Summary
The R enantiomer of salsolinol was detected in the urine of two out of six healthy subjects, whereas 1,2-dehydrosalsolinol was present in the urine of all the subjects. (S)-salsolinol was never detected. Administration of Madopar for 7 days resulted in the presence of large amounts of (R)- and (S)-salsolinol in the urine of five out of the six subjects, the urinary excretion of 1,2-dehydrosalsolinol being generally not markedly increased.
The presence of 1,2-dehydrosalsolinol in urine suggests that the biosynthesis of salsolinol in healthy volunteers should occur by condensation of dopamine with pyruvic acid, in keeping with Hahn's hypothesis. The absence of salsolinol in the urine of one subject after Madopar administration seems to indicate that the biological system(s) involved in the reduction of the C = N bond in 1,2-dehydrosalsolinol can be missing or not, or poorly, functional in some individuals, and suggests that there is no alternative pathway for the formation of salsolinol in healthy volunteers.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Brossi A (1982) Mammalian TIQ's: products of condensation with aldehydes or pyruvic acids? Prog Clin Biol Res 90: 123–133
Cheng BY, Origitano TC, Collins MA (1987) Inhibition of catechol-0-methyltransferase by 6,7-dihydroxy-3,4-dihydro-isoquinolines related to dopamine: demonstration using liquid chromatography and a novel substrate for 0-methylation. J Neurochem 48: 779–786
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
Corrodi H, Hillarp Nå (1964) Fluoreszenzmethoden zur histochemischen Sichtbarmachung von Monoaminen. Identifizierung des fluoreszierenden Produktes aus Dopamin und Formaldehyd. Helv Chim Acta 47: 911–918
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 (1987) 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
Dostert P, Strolin Benedetti M, Dordain G, Vernay D (1989) Enantiomeric composition of urinary salsolinol in Parkinsonian patients after Madopar. J Neural Transm [PD-Sect] 1: 269–278
Hahn G, BÄrwald L, Schales O, Werner H (1935) Synthese von Tetrahydro-harman (4-Carbolin)-Derivaten unter physiologischen Bedingungen. Justus Liebigs Ann Chem 520: 107–123
Hahn G, Stiehl K (1936) über Β-[Oxy-phenyl]-Äthylamine and ihre Umwandlungen. IV Mitteil. Synthese von Tetrahydro-isochinolin-carbonsÄuren und die spontane Decarboxylierung von α-Keto-sÄuren unter physiologischen Bedingungen. Chem Ber 69: 2627–2654
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
Pianezzola E, Bellotti V, Fontana E, Gal J, Desai DM, Moro E (1989) Determination of the enantiomeric composition of salsolinol in biological samples by HPLC with electrochemical detection. J Chromatogr Biomed Appl 495: 205–214
Robbins JH (1968) Alkaloid formation by condensation of biogenic amines with acetaldehyde. Clin Res 16: 350
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
Sourkes TL (1971) Possible new metabolites mediating actions of L-dopa. Nature 229: 413–414
Strolin Benedetti M, Bellotti V, Pianezzola E, Moro E, Carminati P, Dostert P (1989a) Ratio of the R and S enantiomers of salsolinol in food and human urine. J Neural Transm 77: 47–53
Strolin Benedetti M, Dostert P, Carminati P (1989b) Influence of food intake on the enantiomeric composition of urinary salsolinol in man. J Neural Transm [Gen Sect] 78: 43–51
Susilo R, Rommelspacher H (1988) Formation of 1-methyl-Β-carbolines in rats from their possible carboxylic acid precursor. Naunyn Schmiedebergs Arch Pharmacol 337: 566–571
Ung-Chhun N, Cheng BY, Pronger DA, Serrano P, Chavez B, Fernandez Perrez 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
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Dostert, P., Strolin Benedetti, M., Bellotti, V. et al. Biosynthesis of salsolinol, a tetrahydroisoquinoline alkaloid, in healthy subjects. J. Neural Transmission 81, 215–223 (1990). https://doi.org/10.1007/BF01245043
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01245043