Reinvestigation of the chemical structure of bitter-tasting quinizolate and homoquinizolate and studies on their maillard-type formation pathways using suitable 13C-labeling experiments

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 21, 2002, Pages 6027-6036

  Frank, Oliver ^a   Hofmann, Thomas ^a  

^a DEUTSCHE FORSCHUNGSANSTALT FÜR LEBENSMITTELCHEMIE   (Germany)

Author keywords

13C labeling; Bitter taste; Bond labeling; CAMOLA; Carbon module labeling; Homoquinizolate; Maillard reaction; Quinizolate; Taste compounds

Indexed keywords

7 (2 FURYLMETHYL) 2 (2 FURYLMETHYLIDENE) 3 (HYDROXYMETHYL) 1 OXO 2,3 DIHYDRO 1H INDOLIZINIUM 6 OLATE; 7 (2 FURYLMETHYL) 2 (2 FURYLMETHYLIDENE) 3,8 BIS(HYDROXYMETHYL) 1 OXO 2,3 DIHYDRO 1H INDOLIZINIUM 6 OLATE; CARBON 13; HOMOQUINIZOLATE; INDOLIZINE DERIVATIVE; QUINIZOLATE; UNCLASSIFIED DRUG;

ARTICLE; BITTER TASTE; CHEMICAL STRUCTURE; GLYCATION; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; TASTE;

CARBON ISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FURANS; HEAT; INDOLES; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; MAILLARD REACTION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; QUINOLIZINES; TASTE;

EID: 0037048755     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020473k     Document Type: Article

References (21)

1. Schieberle, P.; Grosch, W. Potent odorants of the wheat crumb. Differences to the crust and effect of a longer dough fermentation. Z. Lebensm. Unters. Forsch. 1991, 192, 130-135.
2. Cerny, M.; Grosch, W. Evaluation of potent odorants in roasted beef by aroma extract dilution analysis. Z. Lebensm. Unters. Forsch. 1992, 194, 322-325.
3. Fickert, B.; Schieberle, P. Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses. Food 1998, 42, 371-375.
4. Schieberle, P.; Pfnuer, P. In Flavor Chemistry. Thirty Years of Progress; Teranishi R., Wick, E. L., Hornstein, I., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; pp 147-153.
5. Pickenhagen, W.; Dietrich, P.; Keil, N.; Polonsky, J.; Nouaille, F.; Lederer, E. Identification of the bitter principle of cacoa. Helv. Chim. Acta 1975, 58, 1078.
6. Papst, H. M. E.; Ledl, F.; Belitz, H.-D. Bitter tasting compounds in heated mixtures of sucrose, maltose and L-proline. Z. Lebensm. Unters. Forsch. 1985, 181, 386-390 (in German).
7. Tressl, R.; Helak, B.; Spengler, K.; Schröder, A.; Rewicki, D. Cyclo[b]azepine derivatives-novel proline-specific Maillard reaction products. Liebigs Ann. Chem. 1985, 2017-2027 (in German).
8. Shima, K.; Yamada, N.; Suzuki, E.-I.; Harada, T. Novel brothy taste modifier isolated from beef broth. J. Agric. Food Chem. 1998, 46, 1465-1468.
9. Hofmann, T. Influence of L-cysteine on the formation of bitter-tasting aminohexose reductones from glucose and L-proline: Identification of a novel furo[2,3-b]thiazine. J. Agric. Food Chem. 1999, 47, 4763-4768.
10. Frank, O.; Ottinger, H.; Hofmann, T. Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. J. Agric. Food Chem. 2001, 49, 231-238.
11. Ottinger, H.; Bareth, A.; Hofmann, T. Characterization of natural "cooling" compounds formed from glucose and L-proline in dark malt by application of taste dilution analysis. J. Agric. Food Chem. 2001, 49, 1336-1344.
12. Frank, O.; Jezussek, M.; Hofmann, T. Identification of novel 1H,4H-quinolizinium-7-olate chromophores by application of colour dilution analysis and high-speed countercurrent chromatography on thermally browned pentose/L-alanine solutions. Eur. Food Res. Technol. 2001, 213, 1-7.
13. Hofmann, T.; Schieberle, P. Quantitative model studies on the effectivity of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol. J. Agric. Food Chem. 1998, 46, 235-241.
14. Hofmann, T.; Schieberle, P. Studies on the formation and stability of the roast-flavor compound 2-acetyl-2-thiazoline. J. Agric. Food Chem. 1995, 43, 2946-2950.
15. 13C-labeling experiments. Carbohydr. Res. 1998, 313, 215-224.
16. Frank, O.; Heuberger, S.; Hofmann, T. Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids. J. Agric. Food Chem. 2001, 49, 1595-1600.
17. 13C-NMR spectroscopy for the elucidation of the formation pathway leading to a red colored 1H-pyrrol-3(2H)-one during Maillard reaction of furan-2-carboxaldehyde and L-alanine. J. Agric. Food Chem. 1998, 46, 941-945.
18. Bacher, A.; Rieder, Ch.; Eichinger, D.; Arigoni, D.; Fuchs, G.; Eisenreich, W. Elucidation of novel biosynthetic pathways and metabolite flux patterns by retrobiosynthetic NMR analysis. FEMS Microbiol. Rev. 1999, 22, 567-598.
19. Hofmann, T. Quantitative studies on the role of browning precursors in the Maillard reaction of pentoses and hexoses with L-alanine. Eur. Food Res. Technol. 1999, 209, 113-121.
20. Ledl, F.; Schleicher, E. The Maillard reaction in foods and in the human body-new results of the chemistry, biochemistry and medicine. Angew. Chem. 1990, 102, 597-734 (in German).
21. Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2-methyl-3(2H)-furanone and of α-dicarbonyl compounds in reaction mixtures of hexoses with different amines. Z. Lebensm. Unters. Forsch. 1992, 194, 222-228.