Journal of Chemical Ecology

, Volume 15, Issue 9, pp 2347–2355 | Cite as

Induction of cytochrome P450-mediated detoxification of xanthotoxin in the black swallowtail

  • Michael B. Cohen
  • May R. Berenbaum
  • Mary A. Schuler


Xanthotoxin is a phototoxic allomone found in many of the host plants of the black swallowtail,Papilio polyxenes (Lepidoptera: Papilionidae). When added to the diet of final instar larvae, xanthotoxin can induce the cytochrome P450 monooxygenase (P450) activity in midgut microsomes by which it is detoxified. Induction is dose-dependent, increasing sevenfold when larvae feed on parsley treated topically with xanthotoxin at 0.5 or 1.0% fresh weight. Although xanthotoxin exerts much of its toxic effects when photoactivated by ultraviolet light, induction of P450 activity did not differ in the presence or absence of ultraviolet light. Despite a 4.7-fold induction of xanthotoxin-metabolizing P450 activity, total P450 content measured in the same microsomal samples did not increase significantly. These data indicate that multiple forms of P450 exist in the black swallowtail midgut and that they are differentially induced by xanthotoxin.

Key words

Black swallowtail Papilio polyxenes Lepidoptera Papilionidae microsomal cytochrome P450 induction xanthotoxin furanocoumarins plant defensive compounds 


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  1. Berenbaum, M. 1978. Toxicity of a furanocoumarin to armyworms: A case of biosynthetic escape from insect herbivores.Science 201:532–534.Google Scholar
  2. Berenbaum, M. 1981. Patterns of furanocoumarin distribution and insect herbivory in the Umbelliferae: Plant chemistry and community structure.Ecology 62:1254–1266.Google Scholar
  3. Berenbaum, M. 1985. Brementown revisited: Interactions among allelochemicals in plants.Recent Adv. Phytochem. 19:139–169.Google Scholar
  4. Berenbaum, M., andFeeny, P. 1981. Toxicity of angular furanocoumarins to swallowtail butterflies: escalation in a coevolutionary arms race?Science 212:927–929.Google Scholar
  5. Berenbaum, M., Zangerl, A.R., andNitao, J.K. 1984. Furanocoumarins in seeds of wild and cultivated parsnip.Phytochemistry 23:1809–1810.Google Scholar
  6. Berenbaum, M.R., Zangerl, A.R., andNitao, J.K. 1986. Constraints on chemical coevolution: Wild parsnips and the parsnip webworm.Evolution 40:1215–1228.Google Scholar
  7. Brattsten, L.B. 1987. Inducibility of metabolic insecticide defenses in boll weevils and tobacco budworm caterpillars.Pestic. Bioch. Physiol. 27:13–23.Google Scholar
  8. Brattsten, L.B., Wilkinson, C.F., andEisner, T. 1977. Herbivore-plant interactions: Mixedfunction oxidases and secondary plant substances.Science 196:1349–1352.Google Scholar
  9. Bull, D.L., Ivie, G.W., Beier, R.C., andPryor, N.W. 1986. In vitro metabolism of a linear furanocoumarin (8-methoxypsoralen, xanthotoxin) by mixed-function oxidases of larvae of black swallowtail butterfly and fall armyworm.J. Chetn. Ecol. 12:885–892.Google Scholar
  10. Crankshaw, D.L., Hetnarski, H.K., andWilkinson, C.F. 1979. Microsomal NADPH-cytochrome c reductase from the midgut of the southern armyworm (Spodoptera eridania).Insect Biochem. 9:43–48.Google Scholar
  11. Dowd, P.P., Smith, C.M., andSparks, T.C. 1983. Detoxification of plant toxins by insects.Insect Biochem. 13:453–468.Google Scholar
  12. Feeny, P.P., Blau, W.S., andKareiva, P.M. 1985. Larval growth and survivorship of the black swallowtail butterfly in Central New York.Ecol. Monogr. 55:167–187.Google Scholar
  13. Gould, F. 1984. Mixed function oxidases and herbivore polyphagy: The devil's advocate position.Ecol. Entomol. 9:29–34.Google Scholar
  14. Hodgson, E. 1985. Microsomal mono-oxygenases, pp. 225–321,in G.A. Kerkut and L.I. Gilbert (eds.). Comprehensive Insect Physiology, Biochemistry, and Pharmacology, Vol. 11. Pergamon Press, New York.Google Scholar
  15. Ivie, G.W., Bull, D.L., Beier, R.C., Pryor, N.W., andOertli, E.H. 1983. Metabolic detoxification: Mechanism of insect resistance to plant psoralens.Science 221:374–376.Google Scholar
  16. Lee, K., andBerenbaum, M.R. 1989. Action of antioxidant enzymes and cytochrome P-450 monooxygenases in the cabbage looper in response to plant phototoxins.Arch. Insect Biochem. Physiol. 10:In press.Google Scholar
  17. Murray, R.D.H., Mendez, J., andBrown, S.A. 1982. The Natural Coumarins. J. Wiley & Sons, Ltd., Chichester.Google Scholar
  18. Nebert, D.W., andGonzalez, F.J. 1987. P450 genes: Structure, evolution, and regulation.Annu. Rev. Biochem. 56:945–993.Google Scholar
  19. Nitao, J.K. 1989. Enzymatic adaptation in a specialist herbivore for feeding on furanocoumarin-containing plants.Ecology In press.Google Scholar
  20. Nitao, J.K., andZangerl, A.R. 1987. Floral dgvelopment and chemical defense allocation in wild parsnip (Pastinaca saliva).Ecology 68:521–529.Google Scholar
  21. Omura, T., andSato, R. 1964. The carbon oonozide binding pigment of liver microsomes I. Evidence for its hemoprotein nature.J. Biol. Chetn. 239:2370–2378.Google Scholar
  22. Scott, J.A. 1986. The Butterflies of North America. Stanford University Press, Stanford, California.Google Scholar
  23. Tietz, H.M. 1972. An Index to the Described Life Histories, Early Stages anf Hosvs of the Macrolepidoptera of the Continental United States and Canada. Allyn Museum of Entomology, Sarasota, Florida.Google Scholar
  24. Yu, S.J. 1984. Inveractions of allelochemicals with detoxification enzymes of insecticide-susceptible and resistant fall armyworms.Pestic. Biochem. Physiol. 22:60–68.Google Scholar
  25. Yu, S. 1987. Microsomal oxidation of allelochemicans in generanist (Spodoptera frugiperda) and semispecialist (Cnticarsia gemmatalis) insect.J. Chem. Ecol. 13:423–436.Google Scholar
  26. Zangerl, A.R., andBazzaz, F.A. 1989. Allocation patterns, costs and benefits in plant defense,in R.S. Fritz and E.L. Simms (eds.). Ecology and Evolution of Plant Resistance. University of Chicago Press, Chicago. In press.Google Scholar
  27. Zangerl, A.R., andBerenbaum, M.R. 1987. Furanocoumarins in wild parsnip: effects of photosynthetically active radiation, ultraviolet light, and nutrients.Ecology 68:516–520.Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • Michael B. Cohen
    • 1
  • May R. Berenbaum
    • 1
  • Mary A. Schuler
    • 2
  1. 1.Department of EntomologyUniversity of IllinoisUrbana
  2. 2.Department of Plant BiologyUniversity of IllinoisUrbana

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