Identification of aminoreductones as active components in Maillard reaction mixtures inducing nuclear NF-kappaB translocation in macrophages.
Coffee, a highly processed food, and Maillard mixtures are able to activate nuclear factor kappaB translocation in macrophages via generation of hydrogen peroxide. In this study, a substructure library was prepared and used to identify Maillard products that are responsible for this effect. Three different Maillard reaction products with aminoreductone substructure (C(6)-aminoreductone, C(4)-aminoreductone, and aminohexose reductone) strongly induce nuclear factor kappaB translocation in macrophages. The effect was almost completely blocked by co-incubation with catalase, indicating that cellular activation was mediated by the ability of the test compounds to generate hydrogen peroxide. The cellular effect of a Maillard mixture, which was produced under conditions favoring aminoreductone formation, could be almost completely related to the presence of C(6)-aminoreductone.
Wühr
Andrea
A
Department of Chemistry and Pharmacy, Food Chemistry, Emil Fischer Center, Friedrich-Alexander-University, D-91052 Erlangen-Nuremberg, Germany.
Deckert
Melanie
M
Pischetsrieder
Monika
M
D000818:Animals; D002374:Catalase / Q000378:metabolism; D002460:Cell Line; D002467:Cell Nucleus / Q000187:drug effects* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005511:Food Handling; D006861:Hydrogen Peroxide / Q000378:metabolism; D007661:Ketoses / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D016328:NF-kappa B / Q000378:metabolism*; D009687:Nuclear Proteins / Q000378:metabolism*; D021381:Protein Transport / Q000187:drug effects; D051381:Rats; D019163:Reducing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D054852:Small Molecule Libraries; D013056:Spectrophotometry, Ultraviolet; D051996:Transcription Factor RelA / Q000378:metabolism
C553559:1-(butylamino)-1,2-dehydro-4-deoxy-3-hexulose; D007661:Ketoses; D016328:NF-kappa B; D009687:Nuclear Proteins; D019163:Reducing Agents; D054852:Small Molecule Libraries; D051996:Transcription Factor RelA; D006861:Hydrogen Peroxide; D002374:Catalase