Identification of novel fluorescent pyrrolopyridinium compound formed from maillard reaction of 3-deoxyglucosone and butylamine

• Published in: Bioscience, biotechnology, and biochemistry Vol. 58; no. 10; pp. 1936 - 1937
• Main Authors: Hayase, F. (Meiji Univ., Tokyo (Japan)), Hinuma, H, Asano, M, Kato, H, Arai, S
• Format: Journal Article
• Language: English
• Published: Tokyo Taylor & Francis 1994; Japan Society for Bioscience Biotechnology and Agrochemistry
• Subjects: ALDEHIDOS; ALDEHYDE; ALDEHYDES; AMINAS; AMINE; AMINES; Biological and medical sciences; CETONAS; CETONE; Food industries; Fundamental and applied biological sciences. Psychology; General aspects; IDENTIFICACION; IDENTIFICATION; KETONES; MAILLARD REACTION; Methods of analysis, processing and quality control, regulation, standards; PIRIDINAS; PYRIDINE; PYRIDINES; REACCION DE MAILLARD; REACTION DE MAILLARD; Maillard reaction; Glucose; Lysine; Reaction product; Structural analysis
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.58.1936

A major fluorescent compound (FL-C) was generated in a butylamine-glucose or 3-deoxyglucosone (3DG) reaction system under physiological conditions of 37°C at pH 7.4. FL-C was purified from the butylamine-3DG reaction system and identified as 6,8-dibutyl-3,3a,8,8a-tetrahydro-3a-hydroxy-2-(l,2-dihydroxyethyl)-5-hydroxymethyl-2H-furo[3′,2′:4,5]pyrrolo-[2,3-c]pyridinium. The compound was formed by the loss of five molecules of water from the reaction between 2 molecules of butylamine and 2 molecules of 3DG.