Interaction of free arginine and guanidine with glucose under thermal processing conditions and formation of Amadori-derived imidazolones

卷:220

Zhu, Yuchen ; Yaylayan, Varoujan A.

McGill Univ

关键词: Guanidine;    Arginine;    Glucose;    Imidazolinone;    Amadori product;    1,2-Dicarbonyls;   

DOI  :  10.1016/j.foodchem.2016.09.173

学科分类：食品科学和技术

【 摘 要 】

To investigate the reactivity of free guanidine and arginine in the formation of imidazolinone derivatives, model systems of guanidine or arginine/glucose or (13)[C-6]-glucose were heated in aqueous solutions at110 degrees C for 3 h and the residues were analyzed by ESI/qTOF/MS using MS/MS and isotope labeling techniques. The analysis of the data indicated that guanidine and arginine formed both covalent and non-covalent interaction products. Covalent interactions included Amadori rearrangement at the a-nitrogen with glucose and imidazolinone formation with 3-deoxy-glucosone at the guanidine side-chain. Non-covalent interactions, such as self-interaction and interaction with free guanidine or arginine and glucose, were also observed. Guanidine underwent three sequential Amadori rearrangements and the free and mono-glycated guanidine also formed imidazolinone derivatives and their corresponding dehydration products and at the same time exhibiting various non-covalent interactions. On the other hand, arginine formed free Amadori product, free imidazolinone and Amadori-derived imidazolinone derivative in addition to methylglyoxal-derived hydroimidazolones. (C) 2016 Elsevier Ltd. All rights reserved.