On the Formation of 2-Acylpyrroles and 3-Pyridinols in the Maillard Reaction through Strecker Degradation.

Effect of Maillard reaction products on protein digestion. Studies on pure compounds

“…The formation of pyrroles and pyridinols during the Maillard reaction is not only dependent on the original reactants but also on the reaction conditions. As shown in model studies (Nyhammar et al, 1983), the concentrations of pyrroles pass through a maximum during the course of the reaction and are consumed during later stages, while the pyridinols are accumulated. The effect of pH on the yield differs with the type of pyrrole or pyridinol being formed, and some types are evidently favored by a pH close to that of foodstuffs (Nyhammar et al, 1983).…”

“…As shown in model studies (Nyhammar et al, 1983), the concentrations of pyrroles pass through a maximum during the course of the reaction and are consumed during later stages, while the pyridinols are accumulated. The effect of pH on the yield differs with the type of pyrrole or pyridinol being formed, and some types are evidently favored by a pH close to that of foodstuffs (Nyhammar et al, 1983). However, if not specifically analyzed, it is impossible, at the present state of knowledge, to predict the amount of a pyrrole of furan that is generated in a specific heated foodstuff.…”

“…The latter compound, found to be a weak inhibitor, is one of the major components formed during nonenzymatic browning in food. The simple pyrroles with unsubstituted nitrogen and the pyridinols (compounds 2, 3, 5, 6, 14, and 15) are generally assumed to be formed via a reaction pathway that includes Strecker degradation of amino acids having a free carboxylic acid group (Nyhammar et al, 1983). Since the concentrations of free amino acids are low in most foodstuffs, the majority of amino groups that may participate in the Maillard reaction is probably those of the protein.…”

Analysis of Furanone, Pyranone, and New Heterocyclic Colored Compounds from Sugar−Glycine Model Maillard Systems

“…However, other pyridinones, such as 5,6dihydro-3-hydroxypyridinone, have been isolated from disaccharide-containing model systems (Schoetter et al, 1994;Pischetsrieder and Severin, 1996). Also, methylpyridinols have been reported from a glucose-glycine system (Nyhammar et al, 1983) and glucose/fructoseisoleucine systems by gas chromatography-mass spectrometry of an ether extract (Tressl et al, 1995). Cyclopent[b]azepin-8(1H)-ones have been reported as proline-specific Maillard products (Tressl et al, 1985;Chen et al, 1997), whereas hexahydroimidazo[4,5-b]azepinyl derivatives were identified when glucose was reacted with butylamine and guanidine derivatives (Lederer et al, 1998).…”

Der Abbau von reduzierenden Zuckern und Aminen bei der Maillard-Reaktion

“…Das e-Lysylderivat 46a, das sog. Ffir die Bildung y o n 51 u n d 52 wird ein anderer M e c h a n i s m u s vorgeschlagen (58). Der Einflul3 des Maltosins a u f die S p u r e n e l e m e n t a u f n a h m e und -ausscheidung mul3 n o c h u n t e r s u c h t werden.…”