Contribution of pyrrole formation and polymerization to the nonenzymatic browning produced by amino-carbonyl reactions.
Recent studies have hypothesized that pyrrole formation and polymerization may be contribute to the nonenzymatic browning produced in both oxidized lipid/protein reactions and the Maillard reaction. To develop a methodology that would allow investigation of the contribution of this browning mechanism, the kinetics of formation of color, fluorescence, and pyrrolization in 4, 5(E)-epoxy-2(E)-heptenal/lysine and linolenic acid/lysine model systems were studied. In both cases similar kinetics for the three measurements were observed at the two temperatures assayed (37 and 60 degrees C), and there was a high correlation among color, fluorescence, and pyrrolization measurements obtained as a function of incubation time. Because the color and fluorescence production in the 4,5(E)-epoxy-2(E)-heptenal/lysine system is a consequence of pyrrole formation and polymerization, the high correlations observed with the unsaturated fatty acid also suggest a contribution of the pyrrole formation and polymerization to the development of color and fluorescence observed in the fatty acid/lysine system. Although the contribution of other mechanisms cannot be discarded, all of these results suggest that when the pyrrole formation and polymerization mechanism contributes to the nonenzymatic browning of foods, a high correlation among color, fluorescence, and pyrrolization measurements should be expected.
Zamora
R
R
Instituto de la Grasa, CSIC, Sevilla, Spain.
Alaiz
M
M
Hidalgo
F J
FJ
D000588:Amines / Q000737:chemistry; D008239:Lysine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D013058:Mass Spectrometry; D011108:Polymers; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D017962:alpha-Linolenic Acid / Q000737:chemistry
D000588:Amines; D011108:Polymers; D011758:Pyrroles; D017962:alpha-Linolenic Acid; D008239:Lysine