标示物包括糠氨酸、乳果糖、糠醛类化合物、荧光化合物等。此外，还介绍了可溶性乳清蛋白、碱性磷酸酶和乳过氧化物酶等热处理标示物，这些标示物与Maillard反应之间具有较好的相关性，也是评价乳制品热处理程度以及区分不同乳制品时常用的指标，可与Maillard反应标示物联合应用。     

Effect of Maillard reaction products on oxidation products in ground chicken breast

Three amino acid-sugar solutions were adjusted to pH 8.0, heated and lyophilized prior to addition to ground chicken breast (GCB). GCB with no additives, GCB with 0.01% BHT, GCB with 0.1 or 0.2 mg/g glucose heated with arginine, valine, or histidine were prepared. Thiobarbituric acid reactive substances (TBARS), volatiles determined by gas chromatography, and Hunter L*, a* and b* values were monitored over nine days. Multiple linear regression models were used to determine the effects of the studied factors on the corresponding outcome variables. a* values of GCB ranged from 1.60 to 4.90 over nine days of storage. While Maillard reaction products (MRP) lowered oxidation compared to control, no significant difference in TBARS between MRP solutions heated for 8 or 24 h was found. Further, 0.1 mg/g heated glucose-valine mixture decreased aldehydes up to 72.87%. Therefore, shelf-life of GCB could be extended using 0.1 or 0.2 mg/g MRP.     

木糖与甘氨酸美拉德反应产物抗氧化性能的研究

以木糖和甘氨酸为底物,控制不同的物质的量(木糖与甘氨酸物质的量之比分别为1∶0.1、1∶0.2、1∶0.4)进行美拉德反应,制备了三种不同的美拉德反应产物,并通过还原能力、清除H2O2能力、清除羟基自由基(.OH)、清除超氧阴离子自由基(O2-.)、清除亚硝酸根(NO2-)等体系研究了美拉德反应产物的抗氧化性能。结果表明,三种反应产物均具有较强的抗氧化能力,随着反应产物浓度的增加,抗氧化能力增强;三种产物的还原能力和清除O2-.的能力相当;木糖与甘氨酸物质的量之比为1∶0.2的美拉德反应产物清除H2O2、.OH和NO2-的能力要强于物质的量之比为1∶0.1和1∶0.4的反应产物。     

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.     

利用美拉德反应制备酱油香料

以还原糖和氨基酸为主要原料经美拉德反应制得酱油香料(基料),再经过调配可直接用于酿造酱油的香料。实验结果表明,其最佳反应条件是:氨基酸∶还原糖为3~3.5∶1,反应温度为100~110℃(分段升温),微波下反应时间为10~18min,无微波辐照下120~150min,pH值为3.2~4.2的混合物溶剂下可得到酱油色更深、酱香气味浓郁、味道鲜美的酱油香料。质量测定结果显示,用此法制得的酱油香料各项质量指标均符合要求。应用实验结果表明,经过适当调配后的此香料应用到酿造酱油中效果颇佳。     

酪蛋白-木糖体系美拉德反应产物的抗氧化活性

研究评价了由酪蛋白-木糖模拟体系产生的美拉德反应产物的抗氧化活性,考察了反应过程中体系的pH、褐变和中间产物的变化,并测定了美拉德反应产物对金属离子(Cu2+和Fe2+)的螯合能力、自由基清除能力(.OH、DPPH.和ABTS.)以及其还原能力。结果表明,模拟体系的酸度和褐变均随反映的进行而逐渐增加,中间产物在反应初期大量形成;美拉德反应产物对Fe2+的螯合能力要明显强于对Cu2+的螯合能力;美拉德反应产物对DPPH.和ABTS.具有较强的清除作用,而对.OH的清除作用较弱;美拉德反应产物的还原能力随反应时间的延长而逐渐增大。     

咸味香精中美拉德反应产物的抗氧化性研究

利用膜分离手段从肉味香基中分离得到不同分子量范围的美拉德反应产物(MRPs),考察咸味香精中的肉味香基以及不同分子量的MRPs对卵磷脂脂质体的抗氧化效果。结果表明,肉味香基对脂质体过氧化有抑制能力,其抗氧化能力随反应物浓度的增加而增强。高分子量MRPs的抗氧化能力最强,其次为中分子量MRPs,小分子量MRPs抗氧化能力最弱,并且MRPs的抗氧化能力与其褐色程度成正比。     

美拉德反应产物的褐变、荧光吸收及抗氧化性的研究

采用以还原糖-氨基酸(木糖/葡萄糖分别与甘氨酸、赖氨酸、谷氨酰胺、半胱氨酸)模式美拉德反应(Maillard Reaction,MR)制备得到美拉德反应产物(MRPs),研究反应条件对MRPs的褐变程度、荧光吸收强度以及其抗氧化活性的影响,并分析MRPs的光学特征与抗氧化活性之间的联系。结果表明,还原糖和氨基酸的种类对MR的褐变强度有很大影响,其影响程度由强到弱分别为:Xly>Glc,Lys>Gly>Glu>Cys。随着反应时间的延长,各体系MRPs的褐变程度逐渐变强;而荧光吸收强度随着加热时间的延长而增强,然后在出现最大值后趋于平缓或者表现出下降的趋势。MRPs的抗氧化能力也随反应时间的延长而增强,抗氧化活性与褐变强度呈正相关,与荧光吸收特性没有表现出明显的关联。     

Improvement in emulsifying properties of soy protein isolate by conjugation with maltodextrin using high‐temperature,short‐time dry‐heating Maillard reaction

Soy protein isolate (SPI)–maltodextrin (MD) conjugates were synthesised using Maillard reaction under high‐temperature (90, 115 and 140 °C), short‐time (2 h) dry‐heating conditions. The loss of free amino groups in proteins and sodium dodecyl sulphate polyacrylamide gel electrophoresis (SDS‐PAGE) profile confirmed that SPI‐MD conjugates were formed and higher dry‐heated temperatures could increase the glycosylation degree. The emulsifying properties of SPI and SPI‐MD conjugates were evaluated in oil‐in‐water emulsions. The emulsions stabilised with SPI‐MD conjugates synthesised at 140 °C exhibited higher emulsifying stability and excellent storage stability against pH, ionic strength and thermal treatment compared with those synthesised at 90 °C, 115 °C and SPI stabilised emulsions. This might be due to a greater proportion of conjugated MD in SPI‐MD conjugates synthesised at 140 °C because of the higher glycosylation degree, and more conjugated MD on the droplet surface could provide steric effect and enhance the stability of the droplets in the emulsions.     

Maillard reaction products consumption: Magnesium bioavailability and bone mineralization in rats

The aim of this study was to analyze the influence of the consumption of Maillard reaction products (MRP), derived from glucose-lysine and glucose-methionine mixtures heated for 90 minutes, on magnesium bioavailability and tissue concentration. Magnesium balances were performed in rats. Subsequently, the animals were sacrificed and certain organs removed to analyze the magnesium contents. Glucose-methionine MRP induced increases in magnesium fractional absorption in the last week of the assay (69.2 ± 2.9%) compared with the control group (59.4 ± 1.3%), although no variations in magnesium bioavailability during the total period balance were found. The intake of both MRP assayed seemed to increase renal and hepatic magnesium, decrease calcium bone concentration and mask the positive effect of the free amino acids still present in the samples on bone magnesium. The results show that MRP dietary consumption could lead to changes in bone mineralization. The long-term effects should be more deeply studied to predict possible implications for bone health.     

Shelf-life of fresh noodles as affected by chitosan and its Maillard reaction products

The effects of Maillard reaction products (MRPs) prepared from chitosan and xylose on the shelf-life of fresh noodles were studied. A model system consisting of chitosan and xylose (1:1.5, w/w) dispersed in distilled water with pH values of 5, 6, 7, 9 was used. The systems were heated to 95 °C for up to 60 h. The development of brown color was more pronounced in the model system with a higher initial pH of the water. The antibacterial activity of chitosan increased at the beginning of the Maillard reaction, and the minimum inhibition concentration (MIC) of chitosan against Bacillus subtilis CCRC 10258 decreased to 50 μg/ml of medium from 250 μg as a result of the Maillard reaction. Gram-positive bacteria were more sensitive to chitosan or its MRPs than Gram-negative bacteria. MRP of chitosan/xylose showed a bactericidal effect against Bacillus subtilis CCRC 10258, while chitosan showed a bacteriostatic effect prior to the occurrence of the Maillard reaction. Addition of 0.05 g/100 ml chitosan (in 0.5 ml/100 ml acetic acid) to fresh noodle formulation resulted in an extension of its shelf-life for 6 more days when stored at 4 °C. However, addition of MRP resulted in the longer shelf-life lasting 14 days when stored at 4 °C.     

蛋清蛋白-木糖美拉德反应产物的成膜性及其膜特性的研究

蛋清蛋白具有丰富的营养价值和良好的凝胶性,是可食用膜的重要材料。但蛋清蛋白膜的机械性质和阻湿性较差,因此可以通过美拉德反应用木糖对蛋清蛋白进行糖基化改性,用蛋清蛋白-木糖美拉德反应产物制备膜。然后测定其成膜性、物理性质、机械性质以及水蒸气透过率,并用蛋清蛋白-木糖美拉德反应产物膜和蛋清蛋白膜对核桃仁进行包裹,考察其对核桃仁脂质过氧化的影响。结果表明,与蛋清蛋白膜相比,蛋清蛋白-木糖美拉德反应产物成膜所需的甘油浓度较低;机械性质有所提高,如刺穿强度提高了47%,拉伸强度提高了40%;水蒸气透过率降低了24%。与未包膜组相比,2种膜包裹都可以延缓核桃仁的脂质过氧化,使酸价降低约23%。