Kinetic Study on Peptide‐Bound Pyrraline Formation and Elimination in the Maillard Reaction Using Single‐ and Multiple‐Response Models

Abstract

Pyrraline, an advanced glycation end product (AGE), is related to some chronic diseases and can be employed as an indicator for heat damage in food processing. In this study, the impact of changing the reactant concentration and ratio on the kinetic parameters describing peptide-bound pyrraline (pep-pyr) formation and elimination was evaluated in the Lys-Gly/glucose model systems, with microwave heating treatment ranging from 120 to 200 °C. The maximum pep-pyr concentration increased as follows: 200 °C ˂ 180 °C ˂ 160 °C ˂ 120 °C ˂ 140 °C. First, the pep-pyr formation and elimination was modeled by using a single-response modelling. The formation rate constant (k ) of pep-pyr was independent of the initial concentration of the reactants and ratios. However, the elimination rate constant of pep-pyr (k ) increased with increasing reactant concentrations. Second, a multiresponse modelling was performed to illustrate the pathways of pep-pyr formation and elimination. Two adapted models can fit to the experimental data with the goodness-of-fit ranging from 0.663 to 0.920. Glucose-to-fructose isomerization rather than glucose-to-mannose epimerization was detected in an equimolar model system and the model system with an excess of any of the reactants. The caramelization reaction was negligible in the equimolar systems and the model systems with an excess of peptide. The reaction rate constant of glucose-to-fructose isomerization was independent of the initial reactant ratios. It was more difficult for pep-pyr elimination in the model system with an excess of peptide than that in the other 2 model systems (the equimolar system and the system with an excess of glucose), whereas a reverse result in pep-pyr formation was obtained.

Pyrraline Formation Modulated by Sodium Chloride and Controlled by Encapsulation with Different Coating Materials in the Maillard Reaction

“…However, at >0.50% Na + , the pyrraline concentration decreased gradually. In this study, the maximum pyrraline concentration was obtained at 140 °C, consistent with our past findings [27,28].…”

“…In conventional cooking, the temperatures of the thermal-induced MR range between 100 and 300 °C [25]. Certain AGEs, such as CML and pyrraline, are likely to form at 120–200 °C [26,27,28]. Some studies [29,30,31,32,33] have reported that the sodium content (expressed as a percentage of mass concentration) ranges between 0.00% and 1.00% in foods, including packaged, commercially processed, and restaurant foods.…”

Maillard Proteomics: Opening New Pages

“…The history of the peptide-based Maillard research comes back to the early 1990s, when Smith and Thornalley proposed the simplest dipeptide hippuryl-lysine model to monitor the degradation of Amadori products accompanied with formation of CML [ 263 , 264 ]. Later, longer peptides (representing artificial [ 265 , 266 , 267 , 268 ] and natural [ 266 , 269 , 270 , 271 ] protein sequences) were employed to address kinetic and mechanistic aspects of glycation adduct formation, structure of novel products [ 265 , 266 , 267 , 268 , 272 ], and influence of reaction conditions on AGE patterns [ 269 , 273 , 274 , 275 ]. To understand the mechanisms of AGE formation in such in vitro glycation model systems, and to dissect individual pathways of advanced glycation, analysis of peptide products can be complemented by quantification of carbohydrate [ 47 ] and α-dicarbonyl [ 276 ] intermediates.…”

“… Synthesis of Amadori-modified peptides by global glycation approach and building block strategy. After selective deprotection of the site to be glycated, Amadori moiety can be introduced directly by incubation with reducing sugar [ 273 ] or via the Lobry de Bruyn reaction with acetonide-protected hexodiulose (2,3:4,5-di- O -isopropylidene-aldehydo-β- d -arabino-hexos-2-ulo-2,6-pyranose) in presence of cyanoborohydride in methanol-isopropanol-water mixture (2:2:1 by volume) [ 274 ]. Alternatively, glycated moiety can be introduced with an acetonide-protected N ε -Boc- N ε -fructosyl- N α -Fmoc-lysine building block [ 272 ].…”

Effect of fatty acids and triglycerides on the formation of lysine-derived advanced glycation end-products in model systems exposed to frying temperature

“…1 AGEs are a diverse group of substances formed by reactions between biological molecules with different compositions and structures, such as reducing sugars, dicarbonyl compounds, amino acids, peptides, proteins, lipids and nucleic acids. [2][3][4][5][6] Studies suggest that the intake of dietary AGEs can promote the accumulation of advanced glycation end products in the human body. [7][8][9] Moreover, other studies indicate that ingestion of high levels of dietary AGEs can have an adverse impact on human health, which is linked to their ability to promote inammation, oxidative stress, diabetes, and kidney damage.…”