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Issue 5, 2019
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Catechin inhibits glycated phosphatidylethanolamine formation by trapping dicarbonyl compounds and forming quinone

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Abstract

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.

Graphical abstract: Catechin inhibits glycated phosphatidylethanolamine formation by trapping dicarbonyl compounds and forming quinone

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Article information


Submitted
25 Jan 2019
Accepted
22 Mar 2019
First published
25 Mar 2019

Food Funct., 2019,10, 2491-2503
Article type
Paper

Catechin inhibits glycated phosphatidylethanolamine formation by trapping dicarbonyl compounds and forming quinone

L. Han, Q. Lin, G. Liu, D. Han, L. Niu and D. Su, Food Funct., 2019, 10, 2491 DOI: 10.1039/C9FO00155G

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