, Volume 43, Issue 8, pp 943–946 | Cite as

Pyrrolizidine alkaloids in overwintering monarch butterflies (Danaus plexippus) from mexico

  • R. B. Kelley
  • J. N. Seiber
  • A. D. Jones
  • H. J. Segall
  • L. P. Brower
Short Communications


North American populations of the monarch butterfly,Danaus plexippus, have been found to contain pyrrolizidine alkaloids and their N-oxides. Analytical methods (TLC, GC, and GC/MS) have been developed to isolate, quantitate, and structurally elucidate the alkaloids. Examples of at least two classes of pyrrolizidine alkaloids have been identified, the macrocyclic diesters, senecionine, integerrimine, and seneciphylline, and the monoesters, echinatine, intermedine, and lycopsamine.

Key words

Pyrrolizidine alkaloids macrocyclic diesters monoesters dihydropyrrolizines Lepidoptera Danaus plexippus monarch butterflies overwintering asteraceae Boraginaceae ecological chemistry 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 2.
    Ackery, P.R., and Vane-Wright, R.I., Milkweed Butterflies: Their Cladistics and Biology. British Museum, London 1984.Google Scholar
  2. 3.
    Brower, L.P., Chemical Defence in Butterflies, The Biology of Butterflies. Eds R.I. Vane-Wright and P.R. Ackery. Academic Press, London 1984.Google Scholar
  3. 4.
    Meinwald, J., Chalmers, A.M., Pliske, T.E., and Eisner, T., Tetrahedron Lett.1968, 4893.Google Scholar
  4. 5.
    Edgar, J.A., Culvenor, C.C.J., and Smith, L.W., Experientia27 (1971) 761.Google Scholar
  5. 6.
    Edgar, J.A., Culvenor, C.C.J., and Robinson, G.S., J. Aust. ent. Soc.12 (1973) 144.Google Scholar
  6. 7.
    Edgar, J.A., Cockrum, P.A., and Frahn, J.L., Experientia32 (1976) 1535.CrossRefGoogle Scholar
  7. 8.
    Edgar, J.A., J. Zool. Lond.196 (1982) 385.Google Scholar
  8. 9.
    Rothschild, M., and Edgar, J.A., J. Zool., Lond.186 (1978) 347.Google Scholar
  9. 10.
    Boppré, M., Naturwissenschaften73 (1986) 17.CrossRefGoogle Scholar
  10. 11.
    Edgar, J.A., Culvenor, C.C.J., and Pliske, T.E., Nature250 (1974) 646.PubMedGoogle Scholar
  11. 12.
    Pliske, T.E., Envir. Ent.4 (1975) 455.Google Scholar
  12. 13.
    Rothschild, M., and Marsh, N., Ent. exp. appl.24 (1978) 637.Google Scholar
  13. 14.
    Brower, L.P., Calvert, W.H., Hedrick, L.E., and Christian, J., J. Lepid. Soc.31 (1977) 232.Google Scholar
  14. 15.
    Brower, L.P., Migration: Mechanisms and Adaptive Significance, Marine Science 27 (supplement). Ed. M.A. Rankin. Univ. Texas Contrib., Austin 1985.Google Scholar
  15. 16.
    Huizing, H.J., and Malingre, T.M., J. Chromat.173 (1979) 187.CrossRefGoogle Scholar
  16. 17.
    Huizing, H.J., and Malingre, T.M., J. Chromat.205 (1981) 218.CrossRefGoogle Scholar
  17. 18.
    Pedersen, E., Archs pharmac. chem. Sci.3 (1975) 55.Google Scholar
  18. 19.
    Huizing, H.J., de Boer, F., and Malingre, T.M., J. Chromat.195 (1980) 407.CrossRefGoogle Scholar
  19. 20.
    Molyneux, R.J., and Roitman, J.N., J. Chromat.195 (1980) 412.CrossRefGoogle Scholar
  20. 21.
    Culvenor, C.C.J., Edgar, J.A., Smith, L.W., and Tweeddale, H.J., Aust. J. Chem.23 (1970) 1869.Google Scholar
  21. 22.
    Robins, D.J., Fortschr. Chem. org. NatStoffe41 (1982) 115.Google Scholar
  22. 23.
    Correll, D.S., and Johnston, M.C., Manual of the Vascular Plants of Texas, Texas Research Foundation, vol. 6. Renner, Texas 1970.Google Scholar
  23. 24.
    Seiber, J.N., Lee, S.M., and Benson, J.M., Handbook of Natural Toxins, vol. 1, Plant and Fungal Toxins. Eds R.F. Keeler and A.T. Tu. Marcel Dekker, New York 1983.Google Scholar
  24. 25.
    Marsh, N., and Rothschild, M., J. Zool., Lond.174 (1974) 89.Google Scholar
  25. 26.
    Eisner, T., Chemistry, Defense and Survival: Case Studies and Selected Topics, Insect Biology in the Future. Eds M. Locke and D.S. Smith. Academic Press, London 1980.Google Scholar
  26. 27.
    Brown, K., Revta bras. Biol.44 (1984) 435.Google Scholar
  27. 28.
    Rothschild, M., Alpin, R.T., Cockrum, P.A., Edgar, J.A., Fairweather, P., and Lees, R., Biol. J. Linn. Soc.,12 (1979) 305.Google Scholar
  28. 29.
    Seiber, J.N., Brower, L.P., Lee, S.M., McChesney, M.M., Cheung, H.T.A., Nelson, C.J., and Watson, T.R., J. chem. Ecol.12 (1986) 1157.CrossRefGoogle Scholar

Copyright information

© Birkhäuser Verlag 1987

Authors and Affiliations

  • R. B. Kelley
    • 1
    • 2
  • J. N. Seiber
    • 1
    • 2
  • A. D. Jones
    • 1
    • 2
  • H. J. Segall
    • 1
    • 2
  • L. P. Brower
    • 1
    • 2
  1. 1.Department of Environmental Toxicology, Facility for Advanced Instrumentation and Department of Veterinary Pharmacology and ToxicologyUniversity of CaliforniaDavisUSA
  2. 2.Department of ZoologyUniversity of FloridaGainesvilleUSA

Personalised recommendations