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Volumn 11, Issue 2, 1999, Pages 160-165

Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline and salsolidine by amine N-methyltransferase A from bovine liver

Author keywords

Enantiomers; High performance liquid chromatography; Parkinsonism; Radioassay

Indexed keywords

CELLULOSE; HYDROXYAPATITE; ISOSALSOLINE; LIVER ENZYME; METHYLTRANSFERASE; S ADENOSYLMETHIONINE; SALSOLIDINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032917838     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:2<160::AID-CHIR13>3.0.CO;2-M     Document Type: Article
Times cited : (8)

References (44)
  • 1
    • 0018852663 scopus 로고
    • Biogenic amine-aldehyde condensation products: Tetrahydroisoquinolines and tryptolines (β-carbolines)
    • Deitrich R, Erwin V. Biogenic amine-aldehyde condensation products: tetrahydroisoquinolines and tryptolines (β-carbolines). Annu Rev Pharmacol Toxicol 1980;20:55-80.
    • (1980) Annu Rev Pharmacol Toxicol , vol.20 , pp. 55-80
    • Deitrich, R.1    Erwin, V.2
  • 2
    • 77957038402 scopus 로고
    • Mammalian alkaloids
    • Brossi A, editor. New York: Academic Press
    • Collins MA. Mammalian alkaloids. In: Brossi A, editor. The alkaloids. Vol XXI. New York: Academic Press, 1983. p 329-358.
    • (1983) The Alkaloids , vol.21 , pp. 329-358
    • Collins, M.A.1
  • 3
    • 0015926907 scopus 로고
    • Tetrahydroisoquinoline alkaloids: In vivo metabolites of L-Dopa in man
    • Sandler M, Carter SB, Hunter KR, Stern GM. Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-Dopa in man. Nature (London) 1973; 241:439-443.
    • (1973) Nature (London) , vol.241 , pp. 439-443
    • Sandler, M.1    Carter, S.B.2    Hunter, K.R.3    Stern, G.M.4
  • 5
    • 0018567695 scopus 로고
    • Dopamine-related tetrahydroisoquinolines: Significant urinary excretion by alcoholics after alcohol consumption
    • Collins MA, Nijm WP, Borge GF, Teas G, Goldfarb C. Dopamine-related tetrahydroisoquinolines: significant urinary excretion by alcoholics after alcohol consumption. Science 1979;206:1184-1186.
    • (1979) Science , vol.206 , pp. 1184-1186
    • Collins, M.A.1    Nijm, W.P.2    Borge, G.F.3    Teas, G.4    Goldfarb, C.5
  • 6
    • 0018386678 scopus 로고
    • Accumulation of a tetrahydroisoquinoline in phenylketonuria
    • Lasala JM, Coscia CJ. Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science 1979;203:283-284.
    • (1979) Science , vol.203 , pp. 283-284
    • Lasala, J.M.1    Coscia, C.J.2
  • 7
    • 0023011644 scopus 로고
    • Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline as novel endogenous amines in rat brain
    • Kohno M, Ohta S, Hirobe M. Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline as novel endogenous amines in rat brain. Biochem Biophys Res Commun 1986;140:448-454.
    • (1986) Biochem Biophys Res Commun , vol.140 , pp. 448-454
    • Kohno, M.1    Ohta, S.2    Hirobe, M.3
  • 8
    • 0023935663 scopus 로고
    • An endogenous substance of the brain, tetrahydroisoquinoline, produces Parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterin in the nigrostriatal regions
    • Nagatsu T, Yoshida M. An endogenous substance of the brain, tetrahydroisoquinoline, produces Parkinsonism in primates with decreased dopamine, tyrosine hydroxylase and biopterin in the nigrostriatal regions. Neurosci Lett 1988;87:178-182.
    • (1988) Neurosci Lett , vol.87 , pp. 178-182
    • Nagatsu, T.1    Yoshida, M.2
  • 9
    • 0021030424 scopus 로고
    • The effect of alcoholism on salsolinol and biogenic amines in human brain
    • Sjöquist B, Perdahl E, Winblad B. The effect of alcoholism on salsolinol and biogenic amines in human brain. Drug Alcohol Depend 1983; 12:15-23.
    • (1983) Drug Alcohol Depend , vol.12 , pp. 15-23
    • Sjöquist, B.1    Perdahl, E.2    Winblad, B.3
  • 11
    • 0019161050 scopus 로고
    • Analysis of salsolinol and salsoline in biological samples using deuterium-labelled internal standards and gas chromatography-mass spectrometry
    • Sjöquist B, Magnuson E. Analysis of salsolinol and salsoline in biological samples using deuterium-labelled internal standards and gas chromatography-mass spectrometry. J Chromatogr 1980;183:17-24.
    • (1980) J Chromatogr , vol.183 , pp. 17-24
    • Sjöquist, B.1    Magnuson, E.2
  • 12
    • 0030593511 scopus 로고    scopus 로고
    • A novel enzyme enantio-selectively synthesizes (R)salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl(R)salsolinol
    • Naoi M, Maruyama W, Dostert P, Kohda K, Kaiya T. A novel enzyme enantio-selectively synthesizes (R)salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl(R)salsolinol. Neurosci Lett 1996;212:183-186.
    • (1996) Neurosci Lett , vol.212 , pp. 183-186
    • Naoi, M.1    Maruyama, W.2    Dostert, P.3    Kohda, K.4    Kaiya, T.5
  • 13
    • 0000913871 scopus 로고
    • Metabolism of salsolinol by tissue cultures of some papaveraceae
    • Iwasa K, Kamigauchi M, Takao N. Metabolism of salsolinol by tissue cultures of some papaveraceae. Phytochemistry 1991;30:2973-2975.
    • (1991) Phytochemistry , vol.30 , pp. 2973-2975
    • Iwasa, K.1    Kamigauchi, M.2    Takao, N.3
  • 14
    • 0026843044 scopus 로고
    • Transformations of (±)-salsolinol into optically active O- and/or N-methylaled derivatives by several papaveraceae plants and their tissue-cultured cells
    • Iwasa K, Kamigauchi M, Takao N. Transformations of (±)-salsolinol into optically active O- and/or N-methylaled derivatives by several papaveraceae plants and their tissue-cultured cells. J Nat Prod 1992; 55:491-495.
    • (1992) J Nat Prod , vol.55 , pp. 491-495
    • Iwasa, K.1    Kamigauchi, M.2    Takao, N.3
  • 15
    • 0023003534 scopus 로고
    • Amine N-methyltransferases from rabbit liver
    • Ansher SS, Jakoby WB. Amine N-methyltransferases from rabbit liver. J Biol Chem 1986;261:3996-4001.
    • (1986) J Biol Chem , vol.261 , pp. 3996-4001
    • Ansher, S.S.1    Jakoby, W.B.2
  • 18
    • 0018909049 scopus 로고
    • Selective 7-O-methylation of salsolinol in rat brain and heart in vivo
    • Bail M, Miller S, Cohen G. Selective 7-O-methylation of salsolinol in rat brain and heart in vivo. Life Sciences 1980;26:2051-2060.
    • (1980) Life Sciences , vol.26 , pp. 2051-2060
    • Bail, M.1    Miller, S.2    Cohen, G.3
  • 19
    • 0019308119 scopus 로고
    • Confirmation of an unexpected brain O-methylation pattern for the dopamine-derived tetrahydroisoquinoline, salsolinol
    • Origitano TC, Collins MA. Confirmation of an unexpected brain O-methylation pattern for the dopamine-derived tetrahydroisoquinoline, salsolinol. Life Sciences 1980;26:2061-2065.
    • (1980) Life Sciences , vol.26 , pp. 2061-2065
    • Origitano, T.C.1    Collins, M.A.2
  • 20
    • 1842330846 scopus 로고    scopus 로고
    • O-methylation of (+)-(R)- and (-)-(S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (salsolinol) in the presence of pig brain catechol-O-methyltransferase
    • Hötzl BK, Thomas H. O-Methylation of (+)-(R)- and (-)-(S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (salsolinol) in the presence of pig brain catechol-O-methyltransferase. Chirality 1997;9: 367-372.
    • (1997) Chirality , vol.9 , pp. 367-372
    • Hötzl, B.K.1    Thomas, H.2
  • 21
    • 0018178166 scopus 로고
    • 3,4-Dimethoxyphenylethylamine excretion of normals and schizophrenics, behaviour during total fasting
    • Knoll E, Wisser H, Emrich HM. 3,4-Dimethoxyphenylethylamine excretion of normals and schizophrenics, behaviour during total fasting. Clin Chim Acta 1978;89:493-502.
    • (1978) Clin Chim Acta , vol.89 , pp. 493-502
    • Knoll, E.1    Wisser, H.2    Emrich, H.M.3
  • 22
    • 0020680904 scopus 로고
    • Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis
    • Langston JW, Ballard P, Tetrud JW, Irwin I. Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis. Science 1983;219:979-980.
    • (1983) Science , vol.219 , pp. 979-980
    • Langston, J.W.1    Ballard, P.2    Tetrud, J.W.3    Irwin, I.4
  • 23
    • 0001496694 scopus 로고
    • A primate model of Parkinsonism: Selective destruction of dopaminergic neurons in the pars compacta of the substantia nigra by N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
    • Burns RS, Chiueh CC, Markey SP, Ebert MH, Jacobowitz DM, Kopin IJ. A primate model of Parkinsonism: selective destruction of dopaminergic neurons in the pars compacta of the substantia nigra by N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Proc Natl Acad Sci USA 1983; 80:4546-4550.
    • (1983) Proc Natl Acad Sci USA , vol.80 , pp. 4546-4550
    • Burns, R.S.1    Chiueh, C.C.2    Markey, S.P.3    Ebert, M.H.4    Jacobowitz, D.M.5    Kopin, I.J.6
  • 24
    • 0021137683 scopus 로고
    • Intraneuronal generation of a pyridinium metabolite may cause drug-induced Parkinsonism
    • Markey SP, Johannessen JN, Chiueh CC, Burns RS, Herkenham MA. Intraneuronal generation of a pyridinium metabolite may cause drug-induced Parkinsonism. Nature 1984;311:464-467.
    • (1984) Nature , vol.311 , pp. 464-467
    • Markey, S.P.1    Johannessen, J.N.2    Chiueh, C.C.3    Burns, R.S.4    Herkenham, M.A.5
  • 25
    • 0022541906 scopus 로고
    • A reactive metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is formed in rat brain in vitro by type B monoamine oxidase
    • Corsini GU, Pintus S, Bocchetta A, Piccardi MP, Zompo MD. A reactive metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is formed in rat brain in vitro by type B monoamine oxidase. J Pharmacol Exp Ther 1986;238:648-652.
    • (1986) J Pharmacol Exp Ther , vol.238 , pp. 648-652
    • Corsini, G.U.1    Pintus, S.2    Bocchetta, A.3    Piccardi, M.P.4    Zompo, M.D.5
  • 26
    • 0023224837 scopus 로고
    • Biochemical events in the development of Parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
    • Singer TP, Castagnoli N Jr, Ramsay RR, Trevor AJ. Biochemical events in the development of Parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J Neurochem 1987;49:1-8.
    • (1987) J Neurochem , vol.49 , pp. 1-8
    • Singer, T.P.1    Castagnoli N., Jr.2    Ramsay, R.R.3    Trevor, A.J.4
  • 28
    • 0023697649 scopus 로고
    • Characteristics of the transport of the quaternary ammonium 1-methyl-4-phenylpyridinium by chromaffin granules
    • Darchen F, Scherman D, Desnos C, Henry J-P. Characteristics of the transport of the quaternary ammonium 1-methyl-4-phenylpyridinium by chromaffin granules. Biochem Pharmacol 1988;37:4381-4387.
    • (1988) Biochem Pharmacol , vol.37 , pp. 4381-4387
    • Darchen, F.1    Scherman, D.2    Desnos, C.3    Henry, J.-P.4
  • 29
    • 0021224694 scopus 로고
    • Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors
    • Heikkila RE, Manzino L, Cabbat FS, Duvoisin RC. Protection against the dopaminergic neurotoxicity of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine by monoamine oxidase inhibitors. Nature 1984;311: 467-469.
    • (1984) Nature , vol.311 , pp. 467-469
    • Heikkila, R.E.1    Manzino, L.2    Cabbat, F.S.3    Duvoisin, R.C.4
  • 30
    • 0021182244 scopus 로고
    • Pargyline prevents MPTP-induced Parkinsonism in primates
    • Langston JW, Irwin I, Langston EB, Forno LS. Pargyline prevents MPTP-induced Parkinsonism in primates. Science 1984;225:1480-1482.
    • (1984) Science , vol.225 , pp. 1480-1482
    • Langston, J.W.1    Irwin, I.2    Langston, E.B.3    Forno, L.S.4
  • 31
    • 0021137683 scopus 로고
    • Intraneuronal generation of a pyridinium metabolite may cause drug-induced Parkinsonism
    • Markey SP, Johannessen JN, Chiueh CC, Burns RS, Herkenham MA. Intraneuronal generation of a pyridinium metabolite may cause drug-induced Parkinsonism. Nature 1984;311:464-467.
    • (1984) Nature , vol.311 , pp. 464-467
    • Markey, S.P.1    Johannessen, J.N.2    Chiueh, C.C.3    Burns, R.S.4    Herkenham, M.A.5
  • 32
    • 0021680307 scopus 로고
    • Uptake of MPP(+) by dopamine neurons explains selectivity of Parkinsonism-inducing neurotoxin, MPTP
    • Javitch JA, Snyder SH. Uptake of MPP(+) by dopamine neurons explains selectivity of Parkinsonism-inducing neurotoxin, MPTP. Eur J Pharmacol 1984;106:455-456.
    • (1984) Eur J Pharmacol , vol.106 , pp. 455-456
    • Javitch, J.A.1    Snyder, S.H.2
  • 33
    • 0021804734 scopus 로고
    • Further insight into the mode of action of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)
    • Gessner W, Brossi A, Shen R, Abell CW. Further insight into the mode of action of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Fed Eur Biochem Soc Lett 1985;183:345-348.
    • (1985) Fed Eur Biochem Soc Lett , vol.183 , pp. 345-348
    • Gessner, W.1    Brossi, A.2    Shen, R.3    Abell, C.W.4
  • 34
    • 0021276089 scopus 로고
    • Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase
    • Chiba K, Trevor A, Castagnoli N Jr. Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem Biophys Res Commun 1984;120:574-578.
    • (1984) Biochem Biophys Res Commun , vol.120 , pp. 574-578
    • Chiba, K.1    Trevor, A.2    Castagnoli N., Jr.3
  • 35
    • 0021337873 scopus 로고
    • Selective nigral toxicity after systemic administration of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyrine (MPTP) in the squirrel monkey
    • Langston JW, Forno LS, Rebert CS, Irwin I. Selective nigral toxicity after systemic administration of 1-methyl-4-phenyl-1,2,5,6-tetrahydropyrine (MPTP) in the squirrel monkey. Brain Res 1984;292:390-394.
    • (1984) Brain Res , vol.292 , pp. 390-394
    • Langston, J.W.1    Forno, L.S.2    Rebert, C.S.3    Irwin, I.4
  • 36
    • 0022490928 scopus 로고
    • Role of N-methyltransferases in the neurotoxicity associated with the metabolites of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and other 4-substituted pyridines present in the environment
    • Ansher SS, Cadet, JL, Jakoby WB, Baker JK. Role of N-methyltransferases in the neurotoxicity associated with the metabolites of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and other 4-substituted pyridines present in the environment. Biochem Pharmacol 1986;35: 3359-3363.
    • (1986) Biochem Pharmacol , vol.35 , pp. 3359-3363
    • Ansher, S.S.1    Cadet, J.L.2    Jakoby, W.B.3    Baker, J.K.4
  • 37
    • 0024359987 scopus 로고
    • A N-methyltransferase in human brain catalyses N-methylation of 1,2,3,4-tetrahydroisoquinoline into N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of a dopaminergic neurotoxin, N-methylisoquinolinium ion
    • Naoi M, Matsuura S, Takahashi T, Nagatsu T. A N-methyltransferase in human brain catalyses N-methylation of 1,2,3,4-tetrahydroisoquinoline into N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of a dopaminergic neurotoxin, N-methylisoquinolinium ion. Biochem Biophys Res Commun 1989;161:1213-1219.
    • (1989) Biochem Biophys Res Commun , vol.161 , pp. 1213-1219
    • Naoi, M.1    Matsuura, S.2    Takahashi, T.3    Nagatsu, T.4
  • 38
    • 0025251799 scopus 로고
    • Endogenous synthesis of N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of N-methylisoquinolinium ion, in the brains of primates with Parkinsonism after systemic administration of 1,2,3,4-tetrahydroisoquinoline
    • Niwa T, Yoshizumi H, Tatematsu A, Matsuura S, Yoshida M, Kawachi M, Naoi M, Nagatsu T. Endogenous synthesis of N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of N-methylisoquinolinium ion, in the brains of primates with Parkinsonism after systemic administration of 1,2,3,4-tetrahydroisoquinoline. J Chromatogr 1990;533:145-151.
    • (1990) J Chromatogr , vol.533 , pp. 145-151
    • Niwa, T.1    Yoshizumi, H.2    Tatematsu, A.3    Matsuura, S.4    Yoshida, M.5    Kawachi, M.6    Naoi, M.7    Nagatsu, T.8
  • 39
    • 0024492782 scopus 로고
    • Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methyl-isoquinolinium ion by monoamine oxidase
    • Naoi M, Matsuura S, Parvez H, Takahashi T, Hirata Y, Minami M, Nagatsu T. Oxidation of N-methyl-1,2,3,4-tetrahydroisoquinoline into the N-methyl-isoquinolinium ion by monoamine oxidase. J Neurochem 1989;52:653-655.
    • (1989) J Neurochem , vol.52 , pp. 653-655
    • Naoi, M.1    Matsuura, S.2    Parvez, H.3    Takahashi, T.4    Hirata, Y.5    Minami, M.6    Nagatsu, T.7
  • 40
    • 0026753805 scopus 로고
    • N-methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinollne, (R)-salsolinol, in rat brains: In vivo microdialysis study
    • Maruyama W, Nakahara D, Ota M, Takahashi T, Takahashi A, Nagatsu T, Naoi M. N-Methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinollne, (R)-salsolinol, in rat brains: in vivo microdialysis study. J Neurochem 1992;59:395-400.
    • (1992) J Neurochem , vol.59 , pp. 395-400
    • Maruyama, W.1    Nakahara, D.2    Ota, M.3    Takahashi, T.4    Takahashi, A.5    Nagatsu, T.6    Naoi, M.7
  • 41
    • 0028231575 scopus 로고
    • 2-methyl-1,2,3,4-tetrahydroisoquinoline does dependently reduce the number of tyrosine hydroxylase-immunoreactive cells in the substantia nigra and locus ceruleus of C57BL/6J mice
    • Fukuda T. 2-methyl-1,2,3,4-tetrahydroisoquinoline does dependently reduce the number of tyrosine hydroxylase-immunoreactive cells in the substantia nigra and locus ceruleus of C57BL/6J mice. Brain Res 1994;639:325-328.
    • (1994) Brain Res , vol.639 , pp. 325-328
    • Fukuda, T.1
  • 42
    • 0023894885 scopus 로고
    • Presence of tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline in foods: Compounds related to Parkinson's disease
    • Makino Y, Ohta S, Tachikawa O, Hirobe M. Presence of tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline in foods: compounds related to Parkinson's disease. Life Sci 1988;43:373-378.
    • (1988) Life Sci , vol.43 , pp. 373-378
    • Makino, Y.1    Ohta, S.2    Tachikawa, O.3    Hirobe, M.4
  • 43
    • 0023698218 scopus 로고
    • Migration of tetrahydroisoquinoline, a possible Parkinsonian neurotoxin, into monkey brain from blood as proved by gas chromatography-mass spectrometry
    • Niwa T, Takeda N, Tatematsu A, Matsuura S, Yoshida M, Nagatsu T. Migration of tetrahydroisoquinoline, a possible Parkinsonian neurotoxin, into monkey brain from blood as proved by gas chromatography-mass spectrometry. J Chromatogr 1988;452:85-91.
    • (1988) J Chromatogr , vol.452 , pp. 85-91
    • Niwa, T.1    Takeda, N.2    Tatematsu, A.3    Matsuura, S.4    Yoshida, M.5    Nagatsu, T.6
  • 44
    • 0026073997 scopus 로고
    • Metabolism and penetration through blood-brain barrier of Parkinsonism-related compounds. 1,2,3,4-tetrahydroisoquinoline and 1-methyl-1,2,3,4-tetrahydroisoquinoline
    • Kikuchi K, Nagatsu Y, Makino Y, Mashino T, Ohta S, Hirobe M. Metabolism and penetration through blood-brain barrier of Parkinsonism-related compounds. 1,2,3,4-tetrahydroisoquinoline and 1-methyl-1,2,3,4-tetrahydroisoquinoline. Drug Metab Dispos 1991;19:257-262.
    • (1991) Drug Metab Dispos , vol.19 , pp. 257-262
    • Kikuchi, K.1    Nagatsu, Y.2    Makino, Y.3    Mashino, T.4    Ohta, S.5    Hirobe, M.6


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