Identification and determination of alpha-dicarbonyl compounds formed in the degradation of sugars

The alpha-dicarbonyl compounds formed in the degradation of glucose and fructose were analyzed by HPLC using 2,3-diaminonaphthalene as derivatizing reagent, and identified as glucosone (GLUCO), 3-deoxyglucosone (3DG), 3-deoxyxylosone (3DX), tetrosone (TSO), triosone (TRIO), 3-deoxytetrosone (3DT), g...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2007-10, Vol.71 (10), p.2465-2472
Main Authors: Usui, T.(Meij Univ., Kawasaki, Kanagawa (Japan). Faculty of Agriculture), Yanagisawa, S, Ohguchi, M, Yoshino, M, Kawabata, R, Kishimoto, J, Arai, Y, Aida, K, Watanabe, H, Hayase, F
Format: Article
Language:English
Subjects:
2,3-diaminonaphthalene
ALIMENTOS
AZUCARES
Biological and medical sciences
CARBONYL COMPOUNDS
Chromatography, High Pressure Liquid
COMPOSE CARBONYLE
COMPUESTOS CARBONILADOS
DEGRADACION
DEGRADATION
Deoxyglucose - analogs & derivatives
Deoxyglucose - chemistry
Deoxyglucose - metabolism
FOODS
Fructose - metabolism
Fundamental and applied biological sciences. Psychology
Glucose - metabolism
glucose degradation products
glycation
Glycation End Products, Advanced - analysis
Glycation End Products, Advanced - chemistry
Glycation End Products, Advanced - metabolism
Glyoxal - chemistry
Glyoxal - metabolism
HPLC
IDENTIFICACION
IDENTIFICATION
Ketoses - chemistry
Ketoses - metabolism
MAILLARD REACTION
Models, Chemical
Molecular Structure
PRODUIT ALIMENTAIRE
REACCION DE MAILLARD
REACTION DE MAILLARD
SUCRES
SUGARS
α-dicarbonyl compounds
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Summary:The alpha-dicarbonyl compounds formed in the degradation of glucose and fructose were analyzed by HPLC using 2,3-diaminonaphthalene as derivatizing reagent, and identified as glucosone (GLUCO), 3-deoxyglucosone (3DG), 3-deoxyxylosone (3DX), tetrosone (TSO), triosone (TRIO), 3-deoxytetrosone (3DT), glyoxal (GO), and methylglyoxal (MGO). The results suggest that alpha-dicarbonyl compounds were formed from glucose via non-oxidative 3-deoxyglucosone formation and oxidative glucosone formation in glucose degradation. In addition, TRIO, GO, and MGO were also formed from glyceraldehyde as intermediate. The alpha-dicarbonyl compounds might be formed from glucose via these pathways in diabetes.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.70229