Identification and Quantification of Aminophospholipid-Linked Maillard Compounds in Model Systems and Egg Yolk Products

While the Maillard reaction of free amino acids and proteins is a well-established process, no defined structures from the nonenzymatic browning of aminophospholipids in foodstuffs have been described so far. Phosphatidylethanolamine (PE)-linked glucosylamines (Schiff-PE), Amadori products (Amadori-PE), 5-hydroxymethylpyrrole-2-carbaldehydes (Pyrrole-PE), and carboxymethyl (CM-PE) as well as carboxyethyl (CE-PE) derivatives were detected and quantified by liquid chromatography− electrospray mass spectrometry (LC−(ESI)MS). Model incubations of soy-PE and d-glucose were employed to firmly establish the LC−(ESI)MS procedure. Analyses of spray-dried egg yolk powders and lecithin products derived therefrom show one-fourth of the native d-glucose content of egg yolk to be transformed to Amadori-PE, corresponding to a PE derivatization quota of 11−15.5 mol %. Schiff-PE and Pyrrole-PE were present only in low amounts, no CM-PE and CE-PE could be identified in any of the investigated samples. The high glycation rate of egg yolk PE will influence the emulsifying properties and perhaps even the oxidation resistance of the respective products. Keywords: Maillard reaction; phosphatidylethanolamine; lecithin; egg yolk; Amadori compound; advanced glycation end products (AGEs)