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.

Egg yolk phospholipids: a functional food material to generate deep‐fat frying odorants

“…In addition, both the primary amine group present in phosphatidylethanolamine and aldehydes produced from lipid oxidation can serve as Maillard reaction substrates . It is also consistent with the previous reports that the products of phospholipids oxidation can contribute to the Maillard reaction.…”

Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products

“…A lesser-known pathway for amino acid degradation is that produced by lipid-derived reactive carbonyls. Lipid oxidation is a main source of carbonyl compounds in foods (Bastos, Costa, & Pereira, 2017), and these compounds have been shown to degrade amino acids in a similar way to that of carbohydrate-derived reactive carbonyls (Hidalgo & Zamora, 2016). In fact, the production of Strecker aldehydes (Hidalgo & Zamora, 2004), α-oxoacids (Zamora, Navarro, Gallardo, & Hidalgo, 2006), amines (Zamora, Delgado, & Hidalgo, 2012), and vinyl derivatives (Zamora & Hidalgo, 2008) by amino acid degradation initiated by lipid-derived reactive carbonyls has been shown.…”

Aldehydes as Wort Off-Flavours in Alcohol-Free Beers—Origin and Control

“…After consequent decarboxylation due to an electronic rearrangement, the molecule forms a second imine, which then hydrolyses to the Strecker aldehyde. The 'by-product' of this reaction in turn is unstable and initiates further reactions with amino acids (Hidalgo and Zamora 2016).…”

“…General formation mechanism of Strecker aldehydes from an amino acid and α-dicarbonyl group(Baert et al 2012;Schonberg and Moubacher 1952). b Proposed mechanism of formation of Strecker aldehydes from amino acids in presence of lipid-derived reactive carbonyls(Hidalgo and Zamora 2016) …”