Identification and occurrence of β-carboline alkaloids in raisins and inhibition of monoamine oxidase (MAO)

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 21, 2007, Pages 8534-8540

  Herraiz, Tomás ^a  

^a INSTITUTO DE FERMENTACIONES INDUSTRIALES CSIC   (Spain)

Author keywords

Carbolines; Alkaloids; Harman; Harmane; Heterocyclic amines; MAO inhibition; Monoamine oxidase; Norharman; Norharmane; Raisins; Tetrahydro carbolines

Indexed keywords

ALKALOID; CARBOLINE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR;

ARTICLE; CHEMISTRY; GRAPE;

ALKALOIDS; CARBOLINES; MONOAMINE OXIDASE INHIBITORS; VITIS;

EID: 35548939870     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0719151     Document Type: Article

References (53)

1. Kalgutkar, A. S.; Dalvie, D. K.; Castagnoli, N.; Taylor, T. J. Interactions of nitrogen-containing xenobiotics with monoamine oxidase MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors. Chem. Res. Toxicol. 2001, 14, 1139-1162.
2. Youdim, M. B. H.; Edmondson, D.; Tipton, K. F. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci. 2006, 7, 295-309.
3. Shih, J. C.; Chen, K.; Ridd, M. J. Monoamine oxidase: From genes to behavior. Ann. Rev. Neurosci. 1999, 22, 197-217.
4. Yamada, M.; Yasuhara, H. Clinical pharmacology of MAO inhibitors: Safety and future. Neurotoxicology 2004, 25, 215-221.
5. Cohen, G.; Farooqui, R.; Kesler, N. Parkinson disease: A new link between monoamine oxidase and mitochondrial electron flow. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4890-4894.
6. Hauptmann, N.; Grimsby, J.; Shih, J. C.; Cadenas, E. The metabolism of tyramine by monoamine oxidase A/B causes oxidative damage to mitochondrial DNA. Arch. Biochem. Biophys. 1996, 335, 295-304.
7. +): Identification of a metabolite of MPTP, a toxin selective to the substantia nigra. Neurosci. Lett. 1984, 48, 87-92.
8. Herraiz, T.; Guillén, H.; Arán, V. J.; Idle, J. R.; Gonzalez, F.J. Comparative aromatic hydroxylation and N-demethylation of MPTP neurotoxin and its analogs, N-methylated β-carboline and isoquinoline alkaloids, by human cytochrome P450 2D6. Toxicol. Appl. Pharmacol. 2006, 216, 387-398.
9. Herraiz, T.; Guillén, H.; Galisteo, J. N-Methyltetrahydro- β-carboline analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxin are oxidized to neurotoxic β-carbolinium cations by heme peroxidases. Biochem. Biophys. Res. Commun. 2007, 356, 118-123.
10. Billett, E. E. Monoamine oxidase (MAO) in human peripheral tissues. Neurotoxicology 2004, 25, 139-148.
11. Yan, Z. Y.; Caldwell, G. W.; Zhao, B. Y.; Reitz, A. B. A high-throughput monoamine oxidase inhibition assay using liquid chromatography with tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2004, 18, 834-840.
12. Lee, M.-H.; Lin, R.-D.; Shen, L.-Y.; Yang, L.-L.; Yen, K.-Y.; Hou, W.-C. Monoamine oxidase B and free radical scavenging activities of natural flavonoids in Melastoma candidum D. Don. J. Agric. Food Chem. 2001, 49, 5551-5555.
13. Fowler, J. S.; Volkow, N. D.; Wang, G. J.; Pappas, N.; Logan, J.; MacGregor, R.; Alexoff, D.; Shea, C.; Schlyer, D.; Wolf, A. P.; Warner, D.; Zezulkova, I.; Cilento, R. Inhibition of monoamine oxidase B in the brains of smokers. Nature 1996, 379, 733-736.
14. Fowler, J. S.; Volkow, N. D.; Wang, G. J.; Pappas, N.; Logan, J.; Shea, C.; Alexoff, D.; MacGregor, R. R.; Schlyer, D. J.; Zezulkova, I.; Wolf, A. P. Brain monoamine oxidase A inhibition in cigarette smokers. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14065-14069.
15. Herraiz, T.; Chaparro, C. Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors. Biochem. Biophys. Res. Commun. 2005, 326, 378-386.
16. Castagnoli, K.; Murugesan, T. Tobacco leaf, smoke and smoking, MAO inhibitors, Parkinson's disease and neuroprotection; Are there links? Neurotoxicology 2004, 25, 279-291.
17. Herraiz, T. Relative exposure to β-carbolines norharman and harman from foods and tobacco smoke. Food Addit. Contam. 2004, 21, 1041-1050.
18. Herraiz, T.; Chaparro, C. Human monoamine oxidase enzyme inhibition by coffee and β-carbolines norharman and harman isolated from coffee. Life Sci. 2006, 78, 795-802.
19. Hernan, M. A.; Takkouche, B.; Caamano-Isorna, F.; Gestal-Otero, J. J. A meta-analysis of coffee drinking, cigarette smoking, and the risk of Parkinson's disease. Ann. Neurol. 2002, 52, 276-284.
20. Airaksinen, M. M.; Kari, I. β-Carbolines, psychoactive compounds in the mammalian body. 2. Effects. Med. Biol. 1981, 59, 190-211.
21. Baum, S. S.; Hill, R.; Rommelspacher, H. Harman-induced changes of extracellular concentrations of neurotransmitters in the nucleus accumbens of rats. Eur. J. Pharmacol. 1996, 314, 75-82.
22. Husbands, S. M.; Glennon, R. A.; Gorgerat, S.; Gough, R.; Tyacke, R.; Crosby, J.; Nutt, D. J.; Lewis, J. W.; Hudson, A.L. β-Carboline binding to imidazoline receptors. Drug Alcohol Depend. 2001, 64, 203-208.
23. Kawanishi, K.; Eguchi, N.; Hayashi, T.; Hashimoto, Y. Relationship between occurrence of tremor/convulsion and level of β-carbolines in the brain after administration of β-carbolines into mice. Pharmacol. Biochem. Behav. 1994, 47, 689-699.
24. 3-β- carboline) in the rat brain. Eur. J. Pharmacol. 1988, 147, 163-171.
25. Yu, A. M.; Idle, J. R.; Herraiz, T.; Küpfer, A.; Gonzalez, F. J. Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. Pharmacogenetics 2003, 13, 307-319.
26. Ergene, E.; Schoener, E. P. Effects of harmane (1-methyl-β- carboline) on neurons in the nucleus accumbens of the rat. Pharmacol. Biochem. Behav. 1993, 44, 951-957.
27. Miralles, A.; Esteban, S.; Sastre-Coll, A.; Moranta, D.; Asensio, V. J.; Garcia-Sevilla, J. A. High-affinity binding of β-carbolines to imidazoline I-2B receptors and MAO-A in rat tissues: Norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain. Eur. J. Pharmacol. 2005, 518, 234-242.
28. Östergren, A.; Annas, A.; Skog, K.; Lindquist, N. G.; Brittebo, E. B. Long term retention of neurotoxic β-carbolines in brain neuromelanin. J. Neural. Transm. 2004, 111, 141-157.
29. Parker, C. A.; Anderson, N. J.; Robinson, E. S. J.; Price, R.; Tyacke, R. J.; Husbands, S. M.; Dillon, M. P.; Eglen, R. M.; Hudson, A. L.; Nutt, D. J.; Crump, M. P.; Crosby, J. Harmane and harmalan are bioactive components of classical clonidine-displacing substance. Biochemistry 2004, 43, 16385-16392.
30. 3-harmane, an endogenous β-carboline, in rat brain. Neuropharmacology 2006, 50, 269-276.
31. Herraiz, T. Analysis of the bioactive alkaloids tetrahydro-β- carboline and β-carboline in food. J. Chromatogr. A 2000, 881, 483-499.
32. Herraiz, T. Tetrahydro-β-carboline bioactive alkaloids in beverages and foods. ACS Symp. Ser. 2004, 871, 405-426.
33. Herraiz, T. Occurrence of tetrahydro-β-carboline-3-carboxylic acids in commercial foodstuffs. J. Agric. Food Chem. 1996, 44, 3057-3065.
34. 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, purees, and jams. J. Agric. Food Chem. 1998, 46, 3484-3490.
35. Herraiz, T. Identification and occurrence of the bioactive β-carbolines norharman and harman in coffee brews. Food Addit. Contam. 2002, 19, 748-754.
36. Herraiz, T.; Chaparro, C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by β-carboline alkaloids occurring in foods and plants. J. Chromatogr. A 2006, 1120, 237-243.
37. 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.
38. Herraiz, T.; Galisteo, J. Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. J. Agric. Food Chem. 2003, 51, 7156-7161.
39. Diem, S.; Gutsche, B.; Herderich, M. Degradation of tetrahydro-β- carbolines in the presence of nitrite: HPLC-MS analysis of the reaction products. J. Agric. Food Chem. 2001, 49, 5993-5998.
40. 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.
41. 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.
42. Herraiz, T. 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid and 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in fruits. J. Agric. Food Chem. 1999, 47, 4883-4887.
43. Airaksinen, M. M.; Kari, I. β-Carbolines, psychoactive compounds in the mammalian body. 1. Occurrence, origin and metabolism. Med. Biol. 1981, 59, 21-34.
44. Fekkes, D.; Bode, W. T. Occurrence and partition of the β-carboline norharman in rat organs. Life Sci. 1993, 52, 2045-2054.
45. Matsubara, K.; Gonda, T.; Sawada, H.; Uezono, T.; Kobayashi, Y.; Kawamura, T.; Ohtaki, K.; Kimura, 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.
46. Herraiz, T.; Papavergou, E. Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-β-carbolines in commercial sausages. J. Agric. Food Chem. 2004, 52, 2652-2658.
47. 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.
48. Aricioglu, F.; Altunbas, H. Harmane induces anxiolysis and antidepressant-like effects in rats. Ann. N.Y. Acad. Sci. 2003, 1009, 196-200.
49. Youdim, M. B. H.; Weinstock, M. Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation. Neurotoxicology 2004, 25, 243-250.
50. Heikkila, R. E.; Manzino, L.; Cabbat, F. S.; Duvoisin, R. C. Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6- tetrahydropyridine by monoamine oxidase inhibitors. Nature 1984, 311, 467-469.
51. Spijkerman, R.; van den Eijnden, R.; van de Mheen, D.; Bongers, I.; Fekkes, D. The impact of smoking and drinking on plasma levels of norharman. Eur. Neuropsychopharmacol. 2002, 12, 61-71.
52. +. Neurosci. Res. 2002, 44, 255-265.
53. Collins, M. A.; Neafsey, E. J. β-Carboline analogs of N-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP). Endogenous factors underlying idiopathic Parkinsonism. Neurosci. Lett. 1985, 55, 179-184.