Inhibition of Maillard Reactions by Replacing Galactose with Galacto-Oligosaccharides in Casein Model Systems

Abstract

Lactose reduced dairy products are more prone to Maillard reactions due to the presence of reactive monosaccharides. Conventional β-galactosidases, which are used for lactose hydrolysis in lactose-reduced dairy products, will lead to conversion of lactose into glucose and galactose, where especially galactose is very reactive during Maillard reactions. Some β-galactosidases have transgalactosylating activity and will thus convert lactose into galacto-oligosaccharides (GOS) and hereby limit the release of galactose. The aim of this study was to investigate the extent of participation of GOS in Maillard reactions in comparison to lactose, a 50:50 mixture of glucose and galactose, and galactose exclusively in sodium caseinate-based milk-like model systems heated at 130 and 75 °C at pH 6.8. The GOS system exhibited reduced loss of free amino groups; accumulated less furosine and less of the following advanced glycation end products (AGEs): Nε-carboxyethyl lysine, methylglyoxal-derived hydroimidazolone isomers, glyoxal-derived lysine dimer, and methylglyoxal-derived lysine dimer; and also developed less browning compared to monosaccharide models. However, the GOS–caseinate system accumulated more 3-deoxyglucosone and 3-deoxygalactosone, which resulted in higher concentrations of 5-(hydroxymethyl)­furfural and pyrraline. The results indicated that GOS overall participate less readily in Maillard reactions than the monosaccharides investigated but were more prone to degradation to C6 α-dicarbonyls species. Finally, relationship analysis indicated that C6 α-dicarbonyls seemed to primarily increase concentrations of 5-(hydroxymethyl)­furfural instead of AGEs. Our results suggest that conversion of lactose into GOS instead of monosaccharides in milk by transgalactosylating β-galactosidases could be a useful strategy for production of lactose-free milk for people with lactose intolerance.

Formation and Antioxidant Activity of Maillard Reaction Products Derived from Different Sugar-amino Acid Aqueous Model Systems of Sesame Roasting

“…Within the first 15 min, the amounts of free amino groups de- creased quickly to only 10-20 of the original amounts in the Cys-sugar model systems, while the Lys-sugar model systems had around 40 remaining amino groups and the Arg-sugar model systems had 75 remaining amino groups. When the reaction times were further extended, slow loss of amino groups was found for Cys-, Lys-, and Arg-sugar model systems, which was similar to results from other reported model systems 26,27 . Interestingly, the Argsugar model system exhibited a rapid loss of free amino group firstly, followed by a decrease in the loss rate, such that the final amounts of Arg in the model system were the highest among all studied model systems.…”

Dietary advanced glycation end‐products: Perspectives linking food processing with health implications

“…In fact, a large variety of natural bioactives, primarily phenolics, oligo‐ and polysaccharides have been portrayed as AGEs inhibitors in model systems or processed foods (Khan, Liu, Wang, & Sun, 2019). The following antiglycation mechanisms have been reported: scavenging of free radicals, chelation of metal ions, trapping of reactive carbonyl intermediates (e.g., MG and 3DG), and formation of protein‐bioactive adducts (Anis & Sreerama, 2020; Khan et al., 2019; Tagliazucchi, Martini, & Conte, 2019; Zhang et al., 2018). Compared with aminoguanidine (a synthetic anti‐AGEs drug), some phenolics from different sources even showed higher percent inhibition of glycation in BSA‐fructose/glucose model systems (Abdallah et al., 2016; Liu et al., 2014).…”

Evaluation of the effect of berry extracts on carboxymethyllysine and lysine in ultra-high temperature treated milk

“….As a result, the importance of being able to control MR and reduce the formation of dietary AGEs has emerged and different strategies have been proposed. For example, reactant encapsulation (Troise, Vitiello, Tsang, & Fiore, 2016), application of natural antioxidative compounds (Peng, Ma, Chen, & Wang, 2011), enzymatic approaches (Troise et al, 2014b) or sugars substitution (Zhang, Ray, Poojary, Jansson, Olsen, & Lund, 2018) have already shown promising results in reducing MR derived compounds.…”