Lipeng Han,Qingna Lin,Guoqin Liu,Dongxue Han,Li Niu,Dongxiao Su
It is important to inhibit food-derived potentially hazardous glycated lipids with natural products. A model reaction inhibition system was established, and products were identified with high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS) to study the inhibitory effects of four types of catechins on the formation of glycated 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE) products. The results show that the percentage inhibition of epicatechin (EC), epicatechin gallate (ECG), epigallocatechin (EGC) and epigallocatechin gallate (EGCG) on the formation of carboxymethyl 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (CM-DPPE) are 38.84%, 33.31%, 20.71% and 22.66%, respectively. The percentage inhibition of EC, ECG, EGC and EGCG on the formation of carboxyethyl 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (CE-DPPE) is 42.04%, 41.99%, 31.70% and 36.24%, respectively. In addition, catechin can capture glyoxal (GO) and methylglyoxal (MGO) to produce multiple products. O-Benzoquinone, the oxidation products of catechin, also captures DPPE to produce quinone–DPPE adducts. Therefore, there are two inhibitory mechanisms of tea-derived catechin for glycated DPPE: (1) catechin inhibits the formation of CM-DPPE and CE-DPPE by trapping reactive GO and MGO; and (2) catechin is oxidized to o-benzoquinone. O-Benzoquinone reacts with DPPE through nucleophilic substitution, which competes with the reaction between glucose and DPPE. This study will provide a theoretical basis for the use of natural products to inhibit the formation of food-derived glycated lipids.
Qingna Lin,Lipeng Han,Guoqin Liu,Weiwei Cheng,Liqing Wang
The formation of food-derived glycated phosphatidylethanolamine (PE) in thermal process was investigated by designing a 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (DPPE)-glucose model system heated from 40 to 100 °C for 8 h. The main products of glycated PE were determined by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). Results showed that the glycation of DPPE formed three major glycated compounds: amadori-glycated-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (Amadori-DPPE), carboxymethyl-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (CM-DPPE), and carboxyethyl-1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine (CE-DPPE). Amadori-DPPE was identified to generate CM-DPPE through oxidative cleavage of glycated polar head group under high temperature and extended incubation time. Additionally, during thermal processing, retro-aldol reactions of glucose led to the formation of two reactive dicarbonyl intermediates: glyoxal (GO) and methylglyoxal (MGO), both of them reacted with amino group of DPPE to form CM-DPPE and CE-DPPE, respectively. Thus, the formation pathways of CM-PE might involve the irreversible rearrangements of Amadori-PE following oxidative cleavage, as well as the glycation of amino group of PE with GO. CE-PE could only be formed by reaction of PE with MGO. Moreover, the content of CM-DPPE was higher than that of CE-DPPE in the same incubation conditions, which indicated that CM-PE might be a more useful predictive marker for food-derived glycated amino-phospholipid, rather than Amadori-PE, particularly in thermal processed foodstuffs.
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