Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

J Agric Food Chem. 2020 May 6;68(18):5039-5048. doi: 10.1021/acs.jafc.0c01345. Epub 2020 Apr 21.

Abstract

Acrylamide, acrolein, and 5-hydroxymethylfurfural (HMF) are food-borne toxicants produced during the thermal processing of food. The α,β-unsaturated carbonyl group or aldehyde group in their structure can react easily with the amino, imino, and thiol groups in amino acids, proteins, and DNA via Michael addition and nucleophilic reactions in food and in vivo. This work reviews the interaction pathways of three toxins with amino acids and the cytotoxicity and changes after the digestion and absorption of the resulting adducts. Their interaction with DNA is also discussed. Amino acids ubiquitously exist in foods and are added as nutrients or used to control these food-borne toxicants. Hence, the interaction widely occurring in foods would greatly increase the internal exposure of these toxins and their derived compounds after food intake. This review aims to encourage further investigation on toxin-derived compounds, including their types, exposure levels, toxicities, and pharmacokinetics.

Keywords: 5-hydroxymethylfurfural; DNA; absorption; acrolein; acrylamide; adduct; amino acids; digestion.

Publication types

  • Review

MeSH terms

  • Acrolein / chemistry*
  • Acrylamide / chemistry*
  • Amino Acids / chemistry*
  • Animals
  • DNA / chemistry*
  • Food Analysis
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / chemistry
  • Hot Temperature
  • Humans

Substances

  • Amino Acids
  • Acrylamide
  • 5-hydroxymethylfurfural
  • Acrolein
  • DNA
  • Furaldehyde