L-tryptophan reacts with naturally occurring and food-occurring phenolic aldehydes to give phenolic tetrahydro-β-carboline alkaloids: Activity as antioxidants and free radical scavengers

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 8, 2003, Pages 2168-2173

  Herraiz, Tomas ^a   Galisteo, Juan ^a   Chamorro, Cristina ^a  

^a INSTITUTO DE FERMENTACIONES INDUSTRIALES CSIC   (Spain)

Author keywords

carbolines; ABTS; Aldehydes; Alkaloids; Antioxidant; Phenolic compounds; Tetrahydro carbolines; Tryptophan

Indexed keywords

ALPHA TOCOPHEROL; ANISALDEHYDE; ANTIOXIDANT; ASCORBIC ACID; BENZALDEHYDE; ESSENTIAL AMINO ACID; PHENOL DERIVATIVE; SALICYLALDEHYDE; SCAVENGER; TROLOX C; TRYPTOLINE; TRYPTOPHAN; VANILLIN;

ANTIOXIDANT ACTIVITY; ARTICLE; COOKING; CYCLIZATION; DIASTEREOISOMER; FOOD PROCESSING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALDEHYDES; ANTIOXIDANTS; BENZALDEHYDES; CARBOLINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; FOOD ANALYSIS; FREE RADICAL SCAVENGERS; HEAT; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PHENOLS; STEREOISOMERISM; TRYPTOPHAN;

LETHRINIDAE;

EID: 0037427315     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0210066     Document Type: Article

References (34)

1. Friedman, M.; Cuq, J. L. Chemistry, nutritional value and toxicology of tryptophan in food. A review. J. Agric. Food Chem. 1988, 36, 1079-1093.
2. Herraiz, T. Analysis of the bioactive alkaloids tetrahydro-β-carboline and β-carboline in food. J. Chromatogr. A 2000, 881, 483-499.
3. Airaksinen, M. M.; Kari, I. β-carbolines, psychoactive compounds in the mammalian body. Part 2: effects. Med. Biol. 1981, 59, 190-211.
4. Braestrup, C.; Nielsen, M.; Olsen, C. E. Urinary and brain β-carboline-3-carboxylates as a potent inhibitors of brain benzodiazepine receptors. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2288-2292.
5. Buckholtz, N. S. Neurobiology of tetrahydro-β-carbolines. Life Sci. 1980, 27, 893-903.
6. Melchior, C.; Collins, M. A. The route and significance of endogenous synthesis of alkaloids in animals. In CRC Critical Reviews in Toxicology; CRC Press: Boca Rotan, FL, 1982; pp 313-356.
7. Myers, R. D. Isoquinolines, β-carbolines and alcohol drinking: Involvement of opioid and dopaminergic mechanisms. Experientia 1989, 45, 436-443.
8. Rommelspacher, H.; May, T.; Susilo, R. β-Carbolines and Tetrahydroisoquinolines: detection and function in mammals. Planta Med. 1991, 57, S85-S92.
9. Totsuka, Y.; Ushiyama, H.; Ishihara, J.; Sinha, R.; Goto, S.; Sugimura, T.; Wakabayashi, K. Quantification of the comutagenic β-carbolines, norharman and harman, in cigarette smoke condensates and cooked foods. Cancer Lett. 1999, 143, 139-143.
10. 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.
11. Sen, N. P.; Seaman, S. W.; Lau, B. P. Y.; Weber, D.; Lewis, 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.
12. Brenneman, D. E.; Page, S. W.; Schultzberg, M.; Thomas, F. S.; Zelazowski, P.; Burnet, P.; Avidor, R.; Sternberg, E. M. A decomposition product of a contaminant implicated in L-tryptophan Eosinophilia Myalgia Syndrome affects spinal cord neuronal cell death and survival through stereospecific maturation and partly interleukin-1-dependent mechanisms. J. Pharm. Exp. Ther. 1993, 266, 1029-1035.
13. Collins, M. A.; Neafsey, E. J. β-carboline analogs of N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): endogenous factors underlying idiophatic parkinsonism? Neurosci. Lett. 1985, 55, 179-183.
14. Matsubara, K.; Gonda, T.; Sawada, H.; Uezono, T.; Kobayashi, Y.; Kawamura, T.; Ohtaki, K.; Akaike, A. Endogenously occurring β-carboline induces parkinsonism in nonprimate animals: a possible causative protoxin in idiopathic Parkinson's disease. J. Neurochem. 1998, 70, 727-735.
15. Herraiz, T. Tetrahydro-β-carboline-3-carboxylic acid compounds in fish and meat: possible precursors of co-mutagenic β-carbolines norharman and harman in cooked foods. Food Addit. Contam. 2000, 17, 859-866.
16. Herraiz, T. Occurrence of tetrahydro-β-carboline-3-carboxylic acids in commercial foodstuffs. J. Agric. Food Chem. 1996, 44, 3057-3065.
17. Herraiz, T. Occurrence 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 fruit juices, fruit purees and jams. J. Agric. Food Chem. 1998, 46, 3484-3490.
18. 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.
19. Herraiz, T.; Sanchez, F. Presence of tetrahydro-β-carboline-3-carboxylic acids in foods by gas chromatography-mass spectrometry as their N-methoxycarbonyl methyl ester derivatives. J. Chromatogr. A 1997, 765, 265-277.
20. Tsuchiya, H.; Yamada, K.; Tajima, K.; Hayashi, T. Urinary excretion of tetrahydro-β-carbolines relating to ingestion of alcoholic beverages. Alcohol Alcohol. (Oxford) 1996, 31, 197-203.
21. Gutsche, B.; Herderich, M. HPLC-MS/MS profiling of tryptophan derived alkaloids in food: Identification of tetrahydro-β-carbolinedicarboxylic acids. J. Agric. Food Chem. 1997, 45, 2458-2462.
22. Herraiz, T.; Ough, C. S. Chemical and technological factors determining tetrahydro-β-carboline-3-carboxylic acid content in fermented alcoholic beverages. J. Agric. Food Chem., 1993, 41, 959-964.
23. Feron, V. J.; Til, H. P.; de Vrijer F.; Woutersen, R. A.; Cassee, F. R.; van Bladeren, P. J.; Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat. Res. 1991, 259, 363-385.
24. 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.
25. Ungemach, F.; Soerens, D.; Weber, R.; DiPierro, M.; Campos, O.; Mokry, P.; Cook, J. M.; Silverton, J. V. General method for the assignment of stereochemistry of 1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines by carbon-13-spectroscopy. J. Am. Chem. Soc. 1980, 102, 6976-6984.
26. Re, R.; Pellegrini, A.; Proteggente, A.; Pannala, M.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol. Med. 1999, 26, 1231-1237.
27. Long, L. J.; Halliwell, B. Antioxidant and prooxidant abilities of foods and beverages. Methods Enzymol. 2001, 335, 181-190.
28. Gutsche, B.; Herderich, M. High performance liquid chromatography-electrospray ionisation-tandem mass spectrometry for the analysis of 1,2,3,4-tetrahydro-β-carboline derivatives. J. Chromatogr. A 1997, 767, 101-106.
29. Halliwell, B. Food-derived antioxidants. Evaluating their importance in food and in vivo. Food Sci. Agric. Chem. 1999, 1, 67-109.
30. Huang, M.-T.; Ferraro, T. Phenolic compounds in food and cancer prevention. In Phenolic Compounds in Food and Their Effects on Health II. Antioxidants and Cancer Prevention; Huan, M.-T., Ho, C.-T., Lee, C. Y., Eds.; ACS Symposium Series 507; American Chemical Society: Washington, DC, 1992; pp 8-34.
31. Rice-Evans, C. A.; Miller, N. J. Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 1996, 24, 790-795.
32. Lin, Jen-Kun; Liang, Yu-Chih; Lin, Yu-Li; Ho, Chi-Tang. Cancer prevention properties of tea: biochemical mechanisms. ACS Symp. Ser. 2000, No. 754, 78-86.
33. Herraiz, T.; Galisteo, J. Tetrahydro-β-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay. Free Radical Res. 2002, 36, 923-928.
34. Ogawa, Y.; Adachi, J.; Tatsuno, Y. Accumulation of 1-methyl- tetrahydro-β-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. Arch. Toxicol. 1993, 67, 290-293.