Pyrrolizidine alkaloids: Different acquisition and use patterns in Apocynaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera: Nymphalidae)

Biological Journal of the Linnean Society

Volumn 58, Issue 1, 1996, Pages 99-123

  Trigo, José Roberto ^a   Brown Jr , Keith S ^a   Witte, Ludger ^b   Hartmann, Thomas ^b   Ernst, Ludger ^b   Barata, Lauro Euclides Soares ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b Inst F Pharmazeut Biol Der TU   (Germany)

Author keywords

Aeria olena; Capillary gas chromatography; Chemical defence; Intermedine; Lycopsamine; Mass spectrometry; Mechanitis polymnia; Nephila clavipes; Tithorea harmonia

Indexed keywords

APOCYNACEAE; ARANEAE; ARCTIIDAE; COPROSMA WAIMEAE; DANAINAE; LEPIDOPTERA; MAGNOLIOPHYTA; MECHANITIS POLYMNIA; NEPHILA; NEPHILA CLAVIPES; NYMPHALIDAE; PAPILIONOIDEA; POLYMNIA; PRESTONIA; SOLANACEAE; SOLANUM; TITHOREA HARMONIA;

EID: 0003030122     PISSN: 00244066     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1095-8312.1996.tb01663.x     Document Type: Article

References (32)

1. Abe F, Nagao T, Okabe H, Yamauchi T, Marubayashi N, Ueda I. 1990. Parsonsianine, a macrocyclic pyrrolizidine alkaloid from the leaves of Parsonsia laevigata (Studies on Parsonsia. III). Chemical and Pharmaceutical Bulletin 38: 2127-2129.
2. Abe F, Nagao T, Okabe H, Yamauchi T. 1991a. Macrocyclic pyrrolizidine alkaloids from Parsonsia laevigata. Photochemistry 30: 1737-1739.
3. Abe F, Yamauchi T, Yaga S, Minato K. 1991b. Pyrrolizidine alkaloids from Parsonsia laevigata in Okinawa Island (Studies on Parsonsia. V). Chemical and Pharmaceutical Bulletin 39: 1576-1577.
4. Asibal CF, Glinski JA, Gelbaum LT, Zalkow LH. 1989. Pyrrolizidine alkaloids from Cynoglossum creticum. Synthesis of the pyrrolizidine alkaloids echinatine, rinderine, and analogues. Journal of Natural Products 52: 109-118.
5. Bingley JB. 1968. Solvent and temperature effects in the determination of pyrrolizidine alkaloids with 4-dimethylaminobenzaldehyde. Analytical Chemistry 40: 1166-1167.
6. Boppré M. 1983. Leaf-scratching - a specialized behaviour of danaine butterflies (Lepidoptera) for gathering secondary plant substances. Oecologia 59: 414-116.
7. Boppré M. 1984. Redefining "pharmacophagy". Journal of Chemical Ecology 10: 1151-1154.
8. Boppré M. 1990. Lepidoptera and pyrrolizidine alkaloids. Exemplification of complexity in chemical ecology. Journal of Chemical Ecology 16: 165-185.
9. Bowers MD. 1981. Unpalatability as a defense strategy of western checkerspot butterflies (Euphydryas). Evolution 35: 367-375.
10. Brower LP, Brower JVZ. 1964. Birds, butterflies and plant poisons: a study in ecological chemistry. Zoologica (New York) 49: 137-159.
11. Brown KS, Jr. 1984. Adult-obtained pyrrolizidine alkaloids defend ithomiine butterflies against a spider predator. Nature 307: 707-709.
12. Brown KS, Jr. 1985. Chemical ecology of dehydropyrrolizidine alkaloids in adult Ithomiinae (Lepidoptera: Nymphalidae). Revista Brasileira de Biologia 44: 435-460.
13. Brown KS, Jr. 1987. Chemistry at the Solanaceae/Ithomiinae interface. Annals of the Missouri Botanical Garden 74: 359-397.
14. Brown KS, Jr., Trigo JR. 1995. The ecological activity of alkaloids. In: Cordell GA, ed. The Alkaloids, vol. 47. New York: Academic Press, 227-356.
15. Robinson MH, Mirick H. 1971. The predatory behavior of the golden-web spider Nephila clavipes (Araneae: Araneidae). Psyche 78: 123-139.
16. Roeder E, Breitmaier E, Birecka H, Frohlich MW, Badzies-Crombach A. 1991. Pyrrolizidine alkaloids of Heliotropium spathulatum. Photochemistry 30: 1703-1706.
17. Roeder E, Bourauel T. 1992. Pyrrolizidine alkaloids from Neatostema apulum. Phytochemistiy 31: 3613-3615.
18. Schulz S. 1987. Die Chemie der Duftorgane männlicher Lepidopteren. Unpublished D.Phil, Thesis, Institut für Organische Chemie, Universität Hamburg.
19. Schulz S. 1992. Absolute configuration and synthesis of 2-hydroxy-2-(1-hydroxyethyl)-3-methyI-γ-butyrolactone) a presumed pheromone of ithomiine butterflies. Liebigs Annalen der Chemie 829-834.
20. Schulz S, Francke W, Edgar JA, Schneider D. 1988. Volatile compounds from androconial organs of danaine and ithomiine butterflies. Zeitschrift für Naturforschung 43c: 99-104.
21. Trigo JR. 1988. Ecologia quimica na interação Ithomiinae (Lepidoptera: Nymphalidae) - Echitoideae (Angiospermae: Apocynaceae). Unpublished MSc. Thesis, Institute de Biologia, UNICAMP.
22. Trigo JR. 1993. Alcalóides pirrolizidinicos em borboletas Ithomiinae. Alguns aspectos em ecologia química. Unpublished D.Sc. Thesis, Institute de Química, UNICAMP.
23. Trigo JR, Brown Jr. KS. 1990. Variation of pyrrolizidine alkaloids in Ithomiinae: a comparative study between species feeding on Apocynaceae and Solanaceae. Chemoecology 1: 22-29.
24. Trigo JR, Brown Jr. KS, Barata LES. 1994. Stereochemical inversion of pyrrolizidine alkaloids in Mechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae). Specificity and evolutionary significance. Journal of Chemical Ecology 20: 2883-2899.
25. Trigo JR, Motta PC. 1990. Evolutionary implications of pyrrolizidine alkaloid assimilation by danaine and ithomiine larvae (Lepidoptera: Nymphalidae). Experientia 46: 332-334.
26. Trigo JR, Witte L, Brown Jr. KS, Hartmann T, Barata LES. 1993. Pyrrolizidine alkaloids in the arctiid moth Hyalurga syma. Journal of Chemical Ecology 19: 669-679.
27. Vasconcellos-Neto J, Lewinsohn TM. 1984. Discrimination and release of unpalatable butterflies by Nephila clavipes, a neotropical orb-weaving spider. Ecological Entomology 9: 337-344.
28. Wiedenfield H, Roeder E. 1991. Pyrrolizidine alkaloids from Ageratum conyzoides. Planta Medica 57: 578-579.
29. Williams DH, Stone MS, Hauck PR, Rahman SK. 1989. Why are secondary metabolites (natural products) biosynthesized? Journal of Natural Products 52: 1189-1208.
30. Witte L, Rubiolo P, Bicchi C, Hartmann T. 1993. Comparative analysis of pyrrolizidine alkaloids from natural sources by gas chromatography-mass spectrometry. Phytochemistry 32: 187-196.
31. Zikán-Cardoso M. 1991. Defesa química por alcalóides pirrolizidinicos (PAs) em Lepidoptera: testes com um predador vertebrado. Unpublished M.Sc. Thesis, Institute de Biologia, UNICAMP.
32. Zalkow LH, Glinski JA, Gelbaum L, Fleischmann TJ, McGowan LS, Gordon MM. 1985. Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents. Journal of Medicinal Chemistry 28: 687-694.