Agents and Actions

, Volume 14, Issue 3–4, pp 351–355

N-methyl-N-formylhydrazine: A toxic and mutagenic inhibitor of the intestinal diamine oxidase

  • T. Biegński
  • R. Braun
  • J. Kusche
Distribution and Metabolism of Histamine

Abstract

N-methyl-N-formylhydrazine is the first active intermediate of the poison gyromitrin of the mushroom: false morel. This compound is a non-competitive inhibitor of human intestinal diamine oxidase (ID50=1.6×10−5 mol/l). This concentration corresponds to less than 5g of wet weight of mushroom/l. The diamine oxidases from 5 other sources are inhibited in a similar manner. Semicarbazide and aminoguanidine are 10-respectively 1000-fold more potent inhibitors of the human intestinal diamine oxidase. An involvement of the diamine oxidase inhibitory property ofN-methyl-N-formylhydrazine in toxic and mutagenic effects of the substance is considered.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    D.S. Rampton, R.D. Murdoch andG.E. Sladen,Rectal mucosal histamine release in ulcerative colitis, Clin. Sci.59, 389–391 (1980).PubMedGoogle Scholar
  2. [2]
    D.N. Challacombe, J.P. Edwards andJ.M. Baylis,Histamine release in post-challenge coeliac disease, LancetI, 202 (1980).CrossRefGoogle Scholar
  3. [3]
    H.-J. Reimann, J. Ring, B. Ulsch et al.,Histaminstoffwechsel in Magen und Darmmucosa nach Allergenprovokation bei Patienten mit Nahrungs-mittelunverträglichkeit, Verh. dt. Ges. inn. Med.89, 83–89 (1983).Google Scholar
  4. [4]
    J.S. Lee andJ.W. Silverberg,Effect of histamine in intestinal fluid secretion in the dog. Am. J. Physiol.231, 793–798 (1976).PubMedGoogle Scholar
  5. [5]
    J.P.M. Tutton,The influence of histamine on epithelial cell proliferation in the jejunum of the rat, Clin. Exp. Pharmac. Physiol.3, 369–373 (1976).Google Scholar
  6. [6]
    Ö. V. Sjaastad,Potentiation by aminoguanidine of the sensitivity of sheep to histamine given by mouth. Effect of aminoguanidine of the urinary excretion of endogenous histamine. Q. Jl exp. Physiol.52, 319–330 (1967).Google Scholar
  7. [7]
    J. Kusche, C.-D. Stahlknecht, W. Lorenz, G. Reichert andW. Dietz,Comparison of alterations in the histamine-diamine-oxidase system during intestinal ischemia in pigs, dogs and rabbits: evidence for an uniform pathophysiological mechanism? Agents and Actions,9, 49–52 (1979).PubMedGoogle Scholar
  8. [8]
    J. Kusche, W. Lorenz, C.-D. Stahlknecht, H. Richter et al.,Intestinal diamine oxidase and histamine release in rabbit mesenteric ischemia, Gastroenterology80, 980–987 (1981).PubMedGoogle Scholar
  9. [9]
    K.J. Motil andN.S. Scrimshaw,The role of exogenous histamine in scombroid poisoning. Toxicol. Lett.3, 219–223 (1979).CrossRefGoogle Scholar
  10. [10]
    S.L. Taylor, L.s. Guthertz andE.L. Lieber,Histamine production by Klebsiella pneumoniae and an incident of scombroid fish poisoning, Appl. environm. Microbiol.37, 274–278 (1979).Google Scholar
  11. [11]
    S.L. Taylor andE.R. Lieber,In vitro inhibition of rat intestinal histamine-metabolizing enzymes, Fd Cosmet. Toxicol.17, 237–240 (1979).CrossRefGoogle Scholar
  12. [12]
    L.Y. Foo,Scombroid-type poisoning induced by the ingestion of smoked Kahawai, N.Z. med. J.81, 476–477 (1975).PubMedGoogle Scholar
  13. [13]
    M.H. Merson, W.B. Baine, E.J. Gangarosa andR.C. Swanson,Scombroid fish poisoning, J. Am. med. Ass.228, 1268–1269 (1974).CrossRefGoogle Scholar
  14. [14]
    J. Kusche, H. Richter, J. Schmidt, R. Hesterberg et al.,Diamine oxidase in rabbit small intestine: separation from a soluble monoamine oxidase, properties and pathophysiological significance in intestinal ischemia. Agents and Actions5, 431–439 (1975).PubMedGoogle Scholar
  15. [15]
    J. Kusche, W. Lorenz andJ. Schmidt,Oxidative deamination of biogenic amines by intestinal amine oxidase: histamine is solely inactivated by diamine oxidase. Hoppe-Seyler's Z. physiol. Chem.356, 1485–1496 (1975).PubMedGoogle Scholar
  16. [16]
    S. Franke andU. Freimuth,Über die Giftigkeit der Frühjahrslorchel Gyromitra (Helvella) esculenta Fr., Arch. Tox.22, 293–332 (1967).CrossRefGoogle Scholar
  17. [17]
    W.P. Burkard, K.F. Gey andA. Pletscher,Inhibition of diamine oxidase in vivo by hydrazine derivatives, Biochem. Pharmac.3, 249–255 (1960).CrossRefGoogle Scholar
  18. [18]
    E.A. Zeller, J. Barsky, J.R. Fouts et al.,Influence of isonicotinic acid hydrazide (INH) and 1-isonicotinyl-2-isopropyl hydrazide (IIH) on bacterial and mammalian enzymes, Experientia8, 349–350 (1952).Google Scholar
  19. [19]
    T. Bieganski, J. Kusche, W. Lorenz, R. Hesterberg et al.,Distribution and properties of human intestinal diamine oxidase and its relevance for the histamine catabolism, Biochim. biophys. Acta756, 196–203 (1983).PubMedGoogle Scholar
  20. [20]
    W. Lorenz, H.-J. Reimann, H. Barth, J. Kusche et al.,A sensitive and specific method for the determination of histamine in human whole blood and plasma, Hoppe-Seyler's Z. physiol. Chem.353 911–920 (1972).PubMedGoogle Scholar
  21. [21]
    P.H. List andP. Luft, Gyromitrin, das Gift der Frühjahrslorchel Gyromitra (Helvella) esculenta Fr., Tetrahedron Lett.20 1893–1895 (1967).CrossRefGoogle Scholar
  22. [22]
    T. Okuyama andY. Kobayashi,Determination of diamine oxidase activity by liquid scintillation counting, Archs Biochem. Biophys.,95, 242–250 (1961).CrossRefGoogle Scholar
  23. [23]
    J. Kusche andW. Lorenz, Diamine oxidase. InMethods of Enzymativ Analysis, 3rd edn. (Ed.H.U. Bergmeyer). Verlag Chemie, Weinheim 1983.Google Scholar
  24. [24]
    W.W. Cleland, Steady start kinetics. InThe Enzymes Vol. II, 3rd edn. pp. 1–65 (EdP.D. Boyer). Academic Press, New York, London 1970.Google Scholar
  25. [25]
    M.J.C. Crabbe, R.E. Childs andW.C. Bardsley,Time dependent inhibition of diamine oxidase by carbonyl group reagents and urea, Eur. J. Biochem.60, 325–333 (1975).CrossRefPubMedGoogle Scholar
  26. [26]
    F. Buffoni,Histaminase and related amine oxidases, Pharmac. Rev.18, 1163–1199 (1966).Google Scholar
  27. [27]
    E. Werle, Aminooxidasen., InHoppe Seyler/Thierfelder Handbuch der physiologisch- und pathologisch-chemischen Analyse, 10th edn. VI/A, pp. 691–693, Springer Verlag, Berlin-Göttingen-Heidelberg-New York 1964.Google Scholar
  28. [28]
    E.A. Zeller, L.A. Blanksma andJ.A. Carbon,Über die Wirkung von optisch aktiven Hydraziden auf die Diaminoxydase. 14. Mittl über Aminoxydasen, Helv. chim. Acta40, 257–260 (1957).CrossRefGoogle Scholar
  29. [29]
    W. Schuler,Zur Hemmung der Diaminoxydase/Histaminase, Experientia7, 230–232 (1952).Google Scholar
  30. [30]
    T. Bieganski, J. Kusche, K.-D. Feussner et al.,The importance of human intestinal diamine oxidase in the oxidation of histamine and/or putrescine, Arch. Immunol. Ther. Exp.28, 901–906 (1980).Google Scholar
  31. [31]
    Y. Kuwabara,Experimental studies on food poisoning due to vibrio parahaemolyticus, Chiba Med. J.50, 21–29 (1974).Google Scholar
  32. [32]
    U.S. Goodman andA. Gilman,The Pharmacological Basis of Therapeutics, 6th edn, p. 430. Macmillan Publ. 1980.Google Scholar
  33. [33]
    J.T. LaMont andT.A. O'Gorman,Experimental colon cancer, Gastroenterology75, 1157–1169 (1978).PubMedGoogle Scholar
  34. [34]
    W. Von Der Hude andR. Braun,On the mutagenicity of metabolites derived from the mushroom poison gyromitrin, Toxicology861 (1983) in press.Google Scholar
  35. [35]
    R. Hesterberg, J. Kusche, C.-D. Stahlknecht andK.-D. Feussner,The start of a programme for measuring diamine oxidase activity in biopsy specimens of human rectal mucosa, Agents and Actions11, 33–37 (1981).PubMedGoogle Scholar

Copyright information

© Birkhäuser Verlag 1984

Authors and Affiliations

  • T. Biegński
    • 1
  • R. Braun
    • 2
  • J. Kusche
    • 3
  1. 1.Department of Biogenic AminesInstitute of PharmacologyLódźPoland
  2. 2.Bundesgesundheitsamt BerlinFRG
  3. 3.Biochemical and Experimental Division, II. Department of SurgeryUniversity of CologneKöln 91FRG

Personalised recommendations