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

J Food Sci. 2016 Oct;81(10):C2405-C2424. doi: 10.1111/1750-3841.13428. Epub 2016 Sep 14.

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 (kF ) of pep-pyr was independent of the initial concentration of the reactants and ratios. However, the elimination rate constant of pep-pyr (kE ) 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.

Keywords: Kinetics; peptide-glucose system; pyrraline; the Maillard reaction.

MeSH terms

  • Cooking / methods*
  • Dipeptides / chemistry
  • Fructose / chemistry
  • Glucose / chemistry*
  • Glycation End Products, Advanced
  • Hot Temperature*
  • Humans
  • Kinetics
  • Maillard Reaction*
  • Mannose / chemistry
  • Microwaves
  • Models, Chemical
  • Norleucine / analogs & derivatives*
  • Norleucine / chemistry
  • Peptides / chemistry*
  • Pyrroles / chemistry*

Substances

  • Dipeptides
  • Glycation End Products, Advanced
  • Peptides
  • Pyrroles
  • lysylglycine
  • Fructose
  • 2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
  • Norleucine
  • Glucose
  • Mannose