Ability of amino acids, dipeptides, polyamines, and sulfhydryls to quench hexanal, a saturated aldehydic lipid oxidation product

J Agric Food Chem. 1999 May;47(5):1932-6. doi: 10.1021/jf980939s.

Abstract

Hexanal is a common product arising from the oxidation of omega-6 fatty acids. Because aldehydic lipid oxidation products can react with food components, interactions between hexanal and sulfhydryl- and amine-containing compounds were determined. The polyamines, spermidine and spermine, and the sulfhydryl-containing compounds, glutathione and thioctic acid, decreased headspace hexanal concentrations < or =7.0%. Histidine was the only amino acid tested that was able to quench headspace hexanal. Histidine-containing dipeptides decreased headspace hexanal 3.0-8.5-fold more than histidine. Hexanal quenching by the hisitidine-containing dipeptides increased as the size of the aliphatic side group of the amino acid adjacent to histidine increased, with Leu-His having the greatest hexanal quenching activity. The ability of Leu-His to quench histidine increased with increasing pH. The ability of histidine-containing dipeptides to interact with hexanal suggests that it may be possible to design peptides to alter the concentration of saturated aldehydes in oxidizing lipids.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemistry*
  • Amino Acids / chemistry*
  • Dipeptides / chemistry*
  • Lipid Peroxidation
  • Polyamines / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Aldehydes
  • Amino Acids
  • Dipeptides
  • Polyamines
  • Sulfhydryl Compounds
  • n-hexanal