Molecular Basis for the Simultaneous Enhancement of the Aroma-Generating Capacity and Bioactivity of Maillard Reaction Precursors through Mechanochemistry

J Agric Food Chem. 2022 Oct 26;70(42):13637-13650. doi: 10.1021/acs.jafc.2c05644. Epub 2022 Oct 13.

Abstract

Ball milling at ambient temperatures can accelerate the formation and accumulation of early-stage Maillard reaction intermediates considered important precursors of aromas and antioxidants. In this study, using chemical and biological assays, we explored the potential of sequential milling and heating to enhance the antioxidant and aroma-generating capacity of Maillard model systems. Milling (30 Hz/30 min) followed by dry heating (90 °C/30 min) of glycine or lysine with glucose significantly increased not only the intensity of their aroma-active compounds as analyzed by headspace-gas chromatography/mass spectrometry (HS-GC/MS) but also their free radical scavenging capacity as assessed by 2,2'-azino-bis-(3-ethylbenzothiazoneline-6-sulfonic acid) (ABTS) and oxygen radical absorbance capacity (ORAC) assays. This was attributed to the increased formation of redox-active endiol moieties and precursors of N,N-dialkyl-pyrazinium radical cation in the lysine system assessed by electrospray ionization-quadrupole time-of-flight/tandem mass spectrometry (ESI-QqTOF/MS/MS) analysis. The test samples also inhibited NO generation and cellular oxidative stress in RAW 264.7 murine macrophage cells, indicating size reduction induced by milling promoted paracellular absorption.

Keywords: ABTS; Maillard reaction; ORAC; RAW 264.7; aromas; ball milling; free radical scavenging activity; mechanochemistry.

MeSH terms

  • Animals
  • Antioxidants* / chemistry
  • Free Radicals
  • Glucose
  • Glycine
  • Lysine
  • Maillard Reaction*
  • Mice
  • Odorants
  • Sulfonic Acids
  • Tandem Mass Spectrometry

Substances

  • Antioxidants
  • Lysine
  • Free Radicals
  • Glycine
  • Glucose
  • Sulfonic Acids