Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura

Insect Biochemistry and Molecular Biology

Volumn 35, Issue 10, 2005, Pages 1083-1099

  Hartmann, T ^a   Theuring, C ^a   Beuerle, T ^a   Bernays, E A ^b   Singer, M S ^c  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF ARIZONA   (United States)

^c WESLEYAN UNIVERSITY   (United States)

Author keywords

Alkaloid processing; Alkaloid sequestration; Callimorphines; Chemical defense; Creatonotines; Grammia geneura (Lepidoptera; Arctiidae); Insect alkaloids; Pyrrolizidine alkaloids

Indexed keywords

PYRROLIZIDINE ALKALOID;

ANIMAL; ARTICLE; ASTERACEAE; GROWTH, DEVELOPMENT AND AGING; LARVA; METABOLISM; MOTH; PARASITOLOGY; PATHOGENICITY; PLANT; PLANT DISEASE;

ANIMALS; ASTERACEAE; LARVA; MOTHS; PLANT DISEASES; PLANTS; PYRROLIZIDINE ALKALOIDS;

APOCYNACEAE; ARCTIIDAE; ASTERACEAE; BORAGINACEAE; ESTIGMENE ACREA; EUPATORIEAE; FABACEAE; GRAMMIA GENEURA; INSECTA; LEPIDOPTERA; ORCHIDACEAE; SENECIONEAE;

EID: 23444458235     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibmb.2005.05.011     Document Type: Article

References (48)

1. R.T. Aplin, and M. Rothschild Poisonous alkaloids in the body tissue of the garden tiger moth (Arctia caja L.) (Lepidoptera) and the cinnabar moth (Tyria jacobaeae L.) A. De Vries E. Kochva Toxins of animal and plant origin 1972 Gordon & Breach Science Publication New York 579 595
2. R.T. Aplin, M.H. Benn, and M Rothschild Poisonos alkaloids in the body tissues of the cinnabar moth (Callimorpha jacobaeae L) Nature 219 1968 747 748
3. E.A. Bernays, R.F. Chapman, and T Hartmann A highly sensitive taste receptor cell for pyrrolizidine alkaloids in the lateral galeal sensillum of a polyphagous caterpillar, Estigmene acrea J. Comp. Physiol. A 188 2002 715 723
4. E.A. Bernays, R.F. Chapman, and T. Hartmann A taste receptor neuron dedicated to the perception of pyrrolizidine alkaloids in the medial galeal sensillum of two polyphagous arctiid caterpillars Physiol. Entomol. 27 2002 1 10
5. M. Boppré Insects pharmacophagously utilizing defensive plant chemicals (pyrrolizidine alkaloids) Naturwissenschaften 73 1986 17 26
6. W.E. Conner, and S.J. Weller A quest for alkaloids: the curious relationship between tiger moths and plants containing pyrrolizidine alkaloids R.T. Cardé J.G. Millar Advances in Insect Chemical Ecology 2004 University Press Cambridge 248 282
7. W.E. Conner, B. Roach, E. Benedict, J. Meinwald, and T. Eisner Courtship pheromone production and body size as correlates of larval diet in males of the arctiid moth Utetheisa ornatrix J. Chem. Ecol. 16 2 1990 543 552
8. Davenport, J.W., Conner, W.E., 2003. Dietary alkaloids and the development of androconial organs in Estigmene acrea. J. Insect Sci. Tucson 3:3, available online: insectscience.org/3.3.
9. D.E. Dussourd, C.A. Harvis, J. Meinwald, and T. Eisner Pheromonal Advertisement of a Nuptial gift by a male moth Utetheisa ornatrix Proc. Natl. Acad. Sci. USA 88 1991 9224 9227
10. D.E. Dussourd, K. Ubik, C. Harvis, J. Resch, J. Meinwald, and T. Eisner Biparental defensive endowment of eggs with acquired plant alkaloid in the moth Utetheisa ornatrix Proc. Natl. Acad. Sci. USA 85 1988 5992 5996
11. J.A. Edgar, C.C.J. Culvenor, P.A. Cockrum, and L.W Smith Callimorphine: identification and synthesis of the cinnabar moth "metabolite" Tetrahedron Lett 21 1980 1383 1384
12. A. Ehmke, L. Witte, A. Biller, and T Hartmann Sequestration, N-oxidation and transformation of plant pyrrolizidine alkaloids by the arctiid moth Tyria jacobaeae L Z. Naturforsch. 45c 1990 1185 1192
13. T. Eisner, C. Rossini, A. Gonzalez, V.K. Iyengar, M.V.S. Siegler, and S.R. Smedley Paternal investment in egg defence M. Hilker T. Meiners Chemoecology of Insect Eggs and Egg Deposition 2002 Blackwell Publishing Oxford 91 116
14. H. Frei, J. Lüthy, J. Bräuchli, U. Zweifel, F.E. Wurgler, and C Schlatter Structure/activity relationships of the genotoxic potencies of sixteen pyrrolizidine alkaloids assayed for the induction of somatic mutation and recombination in wing cells of Drosophila melanogaster Chem. Biol. Interact. 83 1992 1 22
15. P.P. Fu, Q. Xia, G. Lin, and M.W. Chou Pyrrolizidine alkaloids - genotoxicity, metabolism enzymes, metabolic activation, and mechanisms Drug Metab. Rev. 36 2004 1 55
16. T Hartmann Chemical ecology of pyrrolizidine alkaloids Planta 207 1999 483 495
17. T. Hartmann, and D. Ober Biosynthesis and metabolism of pyrrolizidine alkaloids in plants and specialized insect herbivores F.J. Leeper J.C. Vederas Topics in Current Chemistry: Biosynthesis - Aromatic Polyketides, Isoprenoids, Alkaloids 2000 Springer Berlin 207 244
18. T. Hartmann, and L. Witte Pyrrolizidine alkaloids: chemical, biological and chemoecological aspects S.W. Pelletier Alkaloids: Chemical and Biological Perspectives 1995 Pergamon Press Oxford 155 233
19. T. Hartmann, and M. Zimmer Organ-specific distribution and accumulation of pyrrolizidine alkaloids during the life history of two annual Senecio species J. Plant Physiol. 122 1986 67 80
20. T. Hartmann, A. Biller, L. Witte, L. Ernst, and M. Boppre Transformation of plant pyrrolizidine alkaloids into novel insect alkaloids by arctiid moths (Lepidoptera) Biochem. Syst. Ecol. 18 1990 549 554
21. T. Hartmann, C. Theuring, L. Witte, and J.M. Pasteels Sequestration, metabolism and partial synthesis of tertiary pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi Insect Biochem. Mol. Biol. 31 2001 1041 1056
22. T. Hartmann, C. Theuring, and E.A. Bernays Are insect-synthesized retronecine esters (creatonotines) the precursors of the male courtship pheromone in the arctiid moth Estigmene acrea? J. Chem. Ecol. 29 2003 2603 2608
23. T. Hartmann, C. Theuring, L. Witte, S. Schulz, and J.M. Pasteels Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi Insect Biochem. Mol. Biol. 33 2003 515 523
24. T. Hartmann, C. Theuring, T. Beuerle, and E.A. Bernays Phenological fate of plant-acquired pyrrolizidine alkaloids in the polyphagous arctiid Estigmene acrea Chemoecology 14 2004 207 216
25. T. Hartmann, C. Theuring, T. Beuerle, L. Ernst, M.S. Singer, and E.A. Bernays Acquired and partially de novo synthesized pyrrolizidine alkaloids in two polyphagous arctiids and the alkaloid profiles of their larval food-plants J. Chem. Ecol. 30 2004 229 254
26. T. Hartmann, C. Theuring, T. Beuerle, N. Klewer, S. Schulz, M.S. Singer, and E.A. Bernays Specific recognition, detoxification and metabolism of pyrrolizidine alkaloids by the polyphagous arctiid Estigmene acrea Insect Biochem. Mol. Biol. 35 2005 391 411
27. V.K. Iyengar, C. Rossini, and T. Eisner Precopulatory assessment of male quality in an arctiid moth (Utetheisa ornatrix): hydroxydanaidal is the only criterion of choice Behav. Ecol. Sociobiol. 49 2001 283 288
28. K. Jenett-Siems, T. Schimming, M. Kaloga, E. Eich, K. Siems, M.P. Gupta, L. Witte, and T. Hartmann Pyrrolizidine alkaloids of Ipomoea hederifolia and related species Phytochemistry 47 1998 1551 1560
29. Jordan, A.T., Jones, T.H., Conner, W.E., 2005. If you've got it, flaunt it: Ingested alkaloids affect corematal display behavior in the salt marsh moth, Estigmene acrea. J. Insect Sci. 5:1, available online: insectscience.org/5.1.
30. K.M. L'Empereur, Y. Li, and F.R. Stermitz Pyrrolizidine alkaloids from Hackelia californica and Gnophaela latipennis, an H. californica-hosted arctiid moth J. Nat. Prod. 54 1989 360 366
31. R. Lindigkeit, A. Biller, M. Buch, H.M. Schiebel, M. Boppré, and T. Hartmann The two faces of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids Eur. J. Biochem. 245 1997 626 636
32. A.R. Mattocks Chemistry and Toxicology of Pyrrolizidine Alkaloids 1986 Academic Press London
33. C. Naumann, T. Hartmann, and D. Ober Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae Proc. Natl. Acad. Sci. USA 99 2002 6085 6090
34. M. Reina, C.A. Gonzalez, C. Gutierrez, R. Cabrera, J. Henriquez, and L. Villarroel Bioactive saturated pyrrolizidine alkaloids from Heliotropium floridum Phytochemistry Oxford 46 1997 845 853
35. D. Schneider The strange fate of pyrrolizidine alkaloids R.F. Chapman E.A. Bernays J.G. Stoffolano Perspectives in chemoreception and behavior 1987 Springer 123 142
36. S. Schulz, W. Francke, M. Boppré, T. Eisner, and J. Meinwald Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae) Proc. Natl. Acad. Sci. USA 90 1993 6834 6838
37. M.S. Singer, and J.O. Stireman III How foraging tactics determine host-plant use by a polyphagous caterpillar Oecologia 129 2001 98 105
38. M.S. Singer, Y. Carriere, C. Theuring, and T. Hartmann Disentangling food quality from resistance against parasitoids: diet choice by a generalist caterpillar Am. Nat. 164 2004 423 429
39. M.S. Singer, D. Rodrigues, J.O. Stireman III, and Y. Carriere Roles of food quality and enemy-free space in host use by a generalist insect herbivore Ecology 85 2004 2747 2753
40. A. Termonia, J.M. Pasteels, D.M. Windsor, and M.C Milinkovitch Dual chemical sequestration: a key mechanism in transitions among ecological specialization Proc. R. Soc. London B 269 2002 1 6
41. J.R. Trigo, L. Witte, K.S. Brown Jr., T. Hartmann, and L.E.S. Barata Pyrrolizidine alkaloids in the arctiid moth Hyalurga syma J. Chem. Ecol. 19 1993 669 679
42. J.R. Trigo, L.E.S. Barata, and K.S. Brown Jr. Stereochemical inversion of pyrrolizidine alkaloids by Mechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance J. Chem. Ecol. 20 1994 2883 2899
43. J.R. Trigo, K.S. Brown, S.A. Henriques, and L.E.S. Barata Qualitative patterns of pyrrolizidine alkaloids in ithomiine butterflies Biochem. Syst. Ecol. 24 1996 181 188
44. S.J. Weller, N.L. Jacobson, and W.E. Conner The evolution of chemical defences and mating systems in tiger moths (Lepidoptera: Arctiidae) Bot. J. Linn. Soc. 68 1999 557 578
45. M. Wink, D. Schneider, and L. Witte Biosynthesis of pyrrolizidine alkaloid-derived pheromones in the arctiid moth, Creatonotos transiens: stereochemical conversion of heliotrine Z. Naturforsch. 43c 1988 737 741
46. L. Witte, A. Ehmke, and T. Hartmann Interspecific flow of pyrrolizidine alkaloids; from plants via aphids to ladybirds Naturwissenschaften 77 1990 540 543
47. L. Witte, P. Rubiolo, C. Bicchi, and T. Hartmann Comparative analysis of pyrrolizidine alkaloids from natural sources by gas chromatography-mass spectrometry Phytochemistry 32 1993 187 196
48. R.T. Yamamoto Mass rearing of the tobacco hornworm II. Larval rearing and pupation J. Econ. Entomol. 62 1969 1427 1431