Lipids Promote Glycated Phospholipid Formation by Inducing Hydroxyl Radicals in a Maillard Reaction Model System

Abstract

Food-derived glycated phospholipids is potentially hazardous to human health. However, there are few studies on the effects of lipids on the formation of glycated phospholipids. In this work, two model systems were established: (1) a model system including 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (PE), glucose, and Fenton reagent and (2) a model system including PE, glucose, and five kind of vegetable oils. The contents of carboxymethyl-PE, carboxyethyl-PE, Amadori-PE, hydroxyl radical (OH•), glyoxal, and methylglyoxal were determined with high-performance liquid chromatography mass spectrometry. The results of the first model system showed that OH• oxidized glucose to produce glyoxal and methylglyoxal, which then reacted with PE to form carboxymethyl-PE and carboxyethyl-PE. OH• also oxidized Amadori-PE to form carboxymethyl-PE. The results of the second model system showed that vegetable oils with higher number of moles of carbon–carbon unsaturated double bond in vegetable oil per kilogram could produce more OH•, which promote the formation of carboxymethyl-PE and carboxyethyl-PE by oxidizing glucose and oil. We elucidated the effects of oils on the formation of glycated phospholipids in terms of OH• and intermediates. This work will contribute to better understanding the formation mechanism of glycated phospholipids with oil.

Sesame oil inhibits the formation of glycidyl ester during deodorization

“…We have proven that both DAG and MAG could significantly increase the formation GE in oil, because they are important precursors for the formation of GE. [17] However, MAG was not detected in this research. Therefore, the concentration of DAG in Figure 3 was closely related to the content of GE in Figure 2.…”

“…In Table 1, N C=C can be used as a general evaluation of unsaturated double bonds in oil. N C=C was proportional to the degree of unsaturated fatty acids in oil [17] and was related to the formation of GE. We have proposed the influence mechanism of lipid oxidation on the formation of GE in the deodorization process, as shown in Figure 1.…”

“…The method was performed according to Han et al [17] A total of 0.06 g oil was dissolved in 4 mL hexane, respectively. A total of 0.2 mL of 2 mol/L potassium hydroxide-methanol solution was added, and the mixture was stirred for 30 min.…”

“…The concentrations of diacylglycerol (DAG) in oil after deodorization were determined by HPLC-RID. The method was performed according to Han et al [17] HPLC conditions were according to Li et al [19] Chromatographic column: Luna silica normalphase HPLC column (2.0 mm × 250 mm, 5 μm); column temperature: 35°C; mobile phase: hexane/2propanol (21:1, v/v) for isocratic elution; flow rate: 1.0 mL/min; injection volume: 10 μL.…”

Synthesis and activity of a coumarin‐based fluorescent probe for hydroxyl radical detection

“…The hydroxyl radical (ÁOH) is the most representative free radical in the human body, [1,2] and it is closely related to the occurrence and development of various diseases because of its strong oxidation ability, high reaction activity, and short half-time. [3][4][5][6][7][8] For example, ÁOH can induce a series of free radical reactions, causing lipid peroxidation of membrane unsaturated fatty acids, resulting in the local destruction and even dissolution of lipid membranes. [9][10][11][12] ÁOH can also change the activity of phosphoric acid and induce the release of arachidonic acid (AA) from membrane phospholipids.…”