title: Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.
abstract: Tryptophan (TRP) and its metabolites are considered as potential precursors of 2-aminoacetophenone (AAP) in different food products causing different off-flavors. AAP is also responsible for the "untypical aging flavor (UTA)" in wine, developing a floor polish-like flavor in white wines within a few months of storage. In this study the formation of AAP was elucidated by GC-MS analysis of volatile components in model systems, grape musts and wines, spiked with TRP and different TRP metabolites like indole-3-acetic acid (IAA) and sulfite. In sulfurized wines and model solutions which were stored at different temperatures (20 degrees C, 45 degrees C) formylaminoacetophenone (FAP) and AAP were formed mainly from IAA with formation rates up to 20 mole%. Minor formation rates of AAP (< 1 mole%) were found in sulfurized solutions of TRP, indole-3-lactic acid, and indole-3-pyruvic acid. The results showed that the formation of AAP in wine can be referred to an oxidative degradation of IAA by superoxide- and hydroxyl-radicals, which can be formed in wine after the sulfuration by cooxidation of sulfite to sulfate. After decarboxylation, pyrrole oxidation, and ring cleavage, FAP was the main volatile compound of the nonenzymatic degradation of IAA by sulfite which was quantitatively hydrolyzed to AAP. The formation of AAP and FAP was significantly lower in white wines than in ethanolic solutions spiked with IAA. However AAP formation rates of up to 5 mole% were still enough for an UTA. Due to the fact that the AAP- and UTA-formation by cooxidation of sulfite and IAA was completely blocked in red wines, it could be deduced that polyphenolic compounds, typical for red wines, have a scavenger effect on the radical oxidation of sulfite. Possibilities for an inhibition of the IAA degradation during winemaking to avoid the UTA in white wines by addition of radical scavengers like grape marc or ascorbic acid are discussed.
authors.affiliation: Landesuntersuchungsamt für das Gesundheitswesen Nordbayern, Würzburg.
authors.forename: N
authors.initials: N
authors.lastname: Christoph
authors.forename: M
authors.initials: M
authors.lastname: Gessner
authors.forename: T J
authors.initials: TJ
authors.lastname: Simat
authors.forename: K
authors.initials: K
authors.lastname: Hoenicke
mesh_terms: D000098:Acetophenones / Q000032:analysis / Q000737:chemistry; D005502:Food; D005504:Food Analysis; D005506:Food Contamination; D008401:Gas Chromatography-Mass Spectrometry; D007210:Indoleacetic Acids / Q000737:chemistry; D013649:Taste; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry*; D014920:Wine / Q000032:analysis
chemical_list: D000098:Acetophenones; D007210:Indoleacetic Acids; C015225:formylaminoacetophenone; C055495:2-aminoacetophenone; C030737:indoleacetic acid; D014364:Tryptophan