Lin Qingna, Han Lipeng, Liu Guoqin, Cheng Weiwei, Wang Liqing
School of Food Science and Engineering, South China University of Technology No. 381 Wushan Road, Tianhe District Guangzhou 510640 China
School of Chemistry and Chemical Engineering, Guangzhou University Guangzhou 510006 China.
RSC Adv. 2018 Mar 21;8(21):11280-11288. doi: 10.1039/c8ra01072b.
The formation of food-derived glycated phosphatidylethanolamine (PE) in thermal process was investigated by designing a 1,2-dipalmitoyl--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--3-phosphoethanolamine (Amadori-DPPE), carboxymethyl-1,2-dipalmitoyl--3-phosphoethanolamine (CM-DPPE), and carboxyethyl-1,2-dipalmitoyl--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.
通过设计一个在40至100°C加热8小时的1,2 - 二棕榈酰 - 3 - 磷酸乙醇胺（DPPE） - 葡萄糖模型系统，研究了热加工过程中食物衍生糖化磷脂酰乙醇胺（PE）的形成。通过高效液相色谱 - 串联质谱（HPLC - MS/MS）测定糖化PE的主要产物。结果表明，DPPE的糖基化形成了三种主要的糖化化合物：阿马多里糖化 - 1,2 - 二棕榈酰 - 3 - 磷酸乙醇胺（阿马多里 - DPPE）、羧甲基 - 1,2 - 二棕榈酰 - 3 - 磷酸乙醇胺（CM - DPPE）和羧乙基 - 1,2 - 二棕榈酰 - 3 - 磷酸乙醇胺（CE - DPPE）。经鉴定，阿马多里 - DPPE在高温和延长孵育时间下通过糖化极性头部基团的氧化裂解生成CM - DPPE。此外，在热加工过程中，葡萄糖的逆羟醛反应导致形成两种活性二羰基中间体：乙二醛（GO）和甲基乙二醛（MGO），它们分别与DPPE的氨基反应形成CM - DPPE和CE - DPPE。因此，CM - PE的形成途径可能涉及阿马多里 - PE在氧化裂解后的不可逆重排，以及PE的氨基与GO的糖基化反应。CE - PE只能通过PE与MGO的反应形成。此外，在相同孵育条件下，CM - DPPE的含量高于CE - DPPE，这表明CM - PE可能是食物衍生糖化氨基磷脂更有用的预测标志物，而不是阿马多里 - PE，特别是在热加工食品中。
