From terpenoids to aliphatic acids: Further evidence for late-instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini

Journal of Chemical Ecology

Volumn 32, Issue 9, 2006, Pages 1999-2012

  Ômura, Hisashi ^a   Honda, Keiichi ^a   Feeny, Paul ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

Aliphatic acid and ester; Chilasa; Lepidoptera; Monoterpene; Osmeterial secretion; Papilio; Papilionidae; Papilionini; Sesquiterpene

Indexed keywords

CARCINOGEN; CYCLOHEXENE DERIVATIVE; ESSENTIAL OIL; FATTY ACID; LIMONENE; TERPENE;

ALIPHATIC HYDROCARBON; BUTTERFLY; CHEMICAL COMPOSITION; CHEMICAL DEFENSE; COMPARATIVE STUDY; HOST PLANT; QUANTITATIVE ANALYSIS; TERPENE;

ANIMAL; ARTICLE; BUTTERFLY; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; LARVA; MASS FRAGMENTOGRAPHY; METABOLISM; PHYSIOLOGY;

ANIMALS; BUTTERFLIES; CARCINOGENS; CYCLOHEXENES; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LARVA; OILS, VOLATILE; TERPENES;

CHILASA; MENTHA; PAPILIO; PAPILIO DEMOLEUS; PAPILIO GLAUCUS; PAPILIO MACILENTUS; PAPILIO PARIS; PAPILIO POLYTES; PAPILIO TROILUS; PAPILIONIDAE; PAPILIONINAE; PAPILIONINI; RUTACEAE;

EID: 33747710117     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-006-9124-x     Document Type: Article

References (51)

1. ALDRICH, J. R., OLIVER, J. R., OLIVER, J. E., LUSBY, W. R., KOCHANSKY, J. P., and LOCKWOOD, J. A. 1987. Pheromone strains of the cosmopolitan pest, Nezara viridula (Heteroptera: Pentatomidae). J. Exp. Zool. 244:171-175.
2. ALDRICH, J. R., LUSBY, W. R., MARRON, B. E., NICOLAU, K. C., HOFFMANN, M. P., and WILSON, L. T. 1989. Pheromone blends of green stink bugs and possible parasitoid selection. Naturwissenschaften 76:173-175.
3. BENGTSSON, M., BÄCKMAN, A.-C., LIBLIKAS, I., RAMIREZ, M. I., BORG-KARLSON, A.-K., ANSEBO, L., ANDERSON, P., LÖFQVIST, J., and WITZGALL, P. 2001. Plant odor analysis of apple: Antennal response of codling moth females to apple volatiles during phenological development. J. Agric. Food Chem. 49:3736-3741.
4. BERENBAUM, M. R., MORENO, B., and GREEN, E. 1992. Soldier bug predation of swallowtail caterpillars: Circumvention of defensive chemistry. J. Insect Behav. 5:547-553.
5. BERNAYS, E. A. and CHAPMAN, R. 1987. The evolution of deterrent responses in plant-feeding insects, pp. 159-173, in R. F. CHAPMAN, E. A. BERNAYS, and J. G. STOFFOLANO (eds.). Perspectives in Chemoreception and Behavior. Springer-Verlag, New York.
6. BLUM, M. S. 1981. Chemical Defenses of Arthropods. Academic Press, New York.
7. BROWER, L. P. 1958. Bird predation and foodplant specificity in closely related procryptic insects. Amer. Natur. 92:183-187.
8. BROWER, L. P. 1984. Chemical defence in butterflies, pp. 109-134, in R. I. VANE-WRIGHT and P. R. ACKERY (eds.). The Biology of Butterflies. Symp. R. Entomol. Soc. Lond., 11. Academic Press, London.
9. BURGER, B. V., MUNRO, Z., RÖTH, M., SPIES, H. S. C., TRUTER, V., GEERTSEMA, H., and HABICH, A. 1985. Constituents of osmeterial secretion of pre-final instars of citrus swallowtail, Papilio demodocus (Esper) (Lepidoptera: Papilionidae). J. Chem. Ecol. 11:1093-1113.
10. CHOW, Y. S. and TSAI, R. S. 1989. Protective chemicals in caterpillar survival. Experientia 45:390-392.
11. DAMMAN, H. 1986. The osmaterial glands of the swallowtail butterfly Eurytides marcellus as a defense against natural enemies. Ecol. Entomol. 11:261-265.
12. EISNER, T. and MEINWALD, Y. C. 1965. Defensive secretion of a caterpillar (Papilio). Science 150:1733-1735.
13. EISNER, T., PLISKE, T. E., IKEDA, M., OWEN, D. F., VÁZQUEZ, L., PÉREZ, H., FRANCLEMONT, J. G., and MEINWALD, J. 1970. Defense mechanisms of arthropods. XXVII. Osemeterial secretions of papilionid caterpillars (Baronia, Papilio, Eurytides). Ann. Entomol. Soc. Am. 63:914-915.
14. EISNER, T., KLUGE, A. F., IKEDA, M. I., MEINWALD, Y. C., and MEINWALD, J. 1971. Sesquiterpenes in the osmeterial secretion of a papilionid butterfly, Battus polydamas. J. Insect Physiol. 17:245-250.
15. FEENY, P., BLAU, W. S., and KAREIVA, P. M. 1985. Larval growth and survivorship of the black swallowtail butterfly in Central New York. Ecol. Monogr. 55:167-187.
16. GERSHENZON, J. and CROTEAU, R. 1991. Terpenoids, pp. 165-219, in G. A. ROSENTHAL and M. R. BERENBAUM (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. Volume 1: The Chemical Participants, 2nd edition. Academic Press, San Diego, CA.
17. HANCOCK, D. L. 1983. Classification of the Papilionidae (Lepidoptera): A phylogenetic approach. Smithersia 2:1-48.
18. HARREWIJN, P., MINKS, A. K., and MOLLEMA, C. 1995. Evolution of plant volatile production in insect-plant relationships. Chemoecology 5/6:55-73.
19. HEGNAUER, R. 1971. Chemical patterns and relationships of Umbelliferae, pp. 267-277, in V. H. HEYWOOD (ed.). The Biology and Chemistry of the Umbelliferae. Academic Press, London.
20. HEGNAUER, R. 1983. Chemical characters and the classification of the Rutales, pp. 401-440, in P. G. WATERMAN and M. F. GRUNDON (eds.). Chemistry and Chemical Taxonomy of the Rutales. Academic Press, London.
21. HIROSE, Y., SUZUKI, Y., TAKAGI, M., HIEHATA, K., YAMASAKI, M., KIMOTO, H., YAMANAKA, M., IGA, M., and YAMAGUCHI, K. 1980. Population dynamics of the Citrus swallowtail, Papilio xuthus Linné (Lepidoptera: Papilionidae): Mechanisms stabilizing its numbers. Res. Popul. Ecol. 21:260-285.
22. HONDA, K. 1980a. Osmeterial secretions of papilionid larvae in the genera Luehdorfia, Graphium and Atrophaneura (Lepidoptera). Insect Biochem. 10:583-588.
23. HONDA, K. 1980b. Volatile constituents of larval osmeterial secretions in Papilio protenor demetrius. J. Insect Physiol. 26:39-45.
24. HONDA, K. 1981. Larval osmeterial secretions of the swallowtail (Papilio). J. Chem. Ecol. 7:1089-1113.
25. HONDA, K. 1983a. Defensive potential of components of the larval osmeterial secretion of papilionid butterflies against ants. Physiol. Entomol. 8:173-179.
26. HONDA, K. 1983b. Evidence for de novo biosynthesis of osmeterial secretions in young larvae of the swallowtail butterflies (Papilio): Deuterium incorporation in vivo into sesquiterpene hydrocarbons as revealed by mass spectrometry. Insect Sci Appl. 4:255-261.
27. 13C-NMR studies on the biosynthesis of terpenoid defensive secretions by the larvae of papilionid butterflies (Luehdorfia and Papilio). Insect Biochem. 20:245-250.
28. HONDA, K. and HAYASHI, N. 1995. Chemical nature of larval osmeterial secretions of papilionid butterflies in the genera Parnassius, Sericinus and Pachliopta. J Chem. Ecol. 21:859-867.
29. IGARASHI, S. 1979. Papilionidae and Their Early Stages. Kodansha, Tokyo, Japan.
30. IGARASHI, S. 1984. The classification of the Papilionidae mainly based on the morphology of their immature stages. Trans. Lepid. Soc. Jpn. 34:41-96.
31. JÄRVI, T., SILLÉN-TULLBERG, B., and WIKLUND, C. 1981. The cost of being aposematic. An experimental study of predation on larvae of Papilio machaon by the great tit Parus major. Oikos 36:267-272.
32. LESLIE, A. J. and BERENBAUM, M. R. 1990. Role of the osmeterial gland in swallowtail larvae (Papilionidae) in defense against an avian predator. J. Lep. Soc. 44:245-251.
33. LOPEZ, A. and QUESNEL, V. C. 1970. Defensive secretions of some papilionid caterpillars. Carib. J. Sci. 10:5-7.
34. MILLER, J. S. 1987. Phylogenetic studies in the Papilioninae (Lepidoptera: Papilionidae). Bull. Am. Nat. Hist. 186:365-512.
35. MUNROE, E. and EHRLICH, P. R. 1960. Harmonization of concepts of higher classification of the Papilionidae. J. Lepidop. Soc. 14:169-175.
36. NIGG, H. N., MALLORY, L. L., SIMPSON, S. E., CALLAHAM, S. B., TOTH, J. P., FRASER, S., KLIM, M., NAGY, S., NATION, J. L., and ATTAWAY, J. A. 1994. Caribbean fruit fly, Anastrepha suspense (Loew), attraction to host fruit and host kairomones. J. Chem. Ecol. 20:727-743.
37. NISHIDA, R. 1995. Sequestration of plant secondary compounds by butterflies and moths. Chemoecology 5/6:127-138.
38. NISHIDA, R. and FUKAMI, H. 1989. Ecological adaptation of an Aristolochiaceae-feeding swallowtail butterfly, Atrophaneura alcinous, to aristolochic acids. J. Chem. Ecol. 15:2549-2563.
39. NISHIDA, R., WEINTRAUB, J. D., FEENY, P., and FUKAMI, H. 1993. Aristolochic acids from Thottea spp. (Aristolochiaceae) and the osmeterial secretions of Thottea-feeding troidine swallowtail larvae (Papilionidae). J. Chem. Ecol. 19:1587-1594.
40. REAVEY, D. 1993. Why body size matters to caterpillars, pp. 248-279, in N. E. STAMP and T. M. CASEY (eds.). Caterpillars: Ecological and Evolutionary Constraints on Foraging. Chapman and Hall, New York.
41. SCRIBER, J. M. 1995. Overview of swallowtail butterflies: taxonomic and distributional latitude, pp. 3-8, in J. M. SCRIBER, Y. TSUBAKI, and R. C. LEDERHOUSE (eds.). Swallowtail Butterflies: Their Ecology and Evolutionary Biology. Scientific Publishers, Gainesville, FL.
42. SELIGMAN, I. M. and DOY, F. A. 1972. β-Hydroxy-n-butyric acid in the defensive secretion of Papilio aegeus. Comp. Biochem. Physiol. 41:341-342.
43. SELIGMAN, I. M. and DOY, F. A. 1973. Biosynthesis of defensive secretions in Papilio aegeus. Insect Biochem. 3:205-215.
44. SIME, K. R. 2002. Chemical defence of Battus philenor larvae against attack by the parasitoid Trogus pennator. Ecol. Entomol. 27:337-345.
45. SIME, K. R., FEENY, P. P., and HARIBAL, M. M. 2000. Sequestration of aristolochic acids by the pipevine swallowtail, Battus philenor (L.): Evidence and ecological implications. Chemoecology 10:169-178.
46. STAMP, N. E. 1986. Physical constraints of defense and response to invertebrate predators by pipevine caterpillars (Battus philenor: Papilionidae). J. Lepidop. Soc. 40:191-205.
47. TAKAGI, M., HIROSE, Y., and YAMASAKI, M. 1995. Antipredator defense in Papilio larvae: effective or not? pp. 85-92, in J. M. SCRIBER, Y. TSUBAKI, and R. C. LEDERHOUSE (eds.). Swallowtail Butterflies: Their Ecology and Evolutionary Biology. Scientific Publishers, Gainesville, FL.
48. WATANABE, M. 1981. Population dynamics of the swallowtail butterfly, Papilio xuthus L., in a deforested area. Res. Popul. Ecol. 23:74-93.
49. YOUNG, A. M. 1973. Notes on the life cycle and natural history of Parides arcas mylotes (Papilionidae) in Costa Rican premontane wet forest. Psyche 80:1-21.
50. YOUNG, A. M., BLUM, M. S., FALES, H. M., and BIAN, Z. 1986. Natural history and ecological chemistry of the neotropical butterfly Papilio anchisiades (Papilionidae). J. Lepidop. Soc. 40:36-53.
51. ZAKHAROV, E. V., CATERINO, M. S., and SPERLING, F. A. H. 2004. Molecular phylogeny, historical biogeography, and divergence time estimates for swallowtail butterflies of the genus Papilio (Lepidoptera: Papilionidae). Syst. Biol. 53:193-215.