Maillard Reaction of d-Glucose:  Identification of a Colored Product with Conjugated Pyrrole and Furanone Rings

Abstract

Formation of colored compounds during the Maillard reaction of D-glucose with butylammonium acetate in aqueous solution has been investigated. Butylamine was used as a model compound analogous to the lysine side chains of proteins. The previously unknown, yellow product, 4-hydroxy-5-methyl-2-(N-butyl-3-hydroxy-5-(2-hydroxyethyl)pyrrolyl-2-methylidene)-2H-furan-3-one (1a), was isolated from the reaction mixtures and identified by spectroscopic data.

Biological and Chemical Assessment of Antioxidant Activity of Sugar‐Lysine Model Maillard Reaction Products

“…Our colorimetric results showed that the pentose sugar ribose produced faster rates of change in color parameters and the highest yield of HMW‐MRPs compared to both aldo‐ and ketohexose sugars. Similar findings have been reported in other studies that tested a number of different Maillard reactants 24. In many of these studies, an absorbance reading at 420 nm was used to monitor the formation of late‐stage MRPs,4,25 which include the presence of furans, pyrroles, pyridine, and pyrazine components 2,24.…”

“…Similar findings have been reported in other studies that tested a number of different Maillard reactants. 24 In many of these studies, an absorbance reading at 420 nm was used to monitor the formation of late-stage MRPs, 4,25 which include the presence of furans, pyrroles, pyridine, and pyrazine components. 2,24 The change in fluorescence noted herein was attributed to the generation of initial MR products, with a variety of fluorogens being precursors for brown pigments that were subsequently generated, as evidenced by the 420-nm absorbance reading.…”

“…24 In many of these studies, an absorbance reading at 420 nm was used to monitor the formation of late-stage MRPs, 4,25 which include the presence of furans, pyrroles, pyridine, and pyrazine components. 2,24 The change in fluorescence noted herein was attributed to the generation of initial MR products, with a variety of fluorogens being precursors for brown pigments that were subsequently generated, as evidenced by the 420-nm absorbance reading. The decrease in L* values and corresponding changes in a* and b* values also represent the formation of brown pigments common to the intermediate and late-stage MR products and are alternative measures to define the progression of yellow to brown pigmentation that is derived from various products of the MR. 26 The greater loss of Rib in MR after 1 and 2 hours of heating with lysine corresponded to the faster reaction rate for pentose than hexoses.…”

Metabolic reconstruction and experimental verification of glucose utilization in Desulfurococcus amylolyticus DSM 16532

“…2 b and Table 1 ). This could be explained by putative unintended by-product formation and accumulation due to the Maillard reaction (Lerche et al 2002 ), which was inhibiting growth of D. amlyolyticus . According to a study on anaerobic bacteria, melanoidins, the product of the Maillard reaction, have strong prebiotic potential and can be used as carbon source by particularly Bifidobacterium spp.…”