Summary
Urinary salsolinol output had been shown to be lower in Parkinsonian patients than in controls and to increase largely after L-dopa therapy. It had also been established that the R enantiomer of salsolinol is either the predominant or the sole enantiomer present in the urine of healthy subjects.
When Madopar was administered to Parkinsonians, the enantiomeric composition of urinary salsolinol showed an S/R ratio around 1. Considering brain and plasma concentrations in dopamine, acetaldehyde and pyruvate, it is suggested that, under physiological conditions, urinary salsolinol should have a central origin in humans. Conversely, urinary salsolinol in Madopar-treated Parkinsonian patients might be predominantly formed at the periphery.
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References
Brossi A (1982) Mammalian TIQ's: products of condensation with aldehydes or pyruvic acids? Prog Clin Biol Res 90: 123–133
Claustre J, Serusclat P, Peyrin L (1983) Glucuronide and sulfate catecholamine conjugates in rat and human plasma. J Neural Transm 56: 265–278
Collins MA (1985) Alkaloids condensation products as biochemical indicators in alcoholism. In: Chang N, Chao H (eds) Early identification of alcohol abuse. (NIAAA monography, vol 17, pp 255–267)
Collins MA, Cheng BY (1988) Oxidative decarboxylation of salsolinol-1-carboxylic acid to 1,2-dehydrosalsolinol: evidence for exclusive catalysis by particulate factors in rat kidney. Arch Biochem Biophys 263: 86–95
Collins MA, Dahl K, Nijm WP, Major LF (1982) Evidence for homologous families of dopamine and serotonin condensation products in cerebrospinal fluids from monkeys. Soc Neurosci Abstr 8: 277
Dannecker JR, Shaskan EG, Philips M (1981) A new highly sensitive assay for breath acetaldehyde: detection of endogenous levels in humans. Anal Biochem 114: 1–7
Da Prada M, Zürcher G (1976) Simultaneous radioenzymatic determination of plasma and tissue adrenaline, noradrenaline and dopamine within the femtomole range. Life Sci 19: 1161–1174
Dordain G, Dostert P, Strolin Benedetti M, Rovei V (1984) Tetrahydroisoquinoline derivatives and Parkinsonism. In: Tipton KF, Dostert P, Strolin Benedetti M (eds) Monoamine oxidase and disease. Prospects for therapy with reversible inhibitors. Academic Press, London, pp 417–426
Dostert P, Strolin Benedetti M, Dedieu M (1987a) Is Salsolinol as a racemic mixture in human urine or does an enantiomer predominates? Pharmacol Toxicol 60 [Suppl 1]: 12
Dostert P, Strolin Benedetti M, Dedieu M (1987b) Ratio of enantiomers of Salsolinol in human urine. Pharmacol Toxicol 60 [Suppl 1]: 13
Dostert P, Strolin Benedetti M, Dordain G (1988) Dopamine-derived alkaloids in alcoholism and in Parkinson's and Huntington's diseases. J Neural Transm 74: 61–74
Elchisak MA (1983) Distribution of free and conjugated dopamine in human caudate nucleus, hypothalamus, and kidney. J Neurochem 41: 893–896
Gal J, Desai DM, Bloedow DC (1986) (S)-1-(naphthyl)ethyl isothiocyanate: a new chiral derivatizing agent in liquid chromatography. In: 10th international symposium on column liquid chromatography, San Francisco, May 18–23 (book of abstracts, p 406)
Gottfries CG, Kjällquist A, Ponten U, Ross BE, Sundbärg G (1974) Cerebrospinal fluid pH and monoamine and glucolytic metabolites in Alzheimer's disease. Br J Psychiat 124: 280–287
Hansen JL, Freier EF (1978) Direct assays of lactate, pyruvate, β-hydroxybutyrate, and acetoacetate with a centrifugal analyser. Clin Chem 24: 475–479
Hardy JA, Wester P, Backstrom I, Gottfries J, Oreland L, Stenstrom A, Windblad B (1987) The regional distribution of dopamine and serotonine uptake and transmitter concentrations in the human brain. Neurochem Int 10: 445–450
Hornykiewicz O, Kish SJ (1986) Biochemical pathophysiology of Parkinson's disease. Adv Neurol 45: 19–34
Johnson GA, Baker CA, Smith RT (1980) Radioenzymatic assay of sulfate conjugates of catecholamines and dopa in plasma. Life Sci 26: 1591–1598
Kapadia GJ, Subba Rao G, Leete E, Fayez MBE, Vaishnav YN, Fales HM (1970) On the origin of carbon 1 in tetrahydroisoquinoline alkaloids. J Am Chem Soc 92: 6943–6951.
Kopin IJ (1985) Catecholamine metabolism: basic aspects and clinical significance. Pharmacol Rev 37: 333–364
Kienzl E, Eichinger K, Jellinger K, Riederer P (1988) Excretion patterns of dopamine sulfoconjugates in patients with Parkinson's disease. In: 9th international symposium on Parkinson's disease, Jerusalem, June 5–9 (book of abstracts, p 25)
Kuruma J, Bartholini G, Tissot R, Plettscher A (1972) Comparative investigation of inhibitors of extracerebral dopa decarboxylase in man and rats. J Pharm Pharmacol 24: 289–294
Myers WD, Ng KT, Singer G, Smythe GA, Duncan MW (1985) Dopamine and salsolinol levels in rat hypothalami and striatum after schedule-induced self-injection of ethanol and acetaldehyde. Brain Res 358: 122–128
Pianezzola E, Bellotti V, Fontana E, Gal J, Desai DM, Moro E (in press) Determination of the enantiomeric composition of salsolinol by HPLC with electrochemical detection. J Chromatogr Biomed Appl
Renskers KJ, Feor KD, Roth JA (1980) Sulfation of dopamine and other biogenic amines by human brain phenol sulfotransferase. J Neurochem 34: 1362–1368
Rinne UK (1980) Levodopa in combination with an extracerebral decarboxylase inhibitor. In: Rinne UK, Klinger M, Stamm G (eds) Parkinson's disease—Current progress, problems and management. Elsevier, North-Holland Biomedical Press, pp 323–334
Rivett AJ, Eddy BJ, Roth JA (1982) Contribution of sulfate conjugation, deamination, and 0-methylation to metabolism of dopamine and norepinephrine in human brain. J Neurochem 39: 1009–1016
Robbins JH (1968) Possible alkaloid formation in alcoholism and other diseases. Clin Res 16: 554
Rossor MN, Watkins J, Brown MJ, Reid JL, Dollery CT (1980) Plasma levodopa, dopamine and therapeutic response following levodopa therapy of Parkinsonian patients. J Neurol Sci 46: 385–392
Rueffer M, El-Shagi H, Nagakura N, Zenk MH (1981) (S)-Norlaudasonoline synthase: the first enzyme in the benzylisoquinoline biosynthetic pathway. FEBS Lett 129: 5–9
Sandler M, Bonham Carter S, Hunter KR, Stern GM (1973) Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-dopa in man. Nature 241: 439–443
Schöpf C, Bayerle H (1934) Zur Frage der Biogenese der Isochinolin-alkaloide—Die Synthese des 1-Methyl-6,7-dioxy-1,2,3,4-tetrahydro-isochinolins unter physiologischen Bedingungen. Justus Liebigs Ann Chem 513: 190–202
Shah RJ, Vaghani DD, Merchant JR (1961) Heterocyclic compounds. I. Synthesis of some isoquinoline derivatives. J Org Chem 26: 3533–3534
Sippel HW (1974) The acetaldehyde content in rat brain during ethanol metabolism. J Neurochem 23: 451–452
Sjöquist B, Ljungquist C (1985) Identification and quantification of 1-carboxysalsolinol and salsolinol in biological samples by gas chromatography-mass spectrometry. J Chromatogr Biomed Appl 343: 1–8
Smythe GA, Duncan MW (1985) Precise GC/MS assays for salsolinol and tetrahydropapaveroline: the question of artifacts and dietary sources and the influence of alcohol. Prog Clin Biol Res 183: 77–84
Stowell AR, Lindros KO, Salaspuro MP (1980) Breath and blood acetaldehyde concentrations and their correlation during normal and calcium carbimide-modified ethanol oxidation in man. Biochem Pharmacol 29: 783–787
Strolin Benedetti M, Dostert P, Dedieu M (1986) Ratio of enantiomers of salsolinol in human urine and effect of food. In: 15th CINP congress, Porto Rico, December 14–17 (book of abstracts, p 56)
Strolin Benedetti M, Dostert P, Carminati P (1989a) Influence of food intake on the enantiomeric composition of urinary salsolinol in man. J Neural Transm [GenSect] 78: 43–51
Strolin Benedetti M, Bellotti V, Pianezzola E, Moro E, Carminati P, Dostert P (1989b) Ratio of the R and S enantiomers of salsolinol in food and human urine. J Neural Transm 77: 47–53
Tyce GM (1976) The effect of L-dopa and an inhibitor of peripheral decarboxylation on glucose metabolism in brain. J Neurochem 27: 1397–1403
Ung-Chhun N, Cheng BY, Pronger DA, Serrano P, Chavez B, Fernandez Perez R, Morales J, Collins MA (1985) Alkaloid adducts in human brain: coexistence of 1-carboxylated and noncarboxylated isoquinolines and β-carbolines in alcoholics and nonalcoholics. Prog Clin Biol Res 183: 125–136
Whaley WH, Govindachari TR (1951) The Pictet-Spengler synthesis of tetrahydroisoquinolines and related compounds. In: Organic reactions, vol 6. Wiley, London, pp 151–190
Westcoot JY, Weiner H, Shultz J, Myers RD (1980) In vivo acetaldehyde in the brain of the rat treated with ethanol. Biochem Pharmacol 29: 411–417
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Dostert, P., Benedetti, M.S., Dordain, G. et al. Enantiomeric composition of urinary salsolinol in Parkinsonian patients after Madopar. J Neural Transm Gen Sect 1, 269–278 (1989). https://doi.org/10.1007/BF02263481
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DOI: https://doi.org/10.1007/BF02263481