Arginine-Derived Advanced Glycation End Products Generated in Peptide–Glucose Mixtures During Boiling

Glycation refers to the reaction of amino groups, for example in proteins, with reducing sugars. Intermediately formed Amadori products can be degraded by oxidation (Maillard reactions) leading to a heterogeneous class of advanced glycation end-products (AGEs), especially during exposure to heat. AG...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2014-04, Vol.62 (16), p.3626-3635
Main Authors: Frolov, Andrej, Schmidt, Rico, Spiller, Sandro, Greifenhagen, Uta, Hoffmann, Ralf
Format: Article
Language:English
Subjects:
advanced glycation end products
Amadori products
Arginine - chemistry
boiling
cooking
glucose
Glucose - chemistry
glutamic acid
glycation
Glycation End Products, Advanced - chemistry
Glycosylation
Glyoxal - chemistry
histidine
Hot Temperature
iron
Maillard Reaction
oxidation
Oxidation-Reduction
peptides
Peptides - chemistry
reducing sugars
temperature
toxicity
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Summary:Glycation refers to the reaction of amino groups, for example in proteins, with reducing sugars. Intermediately formed Amadori products can be degraded by oxidation (Maillard reactions) leading to a heterogeneous class of advanced glycation end-products (AGEs), especially during exposure to heat. AGEs are considered to be toxic in vivo due to their pronounced local and systemic inflammatory effects. At high temperatures, these reactions have been mostly investigated at the amino acid level. Here, we studied the formation of arginine-related AGEs in peptides under conditions simulating household cooking at physiological d-glucose concentrations. High quantities of AGE-modified peptides were produced within 15 min, especially glyoxal-derived products. The intermediately formed dihydroxy-imidazolidine yielded glyoxal- (Glarg) and methylglyoxal-derived hydro-imidazolinones (MG-H), with Glarg being further degraded to carboxymethyl-l-arginine (CMA). Carboxyethyl-l-arginine was not detected. The formation rates and yields were strongly increased in the presence of physiologically relevant concentrations of Fe(II)-ions and ascorbate. A nearby histidine residue increased the content of AGEs, whereas glutamic acid significantly reduced the CMA levels.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf4050183