HPLC-MS/MS Profiling of Tryptophan-Derived Alkaloids in Food: Identification of Tetrahydro-β-carbolinedicarboxylic Acids

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 7, 1997, Pages 2458-2462

  Gutsche, B ^a   Herderich, M ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Electrospray ionization; Neutral loss scanning; Tandem mass spectrometry; Tetrahydro carboline

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0001630515     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf960952h     Document Type: Article

References (19)

1. Adachi, J.; Mizoi, Y.; Naito, T.; Ogawa, Y.; Uetani, Y.; Ninomiya, I. Identification of tetrahydro-β-carboline-3-carboxylic acid in foodstuffs, human urine and human milk. J. Nutr. 1991, 121, 646-652.
2. Arai, S.; Abe, M.; Yamashita, M.; Kato, H.; Fujimaki, M. Applying proteolytic enzymes on soybean. Agric. Biol. Chem. 1971, 35, 552-559.
3. 6. Synthesis of the corresponding β-tetrahydrocarbolines. J. Agric. Food Chem. 1994, 42, 2372-2375.
4. Bailey, P. D.; Hollinshead, S. P.; McLay, N. R.; Morgan, K.; Palmer, S. J.; Prince, S. N.; Reynolds, C. D.; Wood, S. D. Diastereo- and enantioselectivity in the Pictet-Spengler reaction. J. Chem. Soc., Perkin Trans. 1 1993, 431-439.
5. Bosin, T. R.; Krogh, S.; Mais, D. Identification and quantitation of 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in beer and wine. J. Agric. Food Chem. 1986, 34, 843-847.
6. Cox, E. D.; Cook, J. M. The Pictet-Spengler condensation: A new direction for an old reaction. Chem. Rev. 1995, 95, 1797-1842.
7. Gutsche, B.; Herderich, M. High performance liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) for the analysis of 1,2,3,4-tetrahydro-β-carboline derivatives. J. Chromatogr. A 1997, 767, 101-106.
8. Harvey, D. G., Miller, E. J., Robsen, W. The Adamkiewicz, Hopkins and Cole, and Rosenheim tests for Tryptophan. J. Chem. Soc. 1941, 153-158.
9. Herraiz, T. Occurrence of Tetrahydro-β-carboline-3-carboxylic acids in commercial foodstuffs. J. Agric. Food Chem. 1996, 44, 3057-3065.
10. Herraiz, T.; Huang, Z.; Ough, C. S. 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in wines. J. Agric. Food Chem. 1993, 41, 455-459.
11. Jacobs, W. A.; Craig, L. C. The ergot alkaloids: The synthesis of 4-carboline carbonic acids. J. Biol. Chem. 1936, 113, 759-765.
12. McKenna, D. J.; Towers, G. H. N. Biochemistry and pharmacology of tryptamines and β-carbolines: A Minireview. J. Psychoact. Drugs 1984, 16, 347-358.
13. Papavergou, E.; Clifford, M. N. Tetrahydro-β-carbolinecarboxylic acids in smoked foods. Food Addit. Contam. 1992, 9, 83-95.
14. Rommelspacher, H.; Damm, H.; Strauss, S.; Schmidt, G. Ethanol induces an increase of harman in the brain and urine of rats. Naunyn-Schmiedeberg's Arch. Pharmacol. 1984, 327, 107-113.
15. Rommelspacher, H.; May, T.; Salewski, B. Harman (1-methyl-β-carboline) is a natural inhibitor of monoamine oxidase type A in rats. Eur. J. Pharmacol. 1994, 252, 51-59.
16. Sen, N. P.; Seaman, S. W.; Lau, P. P.-Y.; Weber, D. Determination and occurrence of various tetrahydro-β-carboline-3-carboxylic acids and the corresponding N-nitroso compounds in foods and alcoholic beverages. Food Chem. 1995, 54, 327-337.
17. Spies, C. D.; Rommelspacher, H.; Schnapper, C.; Muller, C.; Marks, C.; Berger, G.; Conrad, C.; Blum, S.; Specht, M.; Hannemann, L.; Striebel, H. W.; Schaffartzik, W. β-Carbolines in chronic alcoholics undergoing elective tumor resection. Alcoholism-Clin. Exp. Res. 1995, 19, 969-976.
18. Wakabayashi, K.; Ochiai, M.; Saito, H.; Tsuda, M.; Suwa, Y.; Nagao, M.; Sugimura, T. Presence of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 2912-2916.
19. 4: A new synthetic approach to isoquinoline- and indole-alkaloids. Tetrahedron Lett. 1969, 36, 3105-3108.