Effects of dough formula and baking conditions on acrylamide and hydroxymethylfurfural formation in cookies

The effects of dough formula and baking conditions on the formations of acrylamide and hydroxymethylfurfural (HMF) were studied in a cookie model system. Increasing the sugar concentration in the dough formula increased acrylamide formation during baking at 205 °C for 11 min. The effect of sugar on acrylamide formation was more pronounced for glucose than for sucrose, expectedly. Addition of citric acid into dough formula comprising sucrose increased the susceptibility of acrylamide formation, while it decreased acrylamide formation in the dough formula comprising glucose. Decreasing the pH of dough formula increased the tendency to surface browning and the formation of hydroxymethylfurfural in cookies during baking. The results suggest that a cookie with acceptable texture and colour, but having less than 150 ng/g of acrylamide, can be manufactured by lowering the baking temperature and avoiding reducing sugars in the recipe.     

Mitigation strategies of acrylamide,furans, heterocyclic amines and browning during the Maillard reaction in foods

The Maillard reaction (MR) occurs widely during food manufacture and storage, through controlled or uncontrolled pathways. Its consequences are ambiguous depending on the nature and processing of the food products. The MR is often used by food manufacturer to develop appealing aromas, colour or texture in food products (cereal based food, coffee, meat…). However, despite some positive aspects, the MR could decrease the nutritional value of food, generate potentially harmful compounds (e.g. acrylamide, furans, heterocyclic amines) or modify aroma or colour although it is not desired (milk, fruit juice). This paper presents a review of the different solutions available to control or moderate the MR in various food products from preventive to removal methods. A brief reminder of the role and influence of the MR on food quality and safety is also provided.     

Chemical activation of piperidine by formaldehyde and formation of lysine-specific Maillard reaction products

Piperidine is considered as a lysine-specific Maillard reaction product that can be formed from free lysine through decarboxylation and deamination reactions or through cyclization of pent-4-en-1-amine, the counterpart of acrylamide from lysine. Due to the importance and reactivity of piperidine its further interaction products in glucose/lysine model system was investigated. A useful strategy based on Py-GC/MS analysis was developed using an isotope labelling technique to identify reaction products incorporating piperidine moieties. Products simultaneously possessing five lysine carbon atoms (C2′–C6′) and the Nε-amino group from lysine in addition to glucose carbon atoms were targeted using specifically labelled precursors such as [¹⁵Nα]Lysine·2HCl, [¹⁵Nε]Lysine·2HCl, [U-¹³C₆]Lysine·2HCl, [¹³C-6]Lysine·2HCl and [U-¹³C₆]Glucose. Detailed labelling studies using specifically ¹³C-enriched sugars have shown that the piperidine can form reactive 1-methylidenepiperidinium ion with formaldehyde, which is able to undergo further aldol addition reactions to form compounds, such as 3-(piperidin-1-yl)propanal and 3-(pyridin-1(4H)-yl)propanal. Furthermore, these studies have also demonstrated that oxidation of piperidine into di- and tetrahydropyridine derivatives can generate reactive eneamine moieties capable of nucleophilic attack at carbonyl groups and formation of pyridine derivatives.     

The effects of phytic acid on the Maillard reaction and the formation of acrylamide

Phytic acid, myo-inositol hexaphosphoric acid, exists in substantial (1–5%) amounts in edible plant seeds. In this study the effects of phytic acid on the Maillard reaction and the formation of acrylamide were investigated. Both phytic acid and phosphate enhanced browning in glucose/β-alanine system, but phytic acid was less effective than phosphate. Higher pH favoured the catalytic activities for both of them. The influence of the types of sugar and amino acid on the reaction was also examined. Browning was suppressed by the addition of calcium and magnesium ions, but an additive effect was observed for ferrous ions and phytic acid in glucose/β-alanine solution at pH 8.0. Both phytic acid and phosphate promoted the polymerisation of the reaction intermediates. The kinetics of Maillard reaction was first-ordered reaction in the presence of phytic acid. Phytic acid was less effective than phosphate in the formation of acrylamide. When potato slices were treated with sodium phytate and calcium chloride successively, the formation of acrylamide was greatly suppressed.     

Correlation of methylglyoxal with acrylamide formation in fructose/asparagine Maillard reaction model system

α-Dicarbonyl compounds were highly reactive intermediates formed in Maillard reaction (MR), and o-phenylenediamine (OPD) was widely used as a trapping agent for α-dicarbonyl compounds. Both aqueous fructose/asparagine (Fru/Asn) and fructose/asparagine/o-phenylenediamine (Fru/Asn/OPD) model systems were heated at 150 °C for up to 30 min. Methylglyoxal (MG) was the main α-dicarbonyl compounds formed in MR, which was chosen as a representative of α-dicarbonyl compound to investigate the influence on acrylamide (AA) formation. The concentrations of AA, MG and Asn were detected during MR by HPLC method. The results indicated that the formation of AA increased with the heating time, and nearly 75% of AA was formed through the participation of α-dicarbonyl compounds. The amounts of formation and consumption of MG increased with heating time, and from 12 min of reaction, the consumed amounts of MG accounted for 62.1–90.3% on the basis of total amounts of MG formed in MR, suggesting that most of the MG took part in further reactions. Meanwhile, Asn concentration decreased with heating time in both models. The formation of AA and consumption of Asn were highly correlated with MG. Indeed, as MG concentration in MG/Asn model system decreased during heating at 150 °C, the concentration of AA significantly increased. The coefficient of correlation between consumed amounts of MG and the formed amounts of AA was 0.931, demonstrating that MG plays a role in AA formation.     

Unravelling the kinetics of the formation of acrylamide in the Maillard reaction of fructose and asparagine by multiresponse modelling

A kinetic model for the formation of acrylamide in a fructose–asparagine reaction system at initial pH 5.5 is proposed, based on an approach called multiresponse kinetic modelling. The formation of acetic acid and formic acid from the degradation of fructose and its isomer glucose was included in the proposed kinetic model. The kinetic model suggests that the effect of temperature on acrylamide formation with fructose is more due to the preceding steps with the formation of the Schiff base. The use of fructose and lower pH resulted in a higher yield of acrylamide (3%), suggesting that both can play an important role in acrylamide mitigation. Furthermore, these models have shown that, at high temperatures (120–200 °C), the Maillard reaction rapidly goes into the advanced stages, forming high amounts of organic acids and high molecular weight melanoidins. Overall, these mechanistic models provide more insight of the formation of acrylamide in a quantitative way.     

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.     

Resistant starch formation during baking -effect of baking time and temperature and variations in the recipe

Summary The dietary fibre content in white wheat bread, measured with an enzymatic, gravimetric method, was almost 20% higher than in the corresponding flour. The increment was largely explained by the formation of resistant starch, i.e. starch available to amyloglucosidase only after solubilization with 2m-KOH. The resistant starch was formed in the oven or upon cooling of the finished bread. The water content in the dough seemed to influence the extent of the resistant starch formation, whereas changes in the fat content had no effect. The results indicate that the resistant starch might be hard retrograded starch, possibly amylose.

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Bildung von resistenter Stärke während des Backens in Abhängigkeit von Backzeit, Backtemperatur und Rezeptvariationen

Zusammenfassung Die Menge an Ballaststoffen, die nach einer enzymatisch-gravimetrischen Methode bestimmt wurde, war in weißem Weizenbrot fast 20% höher als in dem entsprechendem Mehl. Die Erhöhung konnte zum großen Teil auf die Bildung von resistenter Stärke zurückgeführt werden, d. h. auf eine Stärkefraktion, die nur nach Auflösung mit 2m-KOH für Amyloglucosidase zugänglich ist. Die resistente Stärke wird während des Backens oder während der Abkühlung des Brotes gebildet, und die Menge scheint vom Wassergehalt des Teiges, aber nicht vom Fettgehalt abhängig zu sein. Die Resultate dieser Untersuchung weisen darauf hin, daß die resistente Stärke retrogradierte Stärke, möglicherweise Amylose, ist.

     

Effect of leavening agents and sugars on the formation of hydroxymethylfurfural in cookies during baking

The effects of recipe compositions in terms of leavening agent (ammonium and sodium bicarbonates) and sugars (sucrose and glucose), and baking conditions (temperature and time) on HMF formation in cookies were studied. Five recipes were prepared by varying the types of leavening agent and sugar. The cookies were baked at different temperatures (180, 200, 210 and 220 °C) for different time (10, 15, 20 and 25 min) to monitor physical and chemical changes in cookie composition in terms of water activity, pH, surface browning, sugar decomposition, and hydroxymethylfurfural (HMF) formation. Decreasing moisture to a level under a water activity of 0.4 appeared as the critical point in baking where the rate of HMF formation drastically increased after this point. After this stage, sucrose decomposed very rapidly if ammonium bicarbonate was used as the leavening agent at temperatures greater than 200 °C. Replacing ammonium bicarbonate with sodium bicarbonate maintained pH of cookies ranging between 9.0 and 10.0 during baking, which limited the decomposition of sucrose.     

Antioxidant activity of oligochitosan Maillard reaction products using oligochitosan as the amino or carbonyl groups donors

The purpose of this study was to evaluate the influence of oligochitosan (COS) as amino (–NH₂) or carbonyl group (–C=O) donors on the antioxidant activities of COS Maillard reaction (MR) products. Two kinds of COS MR products (COS MRPs) were prepared by using COS and glucose/α-alanine, respectively. Their structures were characterized by Fourier transform infrared spectroscopy (FT-IR), their molecular weights (Mws) were measured by gel permeation chromatography, and the –NH₂ contents of COS MRPs were determined. The antioxidant activities of COS MRPs were evaluated by measuring the scavenging activity of superoxide anion radical (O₂^?), 1,1-diphenyl-2-picrylhydrazyl radical, and the reducing power. The result showed that C=N absorbance can be observed in CG (MRPs of COS and glucose) and CA (MRPs of COS and α-alanine). The Mw of COS increased after MR. CG and CA showed dramatically enhanced antioxidant activity compared to COS, and the antioxidant activity of CG was better than that of CA. In other words, MR is an efficient way to enhance the antioxidant activity of COS. Moreover, it is a more efficient way to enhance the antioxidant activity of COS by using COS as amino group donor involved in MR. The results may provide some references to the modification and application of COS.     

Recent developments in pasteurising seeds and their products using radio frequency heating: a review

Food-borne or plant diseases mainly rely on the spread of seeds with pathogens. It is vital to eliminate food/seed-borne pathogens of seeds and their products before commercial import/export or circulation. Radio frequency (RF) heating is identified as an effective method with lack of chemical residues, rapid or volumetric heating and large penetration depth, and also validated as a potential physical method to eliminate pests or pathogens in agricultural products or foods. Although, many reviews have summarised the applications of RF treatment during the process of foods, little comprehensive review has been focused on seeds and their products pasteurised by the RF energy. Comprehensive summary about principles and main applications of RF energy for pasteurising seeds and their products was reported in this review. This review also introduced some typical RF heating systems, thermal death kinetics of pathogens, influences of RF heating on germination rate of seeds and some ways for improving uniformity of RF heating. Furthermore, this review recommended the future research directions about treatment of seeds and their products using RF energy, especially for seed industry to control the pathogens in seeds without reducing their quality after RF treatments.     

Acrylamide formation and colour development in low-fat baked potato products as influenced by baking conditions and oil type

The objective of this study was to investigate the effect of oil type and oxidation status on acrylamide (AA) formation and colour development in potato products under domestic baking conditions. Sunflower, soybean and olive oil were used; the first one was thermally oxidized to obtain different oxidation status. A potato dough containing 10 % oil, potato powder, flour and water was shaped into thin discs and baked at 180 °C for different heating times. AA concentration, moisture content and surface colour were determined. Results obtained showed that neither the nature of lipids present, in terms of content of unsaturated fatty acids, nor the degree of fat oxidation influenced AA formation in low-fat baked potato products. Browning ratio higher than 45 % and moisture content lower than 17 % resulted in dark brown, almost burnt, products. Moreover, in those cases, no correlation could be found between those variables and AA content, since formation and degradation simultaneously occur. When the browning ratio ranged between 0 and 45 %, a good linear correlation with AA formation was observed, suggesting that the browning ratio may be considered as a reliable indicator of AA concentration. Finally, AA less than 1000 μg/kg, which is an indicative value that has been recently set for potato crisps by the European Commission, corresponds to a browning ratio of less than 8 % and moisture content more than 23.5 %.     

Maillard reaction products as "natural antibrowning" agents in fruit and vegetable technology

The effects of Maillard reaction products (MRPs), synthesized from a sugar (pentose, hexose, or disaccharide) and either a cysteine-related compound, an amino acid, or a sulfur compound, were investigated on polyphenoloxidase (PPO) activity from apple, mushroom, and eggplant. The optimal conditions for the production of inhibitory MRPs were performed using two-factor and five-level central experimental designs. It resulted that thiol-derived MRPs were highly prone to give rise to inhibitory compounds of PPO activity. Technological assays were also performed to test the efficiency of selected MRPs in the prevention of enzymatic browning in raw and minimally processed fruits and vegetables.     

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 flour type on Maillard reaction and acrylamide formation during toasting of bread crisp model systems and mitigation strategies

Maillard reaction along with caramelisation are the main chemical reactions occurring in bakery products. They are referred to as non enzymatic browning. In this work, the effect of flour type (wheat, rye and whole-wheat flours) and process conditions were investigated by using a bread crisp model system made up of flour, water and yeast. The bread was toasted at different temperature for different times. In a second set of experiments several additives (glycine, 0.1% on flour; asparaginase, 2000 U kg⁻¹ of flour and an antioxidant extract from green tea) were added to the basic formulations in order to test their ability in reducing the formation of potentially harmful Maillard reaction compounds such as HMF and acrylamide. Browning development and water content along with antioxidant activity were also monitored.Rye model systems produced more HMF and acrylamide at all temperature tested, while wholewheat systems produced less HMF, but more acrylamide than wheat one. The addition of glycine was effective in reducing acrylamide formation, and it increased browning development, antioxidant activity and HMF formation. Asparaginase reduced acrylamide formation up to 88% and had no effect on browning development and antioxidant activity. The addition of exogenous antioxidant compounds from green tea did not produce clear effect on acrylamide formation, thus it was not useful as mitigation strategy in bakery products, likely because of the low fat content.     

SPME-GC-MS分析谷朊粉酶解物Maillard反应产物的风味成分

利用碱性蛋白酶水解谷朊粉,得到一定水解时间的酶解粉作为Maillard反应生产香精基料的前体物质.氨基酸分析结果表明,随水解时间延长,水解物中总游离氨基酸的含量逐步增大,从37.71 mg/100mL提高到78.15mg/100mL.酶解粉与葡萄糖反应后采用固相微萃取气质联用分析,通过谱库检索定性,共鉴定出87种肉香味成分,包括吡嗪类、呋喃类、含硫类、醛类、酮类,醇类、酚类等.实验结果表明,水解30min的谷朊粉酶解物参与的Maillard反应中,生成物的峰面积最小,种类最少,另外四组主要风味物质没有发生较大变化,只是强度会发生改变.水解180min的谷朊粉酶解物Maillard反应产物中杂环化合物含量最高.