Comparison of the antioxidant activity of melatonin and pinoline in vitro

Journal of Pineal Research

Volumn 24, Issue 2, 1998, Pages 96-101

  Pähkla, Rein ^a   Zilmer, Mihkel ^a   Kullisaar, Tiiu ^a   Rägo, Lembit ^a  

^a UNIVERSITY OF TARTU   (Estonia)

Author keywords

6 methoxy tetrahydro beta carboline; Antioxidant; Hydroxyl radical; Lipid peroxidation; Melatonin; Pinoline

Indexed keywords

6 METHOXYTRYPTOLINE; AMITRIPTYLINE; ANTIDEPRESSANT AGENT; ANTIOXIDANT; IMIPRAMINE; MELATONIN; PINOLINE; TRICYCLIC ANTIDEPRESSANT AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DEPRESSION; INTRAPERITONEAL DRUG ADMINISTRATION; LIPID PEROXIDATION; MOUSE; NEUROENDOCRINOLOGY; NONHUMAN; PINEAL BODY; PSYCHOPHARMACOLOGY; STRUCTURE ACTIVITY RELATION;

ALPHA-LINOLENIC ACID; ANTIOXIDANTS; CARBOLINES; DOSE-RESPONSE RELATIONSHIP, DRUG; FREE RADICAL SCAVENGERS; HYDROXYL RADICAL; LIPID PEROXIDATION; MELATONIN;

EID: 0031981238     PISSN: 07423098     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1600-079X.1998.tb00373.x     Document Type: Article

References (42)

1. AIRAKSINEN, M.M., J.C. CALLAWAY, P. NYKVIST, L. RÄGO, E. KARI, J. GYNTHER (1993) Binding sites for [3H]pinoline. In: Melatonin and the Pineal Gland: From Basic Science to Clinical Application. Y. Touitou, J. Arendt, P. Pévet, eds. Elsevier Science Publishers, Amsterdam, pp. 83-86.
2. AIRAKSINEN, M.M., B.T. Ho, R. AN, D. TAYLOR (1978) Major pharmacological effects of 6-methoxytetrahydro-β-carboline, a drug elevating the tissue 5-hydroxytryptamine level. Arzneim-Forsch. Drug Res. 28:42-46.
3. BARKER, S.A., R.E. HARRISON, J.A. MONTI, G.B. BROWN, S.T. CHRISTIAN (1981) Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland. Biochem. Pharmacol. 30:9-17.
4. BARRETO, J.C., G.S. SMITH, N.H.P. STROBEL, P.A. MCQUILLIN, T.A. MILLER (1995) Terephthalic acid: a dosimeter for the detection of hydroxyl radicals in vitro. Life Sci. 56:PL89-96.
5. BOSIN, T R, B. HOLMSTEDT, A. LUNDMAN, O. BECK (1983) Presence of formaldehyde in biological media and organic solvents. Artifactual formation of tetrahydro-β-carbolines. Anal. Biochem. 128:287-293.
6. CALLAWAY, J.C., J. GYNTHER, A. Poso, J. VEPSALAINEN, M.M. AIRAKSINEN (1994) The Pictet-Spengler reaction and biogenic tryptamines: Formation of tetrahydro-β-carbolines at physiological pH. J. Heterocyclic Chem. 31:431-435.
7. CHEN, L.D., D. MELCHIORRI, E. SEWERYNEK, R.J. REITER (1995) Retinal lipid peroxidation in vitro is inhibited by melatonin. Neurosci. Res. Commun. 17:151-158.
8. DANIELS, W.M.U., S.J. VAN RENSBURG, J.M. VAN ZYL, B.J. VAN DER WALT, J.J.F. TALJAARD (1996) Free radical scavenging effects of melatonin and serotonin: possible mechanism. NeuroReport 7:1593-1596.
9. FAULL, K.F., R.B. HOLMAN, G.R. ELLIOTT, J.D. BARCHAS (1992) Tryptolines - artifact or reality - a new method of analysis using GC MS. In: Beta-carbolines and Tetrahydroisoquinolines: Progress in Clinical and Biological Research, Vol. 90. F. Bloom, J. Barchas, M. Sandler, E. Usdin, eds. Alan R. Liss, Inc., New York, pp. 135-154.
10. HARDELAND, R., R.J. REITER, B. POEGGLER, D-X. TAN (1993) The significance of metabolism of the neurohormone melatonin: Antioxidative protection and formation of bioactive substances. Neurosci. Biobehav. Rev. 17:347-357.
11. KARI, I. (1981) 6-Methoxy-1,2,3,4-tetrahydro-β-carboline in pineal gland of chicken and cock. FEBS Lett. 127:277-280.
12. KARI, I., M.M. AIRAKSINEN, J. GYNTHER, A. HUHTIKANGAS (1983) Mass spectrometric identification of 6-methoxy-1,2,3,4-tetrahydro-β-carboline in pineal gland. In: Recent Developments in Mass Spectrometry in Biochemistry, Medicine and Environmental Research, vol. 8. Frigerio A, ed. Elsevier, Amsterdam. pp. 19-24.
13. KAWASHIMA, Y., A. HORIGUCHI, M. TAGUCHI, Y. TUYUKI, Y. KARASAWA, H. ARAKI, K. HATAYAMA (1995) Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydro-β-carboline derivatives. Chem. Pharmacol. Bull. 43:783-787.
14. 3H]imipramine recognition site. Eur. J. Pharmacol. 102:379-380.
15. LANGER, S.Z., A.M. GALZIN, C.R. LEE, H. SCHOEMAKER (1986) Antidepressant-binding sites in brain and platelets. Ciba Found. Symp. 123:3-29.
16. LEINO, M., I. KARI, M.M. AIRAKSINEN, J. GYNTHER (1983) 6-Methoxy-tetrahydro-β-carboline in the retinae of rabbits and pigs. Exp. Eye Res. 36:135-138.
17. LEINO, M. (1984) 6-Methoxy-tetrahydro-β-carboline and melatonin in the human retina. Exp. Eye Res. 38:325-330.
18. MARSHALL, K.-A., R.J. REITER, B. POEGGELER, O.I. ARUOMA, B. HALLIWELL (1996) Evaluation of the antioxidant activity of melatonin in vitro. Free Rad. Biol. Med. 21:307-315.
19. MATUSZAK, Z., K.J. RESZKA, C.F. CHIGNELL (1997) Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations. Free Rad. Biol. Med. 23:367-372.
20. MCISAAC, W.M., D. TAYLOR, K.E. WALKER, B.T. HO (1972) 6-Methoxy-1,2,3,4-tetrahydro-β-carboline: A serotonin elevator. J. Neurochem. 19:1203-1206.
21. MELCHIORRI, D., R.J. REITER, E. SEWERYNEK, L.D. CHEN, G. NISTICO (1995) Melatonin reduces kainate-induced lipid peroxidation in homogenates of different brain regions. FASEB J. 9:1205-1210.
22. MENENDEZ-PELAEZ, A., B. POEGGELER, R.J. REITER, L.R. BARLOW-WALDEN, M.I. PABLOS, D.X. TAN (1993) Nuclear localization of melatonin in different mammalian tissues: Immunological and radioimmunoassay evidence. J. Cell. Biochem. 53:373-382.
23. MORTON, D.J., B. POTGEITER (1982) Relationships between methoxyindoles and hydroxyindoles formed from 5-hydroxytryptamine in rat pineal gland. J. Endocrinol. 95:253-256.
24. OHKAWA, H., N. OHISHI, K. YAGI (1979) Assay for lipid peroxidation in animal tissues by thiobarbituric acid reaction. Anal. Biochem. 95:351-358.
25. 3H]pinoline binding sites in mouse tissues. Methods Find. Exp.Clin. Pharmacol. 18:359-366.
26. PÄHKLA, R., J. HARRO, L. RÄGO (1996b) Behavioural effects of pinoline in the rat forced swimming, open field and elevated plus-maze tests. Pharmacol. Res. 34:73-78.
27. PÄHKLA, R., M. ZILMER, T. KULLISAAR, L. RÄGO (1997a) Antioxidative capacity of pinoline in three in vitro assay systems. Pharmacol. Toxicol. 80 Suppl. 1: Abstr. 71.
28. 3H]citalopram. Pharmacol. Toxicol. 80:122-126.
29. PIERI, C., M. MARRA, F. MORONI, R. RECCHIONI, F. MARCHESELLI (1994) Melatonin: A peroxyl radical scavenger more effective than vitamin E. Life Sci. 55:271-276.
30. PIERI, C., F. MORONI, M. MARRA, F. MARCHESELLI, R. RECCHIONI (1995) Melatonin as an efficient antioxidant. Arch. Gerontol. Geriatr. 20:159-165.
31. POEGGELER, B., R.J. REITER, R. HARDELAND, E. SEWERYNEK, D. MELCHIORRI, L.R. BARLOW-WALDEN (1995) Melatonin, a mediator of electron transfer and repair actions, acts synergistically with the chain-breaking antioxidants ascorbate, trolox and glutathione. Neuroendocrinol. Lett. 17:87-92.
32. REITER, R. J. (1997) Antioxidant actions of melatonin. Adv. Pharmacol. 38:103-117.
33. REITER, R.J., D-X. TAN, B. POEGGELER, A. MENENDEZ-PELAEZ, L-D. CHEN, S. SAARELA (1994) Melatonin as a free radical scavenger: implications for aging and age-related diseases. Ann. N. Y. Acad. Sci. 719:1-12.
34. REITER, R. J., M.I. PABLOS, T.T. AGAPITO, J.M. GUERRERO (1996) Melatonin in the context of free radical theory of aging. Ann. N. Y. Acad. Sci. 786:362-378.
35. RIMÓN, R., M.M. AIRAKSINEN, I. KARI, J. GYNTHER, E. VENÄLÄINEN, L. HEIKKILÄ, J. RYYPPO, J. PALO (1984) Pinoline, a β-carboline derivative in the serum and cerebrospinal fluid of patients with schizophrenia. Ann. Clin. Res. 16:171-175.
36. SCAIANO, J.C. (1995) Exploratory laser flash photolysis study of free radical reactions and magnetic field effects in melatonin chemistry. J. Pineal Res. 19:189-195.
37. SHOEMAKER, D.W., J.T. CUMMINS, T.G. BIDDER (1978) β-Carbolines in rat arcuate nucleus. Neuroscience 3:233-239.
38. STARKOPF, J., K. ZILMER, T. VIHALEMM, T. KULLISAAR, M. ZILMER, J. SAMARÜTEL (1995) Time course study of oxidative stress during open heart surgery. Scand. J. Thoracic Cardiovasc. Surg. 29:181-186.
39. TAN, D-X., L-D. CHEN, B. POEGGELER, L.C. MANCHESTER, R.J. REITER (1993) Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocrine J. 1:57-60.
40. TANG, L., R.J. REITER, Z.R. LI, G.G. ORTIZ, B.P. Yu, J.J. GARCIA (1997) Melatonin reduces the increase in 8-hydroxydeoxyguanosine levels in the brain and liver of kainic acid-treated rats. Molec. Cell. Biochem., in press.
41. TOBE, A., Y. YOSHIDA, H. IKOMA, S. TONOMURA, R. KIKUMOTO (1981) Pharmacological evaluation of 2-(4-methylaminobutoxy)diphenylmethane hydrochloride (MCI-2016), a new psychotropic drug with antidepressant activity. Arzneimittel-Forschung 31:1278-1285.
42. TSE, S.Y., I.T. MAK, B.F. DICKENS (1991) Antioxidative properties of harmane and beta-carboline alkaloids. Biochem. Pharmacol. 42:459-464.