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Food Chem Toxicol. 2013 Oct;60:536-41. doi: 10.1016/j.fct.2013.07.081. Epub 2013 Aug 16.

Hydroxyl radical induced by lipid in Maillard reaction model system promotes diet-derived N(ε)-carboxymethyllysine formation.

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  • 1College of Light Industry and Food Sciences, South China University of Technology, 381# Wushan Road, Tianhe District, Guangzhou 510640, China; School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.


N(ε)-carboxymethyllysine (CML) is commonly found in food, and is considered as a potential hazard to human health. However, the effect of lipids on CML formation in Maillard reaction is still not clarified. In this study, the content of diet-derived CML and its key intermediates, epsilon-fructoselysine (FL) and glyoxal (GO), is determined with high performance liquid chromatography mass spectrum (HPLC-MS) in model system containing lipid compounds. According to the results, hydroxyl radical (OH) induced by Fenton reagent can promote the three pathways of CML formation. Moreover, in the Maillard reaction system, linoleic acid (Lin), oleic acid (Ole) and glycerol trioleate (Tri) can induce more OH·, which promotes CML formation. Their level of promoting CML formation is in the order of Ole>Lin>Tri. On the contrary, glycerol (Gly) can scavenge OH·, which inhibit the CML formation. Finally, it is proved that FL content and GO content decreases with heating time in model system, while CML content increases with heating time. Thus, it is concluded that in the Maillard reaction system lipids can induce more OH·, which promotes the conversion from FL and GO to CML. Our research may contribute to the development of inhibitory methods for diet-derived CML by scavenging OH·.

Copyright © 2013 Elsevier Ltd. All rights reserved.


1-deoxy-1-morpholino-D-fructose; 2,3-DHBA; 2,3-Diaminonaphthalene; 2,3-dihydroxy benzoic acid; 2,4-DHBA; 2,4-dihydroxy benzoic acid; 2,5-DHBA; 2,5-dihydroxy benzoic acid; AGEs; Advanced glycation end products; CML; Carboxymethyllysine; DAN; DMF; FL; GO; Glu; Gly; HPLC-MS; Hydroxyl radical; Lin; Lipid; Lys; N(ε)-carboxymethyllysine; NBT; OH; Ole; SA; SIR; Single Ion Recording; Tri; advanced glycation end products; alpha-Boc-lysine; epsilon-fructoselysine; glucose; glycerol; glycerol trioleate; glyoxal; high performance liquid chromatography mass spectrum; hydroxyl radical; linoleic; nitroblue tetrazolium; oleic acid; salicylic acid

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