Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 66, Issue 15, Pages 3957-3965Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.8b00937
Keywords
methylglyoxal; Maillard reaction; advanced glycation endproducts; collagen; glycation cross-links; connective tissue stiffening
Funding
- Deutsche Forschungsgemeinschaft (DFG, Germany) Research Training Group 2155, ProMoAge
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Methylglyoxal is a major 1,2-dicarbonyl compound in vivo and leads to nonenzymatic protein modifications, known as advanced glycation endproducts. Especially long-lived proteins like collagen are prone to changes of the mechanical or biological function, respectively, by accumulation of Maillard-derived modifications. Specifically, the resulting nonenzymatic cross-link structures in parallel to the natural maturation process of collagen fibrils lead to complications with age or during disease. A novel lysine-lysine amide cross-link derived from methylglyoxal, 2,15-diamino-8-methyl-9-oxo-7,10-diaza-1,16-hexadecanedioic acid, named MOLA, was synthesized and identified in vitro and in vivo. Tail tendons of young, adult, and old rats (3, 12, and 22 months) were enzymatically digested prior to analysis of acid-labile glycation products via liquid chromatography-tandem mass spectrometry (LC-MS/MS). As a result, nine monovalent amino acid modifications, mostly originating from methylglyoxal (36 mu mol/mot leucine-equivalents in total), and four glycation cross-links (0.72 mu mol/mol glucosepane, 0.24 mu mol/mol DODIC (3-deoxyglucosone-derived imidazoline cross-link), 0.04 mu mol/mol MODIC (methylglyoxal-derived imidazoline cross-link), 0.34 mu mol/mol MOLA) were quantitated in senescent tendon collagen. The results correlated with increased tail tendon breaking time from 10 to 190 min and indicate that methylglyoxal is a major player in the aging process of connective tissue.
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