Papilio polyxenes

CYP6D1 of the housefly (Musca domestica) has been found to hydroxylate cyper-methrin and thereby provide a resistance mechanism to this compound and other pyrethroids in this species (Scott et al. 1998 see also Chapter 12). Also, this insect P450 can metabolize plant toxins such as the linear furanocoumarins xanthotoxin and bergapten (Ma et al. 1994). This metabolic capability has been found in the lepi-dopteran Papilio polyxenes (black swallowtail), a species that feeds almost exclusively on plants containing furanocoumarins. 

FIGURE 25.1 (See color insert following page 336.) Larval butterflies have distinctive coloration patterns (a) Monarch (Danaus plexippus yellow, white, and black), (b) Swallowtail (Papilio polyxenes asterius yellow, black, and green), (c) Queen (Danaus gillipus black, white, and yellow, some red coloration is also observable in this specimen), and (d) Atala (Eurnaceus atala florida red with yellow spots). 

Butterfly larvae (Monarch, Danaus plexippus Queen, Danaus gillipus Eastern Black Swallowtail, Papilio polyxenes asterius and Atala, Eurnaceus atala florida) were collected in South Florida approximately seven to eight days after hatching. The larvae were carefully dissected to remove the gut to prevent the contamination of the epidermis with the intestinal contents. The epidermis was... 

Most insect herbivores appear to be rather effectively repelled by furanocoumarin-containing plants (21-24). A notable exception to this generalization occurs among some butterflies of the family Paplllonldae, whose caterpillars are adapted to feed successfully and in fact preferentially on plants that contain linear, but not angular, furanocoumarlns (22). These circumstances prompted us to undertake studies with the black swallowtail butterfly (Papilio polyxenes) and radiolabeled furanocoumarlns in attempts to elucidate the nature of the Insect/furanocoumarln Interactions Involved. 

Metabolic Basis for Papilio polyxenes Resistance to Linear Furanocoumarlns... 

Figure 2. Major metabolites of xanthotoxin (8-methoxypsoralen) in last-stage larvae of the black swallowtail butterfly (Papilio polyxenes) and the fall armyworm (Spodoptera frugiperda).

The majority of swallowtail butterflies of the genus Papilio (family Papilionidae) exclusively utilize plants of the family Rutaceae as hosts, with a few species exploiting limited plant species of the families Apiaceae or Lauraceae. The North American black swallowtail butterfly, Papilio polyxenes, a specialist on members of carrot family (Apiaceae), has already been shown to lay eggs in response to a mixture of two chemotactile stimulants, luteolin 7-0-(6"-0-malonyl)-/3-D-glucoside and trawr-chlorogenic acid, identified from one of its major host plants, Daucus carota (wild carrot). Further study revealed that the oviposition response by the butterfly to another host plant, Pastinaca sativa (wild parsnip), was evoked by a combination of tyramine (1), trans-chlorogenic acid, and a neutral fraction from the plant.4... 

Ma, R., Cohen, M.B., Berenbaum, M.R., and Schuler, M.A., Black swallowtail (Papilio polyxenes) alleles encode cytochrome P450s that selectively metabolize linear furanocoumarins, Arch. Biochem. Biophys., 310, 332,1994. 

Hung, C.F., Harrison, T.L., Berenbaum, M.R. and Schuler, M.A. (1995) CYP6B3 a second furanocoumarin-inducible cytochrome P450 expressed in Papilio polyxenes. Insect Mol. Biol., 4, 149-60. 

Ivie, G.W., Bull, D.L., Beier, R.C. and Pryor, N.W. (1986) Comparative metabolism of [ H]psoralen and [ H]isopsoralen by black swallowtail butterfly (Papilio polyxenes Fabr.) caterpillars. /. Chem. Ecol., 11,869-82. 

Butterflies of the genus Papilio (Lepidoptera) often are associated with members of the Apiaceae. Xanthotoxin (19), a linear furanocoumarin, occurs in many plants of the Apiaceae. This compound is not appreciably toxic to the larvae of Papilio polyxenes which normally feed on umbelliferous plants. Most of these insects feed only on plants that have linear furanocoumarins and, in general, do not consume plants that make angular furanocoumarins. Angelicin (30)... 

Steinly, B. a. and M. Berenbaum, Histopathological effects of tannins on the midgut epithelium of Papilio polyxenes and Papi-lio glaucus, Entomol. Exp. Appl., 39, 3-9 (1985). 

Butterflies of the genus Papilio normally do not feed on plants that contain glucosinolates. Glucosinolates are toxic to the black swallowtail Papilio polyxenes) when larvae of this insect eat celery leaves that have been infiltrated with potassium allylglucosinolate (sinigrin) (Fig. 17.1) (15) at a concentration of 0.1% fresh weight (Chew, 1988 David and Gardiner, 1966). 

Wen Z, Pan L, Berenbaum MR, Schuler MA(2003) Metabolism of linear and angular furanocoumarins by Papilio polyxenes CYP6B1 co-expressed with NADPH cytochrome P450 reductase. Insect Biochem Mol Biol 33 937-947... 

Wen Z, Rupasinghe S, Niu G, Berenbaum MR, Schuler MA (2006) CYP6B1 and CYP6B3 of the black swallowtail (Papilio polyxenes) adaptive... 

Table 7.2 Larval growth performance of penultimate instar Papilio polyxenes larvae. Ithaca, N.Y...

Erickson, J. M. and Feeny, P. P. (1974) Sinigrin A chemical barrier to the black swallow-tail butterfly, Papilio polyxenes. Ecology, 55, 103-11. 

Finke, M. D. (1977) Factors controlling the seasonal foodplant utilization by larvae of the specialized herbivore, Papilio polyxenes (Lepidoptera). MS Thesis, Wright State University, Dayton, Ohio. 

Later, Feeny and collaborators (Feeny et al. 1983, 1988) compared several bioassays to determine the chemical(s) in wild carrot, Daucus carota, eliciting oviposition by the black swallowtail butterfly, Papilio polyxenes. A number of artificial substrates were tried, including artificial leaves made of (1) green construction paper (2) agar, cellulose powder, and green food coloring (following... 

Figure 5.5. A female Papilio polyxenes preparing to oviposit on an artificial leaf during a free-flight bioassay experiment. Reprinted from Feeny et al. (1983) with permission.

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