Amino Acid Degradations Produced by Lipid Oxidation Products

Abstract

Differently to amino acid degradations produced by carbohydrate-derived reactive carbonyls, amino acid degradations produced by lipid oxidation products are lesser known in spite of being lipid oxidation a major source of reactive carbonyls in food. This article analyzes the conversion of amino acids into Strecker aldehydes, α-keto acids, and amines produced by lipid-derived free radicals and carbonyl compounds, as well as the role of lipid oxidation products on the reactions suffered by these compounds: the formation of Strecker aldehydes and other aldehydes from α-keto acids; the formation of Strecker aldehydes and olefins from amines; the formation of shorter aldehydes from Strecker aldehydes; and the addition reactions suffered by the olefins produced from the amines. The relationships among all these reactions and the effect of reaction conditions on them are discussed. This knowledge should contribute to better control food processing in order to favor the formation of desirable beneficial compounds and to inhibit the production of compounds with deleterious properties.

Keywords:

• Acrylamide
• carbonyl–amine reactions
• flavor formation
• lipid oxidation
• Maillard reaction
• Strecker aldehydes
• styrene

ACKNOWLEDGMENT

We are indebted to José L. Navarro for technical assistance.

Funding

This study was supported in part by the European Union (FEDER funds) and the Plan Nacional de I + D of the Ministerio de Economía y Competitividad of Spain (projects AGL2009-07638 and AGL2012-35627).