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Neuroamine Condensations in Human Subjects

  • Michael A. Collins
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 126)

Abstract

Non-enzymatic reactions have held relatively little appeal for biomedical researchers who work with mammalian tissues and eucharyotic cells, and understandably so. When confronted with the splendid array and catalytic efficiencies of enzymes, it can be argued that “uncatalyzed” reactions should be rare in occurrence and probably minor in significance. Accumulated studies indicate however, that presumably non-enzymatic reactions — in particular, bimolecular condensations between amino compounds and aldehydes or α-keto acids — are not as uncommon as assumed. In part, this revelation is due to the new and highly sensitive chromatography methods which have developed recently (Collins, 1977). And other studies, neuropharmacological, enzymological, and behavioral in nature, demonstrate that certain condensation “products” are clearly not insignificant or innocuous agents.

Keywords

High Performance Liquid Chromatography Schiff Base Condensation Product Pyridoxal Phosphate Phenylpyruvic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. ALPERS, H.S., MCLAUGHLIN, B., NIX, W.M., AND DAVIS, V.E., 1975, Inhibition of catecholamine uptake and retention in synaptosomal preparations by tetrahydroisoquinoline and tetrahydroprotoberberine alkaloids. Biochem. Pharmacol., 24, 1391–1396.CrossRefGoogle Scholar
  2. BENESCH, R.E., YUNG, S., SUZUKI, T., BAUER, C., and BENESCH, R., 1973, Pyridoxal compounds as specific reagents for the α and β N-termini of hemoglobin. Proc, Nat. Acad. Sci, USA, 70, 2595–2599.CrossRefGoogle Scholar
  3. BIGDELI, M. and COLLINS, M.A., 1975, Tissue catecholamines and potential tetrahydroisoqulnoline alkaloid metabolites: A gas chromatographic assay method with electron capture detection. Biochem. Med., 12, 55–65.PubMedCrossRefGoogle Scholar
  4. BROSSI, A., FOCELLA, A, and TEXTEL, S., 1972, Condensation of L-DOPA and its two mono-methyl ethers with formaldehyde and acetalde- hyde. Helv. Chim. Acta, 55, 15–21.PubMedCrossRefGoogle Scholar
  5. CASHAW, J.L., MCMURTREY, K., BROWN, H, and DAVIS, V.E., 1974, Identification of catecholamine-derived alkaloids in mammals by gas chromatography and mass spectrometry. J. Chromatog., 99, 567–573.CrossRefGoogle Scholar
  6. COHEN, G., 1976, Alkaloid products in the metabolism of alcohol and biogenic amines. Biochem. Pharmacol., 25, 1123–1128.PubMedCrossRefGoogle Scholar
  7. COHEN, G, and COLLINS, M.A., 1970, Alkaloids from catecholamines in adrenal tissue: Possible role in alcoholism, Science, 167, 1749–1751.PubMedCrossRefGoogle Scholar
  8. COLLINS, M.A., 1977, Identification of isoquinoline alkaloids during alcohol intoxication, in Alcohol and Opiates: Neurochem. Behav. Mech. (Ed. K. Blum), Acad. Press, N.Y., 155–166.Google Scholar
  9. COSCIA, C.J., BURKE, W., JAMROZ, G., LASALA, J., MCFARLANE, J., MITCHELL, J., OTOOLE, M., and WILSON, M., 1977, Occurrence of a new class of tetrahydroisoqulnoline alkaloids in L-DOPA- treated parkinsonian patients. Nature, 269, 617–619.PubMedCrossRefGoogle Scholar
  10. DOUGAN, D., WADE, D., and MEARRICK, P., 1975, Effects of L-DOPA metabolites at a dopamine receptor suggest a basis for ’on-off effects in Parkinson’s disease. Nature, 254, 70–72.PubMedCrossRefGoogle Scholar
  11. DILLON, J., SPECTOR, A., and NAKANISHI, K., 1976, Identification of beta-carbolines isolated from fluorescent human lens protein. Nature, 259, 422–423.PubMedCrossRefGoogle Scholar
  12. FARRELL, G. and MCISAAC, W.M., 1961, Adrenoglomerulotropin. Arch. Biochem. Biophys., 94, 543–544.PubMedCrossRefGoogle Scholar
  13. FLÜCKIGER, R. and WINTERHALTER, K.H., 1976, In vitro synthesis of hemoglobin Ai, FEBS Letts., 71, 356–360.CrossRefGoogle Scholar
  14. GALLAGHER, B., 1971, The influence of tyrosine, phenylpyruvate and vitamin Bfupon Scizure thresholds, J. Neurochem., 18, 799–808.PubMedCrossRefGoogle Scholar
  15. GALLOWAY, M.P. BURKE, W.J., KOSLOFF, A., LIEBERMAN, D.L., MITCHELL, J., and COSCIA, C.J., 1978, Effect of a class of naturally-occurring tetrahydroisoquinolines on catecholamine metabolism in rat adrenal medulla; Importance of methylation. Neurosci. Abst. 4, 315.Google Scholar
  16. GRAF, R.J., HALTER, J.B., and PORTE, D., 1978, Glycosylated hemoglobin in normal and diabetic subjects. Diabetes, 27, 834–839.PubMedCrossRefGoogle Scholar
  17. HANEY, and BUM, H.F., 1976, Glycosylation of haemoglobin in vitro: affinity labeling of hemoglobin by glucose -6- phosphate, Proc. Nat, Acad. Sci. USA, 73, 3534–3538.CrossRefGoogle Scholar
  18. HSIA, Y.E., 1976, Disorders of amino acid metabolism, in Basic Neurochemistry (Eds. Siegel, G., Albers, R.W., Ratzman, R, and Agranoff, B.), Little, Brown and Co., 2nd Ed., 500–541.Google Scholar
  19. KAMETANI, T., TAKEMURA, M., XHARA, M., TAKAHASHI, K., and FUKUMOTO, K., 1976, Biotransformation of 1-benzyl-l,2,3,4- tetrahydro-2-methyl-isoquinolines into tetrahydroprotoberberlnes with rat liver enzymes. J, Amer. Chem. Soc, 98, 1956–1959CrossRefGoogle Scholar
  20. KOENIG, R., PETERSON, C.M., JONES, R.L., SAUDEK, C., LEHRHAN, M., and CERAMI, A., 1976, Correlation of glucose regulation and hemoglobin Aic in diabetes mellitus, N. Engl. J. Med., 295, 417–420.PubMedCrossRefGoogle Scholar
  21. LASAX, A.J.M., COSCIA, C.J. and CICERO, T.J., 1978, Inhibition of catecholamine-uptake by naturally-occurring tetrahydroisoquino- lines and its possible relevance to both L’-DOPA chemotherapy in Parkinsonism and to phenylketonuria. Neurosci. Abst., 4, 428.Google Scholar
  22. LOO, Y.H., 1967, Characterization of a new phenylalanine metabolite in phenylketonuria, J. Neurochem., 14, 813–821CrossRefGoogle Scholar
  23. LOO, Y.H., 1974, Serotonin deficiency in experimental hyperphenylalaninemia, J. Neurochem., 23, 139–147.PubMedCrossRefGoogle Scholar
  24. LOO, Y.H, and MACK, K., 1972, Effect of hyperphenylalaninemia on vitamin B5 metabolism in developing rat brain, J. Neurochem., 19, 2385–2394.PubMedCrossRefGoogle Scholar
  25. LOO, Y.H. and WHITTAKER, V.P., 1967, Pyridoxal kinase in brain and its inhibition by pyridoxylidene-3-phenylethylamine, J. Neurochem., 14, 997–1011.PubMedCrossRefGoogle Scholar
  26. MARKLEY, H.G. and MEZEY, E., 1978, Induction of alcohol withdrawal symptoms by nalorphine in chronic alcoholic patients, Int. J. Addict., 13, 395–402.PubMedGoogle Scholar
  27. MEYERSON, L.R., GEORGE, B., ABEL, M., PHILIPS, H., DAVIS, V.E, and CLEMENT-CORMIER, Y.C., 1978A, Characterization of striatal 3H-apomorphine and 3H-spiroperidol binding and dopamine- sensitive adenylate cyclase activity utilizing protoberberine alkaloids. Neurosci, Abst., 4, 516.Google Scholar
  28. MEYERSON, L.R., McMURTREY, K.D., and DAVIS, V.E., 1978B, Isoquinoline alkaloids: Inhibitory actions on cation-dependent ATP- phosphohydrolases. Neurochem. Res., 3, 239–257.PubMedCrossRefGoogle Scholar
  29. NIJM, W.P., BORGE, G.F., ORIGITANO, T., TEAS, G., GOLDFARB, C. and COLLINS, M.A., 1978, Lack of evidence for sustained blood acetaldehyde concentrations during alcohol detoxification. Res. Comm. Chem. Path. Pharmacol., 20, 178–190.Google Scholar
  30. NIJM, W.P., RIGGIN, R., TEAS, G., KISSINGER, P.T., BORGE, G., and COLLINS, M.A., 1977, Urinary dopamine-related tetrahydroiso- quinolines: Studies of alcoholics and non-alcoholics. Fedn. Proc., 36, 334.Google Scholar
  31. RAHWAN, R., 1975, Toxic effects of ethanol. Possible role of acetaldehyde, tetrahydroisoquinolines and tetrahydro-β-carbolines, Toxicol. Appl. Pharmacol. 34, 3–27.PubMedCrossRefGoogle Scholar
  32. RIGGIN, R.M. and KISSINGER, P.T., 1977, Determination of tetrahydroisoquinoline alkaloids in biological materials with high performance liquid chromatography. Anal. Chem., 49, 530–533.PubMedCrossRefGoogle Scholar
  33. ROBBINS, J.H., 1968, Possible alkaloid formation in alcoholism and other diseases. Clin. Res., 16, 554.Google Scholar
  34. SANDLER, M., 1973, The DOPA effect: Possible significance of transamination and tetrahydroisoquinoline formation. Adv. Neurol. 2, 255–264.Google Scholar
  35. SANDLER, M., CARTER, S.B., HUNTER, K.R., and STERN, G.M., 1973, Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-DOPA in man. Nature, 241, 439–443.PubMedCrossRefGoogle Scholar
  36. SHOEMAKER, D.W., CUMMINS, J.T., and BIDDER, T.G., 1978, Beta- carbolines in rat arcuate nucleus, Neurosci., 3, 233–239.CrossRefGoogle Scholar
  37. SOURKES, T., 1969, On the mode of action of L-DOPA in Parkinson’s disease. Biochem. Med., 3, 321–325.CrossRefGoogle Scholar
  38. SMITH, A.A., 1975, Interaction of biogenic amines with ethanol, in Biochem. Pharmacol, of Ethanol (Ed. E. Majchrowicz), Plenum Press, N.Y., 265–275.CrossRefGoogle Scholar
  39. STEVENS, V.J., ROUGER, C., MONNIER, V., and CERAMI, A., 1978, Diabetic cataract formation: Potential role of lens crystallins, Proc. Nat. Acad. Sci. USA, 75, 2915–2922.CrossRefGoogle Scholar
  40. STEVENS, V.J., VLASSARA, H., ABATI, A., and CERAMI, A., 1977, Non- enzymatic glycosylation of hemoglobin, J. Biol. Chem., 252, 2998–3002.PubMedGoogle Scholar
  41. TATTERSALL, R.B., PYKE, D.A., RANNEY, H., and BRUCKHEIMER, S.M., 1975, Hemoglobin components in diabetes mellitus. Studies in identical twins, N. Eng. J. Med., 293, 1171–1173.CrossRefGoogle Scholar
  42. WILLIAMSON, B. and CONIGLIO, J.G., 1971, The effects of pyridoxine deficiency and of caloric restriction on lipids in the developing rat brain, J. Neurochem., 18, 267–276.PubMedCrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1980

Authors and Affiliations

  • Michael A. Collins
    • 1
  1. 1.Department of Biochemistry and BiophysicsLoyola University Stritch School of MedicineMaywoodUSA

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