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Creatine Is a Scavenger for Methylglyoxal under Physiological Conditions via Formation of N-(4-Methyl-5-oxo-1-imidazolin-2-yl)sarcosine (MG-HCr)

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Institute of Food Chemistry, Technische Universität Dresden, D-01062 Dresden, Germany
*Tel: +49-351-463-34647. Fax: +49-351-463-34138. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2015, 63, 8, 2249–2256
Publication Date (Web):February 6, 2015
https://doi.org/10.1021/jf505998z
Copyright © 2015 American Chemical Society

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    Abstract

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    Following incubation of methylglyoxal and creatine under physiological conditions, N-(4-methyl-5-oxo-1-imidazolin-2-yl)sarcosine (MG-HCr) was isolated and identified by NMR and mass spectrometry. Due to its rapid formation, MG-HCr represents a specific product following “scavenging” of methylglyoxal by creatine. Using hydrophilic interaction chromatography coupled to mass spectrometry, MG-HCr was analyzed in urine samples of healthy volunteers. Daily MG-HCr excretion of nonvegetarians ranged from 0.35 to 3.84 μmol/24 h urine (median: 0.90 μmol/24 h urine) and of vegetarians from 0.11 to 0.31 μmol/24 h urine (median: 0.19 μmol/24 h urine), indicating that formation of MG-HCr in vivo is influenced by the dietary intake of creatine. The trapping of methylglyoxal by creatine may delay the formation of advanced glycation compounds in vivo and, therefore, could be of special importance in situations in which the body has to deal with pathophysiologically increased amounts of dicarbonyl compounds (“carbonyl stress”), for instance in diabetic patients.

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    Figure I, possible tautomeric forms of N-(4-methyl-5-oxo-1-imidazolin-2-yl)sarcosine (MG-HCr). Figure II, identification of MG-HCr by HPLC-ESI-MS/MS in the model incubation of CR and MG. Figure III, HPLC-ESI-MS/MS and HPLC-UV chromatograms of a MG-HCr standard and a urine sample. This material is available free of charge via the Internet at http://pubs.acs.org.

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