Pyrrolizidine alkaloids and pharmacophagous Lepidoptera visitors of Prestonia amabilis (Apocynaceae) in a montane rainforest in Ecuador

Annals of the Missouri Botanical Garden

Volumn 94, Issue 2, 2007, Pages 463-473

  Brehm, Gunnar ^a,b   Hartmann, Thomas ^c   Willmott, Keith ^d  

^a UNIVERSITY OF BAYREUTH   (Germany)

^b Institut für Spezielle Zoologie   (Germany)

^c TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^d UNIVERSITY OF FLORIDA   (United States)

Author keywords

Apocynaceae (Echiteae); Arctiidae; Chemical defense; Ctenuchini; Euchromiini; Ithomiinae; Prestonia; Pyrrolizidine alkaloid

Indexed keywords

APOCYNACEAE; ARCTIIDAE; DANAINAE; ECHITEAE; LEPIDOPTERA; NYMPHALIDAE; PAPILIONOIDEA; PRESTONIA; PRESTONIA AMABILIS;

EID: 34547650732     PISSN: 00266493     EISSN: None     Source Type: Journal    
DOI: 10.3417/0026-6493(2007)94[463:PAAPLV]2.0.CO;2     Document Type: Article

References (55)

1. Ackery, P. R. & R. I. Vane-Wright. 1984. Milkweed Butterflies: Their Cladistics and Biology. British Museum, London.
2. Beebe, W. 1955. Two little-known selective insect attractants. Zoologica 40: 27.
3. _ & R. Kenedy. 1957. Habits, palatability and mimicry in thirteen ctenuchid moth species from Trinidad, B.W.I. Zoologica 42: 147-158.
4. Bernays, E. & M. S. Singer. 2005. Taste alteration and endoparasites. Nature 436: 476.
5. _, R. F. Chapman & T. Hartmann. 2002. A highly sensitive taste receptor cell for pyrrolizidine alkaloids in the lateral galeal sensillum of a polyphagous caterpillar, Estigmene acrea. J. Comp. Physiol. A Neuroethol. Sens. Neural Behav. Physiol. 188: 715-723.
6. Boppré, M. 1984. Redefining "Pharmacophagy." J. Chem. Ecol. 10: 1151-1154.
7. _. 1990. Lepidoptera and pyrrolizidine alkaloids: Exemplification of complexity in chemical ecology. J. Chem. Ecol. 16: 165-185.
8. Brehm, G., L. M. Pitkin, N. Hilt & K. Fiedler. 2005. Montane Andean rain forests are a global diversity hotspot of geometrid moths. J. Biogeogr. 32: 1621-1627.
9. Brower, A. V. Z. 2000. Phylogenetic relationships among the Nymphalidae (Lepidoptera) inferred from partial sequences of the wingless gene. Proc. Roy. Soc. London, Ser. B, Biol. Sci. 267: 1201-1211.
10. Brown Jr., K. S. 1984. Adult-obtained pyrrolizidine alkaloids defend Ithomiine butterflies against a spider predator. Nature 309: 707-709.
11. _. 1985. Chemical ecology of dehydropyrrolizidine alkaloids in adult Ithomiinae (Lepidoptera: Nymphalidae). Revista Brasil. Biol. 44: 435-460.
12. _. 1987. Chemistry at the Solanaceae/Ithomiinae interface. Ann. Missouri Bot. Gard. 74: 359-397.
13. Brückmann, M., J. R. Trigo, M. A. Foglio & T. Hartmann. 2000. Storage and metabolism of radioactively labeled pyrrolizidine alkaloids by butterflies and larvae of Mechanitis polymnia (Lepidoptera: Nymphalidae, Ithomiinae). Chemoecology 10: 25-32.
14. Collins, C. T. & A. Watson. 1983. Field observations of bird predation on neotropical moths. Biotropica 15: 53-60.
15. DeVries, P. J. 1987. The butterflies of Costa Rica, Vol. 1. Princeton Ujniv. Press, Princeton.
16. _ & F. G. Stiles. 1990. Attraction of pyrrolizidine alkaloid seeking Lepidoptera to Epidendrum paniculatum orchids. Biotropica 22: 290-297.
17. Drummond, B. A. & K. S. Brown Jr. 1987. Ithomiinae (Lepidoptera; Nymphalidae): Summary of known larval foodplants. Ann. Missouri Bot. Gard. 74: 341-358.
18. Edgar, J. A. 1984. Parsonsieae: Ancestral larval foodplants of the Danainae and Ithomiinae. Pp. 91-93 in P. R. Ackery & R. I. Vane-Wright (editors), The Biology of Butterflies. The Royal Entomological Society, London.
19. _ & T. E. Pliske. 1976. Isolation of a lactone structurally related to the esterifying acids of pyrrolizidine alkaloids from the costal fringes of male Ithomiiinae. J. Chem. Ecol. 2: 263-270.
20. Ehmke, A., M. Rahier, J. M. Pasteels, C. Theuring & T. Hartmann. 1999. Sequestration, maintenance, and tissue distribution of pyrrolizidine alkaloid N-oxides in larvae of two Oreina species. J. Chem. Ecol. 25: 2385-2395.
21. Ehrlich, P. R. 1958. The comparative morphology, phylogeny and classification of the butterflies (Lepidoptera: Papilionoidea). Univ. Kansas Sci. Bull. 39: 305-370.
22. Eisner, T., C. Rossini, A. Gonzalez, V. K. Iyengar, M. V. S. Siegler & S. R. Smedley. 2002. Paternal investment in egg defence. Pp. 91-116 in M. Hilker & T. Meiners (editors), Chemoecology of Insect Eggs and Egg Deposition. Blackwell, Oxford.
23. Freitas, A. V. L. & K. S. Brown Jr. 2004. Phylogeny of the Nymphalidae (Lepidoptera). Syst. Biol. 53: 363-383.
24. Goss, G. J. 1979. The interaction between moths and plants containing pyrrolizidine alkaloids. Environm. Entomol. 8: 487-493.
25. Hartmann, T. & D. Ober. 2000. Biosynthesis and metabolism of pyrrolizidine alkaloids in plants and specialized insect herbivores. Pp. 207-244 in F. J. Leeper & J. C. Vederas (editors), Topics in Current Chemistry: Biosynthesis-Aromatic Polyketides, Isoprenoids, Alkaloids. Springer, Berlin.
26. _ & L. Witte. 1995. Chemistry, biology and chemoecology of the pyrrolizidine alkaloids. Pp. 155-233 in S. W. Pelletier (editor), Alkaloids: Chemical and Biological Perspectives. Pergamon Press, Oxford.
27. _, C. Theuring, J. Schmidt, M. Rahier & J. M. Pasteels. 1999. Biochemical strategy of sequestration of pyrrolizidine alkaloids by adults and larvae of chrysomelid leaf beetles. J. Insect Physiol. 45: 1085-1095.
28. _, L. Witte, S. Schulz & J. M. Pasteels. 2003. Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. Insect Biochem. Molec. Biol. 33: 515-523.
29. _, T. Beuerle, N. Klewer, S. Schulz, M. S. Singer & E. A. Bernays. 2005. Specific recognition, detoxification and metabolism of pyrrolizidine alkaloids by the polyphagous arctiid Estigmene acrea. Insect Biochem. Molec. Biol. 35: 391-411.
30. Häuser, C. L. & M. Boppré. 1997. Pyrrolizidine alkaloid-related pharmacophagy in neotropical moths (Lepidoptera). Pp. 291-296 in H. Ulrich (editor), Tropical Biodiversity and Systematics. Proceedings of the International Symposium on Biodiversity and Systematics in Tropical Ecosystems, 2-7 May 1994, Bonn. Zoologisches Forschungsinstitut und Museum Alexander König, Bonn.
31. Harvey, D. J. 1991. Higher classification of the Nymphalidae. Pp. 255-273 in H. F. Nijhout (editor), The Development and Evolution of Butterfly Wing Patterns. Smithsonian Institution, Washington, DC.
32. Hilt, N. & K. Fiedler. 2006. Arctiid moth ensembles along a succession gradient in the Ecuadorian montane rainforest zone: How different are subfamilies and trihes? J. Biogeogr. 33: 108-120.
33. Jörgensen, P. 1913. Zur Kenntnis der Syntomiden Argentiniens (Lep.). Z. Wiss. Insektenbiol. 9: 3-7, 33-37, 74-77.
34. Lindigkeit, R., A. Biller, M. Buch, H. M. Schiebel, M. Boppré & T. Hartmann. 1997. The two faces of pyrrolizidine alkaloids: The role of the tertiary amine and its N-oxide in chemical defense of insects with aquired plant alkaloids. Eur. J. Biochem. 245: 626-636.
35. Morales, J. F. 2004. Estudios en las Apocynaceae neotropicales IV: Notas taxonómicas en Prestonia (Apocynoideae, Echiteae) con una nueva especie de Ecuador. Sida 21: 159-163.
36. Moss, A. M. 1947. Notes on the Syntomidae of Pará, with special reference to wasp mimicry and fedegoso, Heliotropium indicum (Boraginaceae), as an attractant. Entomologist 80: 30-35.
37. Naumann, C., T. Hartmann & D. Ober. 2002. 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. Nat. Acad. Sci. U.S.A. 99: 6085-6090.
38. Nishida, R. 2002. Sequestration of defensive substances from plants by Lepidoptera. Annual Rev. Entomol. 47: 57-92.
39. _, C. S. Kim, H. Fukami & R. Irie. 1991. Ideamine N- oxide: Pyrrolizidine alkaloids sequestered by the danaine butterfly, Idea leuconoe. Agric. Biol. Chem. 55: 1787-1792.
40. Pasteels, J. M., C. Theuring, L. Witte & T. Hartmann. 2003. Sequestration and metabolism of pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults. J. Chem. Ecol. 29: 337-355.
41. Pinheiro, C. E. G. 1996. Palatability and escaping ability in Neotropical butterflies: Tests with wild kingbirds (Tyrannus melancholicus, Tyrannidae). Biol. J. Linn. Soc. 59: 351-365.
42. Pliske, T. E. 1975a. Attraction of Lepidoptera to plants containing Pyrrolizidine alkaloids. Environm. Ecol. 4: 455-473.
43. _. 1975b. Pollination of pyrrolizdine alkaloid-containing plants by male Lepidoptera. Environm. Ecol. 4: 474-479.
44. Schulz, S. 1998. Insect-plant interactions: Metabolism of plant compounds to pheromones and allomones by Lepidoptera and leaf beetles. Eur. J. Org. Chem. 1998: 13-20.
45. _, G. Beccaloni, K. S. Brown Jr., M. Boppré, A. V. L. Freitas, P. Ockenfels & J. R. Trigo, 2004. Semiochemicals derived from pyrrolizidine alkaloids in male ithomiine butterflies (Lepidoptera: Nymphalidae: Ithomiinae). Biochem. Syst. Ecol. 32: 699-713.
46. Silva, K. L. & J. R. Trigo. 2002. Structure-activity relationships of pyrrolizidine alkaloids in insect chemical defense against the orb-weaving spider Nephila clavipes. J. Chem. Ecol. 28: 657-668.
47. Singer, M. S., D. Rodrigues, J. O. Stireman III & Y. Carrière. 2004. Roles of food quality and enemy-free space in host use by a generalist insect herbivore. Ecology 85: 2747-2753.
48. Trigo, J. R. & K. S. Brown Jr. 1990. Variation of pyrrolizidine alkaloids in Ithomiinae: A comparative study between species feeding on Apocynaceae and Solanaceae. Chemoecology 1: 22-29.
49. _, L. E. S. Barata & K. S. Brown Jr. 1994. Stereochemical inversion of pyrrolizidine alkaloids by Mechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance. J. Chem. Ecol. 20: 2883-2899.
50. _, K. S. Brown Jr., S. A. Henriques & L. E. S. Barata. 1996a. Qualitative patterns of pyrrolizidine alkaloids in Ithomiinae butterflies. Biochem. Syst. Ecol. 24: 181-188.
51. _, L. Witte, T. Hartmann, L. Ernst & L. E. S. Barata. 1996b. Pyrrolizidine alkaloids: Different acquisition and use patterns in Apocyanaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera: Nymphalidae). Biol. J. Linn. Soc. 58: 99-123.
52. Weber, S., W. Eisenreich, A. Bacher & T. Hartmann. 1999. Pyrrolizidine alkaloids of the lycopsamine type: Biosynthesis of trachelanthic acid. Phytochemistry 50: 1005-1014.
53. Weller, S. J., N. L. Jacobson & W. E. Conner. 1999. The evolution of chemical defences and mating systems in tiger moths (Lepidoptera: Arctiidae). Biol. J. Linn. Soc. 68: 557-578.
54. Willmott, K. R. & A. V. L. Freitas. 2006. Higher level phylogeny of the Ithomiinae (Lepidoptera: Nymphalidae): Classification, patterns of larval hostplant colonisation and diversification. Cladistics 22: 297-368.
55. Witte, L., P. Rubiolo, C. Bicchi & T. Hartmann. 1993. Comparative analysis of pyrrolizidine alkaloids from natural sources by gas chromatography-mass spectrometry. Phytochemistry 32: 187-196.