Quantitation of α-Dicarbonyls and Advanced Glycation Endproducts in Conventional and Lactose-Hydrolyzed Ultrahigh Temperature Milk during 1 Year of Storage

J Agric Food Chem. 2019 Nov 20;67(46):12863-12874. doi: 10.1021/acs.jafc.9b05037. Epub 2019 Nov 12.

Abstract

A comprehensive quantitative characterization of Maillard reaction products was carried out for conventional (CON) and lactose-hydrolyzed (LH) ultrahigh temperature (UHT) milk during storage at 20, 30, and 40 °C for 1 year. The accumulation of 3-deoxyglucosone (3-DG) and 3-deoxygalactosone (3-DGal) in LH-UHT milk ranged from 20-fold (at 20 °C) to 44-fold (at 40 °C) higher than that in CON-UHT milk. High temperature storage (40 °C) significantly accelerated the accumulation of 3-DG, 3-DGal, and 5-hydroxymethyl furfural but not the majority of the analyzed advanced glycation endproducts (AGEs). The concentrations of major AGEs including N-ε-carboxymethyllysine (CML), N-ε-carboxyethyllysine (CEL), methylglyoxal-hydroimidazolone isomers (MG-H1/H3), glyoxal-hydroimidazolone isomers (G-H1/H3), and G-H2 detected in CON milk during storage were in the range 12-700, 1-14, 8-45, 4-13, and 1-30 μM, respectively, while they were 30-570, 2-88, 17-150, 9-20, and 5-34 μM, respectively, in LH milk. Pyrraline, S-(carboxymethyl)cysteine (CMC), and glyoxal-lysine dimer were detected in lower levels, while MG-H2, methylglyoxal-lysine dimer, argpyrimidine, glyoxal-lysine-amide, glycolic acid-lysine-amide, and pentosidine were not detected in any of the milk samples. This work demonstrates for the first time that five of the analyzed AGEs (CML, CEL, MG-H1/H3, G-H1/H3, and G-H2) could be selected as markers for evaluation of the extent of the Maillard reaction in UHT milk. These results contribute to a better understanding of how Maillard reactions progress during storage of UHT milk and can be used to develop strategies to inhibit Maillard reactions in LH milk.

Keywords: 5-(hydroxymethyl)furfural; Maillard reaction; N-ε-carboxyethyllysine; N-ε-carboxymethyllysine; hydroimidazolone isomers; lactose-hydrolyzed UHT milk; pyrraline.

MeSH terms

  • Animals
  • Cattle
  • Deoxyglucose / analogs & derivatives
  • Deoxyglucose / analysis
  • Food Storage
  • Galactose / analogs & derivatives
  • Galactose / analysis
  • Glycation End Products, Advanced / analysis*
  • Isomerism
  • Lactose / chemistry*
  • Lysine / analogs & derivatives
  • Lysine / analysis
  • Maillard Reaction
  • Milk / chemistry*
  • Pyruvaldehyde / analysis
  • Temperature

Substances

  • 3-deoxygalactosone
  • Glycation End Products, Advanced
  • N(6)-(1-carboxyethyl)lysine
  • N(6)-carboxymethyllysine
  • Pyruvaldehyde
  • Deoxyglucose
  • 3-deoxyglucosone
  • Lactose
  • Lysine
  • Galactose