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: Plamen Y Nikolov, Varoujan A Yaylayan
• Journal: Journal of agricultural and food chemistry (J Agric Food Chem) Vol. 60 Issue 40 Pg. 10155-61 (Oct 10 2012) ISSN: 1520-5118 [Electronic] United States
• PMID: 22994507 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Amino Acids
• Furans
• Pyrroles
• furfurylamine
• Ribose
• Hydroxyproline

Topics

• Amino Acids (chemistry)
• Coffea (chemistry)
• Furans (analysis, chemistry)
• Hydroxyproline (chemistry)
• Odorants (analysis)
• Pyrroles (analysis, chemistry)
• Ribose (chemistry)
• Seeds (chemistry)
• Smell