Studies on the Formation of Maillard and Caramelization Products from Glucosamine Incubated at 37 °C

Abstract

This experiment compared the in vitro degradation of glucosamine (GlcN), N-acetylglucosamine, and glucose in the presence of NH3 incubated at 37 °C in phosphate buffer from 0.5 to 12 days. The reactions were monitored with UV-vis absorption and fluorescence emission spectroscopies, and the main products of degradation, quinoxaline derivatives of α-dicarbonyl compounds and condensation products, were determined using UHPLC-UV and Orbitrap mass spectrometry. GlcN produced two major dicarbonyl compounds, glucosone and 3-deoxyglucosone, ranging from 709 to 3245 mg/kg GlcN and from 272 to 4535 mg/kg GlcN, respectively. 3,4-Dideoxyglucosone-3-ene, glyoxal, hydroxypyruvaldehyde, methylglyoxal, and diacetyl were also detected in lower amounts compared to glucosone and 3-deoxyglucosone. Several pyrazine condensation products resulting from the reaction between dicarbonyls and GlcN were also identified. This study determined that GlcN is a significantly unstable molecule producing a high level of degradation products at 37 °C.

A preliminary study on the formation pathways of glycated phosphatidylethanolamine of food rich in phospholipid during the heat-processing

“…13 C-glucose could undergo retro-aldol reactions leading to 13 C-MGO. 21,27 13 C-MGO was highly reactive with DPPE to form 13 C-CE-DPPE. At the same time, the produced glyceraldehyde could also go through retro-aldol reactions to generate GO leading to the formation of CM-DPPE (as shown in Fig.…”

Engineering of the Hyperthermophilic Archaeon Thermococcus kodakarensis for Chitin-Dependent Hydrogen Production

“…In the case of strain KC04, chitin degradation was enhanced, but accumulation of GlcN in the culture supernatant as well as browning of the medium was observed, suggesting that the excess GlcN was subjected to the Maillard reaction (31,32). Gene disruption of tgr (TK1769) was previously shown to increase activity levels of ADP-dependent GK (the TK1110 protein) in the cell extract of T. kodakarensis (29).…”

Inhibitory activity of a Concanavalin-isolated fraction from a glucosamine-peptides reaction system against heat resistant E. coli

“…The quinoxaline derivatives were eluted from another SPE cartridge with 4 mL of a MeOH/H 2 O mixture (90/10, v/v). Alpha-DCs were identified using reversed-phase ultra-high performance liquid chromatography with photodiode array detection (RP-UHPLC–PDA) following the conditions described by Hrynets et al (2015a, b). The elution of α-DCs was performed using Ascentis Express ES-C18 column (Sigma-Aldrich, MO, USA) with the gradient mixture of 0.1% formic acid in water (eluent A) and 100% methanol (eluent B) at a flow rate of 0.3 mL/min and injection volume of 5 μL.…”

“…The elution of α-DCs was performed using Ascentis Express ES-C18 column (Sigma-Aldrich, MO, USA) with the gradient mixture of 0.1% formic acid in water (eluent A) and 100% methanol (eluent B) at a flow rate of 0.3 mL/min and injection volume of 5 μL. Identification of extracted α-DCs was based on comparison with the retention time and absorption spectra of authentic α-DCs standards (Hrynets et al, 2015a, b). …”