Clarification of the Mechanism of Inhibiting the Maillard Reaction between Phosphatidylethanolamine and Sugars by Adding Fatty Acid Calcium Salts

Lecithin is known to undergo heat induced deterioration by the Maillard reaction between 1 mol of any sugar, except 2-deoxy sugar, and 2 mol of phosphatidylethanolamine (PE). However, we have previously reported that adding fatty acid metal salts can inhibit heat deterioration of soybean lecithin (SL). To clarify the mechanism of inhibition, 1,2-di-O-stearoyl-sn-glycero-3-phosphatidylethanolamine (DSPE), d -glucose, and calcium stearate or calcium decanoate were heated in octane. When DSPE and d -glucose with calcium stearate or calcium decanoate were heated in the octane, the heat deterioration of DSPE was significantly inhibited, and no increase in UV absorption at 350 nm was observed. From these reactant solutions, one compound having a phosphate group and no primary amine was isolated, and NMR spectra confirmed that two molar of stearic acid derived from DSPE were coordinated to the amino group and phosphate group of DSPE. Therefore, we concluded that adding fatty acid metal salts reduced the nucleophilic reactivity of the amino group of PE and inhibited the Maillard reaction with sugars because two molar of fatty acid derived from PE coordinated to the amino group and phosphate group of PE.