Isolation and characterization of CYP6B4, a furanocoumarin-inducible cytochrome P450 from a polyphagous caterpillar (Lepidoptera: Papilionidae)

Insect Biochemistry and Molecular Biology

Volumn 27, Issue 5, 1997, Pages 377-385

  Hung, Chien Fu ^a   Berenbaum, May R ^a   Schuler, Mary A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Baculovirus expression; Cytochrome P450 monooxygenases; Furanocoumarin metabolism; Papilio glaucus

Indexed keywords

5-METHOXYPSORALEN; ANGELICIN; BERGAPTEN; COMPLEMENTARY DNA; COUMARIN DERIVATIVE; CYTOCHROME P450; DRUG DERIVATIVE; FUROCOUMARIN DERIVATIVE; ISOPIMPINELLIN; METHOXSALEN; PENTOSALEN; PSORALEN; PSORALEN DERIVATIVE; SPHONDIN; TRIOXYSALEN;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; BACULOVIRUS; BUTTERFLY; CELL LINE; CHEMISTRY; CLONING VECTOR; CONTROLLED STUDY; ENZYME INDUCTION; ENZYMOLOGY; FEMALE; GENETIC RECOMBINATION; GENETICS; ISOLATION AND PURIFICATION; LEPIDOPTERA; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NONHUMAN; PROTEIN EXPRESSION; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; ANIMALS; BACULOVIRIDAE; BUTTERFLIES; CELL LINE; CLONING, MOLECULAR; COUMARINS; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; ENZYME INDUCTION; FEMALE; GENETIC VECTORS; METHOXSALEN; MOLECULAR SEQUENCE DATA; PSORALENS; RECOMBINATION, GENETIC; SEQUENCE HOMOLOGY, AMINO ACID;

ANIMALIA; DROSOPHILA MELANOGASTER; GLAUCUS; INSECTA; LEPIDOPTERA; MELANOGASTER; MUSCA DOMESTICA; PANTHERA TIGRIS; PAPILIO GLAUCUS; PAPILIO POLYXENES; PAPILIONIDAE; UNIDENTIFIED BACULOVIRUS;

EID: 0031149268     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0965-1748(97)00009-X     Document Type: Article

References (26)

1. Berenbaum M. R. (1991a) Coumarins. In Herbivores: Their Interactions with Secondary Plant Metabolites (edited by Rosenthal G. and Berenbaum M.), Vol. 1, pp. 221-249. Academic Press, San Diego.
2. Berenbaum M. R. (1991b) Comparative processing of allelochemicals in the Papilionidae (Lepidoptera). Arch. Insect Biochem. Physiol. 17, 213-222.
3. Berenbaum M. R. (1995) Metabolic detoxification of plant prooxidants. In Oxidative Stress and Antioxidant Defenses' in Biology (edited by Ahmad S.), pp. 181-209. Chapman and Hall, New York.
4. Berenbaum M. R. and Zangerl A. R. (1993) Furanocoumarin metabolism in Papilio polyxenes: genetic variability, biochemistry and ecological significance. Oecologia 95, 370-375.
5. Berenbaum M. R. and Zangerl A. R. (1996) Phytochemical diversity: adaptation or random variation? Recent Adv. Phytochem. 30, 1-24.
6. Berenbaum M. R., Favret C. and Schuler M. A. (1996) On defining "key innovations" in an adaptive radiation; cytochrome P450s and Papilionidae. Am. Naturalist 148, S139-S155.
7. Bossart J. L. and Scriber J. M. (1995) Genetic variation in oviposition preference in tiger swallowtail butterflies: interspecific, interpopulation and interindividual comparisons. In Swallowtail Butterflies: Their Ecology and Evolutionary Biology (edited by Scriber J. M., Tsubaki Y. and Lederhouse R. C.), pp. 183-193. Scientific Pub., Gainesville, FL.
8. Cohen M. B., Berenbaum M. R. and Schuler M. A. (1989) Induction of cytochrome P450-mediated metabolism of xanthotoxin in the black swallowtail. J. Chem. Ecol. 15, 2347-2355.
9. Cohen M. B., Schuler M. A. and Berenbaum M. R. (1992) A host-inducible cytochrome P450 from a host-specific caterpillar: molecular cloning and evolution. Proc. Natl. Acad. Sci. U.S.A. 89, 10920-10924.
10. Feyereisen R., Koener J. F., Farnsworth D. E. and Nebert D. W. (1989) Isolation and sequence of a cDNA encoding a cytochrome P-450 from an insecticide-resistant strain of the house fly, Musca domestica. Proc. Natl. Acad. Sci. U.S.A. 86, 1465-1469.
11. Gotoh O. (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 267, 83-90.
12. Hung C.-F., Prapaipong H., Berenbaum M. R. and Schuler M. A. (1995a) Differential induction of cytochrome P450 transcripts in Papilio polyxenes by linear and angular furanocoumarins. Insect Biochem. Molec. Biol. 25, 89-99.
13. Hung C.-F., Harrison T. L., Berenbaum M. R. and Schuler M. A. (1995b) CYP6B3: a second furanocoumarin-inducible cytochrome P450 expressed in Papilio polyxenes. Insect Molec. Biol. 4, 149-160.
14. Hung C.-F., Holzmacher R., Connolly E., Berenbaum M. R. and Schuler M. A. (1996) Conserved promoter elements in the CYP6B gene family suggest common ancestry for cytochrome P450 monooxygenases mediating furanocoumarin detoxification. Proc. Natl. Acad. Sci. U.S.A. 93, 12200-12205.
15. Ma R., Cohen M. B., Berenbaum M. R. and Schuler M. A. (1994) Black swallowtail (Papilio polyxenes) alleles encode cytochrome P450s that selectively metabolize linear furanocoumarins. Arch. Biochem. Biophys. 310, 332-340.
16. Murray R. D. H., Mendez J. and Brown S. A. (1982) The Natural Coumarins. 702 pp. J. Wiley and Sons, Chichester, U.K.
17. Nelson D. R., Kamataki T., Waxman D. J., Guengerich F. P., Estabrook R. W., Feyereisen R., Gonzalez F. J., Coon M. J., Gunsalus I. C., Gotoh O., Okuda K. and Nebert D. W. (1993) The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol. 12, 1-51.
18. Nelson D. R., Koymans L., Kamataki T., Stegeman J. J., Feyereisen R., Waxman D. J., Waterman M. R., Gotoh O., Coon M. J., Estabrook R. W., Gunsalus I. C. and Nebert D. W. (1996) P450 superfamily: update on new sequences, gene mapping, accession numbers, and nomenclature. Pharmacogenetics 6, 1-41.
19. O'Reilly D. R., Miller L. K. and Luckow V. A. (1992) Baculovirus Expression Vectors: a Laboratory Manual. W. H. Freeman and Co., N.Y.
20. Prapaipong H., Berenbaum M. R. and Schuler M. A. (1994) Transcriptional regulation of the Papilio polyxenes CYP6B1 gene. Nucl. Acids Res. 22, 3210-3217.
21. Prapaipong H., Berenbaum M. R. and Schuler M. A. (1997) Regulatory elements in the promoter of CYP6B1v3, an insect P450 gene induced by plant furanocoumarins. Submitted.
22. Scriber J. M. (1988) Tale of the tiger: beringial biogeography, binomial classification, and breakfast choices in the Papilio glaucus complex of butterflies. In Chemical Mediation of Coevolution (edited by Spencer K. C.), pp. 241-301. Academic Press, New York.
23. Scriber J.M. (1995) Overview of swallowtail butterflies: taxonomic and distributional latitude. In Swallowtail Butterflies: Their Ecology and Evolutionary Biology (edited by Scriber J. M., Tsubaki Y. and Lederhouse R. C.), pp. 3-8. Scientific Pub., Gainesville, FL.
24. Scriber J. M., Lederhouse R. C. and Hagen R. H. (1991) Foodplant and evolution within Papilio glaucus and Papilio troilus species groups (Lepidoptera: Papilionidae). In Plant-Animal Interactions: Evolutionary Ecology in Tropical and Temperate Regions (edited by Price P. W., Lewinsohn T. M., Fernandes G. W. and Benson W. W.), pp. 341-373. J. Wiley and Sons, New York.
25. Wang X.-P. and Hobbs A. A. (1995) Isolation and sequence analysis of a cDNA clone for a pyrethroid inducible cytochrome P450 from Helicoverpa armigera. Insect Biochem. Molec. Biol. 25, 1001-1009.
26. Waters L. C., Zelhof A. C., Shaw B. J. and Ch'ang L.-Y. (1992) Possible involvement of the long terminal repeat of transposable element 17.6 in regulating expression of an insecticide resistance-associated P450 gene in Drosophila. Proc. Natl. Acad. Sci. U.S.A. 89, 4855-4859.