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

Zhou, S., Decker, E.A.
Journal of agricultural and food chemistry 1999 v.47 no.5 pp. 1932-1936
aldehydes, chemical reactions, spermidine, spermine, glutathione, dipeptides, free amino acids, histidine, lipoic acid
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 less than or equal to 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.