title: Role of the ribose-specific marker furfuryl-amine in the formation of aroma active 1-(furan-2-ylmethyl)-1H-pyrrole (or furfuryl-pyrrole) derivatives.
abstract: Furfuryl-pyrroles possess a diverse range of organoleptic properties described as roasted, chocolaty, green, horseradish-like, and mushroom-like and are detected in various foods such as coffee, chocolate, popcorn, and roasted chicken. Although their origin in food was attributed to furfuryl-amine, the latter has not been detected so far in Maillard model systems or in foods. In this study, furfuryl-amine was shown to be formed specifically from ribose through nitrogen atom transfer from the α-amino group of any amino acid. Such a transfer can be achieved through decarboxylation of the Schiff base adduct and isomerization followed by hydrolysis. Through the use of (15)Nα-lysine it was revealed that only the (15)Nα nitrogen atom was incorporated into its structure, indicating a specific role for the carboxylate moiety in the mechanism of its formation. Furthermore, isotope labeling studies have indicated that furfuryl-pyrrole derivatives can be formed by the interaction of 2 mol of furfuryl-amine with 3-deoxyribosone followed by dehydration and cyclization to form 1-(furan-2-yl)-N-{[1-(furan-2-ylmethyl)-1H-pyrrol-2-yl]methylidene}methanamine. After hydrolysis, this intermediate can generate furfuryl-formyl-pyrrole, furfuryl-pyrrole carboxylic acid, and furfuryl-pyrrole. In this study, the furfuryl-amine derivatives were also detected in different coffee beans after pyrolysis and analysis by GC-MS. The potential of these compounds to form in aqueous model systems at a temperature of 120 °C was also demonstrated.
authors.affiliation: Department of Food Science and Agricultural Chemistry, McGill University , 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada H9X 3V9.
authors.forename: Plamen Y
authors.initials: PY
authors.lastname: Nikolov
authors.forename: Varoujan A
authors.initials: VA
authors.lastname: Yaylayan
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D040503:Coffea / Q000737:chemistry; D005663:Furans / Q000032:analysis / Q000737:chemistry*; D006909:Hydroxyproline / Q000737:chemistry; D009812:Odorants / Q000032:analysis*; D011758:Pyrroles / Q000032:analysis / Q000737:chemistry*; D012266:Ribose / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D012903:Smell
chemical_list: D000596:Amino Acids; D005663:Furans; D011758:Pyrroles; C439622:furfurylamine; D012266:Ribose; D006909:Hydroxyproline