Chemistry and some biological effects of model melanoidins and pigments as Maillard intermediates

Abstract

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.