, Volume 29, Issue 11, pp 1319–1327 | Cite as

Chemistry of some potent animal toxins

  • Evert Karlsson


I have discussed in this article only the most active toxins, with the result that many interesting substances have been omitted, e.g. the toxins from bee and wasp venoms (apamin, melittin, etc.), of many amphibians (bufotoxins, etc.), ciguatoxins, and many more. Poisons are found in every phylum except birds. Shrews exemplify venomous mammals. One gets a good illustration of the number of poisonous animals by studying the monumental and impressive work byHalstead106 which consequently excludes terrestrial animals. An interesting fact in this connection is that there are about 20,000 species of spiders, most of which are poisonous.

A toxin ranking list has to be included in an article of this kind. The list is, of course, far from complete. Data on molecular weights, mouse lethal doses, etc. are lacking for many potent toxins, such as the dysentery toxin, a neurotoxin with a toxicity comparable to that of the botulinus toxins107, the toxins from the jelly fishChironex fleckeri106.

A comparison on molar basis gives a better notion of the toxicities. Curare has about 1/30 of the toxicity of the curarimimetic snake venom neurotoxins, clearly indicating that curare has a much lower affinity for the acetylcholine receptor.

Toxic organisms have developed during millions of years more and more refined toxins, and this evolution has probably brought into existence toxins against every physiological function. Neurochemistry is to a great extent unexplored. Progress in this field will in the nearest future depend on specific toxins from various natural sources. Toxins from spiders, scorpions, snakes, frogs, and fishes are therefore not mere curiosities but valuable tools for research on the molecular mechanisms of neural function and synaptic transmission.


Botulinus Toxins107 Melittin Snake Venom Dysentery Ranking List 
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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  1. 1.
    R. Morris andD. Morris,Men and Snakes (Hutchinson and Co. Ltd, London 1965).Google Scholar
  2. 2.
    A. T. Tu, B. S. Hong andT. N. Solie, Biochemistry10, 1295 (1971).PubMedGoogle Scholar
  3. 3.
    C. C. Yang, Biochim. biophys. Acta133, 346 (1967).PubMedGoogle Scholar
  4. 4.
    N. Tamiya, Toxicon11, 95 (1973).PubMedGoogle Scholar
  5. 5.
    E. Karlsson, H. Arnberg andD. Eaker, Eur. J. Biochem.21, 1 (1971).PubMedGoogle Scholar
  6. 6.
    D. Cooper andE. Reich, J. biol. Chem.247, 3008 (1972).PubMedGoogle Scholar
  7. 7.
    C. Su, C. C. Chang andC. Y. Lee, inAnimal Toxins (Eds.F. E. Russell andP. R. Saunders; Pergamon, Oxford and New York 1967), p. 259.Google Scholar
  8. 8.
    F. Tazieff-Depierre andJ. Pierre, C. r. Acad. Sci., Paris263, 1785 (1966).Google Scholar
  9. 9.
    C. Y. Lee, C. C. Chang andY. M. Chen, J. Formosan med. Ass.71, 344 (1971).Google Scholar
  10. 10.
    C. C. Chang andC. C. Lee, Archs int. Pharmacodyn.144, 241 (1963).Google Scholar
  11. 11.
    C. Y. Lee andC. C. Chang, Mem. Inst. Butantan, Simp. Internac.33, 555 (1966).Google Scholar
  12. 12.
    H. Lester, Nature, Lond.227, 727 (1970).Google Scholar
  13. 13.
    P. Boquet, Y. Izard andA. M. Ronsseray, J. Formosan med. Ass.71, 307 (1972).Google Scholar
  14. 14.
    P. Boquet, G. Poilleux, C. Dumarey, Y. Izard andA. M. Ronsseray, Toxicon11, 333 (1973).PubMedGoogle Scholar
  15. 15.
    E. Karlsson, D. Eaker andH. Drevin, Biochim. biophys. Acta293, 1 (1973).PubMedGoogle Scholar
  16. 16.
    E. Karlsson, D. Eaker, L. Fryklund andS. Kadin, Biochemistry11, 4628 (1972).PubMedGoogle Scholar
  17. 17.
    D. J. Strydom, Toxicon10, 39 (1972).PubMedGoogle Scholar
  18. 18.
    D. J. Strydom, Dissertation, University of South Africa, Pretoria (1973).Google Scholar
  19. 19.
    P. G. Lankisch, K. Schoner, W. Schoner, H. Kunze, E. Bohn andW. Vogt, Biochim. biophys. Acta266, 133 (1972).PubMedGoogle Scholar
  20. 20.
    A. C. T. North, Nature, Lond.239, 76 (1972).Google Scholar
  21. 21.
    S. Sato andN. Tamiya, Biochem. J.122, 453 (1971).PubMedGoogle Scholar
  22. 22.
    Y. Endo, S. Sato, S. Ishii andN. Tamiya, Biochem. J.122, 463 (1971).PubMedGoogle Scholar
  23. 23.
    C. C. Yang, H. J. Yang andJ. S. Huang, Biochem. biophys. Acta188, 65 (1969).PubMedGoogle Scholar
  24. 24.
    C. C. Yang, H. J. Yang andR. H. C. Chiu, Biochim. biophys. Acta214, 355 (1970).PubMedGoogle Scholar
  25. 25.
    D. Eaker andJ. Porath, Japan. J. Microbiol.11, 353 (1967).Google Scholar
  26. 26.
    D. P. Botes andD. J. Strydom, J. biol. Chem.244, 4147 (1969).PubMedGoogle Scholar
  27. 27.
    D. P. Botes, D. J. Strydom, C. G. Anderson andP. A. Christensen, J. biol. Chem.246, 3132 (1971).PubMedGoogle Scholar
  28. 28.
    A. J. C. Strydom andD. P. Botes, J. biol. Chem.246 1341 (1971).PubMedGoogle Scholar
  29. 29.
    H. Arnberg, D. Eaker, L. Fryklund andE. Karlsson, to be published.Google Scholar
  30. 30.
    D. P. Botes, J. biol. Chem.246, 7383 (1971).PubMedGoogle Scholar
  31. 31.
    D. P. Botes, J. biol. Chem.246, 2866 (1971).Google Scholar
  32. 32.
    A. J. C. Strydom andD. P. Botes, personal communication.Google Scholar
  33. 33.
    D. J. Strydom, J. biol. Chem.246, 4029 (1971).Google Scholar
  34. 34.
    L. Fryklund, D. Eaker andE. Karlsson, Biochemistry11, 4633 (1973).Google Scholar
  35. 35.
    D. Mebs, K. Narita, S. Iwanaga, Y. Samejima andC. Y. Lee, Hoppe-Seylers Z. physiol. Chem.353, 243 (1972).PubMedGoogle Scholar
  36. 36.
    F. J. Joubert, personal communication.Google Scholar
  37. 37.
    H. Arnberg, D. Eaker andE. Karlsson, to be published.Google Scholar
  38. 38.
    L. Fryklund andD. Eaker, Biochemistry12, 661 (1973).PubMedGoogle Scholar
  39. 39.
    K. Narita andC. Y. Lee, Biochem. biophys. Res. Commun.41, 339 (1970).PubMedGoogle Scholar
  40. 40.
    L. Fryklund andD. Eaker, to be published.Google Scholar
  41. 41.
    K. Hayashi, M. Takechi andT. Sasaki, Biochem. biophys. Res. Commun.45, 1357 (1971).PubMedGoogle Scholar
  42. 42.
    C. C. Chang, C. C. Yang, K. Hamaguchi, K. Nakai andK. Hayashi, Biochim. biophys. Acta236, 164 (1971).PubMedGoogle Scholar
  43. 43.
    J. S. Huang, S. S. Liu, K. H. Ling, C. C. Chang andC. C. Yang, Toxicon11, 39 (1973).PubMedGoogle Scholar
  44. 44.
    E. Karlsson andD. Eaker, J. Formosan med. Ass.71, 358 (1972).Google Scholar
  45. 45.
    R. Chicheportiche, C. Rochat, F. Sampieri andM. Lazdunski, Biochemistry11, 1681 (1972).PubMedGoogle Scholar
  46. 46.
    E. Karlsson, D. Eaker andG. Ponterius, Biochim. biophys. Acta257, 235 (1972).PubMedGoogle Scholar
  47. 47.
    F. Miranda, C. Kupeyan, H. Rochat, C. Rochat andS. Lissitzky, Eur. J. Biochem.17, 477 (1970).PubMedGoogle Scholar
  48. 48.
    C. C. Chang, C. C. Yang, K. Nakai andK. Hayashi, Biochim. biophys. Acta251, 334 (1971).PubMedGoogle Scholar
  49. 49.
    E. Karlsson, E. Heilbronn andL. Widlund, FEBS Lett.28, 107 (1972).PubMedGoogle Scholar
  50. 50.
    J. Schmidt andM. A. Raftery, Biochem. biophys. Res. Commun49, 572 (1972).PubMedGoogle Scholar
  51. 51.
    R. W. Olsen, J. C. Meunier andJ. P. Changeux, FEBS Lett.28, 96 (1972).PubMedGoogle Scholar
  52. 52.
    J. C. Meunier, R. W. Olsen, A. Menez, P. Fromageot, P. Boquet andJ. P. Changeux, Biochemistry11, 1200 (1972).PubMedGoogle Scholar
  53. 53.
    R. Miledi, R. Molinoff andL. T. Potter, Nature, Lond.229, 554 (1971).Google Scholar
  54. 54.
    K. Slotta andH. Fraenkel-Conrat, Chem. Ber.71, 1076 (1938).Google Scholar
  55. 55.
    N. Gralén andT. Svedberg, Biochem. J.32, 1375 (1938).Google Scholar
  56. 56.
    C. H. Li andH. Fraenkel-Conrat, J. Am. chem. Soc.64, 1586 (1942).Google Scholar
  57. 57.
    R. A. Hendon andH. Fraenkel-Conrat, Proc. natn. Acad. Sci.68, 1560 (1971).Google Scholar
  58. 58.
    K. Rübsamen, H. Breithaupt andE. Habermann, Naunyn-Schmiedebergs Arch. Pharmak.270, 274 (1971).Google Scholar
  59. 59.
    O. V. Brazil, J. Formosan med. Ass.71, 394 (1972).Google Scholar
  60. 60.
    O. V. Brazil andB. J. Excell, J. Physiol., Lond.212, 34p (1970).Google Scholar
  61. 61.
    C. C. Chang andC. Y. Lee, Arch. Int. Pharmacodyn.144, 241 (1963).PubMedGoogle Scholar
  62. 62.
    C. Y. Lee, S. L. Chang, S. T. Kau andS. H. Luh, J. Chromatogr.72, 71 (1972).PubMedGoogle Scholar
  63. 63.
    C. C. Chang, T. F. Chen andC. Y. Lee, J. Pharmac. exp. Ther.184, 339 (1973).Google Scholar
  64. 64.
    E. Karlsson, D. Eaker andL. Rydén, Toxicon10, 405 (1972).PubMedGoogle Scholar
  65. 65.
    J. B. Harris, E. Karlsson andS. Thesleff, Br. J. Pharmac.47, 141 (1973).Google Scholar
  66. 66.
    J. B. Harris, to be published.Google Scholar
  67. 67.
    D. Eaker, personal communication.Google Scholar
  68. 68.
    J. Fohlman, D. Eaker andE. Karlsson. to be published.Google Scholar
  69. 69.
    M. Kaminskaya andS. Thesleff, to be published.Google Scholar
  70. 70.
    J. E. Longenecker, W. P. Hurlbut, A. Mauro andA. W. Clark, Nature, Lond.225, 701 (1970).Google Scholar
  71. 71.
    V. d'Ajello, F. Magni andS. Bettini, Toxicon9, 103 (1979).Google Scholar
  72. 72.
    M. Okamoto, H. Longenecker, W. F. Riker andA. W. Clark, Science172, 733 (1971).PubMedGoogle Scholar
  73. 73.
    L. Mazzotti andM. A. Bravo-Becherelle, inVenomous and Poisonous Animals and Noxious Plants in the Pacific Region (Eds.H. L. Keegan andW. V. MacFarlane; Pergamon, Oxford and New York 1963), p. 119.Google Scholar
  74. 74.
    C. Rochat, H. Rochat, F. Miranda andS. Lissitzky, Biochemistry6, 578 (1967).PubMedGoogle Scholar
  75. 75.
    F. Miranda, C. Kupeyan, H. Rochat, C. Rochat andS. Lissitzky, Eur. J. Biochem.16, 514 (1970).PubMedGoogle Scholar
  76. 76.
    D. D. Watt andM. E. McIntosh, Toxicon10, 173 (1972).PubMedGoogle Scholar
  77. 77.
    H. Rochat, C. Rochat, C. Kupeyan, F. Miranda, S. Lissitzky andP. Edman, FEBS Lett.10, 349 (1970).PubMedGoogle Scholar
  78. 78.
    E. Zlotkin andA. S. Shulov, Toxicon7, 217 (1969).PubMedGoogle Scholar
  79. 79.
    J. Cheymol, F. Bourillet andM. Roch-Arveiller, Actual. Pharmac.25, 241 (1972).Google Scholar
  80. 80.
    K. R. Adam, H. Schmidt, R. Stampfli andC. Weiss, Br. J. Pharmac.26, 666 (1966).Google Scholar
  81. 81.
    K. R. Adam andC. Weiss, Mem. Inst. Butantan, Simp. Internac.33, 603 (1966).Google Scholar
  82. 82.
    E. Koppenhöfer andH. Schmidt, Experientia24, 41 (1968).PubMedGoogle Scholar
  83. 83.
    J. Cheymol, F. Bourillet, M. Roch-Arveiller andJ. Heckle, Toxicon11, 277 (1973).PubMedGoogle Scholar
  84. 84.
    F. Tazieff-Depierre, M. Lievremont andM. Czajka, C. r. Acad. Sci., Paris267, 1477 (1968).Google Scholar
  85. 85.
    F. Tazieff-Depierre, C. r. Acad. Sci., Paris271, 1655 (1970).Google Scholar
  86. 86.
    H. Rochat, C. Rochat, F. Miranda, S. Lissitzky andP. Edman, Eur. J. Biochem.17, 262 (1970).PubMedGoogle Scholar
  87. 87.
    C. Y. Kao, Pharmac. Rev.18, 997 (1966).Google Scholar
  88. 88.
    J. W. Moore andT. Narahashi, Fedn. Proc.26, 1655 (1967).Google Scholar
  89. 89.
    Y. Ogura, inNeuropoisons. Their Pathophysiological Action. Poisons of Animal Origin (Ed.L. L. Simpson; Plenum Press, New York and London 1971), vol. 1, p. 139.Google Scholar
  90. 90.
    W. D. Detbarn, inNeuropoisons. Their Pathophysiological Action Poisons of Animal Origin (Ed.L. L. Simpson; Plenum Press, New York and London 1971), vol. 1, p. 169.Google Scholar
  91. 91.
    P. W. Gage, inNeuropoisons. Their Pathophysiological Action. Poisons of Animal Origin (Ed.L. L. Simpson; Plenum Press, New York and London 1971), vol. 1, p. 187.Google Scholar
  92. 92.
    C. Y. Kao, Fedn. Proc.31, 1117 (1972).Google Scholar
  93. 93.
    T. Narahashi, Fedn. Proc.31, 1124 (1972).Google Scholar
  94. 94.
    E. X. Albuquerque, J. W. Daly andB. Witkop, Science172, 995 (1971).PubMedGoogle Scholar
  95. 95.
    E. X. Albuquerque, Fedn. Proc.31, 1133 (1972).Google Scholar
  96. 96.
    H. S. Mosher, F. A. Fuhrman, H. D. Buchwald andH. G. Fischer, Science144, 1100 (1964).PubMedGoogle Scholar
  97. 97.
    J. L. Wong, R. Oesterlin andH. Rapoport, J. Am. Chem. Soc.93, 7344 (1971).PubMedGoogle Scholar
  98. 98.
    E. J. Schantz, J. M. Lynch, G. Vayvada, K. Matsumoto andH. Rapoport, Biochemistry5, 1191 (1966).PubMedGoogle Scholar
  99. 99.
    T. Goto, Y. Kishi, S. Takahashi andY. Hirata, Tetrahedron21, 2059 (1965).PubMedGoogle Scholar
  100. 100.
    H. S. Mosher, F. A. Fuhrman, H. D. Buchwald andH. G. Fischer, Science144, 1100 (1964),PubMedGoogle Scholar
  101. 101.
    K. Tsuda, Naturwissenschaften53, 171 (1966).PubMedGoogle Scholar
  102. 102.
    R. B. Woodward, Pure appl. Chem.9, 49 (1964).Google Scholar
  103. 103.
    T. I. Benzer andM. A. Raftery, Proc. natn. Acad. Sci. USA69, 3634 (1972).Google Scholar
  104. 104.
    T. Tokuyama, J. Daly andB. Witkop, J. Am. chem. Soc.91, 3931 (1972).Google Scholar
  105. 105.
    R. E. Moore andP. J. Scheuer, Science172, 495 (1971).PubMedGoogle Scholar
  106. 106.
    B. W. Halstead,Poisonous and Venomous Marine Animals of the World (U.S. Government Printing Office, Washington, D.C. 1965–1970), vol. 1–3.Google Scholar
  107. 107.
    W. E. Van Heyningen, Schweiz. Z. Path. Bakt.18, 1018 (1955).Google Scholar
  108. 108.
    B. R. Das Gupta andD. A. Boroff, Biochim. biophys. Acta147, 603 (1967).PubMedGoogle Scholar
  109. 109.
    W. H. Beers andE. Reich, J. biol. Chem.244, 4473 (1969).PubMedGoogle Scholar
  110. 110.
    M. J. B. Holmes andW. L. Ryan, Infect. Immun.3, 133 (1971).Google Scholar
  111. 111.
    S. Olsnes andA. Pihl, Eur. J. Biochem.35, 179 (1973).PubMedGoogle Scholar
  112. 112.
    Acknowledgements. This work was supported by the Swedish Natural Science Research Council. I thank my colleagues Dr.David Eaker and Dr.Jan Fohlman for many discussions and valuable suggestions during the writing of this article.Google Scholar

Copyright information

© Birkhäuser Verlag 1973

Authors and Affiliations

  • Evert Karlsson
    • 1
  1. 1.Biokemiska InstitutionenUppsala 1Sweden

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