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The role of ribose-specific marker furfuryl-amine in the formation of aroma active 1-(furan-2yl-methyl)-1H-pyrrole (or furfuryl-pyrrole) derivatives.
MedLine Citation:
PMID:  22994507     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Furfuryl-pyrroles possess a diverse range of organoleptic properties described as roasted, chocolaty, green, horseradish-like, 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, however 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 15Nα-lysine it was revealed that only the 15Nα 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 two moles 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 120oC was also demonstrated.
Authors:
Plamen Y Nikolov; Varoujan A Yaylayan
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-20
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  -     ISSN:  1520-5118     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-21     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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