Novel yellow compounds, dilysyldipyrrolones A and B, formed from xylose and lysine by the Maillard reaction.
When a solution containing xylose and L-lysine is heated under weakly acidic conditions, it turns brown by the Maillard reaction. We isolated here two novel yellow compounds from a heated solution containing xylose and lysine, and identified pyrrolyl-methylidene-pyrrolone derivatives named dilysyldipyrrolones A and B. Their chemical structures were elucidated by instrumental analyses as 6-[[1-[(S)-5-amino-1-carboxypentyl]-3-hydroxy-pyrrol-2-yl]-(E)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-ly]-(S)-2-amino-hexanoic acid (dilysyldipyrrolone A) and 6-[[1-[(S)-5-amino-5-carboxypentyl]-3-hydroxy-pyrrol-2-yl]-(E)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-yl]-(S)-2-amino-hexanoic acid (dilysyldipyrrolone B). These were the major pigments in the heated solution.
Sakamoto
Junko
J
Department of Nutrition and Food Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan.
Takenaka
Makiko
M
Ono
Hiroshi
H
Murata
Masatsune
M
D000614:Aminocaproates; D015119:Aminocaproic Acid / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D008239:Lysine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D008958:Models, Molecular; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014994:Xylose / Q000737:chemistry*
C545999:6-((1-(5-amino-1-carboxypentyl)-3-hydroxypyrrol-2-yl)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-ly)-2-aminohexanoic acid; C546000:6-((1-(5-amino-5-carboxypentyl)-3-hydroxy-pyrrol-2-yl)-2-methylidene-5-methyl-1,2H-pyrrol-3-one-1-yl)-2-amino-hexanoic acid; D000614:Aminocaproates; D011758:Pyrroles; D014994:Xylose; D008239:Lysine; D015119:Aminocaproic Acid