Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases

Biochemical and Biophysical Research Communications

Volumn 451, Issue 1, 2014, Pages 42-47

  Herraiz, Tomás ^a   Galisteo, Juan ^a  

^a INSTITUTE OF FOOD SCIENCE   (Spain)

Author keywords

Alkaloids; Horseradish peroxidase; Lactoperoxidase; Myeloperoxidase; Tetrahydro carboline; Carboline

Indexed keywords

ASCORBIC ACID; BETA CARBOLINE DERIVATIVE; CARBOXYLIC ACID; CATALASE; CYTOCHROME P450; GLUTATHIONE PEROXIDASE; HEME PEROXIDASE; HYDROGEN PEROXIDE; HYDROXYLAMINE; INDOLE ALKALOID; PEROXIDASE; REACTIVE OXYGEN METABOLITE; SODIUM AZIDE; TRYPTOPHAN; UNCLASSIFIED DRUG; 1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID; 1-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID; BETA CARBOLINE; CARBOLINE DERIVATIVE; ENZYME INHIBITOR; HARMAN; HARMINE; HEME; HORSERADISH PEROXIDASE; LACTOPEROXIDASE;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; ENZYME METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; KINETICS; MASS SPECTROMETRY; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY;

ARMORACIA RUSTICANA; MAMMALIA;

ASCORBIC ACID; CARBOLINES; ENZYME INHIBITORS; HARMINE; HEME; HORSERADISH PEROXIDASE; HYDROXYLAMINE; KINETICS; LACTOPEROXIDASE; OXIDATION-REDUCTION; PEROXIDASE; PEROXIDASES; SODIUM AZIDE; TRYPTOPHAN;

EID: 84906252944     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2014.07.047     Document Type: Article

References (53)

1. H.B. Dumford Heme Peroxidases 1999 Wiley-VCH New York
2. J. Arnhold, P.G. Furtmüller, G. Regelsberger, and C. Obinger Redox properties of the couple compound I/native enzyme of myeloperoxidase and eosinophil peroxidase Eur. J. Biochem. 268 2001 5142 5148
3. S.J. Klebanoff Myeloperoxidase: friend and foe J. Leukoc. Biol. 77 2005 598 625
4. P.S. Green, A.J. Mendez, J.S. Jacob, J.R. Crowley, W. Growdon, B.T. Hyman, and J.W. Heinecke Neuronal expression of myeloperoxidase is increased in Alzheimer's disease J. Neurochem. 90 2004 724 733
5. J. Everse, and P.W. Coates Role of peroxidases in Parkinson disease: a hypothesis Free Radical Biol. Med. 38 2005 1296 1310
6. A. De Iuliis, A.P. Burlina, R. Boschetto, P. Zambenedetti, P. Arslan, and L. Galzigna Increased dopamine peroxidation in postmortem Parkinsonian brain Biochim. Biophys. Acta Gen. Subj. 1573 2002 63 67
7. P.J. O'Brien Peroxidases Chem. Biol. Interact. 129 2000 113 139
8. S. Tafazoli, and P.J. O'Brien Peroxidases: a role in the metabolism and side effects of drugs Drug Discov. Today 10 2005 617 625
9. T. Herraiz, H. Guillén, and J. Galisteo 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. 356 2007 118 123
10. T. Herraiz β-Carbolines in foods J. Gilbert, H.Z. Şenyuva, Bioactive Compounds in Foods 2008 Blackwell Publishing 199 223
11. E.S.J. Robinson, N.J. Anderson, J. Crosby, D.J. Nutt, and A.L. Hudson Endogenous β-carbolines as clonidine-displacing substances Ann. N. Y. Acad. Sci. 1009 2003 157 166
12. D. Fekkes, and W.T. Bode Occurrence and partition of the β-carboline norharman in rat organs Life Sci. 52 1993 2045 2054
13. K. Matsubara, T. Gonda, H. Sawada, T. Uezono, Y. Kobayashi, T. Kawamura, K. Ohtaki, K. Kimura, and A. Akaike Endogenously occurring β-carboline induces parkinsonism in nonprimate animals: a possible causative protoxin in idiopathic Parkinson's disease J. Neurochem. 70 1998 727 735
14. M.M. Airaksinen, and I. Kari β-Carbolines, psychoactive compounds in the mammalian body. 1. Occurrence, origin and metabolism Med. Biol. 59 1981 21 34
15. T. Herraiz Relative exposure to β-carbolines norharman and harman from foods and tobacco smoke Food Addit. Contam. 21 2004 1041 1050
16. T. Herraiz, and C. Chaparro Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors Biochem. Biophys. Res. Commun. 326 2005 378 386
17. T. Herraiz 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. 46 1998 3484 3490
18. T. Herraiz β- Carbolines as neurotoxins L. Antkiewicz-Michaluk, H. Rommelspacher, Isoquinolines and β-carbolines as neurotoxins and neuroprotectants. New vistas in ParkinsonÍs disease theraphy Current Topics in Neurotoxicity vol. 1 2012 Springer 77 103
19. R.H. Cao, W.L. Peng, Z.H. Wang, and A.L. Xu β-Carboline alkaloids: biochemical and pharmacological functions Curr. Med. Chem. 14 2007 479 500
20. C.C. Shi, S.Y. Chen, G.J. Wang, J.F. Liao, and C.F. Chen Vasorelaxant effect of harman Eur. J. Pharmacol. 390 2000 319 325
21. E.D. Cox, and J.M. Cook The Pictet-Spengler condensation - a new direction for an old reaction Chem. Rev. 95 1995 1797 1842
22. W. Jantschko, P.G. Furtmüller, M. Allegra, M.A. Livrea, C. Jakopitsch, G. Regelsberger, and C. Obinger Redox intermediates of plant and mammalian peroxidases: a comparative transient-kinetic study of their reactivity toward indole derivatives Arch. Biochem. Biophys. 398 2002 12 22
23. T. Michon, M. Chenu, N. Kellershon, M. Desmadril, and J. Gueguen Horseradish peroxidase oxidation of tyrosine-containing peptides and their subsequent polymerization: a kinetic study Biochemistry 36 1997 8504 8513
24. M. Allegra, P.G. Furtmüller, G. Regelsberger, M.L. Turco-Liveri, L. Tesoriere, M. Perretti, R.A. Livrea, and C. Obinger Mechanism of reaction of melatonin with human myeloperoxidase Biochem. Biophys. Res. Commun. 282 2001 380 386
25. J. Soubhye, I. Aldib, B. Elfving, M. Gelbcke, P.G. Furtmüller, M. Podrecca, R. Conotte, J.M. Colet, A. Rousseau, F. Reye, A. Sarakbi, M. Vanhaeyerbeek, J.M. Kauffmann, C. Obinger, J. Neve, M. Prevost, K.Z. Boudjeltia, F. Dufrasne, and P. Van Antwerpen Design, synthesis, and structure-activity relationship studies of novel 3-alkylindole derivatives as selective and highly potent myeloperoxidase inhibitors J. Med. Chem. 56 2013 3943 3958
26. W. Jantschko, P.G. Furtmüller, M. Zederbauer, K. Neugschwandtner, I. Lehner, C. Jakopitsch, J. Arnhold, and C. Obinger Exploitation of the unusual thermodynamic properties of human myeloperoxidase in inhibitor design Biochem. Pharmacol. 69 2005 1149 1157
27. H.R. Hallingback, R.R. Gabdoulline, and R.C. Wade Comparison of the binding and reactivity of plant and mammalian peroxidases to indole derivatives by computational docking Biochemistry 45 2006 2940 2950
28. A.G. Turjanski, R.E. Rosenstein, and D.A. Estrin Reactions of melatonin and related indoles with free radicals: a computational study J. Med. Chem. 41 1998 3684 3689
29. T. Herraiz, and J. Galisteo Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers J. Agric. Food Chem. 51 2003 7156 7161
30. T. Herraiz, and J. Galisteo Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay Free Radic. Res. 38 2004 323 331
31. T. Herraiz, and J. Galisteo Tetrahydro-β-carboline alkaloids that occur in foods and biological systems act as radical scavengers and antioxidants in the ABTS assay Free Radic. Res. 36 2002 923 928
32. J.M. Bobbitt, and J.P. Willis Electrochemistry of natural products. 7. Oxidative decarboxylation of some tetahydro-β-carbolinecarboxylic acids J. Org. Chem. 45 1980 1978 1984
33. B. Halliwell, and J.M.C. Gutteridge Free Radicals in Biology and Medicine 1999 Oxford University Press
34. S.E. O'Connor, and J.J. Maresh Chemistry and biology of monoterpene indole alkaloid biosynthesis Nat. Prod. Rep. 23 2006 532 547
35. S. Kumar, A. Dutta, A.K. Sinha, and J. Sen Cloning, characterization and localization of a novel basic peroxidase gene from Catharanthus roseus FEBS J. 274 2007 1290 1303
36. H.N. Matsuura, M.R. Rau, and A.G. Fett-Neto Oxidative stress and production of bioactive monoterpene indole alkaloids: biotechnological implications Biotechnol. Lett. 36 2014 191 200
37. H. Parker, A.M. Albrett, A.J. Kettle, and C.C. Winterbourn Myeloperoxidase associated with neutrophil extracellular traps is active and mediates bacterial killing in the presence of hydrogen peroxide J. Leukoc. Biol. 91 2012 369 376
38. D. Roos, and C.C. Winterbourn Immunology - Lethal weapons Science 296 2002 669 671
39. J. Arnhold, and J. Flemmig Human myeloperoxidase in innate and acquired immunity Arch. Biochem. Biophys. 500 2010 92 106
40. D.K. Choi, S. Koppula, M. Choi, and K. Suk Recent developments in the inhibitors of neuroinflammation and neurodegeneration: inflammatory oxidative enzymes as a drug target Expert Opin. Ther. Pat. 20 2010 1531 1546
41. J. Flemmig, J. Remmler, F. Rohring, and J. Arnhold (-)-Epicatechin regenerates the chlorinating activity of myeloperoxidase in vitro and in neutrophil granulocytes J. Inorg. Biochem. 130 2014 84 91
42. D.L. Lefkowitz, and S.S. Lefkowitz Microglia and myeloperoxidase: a deadly partnership in neurodegenerative disease Free Radic. Biol. Med. 45 2008 726 731
43. D.-K. Choi, S. Pennathur, C. Perier, K. Tieu, P. Teismann, D.-C. Wu, V. Jackson-Lewis, M. Vila, J.-P. Vonsattel, J.W. Heinecke, and S. Przedborski Ablation of the inflammatory enzyme myeloperoxidase mitigates features of Parkinson's disease in mice J. Neurosci. 25 2005 6594 6600
44. P. Teismann Myeloperoxidase in the neurodegenerative process of Parkinson's disease Dtsch. Med. Wochenschr. 139 2014 99 102
45. N. Stefanova, B. Georgievska, H. Eriksson, W. Poewe, and G.K. Wenning Myeloperoxidase inhibition ameliorates multiple system atrophy-like degeneration in a transgenic mouse model Neurotox. Res. 21 2012 393 404
46. D. Farzin, and N. Mansouri Antidepressant-like effect of harmane and other β-carbolines in the mouse forced swim test Eur. Neuropsychopharmacol. 16 2006 324 328
47. H. Rommelspacher, L.G. Schmidt, and T. May Plasma norharman (β-carboline) levels are elevated in chronic alcoholics Alcohol. Clin. Exp. Res. 15 1991 553 559
48. E.D. Louis, E. Rios, K.M. Pellegrino, W. Jiang, P. Factor-Litvak, and W. Zheng Higher blood harmane (1-methyl-9H-pyrido-3,4-b-indole) concentrations correlate with lower olfactory scores in essential tremor Neurotoxicology 29 2008 460 465
49. M.A. Collins Alkaloids, alcohol and Parkinson's disease Parkinsonism Relat. Disord. 8 2002 417 422
50. A. Östergren, A. Annas, K. Skog, N.G. Lindquist, and E.B. Brittebo Long term retention of neurotoxic β-carbolines in brain neuromelanin J. Neural Transm. 111 2004 141 157
51. D.A. Gearhart, M.A. Collins, J.M. Lee, and E.J. Neafsey Increased β-carboline 9N-methyltransferase activity in the frontal cortex in Parkinson's disease Neurobiol. Dis. 7 2000 201 211
52. T. Herraiz, H. Guillén, and J. Galisteo Metabolite profile resulting from the activation/inactivation of 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine and 2-methyltetrahydro-β-carboline by oxidative enzymes Biomed. Res. Int. 248608 2013
53. W. Kuhn, T. Muller, H. Grosse, and H. Rommelspacher Elevated levels of harman and norharman in cerebrospinal fluid of parkinsonian patients J. Neural Transm. 103 1996 1435 1440