Chemistry and some biological effects of model melanoidins and pigments as Maillard intermediates.
Various pigments were formed in the D-xylose-glycine reaction system. Blue pigments (Blue-M1 and Blue-M2) and red pigments (Red-M1 and Red-M2) were generated in the Maillard reaction. Blue-M2 is presented to have been generated by the reaction between Blue-M1, which involved two pyrrolopyrrole structures as the major blue pigment, and di-D-xyluloseglycine. We identified red pigments as the isomers of addition compounds of D-xyluloseglycine to condensated compound between pyrroropyrrole-2-carbaldehyde and pyrrole-2-carbaldehyde compounds. These pigments have polymerizing activities, suggesting that they are important Maillard reaction intermediates through the formation of melanoidins. Blue-M1 as well as melanoidins effectively suppressed the peroxidation of linoleic acid. The scavenging activity toward Blue-M1 on hydroxyl and DPPH radicals was also as strong as that of melanoidins. Furthermore, Blue-M1 prevents the oxidative cell injury. Therefore, Blue-M1 will be an antioxidant which protects against the oxidative stress in biological systems. Melanoidins induced IFN-gamma mRNA and IL-12 mRNA expressions in spleen cells exposed to allergen and in macrophage-like J774.1 cells, respectively. These findings suggest that melanoidins have suppressive effect on allergic reaction as a novel physiological effect.
Hayase
Fumitaka
F
Department of Agricultural Chemistry, Meiji University, Kawasaki, Kanagawa, Japan. fumi@isc.meiji.ac.jp
Usui
Teruyuki
T
Watanabe
Hirohito
H
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D002082:Butylamines / Q000737:chemistry; D019556:COS Cells; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D002478:Cells, Cultured; D002522:Chlorocebus aethiops; D005990:Glycerol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D005998:Glycine / Q000737:chemistry; D006967:Hypersensitivity / Q000517:prevention & control; D015227:Lipid Peroxidation / Q000187:drug effects; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D015416:Maillard Reaction; D051379:Mice; D010860:Pigments, Biological / Q000737:chemistry* / Q000494:pharmacology*; D011108:Polymers / Q000737:chemistry* / Q000494:pharmacology*; D011758:Pyrroles / Q000138:chemical synthesis / Q000494:pharmacology; D013154:Spleen / Q000187:drug effects / Q000276:immunology; D014994:Xylose / Q000737:chemistry
C492601:5-((1,4-(dicarboxymethyl)-5-(2,3-dihydroxypropyl)-2-pyrrolo(3,2-b)pyrrolyl)methine)-1,4-(dicarboxymethyl)-2-(1,2,3-trihydroxypropyl)pyrrolo(3,2-b)pyrrolylium; D000975:Antioxidants; D002082:Butylamines; D010860:Pigments, Biological; D011108:Polymers; D011758:Pyrroles; C011908:melanoidin polymers; D014994:Xylose; D005990:Glycerol; D005998:Glycine