Abstract
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.
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References
Berenbaum, M. 1978. Toxicity of a furanocoumarin to armyworms: A case of biosynthetic escape from insect herbivores.Science 201:532–534.
Berenbaum, M. 1981. Patterns of furanocoumarin distribution and insect herbivory in the Umbelliferae: Plant chemistry and community structure.Ecology 62:1254–1266.
Berenbaum, M. 1985. Brementown revisited: Interactions among allelochemicals in plants.Recent Adv. Phytochem. 19:139–169.
Berenbaum, M., andFeeny, P. 1981. Toxicity of angular furanocoumarins to swallowtail butterflies: escalation in a coevolutionary arms race?Science 212:927–929.
Berenbaum, M., Zangerl, A.R., andNitao, J.K. 1984. Furanocoumarins in seeds of wild and cultivated parsnip.Phytochemistry 23:1809–1810.
Berenbaum, M.R., Zangerl, A.R., andNitao, J.K. 1986. Constraints on chemical coevolution: Wild parsnips and the parsnip webworm.Evolution 40:1215–1228.
Brattsten, L.B. 1987. Inducibility of metabolic insecticide defenses in boll weevils and tobacco budworm caterpillars.Pestic. Bioch. Physiol. 27:13–23.
Brattsten, L.B., Wilkinson, C.F., andEisner, T. 1977. Herbivore-plant interactions: Mixedfunction oxidases and secondary plant substances.Science 196:1349–1352.
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.
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.
Dowd, P.P., Smith, C.M., andSparks, T.C. 1983. Detoxification of plant toxins by insects.Insect Biochem. 13:453–468.
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.
Gould, F. 1984. Mixed function oxidases and herbivore polyphagy: The devil's advocate position.Ecol. Entomol. 9:29–34.
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.
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.
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.
Murray, R.D.H., Mendez, J., andBrown, S.A. 1982. The Natural Coumarins. J. Wiley & Sons, Ltd., Chichester.
Nebert, D.W., andGonzalez, F.J. 1987. P450 genes: Structure, evolution, and regulation.Annu. Rev. Biochem. 56:945–993.
Nitao, J.K. 1989. Enzymatic adaptation in a specialist herbivore for feeding on furanocoumarin-containing plants.Ecology In press.
Nitao, J.K., andZangerl, A.R. 1987. Floral dgvelopment and chemical defense allocation in wild parsnip (Pastinaca saliva).Ecology 68:521–529.
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.
Scott, J.A. 1986. The Butterflies of North America. Stanford University Press, Stanford, California.
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.
Yu, S.J. 1984. Inveractions of allelochemicals with detoxification enzymes of insecticide-susceptible and resistant fall armyworms.Pestic. Biochem. Physiol. 22:60–68.
Yu, S. 1987. Microsomal oxidation of allelochemicans in generanist (Spodoptera frugiperda) and semispecialist (Cnticarsia gemmatalis) insect.J. Chem. Ecol. 13:423–436.
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.
Zangerl, A.R., andBerenbaum, M.R. 1987. Furanocoumarins in wild parsnip: effects of photosynthetically active radiation, ultraviolet light, and nutrients.Ecology 68:516–520.
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Cohen, M.B., Berenbaum, M.R. & Schuler, M.A. Induction of cytochrome P450-mediated detoxification of xanthotoxin in the black swallowtail. J Chem Ecol 15, 2347–2355 (1989). https://doi.org/10.1007/BF01012086
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DOI: https://doi.org/10.1007/BF01012086