The role of macrozamin and cycasin in cycads (Cycadales) as antiherbivore defenses

Journal of the Torrey Botanical Society

Volumn 130, Issue 3, 2003, Pages 206-217

  Castillo Guevara, Citlalli ^a   Rico Gray, Victor ^a  

^a INSTITUTO DE ECOLOGÍA   (Mexico)

Author keywords

Association of characters; Azoxyglycosides; Cycads; Cycasin; Herbivores; Herbivory; Independent contrasts; Macrozamin

Indexed keywords

CHEMICAL DEFENSE; PHYTOCHEMISTRY; PLANT-HERBIVORE INTERACTION;

ANIMALIA; BOWENIA; COLEOPTERA; CURCULIONIDAE; CYCADALES; CYCADOPSIDA; CYCAS; LEPIDOPTERA; MACROZAMIA; PHACELIA CONGESTA; STANGERIA;

EID: 0141959839     PISSN: 10955674     EISSN: None     Source Type: Journal    
DOI: 10.2307/3557555     Document Type: Article

References (78)

1. ALEJANDRE, R. J. 1989. Algunos aspectos de la demografía de Ceratozamia mexicana Bröng. (Zamiaceae) en un bosque mesófilo de montaña. B.Sc. thesis. Universidad Veracruzana-Xalapa. México.
2. BANK, H., M. WINK., P. VORSTER, J. TREUTLEIN, L. BRAND, M. BANK, AND J. HURTER. 2001. Allozyme and DNA sequence comparisons of nine species of Enchephalartos (Zamiaceae). Biochem. Syst. Ecol. 29: 241-266.
3. BECERRA, J. X. 1997. Insects on plants: macroevolutionary chemical trends in host use. Science 276: 253-256.
4. BELTRAN, V. J. M. 1993. Aspectos cualitativos de la herbivoría Eumaeus debora Hubner. (Lycaenidae) sobre Ceratozamia mexicana Brong. (Zamiaceae) en la localidad de Coacoatzintla, Veracruz. B.Sc. thesis. Universidad Veracruzana-Xalapa. México.
5. BEUTELSPACHER, C. R. B. 1975. Como hacer una colección de mariposas. Universidad Nacional Autónoma de México. México.
6. BEUTELSPACHER, C. R. B. 1980. Mariposas diurnas del Valle de México. Ediciones Científicas: L.P.M.M. México.
7. BOGACHEVA, I. A. 1994. Leaf size selection by insects: a phenomenon created by random sampling. Oikos 69: 119-124.
8. BOGLER, D. J., AND J. FRANCISCO-ORTEGA. In press. Molecular systematic studies in cycads: evidence from trnL intron and ITS2 rDNA sequences. Mem. New York Bot. Gar.
9. BOWERS, M. D., AND Z. LARIN. 1989. Acquired chemical defence in the lycaenid butterfly, Eumaeus atala. J. Chem. Ecol. 15: 1133-1146.
10. BOWERS, M. D., AND S. FARLEY. 1990. The behaviour of grey jays, Perisoreus canadensis, towards palatable and unpalatable Lepidoptera. Anim. Behav. 39: 699-705.
11. CAPUTO, P., D. W. STEVENSON, AND E. T. WURTZEL. 1991. A phylogenetic analysis of American Zamiceae (Cycadales) using chloroplast DNA restriction fragment length polymorphisms. Brittonia 43: 135-145.
12. CAPUTO, P., C. MARQUIS, T. WURTZEL, D. W STEVENSON, AND E. T. WURTZEL. 1993. Molecular biology in cycad systematic. In D. W. Stevenson DW, and K. J. Norstog. (eds.), Proceedings of CYCAD 90, The second International Conference on Cycad Biology. Palm & Cycad Societies of Australia, Ltd.
13. CLARK, D. B., AND D. A. CLARK. 1991. Herbivores, herbivory, and plant phenology: patterns and consequences in a tropical rain-forest cycad, pages 209-225. In P. W. Price, T. M. Lewinsohn, G. W. Fernandes, and W. W. Benson. (eds.), Plant-Animal Interactions: Evolutionary Ecology in Tropical and Temperate Regions. John Wiley & Sons, New York.
14. CLARK, D. B., C. A. CLARK, AND M. H. GRAYUM. 1992. Leaf demography of a neotropical cycad, Zamia skinneri. Am. J. Bot. 79: 28-33.
15. CRANE, P. P. 1985. Phylogenetic analysis of seed plants and the origin of angiosperms. Ann. Missouri Bot. Gar. 72: 716-793.
16. CRANE, P. P. 1988. Major clades and relationships in the "higher" gymnosperms, pages 218-272. In Beck, C. B. (ed.), Origin and evolution of gymnosperms. Columbia University Press, New York.
17. DE LUCA, P., A. MORETTI, S. SABATO, AND G. SINISCALCO GIGLIANO. 1980. The ubiquity of cycasin in cycads. Phytochem. 19: 2230-2231.
18. DEVRIES, P. J. 1976. Notes on the behavior of Eumaeus minyas (Hübn.) (Lepidoptera: Lycaenidae) in Costa Rica. Brenesia 8: 103.
19. DEVRIES, P. J. 1977. Eumaeus minyas Hubner: an aposematic lycaenid butterfly. Brenesia 12: 269-270.
20. DEVRIES, P. J. 1983. Checklist of butterflies, pages 654-678. In D. H. Janzen (ed.), Costa Rican Natural History. University of Chicago Press, Chicago.
21. DEVRIES, P. J. 1994. Patterns of butterfly diversity and promising topics in natural history and ecology, pages 187-194. In L. A. McDade, K. S. Bawa, H. A. Hespenheide, and G. S. Hartshorn (eds.) La Selva. Ecology and Natural History of a Neotropical Rain Forest. University of Chicago Press, Chicago.
22. DONALDSON, J. S. 1997. Is there a floral parasite mutualism in cycad pollination? The pollination biology of Encephalartos villosus (Zamiaceae). Am. J. Bot. 84: 1389-1406.
23. FELSENSTEIN, J. 1985. Phytogenies and the comparative method. Am. Nat. 125: 1-15.
24. FREITAS, A. V. L., I. R. LEAL, AND S. O. FERREIRA. 1999. Selection of oviposition sites by a lepidopteran community of a tropical forest in southeastern Brazil. Biotropica 31: 372-375.
25. GASCO, A., A. SERAFINO, V. MORTARINI, E. MENZIANI, M. A. BIANCO, AND J. CERUTI SCURTI. 1974. An bacterial and antifungal compound from Calvatia lilacina. Tetrahedron Lett. 38: 3431-3432.
26. GIDDY, C. 1978. Cycads of Southafrica. Burnell and sons, Capetown.
27. GONZÁLEZ, S. E., R. DIRZO, AND R. C. VOGT. 1997. Historia Natural de Los Tuxtlas. Universidad Autónoma de México, México.
28. GOULD, S. J., AND E. VRBA. 1982. Exaptation - a missing term in the science of form. Paleobiol. 8: 4-15.
29. HARVEY, P. H., AND D. M. D. PAGEL. 1991. The comparative method in evolutionary biology. Oxford University Press, Oxford.
30. HOFFAMNN, G. R., AND R. W. MORGAN. 1984. Review: Putative mutagens and carcinogens in foods. V. Cycad Azoxyglycosides. Environ. Mutat. 6: 103-116.
31. HOWARD, F. W., A. HAMON, M. MCLAUGHLIN, T. WEISSLING, AND S. YANG. 1999. Aulacaspis yasumatsui (Hemiptera: Sternrrhyncha: Diaspididae), a scale insect pest of cycads recently introduced into Florida. Fla. Entomol. 82: 14-27.
32. JANZEN, D. H. 1983. Costa Rican Natural History. The University Chicago Press, Chicago.
33. JONES, D. L. 2000. Cycads of the World. Smithsonian Institution Press, Washington.
34. KLOTS, A. B. 1951. A field guide to the butterflies of North America, East of the Great Plains. The Peterson field guide series. Houghton Mifflin Company, Boston.
35. KOBAYASHI, A., AND H. MATSUMOTO. 1965. Studies on methylazoxymethanol, the aglycone of cycasin. Isolation, biological, and chemical properties. Archiv. Biochem. Biophys. 110: 373-380.
36. LOSOS, J. B., AND D. B. MILES. 1994. Adaptation, constraint, and the comparative method: phylogenetic issues and methods, pages 60-98. In P. C. Wainwright, S. M. Reilly (eds.), Ecological morphology. University of Chicago Press, Chicago.
37. LTHGOE, B., AND N. V. RIGGS. 1949. Macrozamin. Part I. The identity of the carbohydrate component. J. Chem. Soc. 4: 2716-2718.
38. MARTINS, E. P., AND T. F. HANSEN. 1996. The statistical analysis of interspecific data: a review and evaluation of phylogenetic comparative methods, pages 22-75. In E. P. Martins (ed.), Phylogenies and the comparative method in animal behavior. University Press, Oxford.
39. MATSUMOTO, H., AND F. M. STRONG. 1963. The occurrence of methylazoxymethanol in Cycas circinalis L. Archiv. Biochem. Biophys. 101: 229-310.
40. MCDADE, L. A, K. S. BAWA, H. A. HESPENHEIDE, AND G. S. HARTSHURA. 1994. La Selva. Ecology and natural history of a Neoptropical rain forest. The University of Chicago Press, Chicago.
41. MORETTI, A., S. SABATO, AND G. SINISCALCO GIGLIANO. 1981. Distribution of macrozamin in Australasian cycads. Phytochem. 20: 1415-1416.
42. MORETTI, A., S. SABATO, AND G. SINISCALCO GIGLIANO. 1983. Taxonomic significance of methilazoxymethanol glycosides in the Cycads. Phytochem. 22: 115-117.
43. MORETTI, A., P. CAPUTO, S. COZZOLINO, P. DE LUCA, L. GAUDIO, G. SINISCALCO GIGLIANO, AND D. W. STEVENSON. 1993. A phylogenetic analysis of Dioon (Zamiaceae). Am. J. Bot. 80: 204-214.
44. MORGAN, R. W, AND G. R. HOFFMANN. 1983. Cycasin and its mutagenic metabolites. Mutat. Res. 114: 19-58.
45. NAGAHAMA, T. 1964. Studies on neocycasins, new glycosides of cycads. Fac. Agr. Kagoshima Univ. Bull. 14: 1-50.
46. NASH, R. J., A. BELL, AND P. R. ACKERY. 1992. The protective role of cycasin in cycad-feeding lepidoptera. Phytochem. 31: 1955-1957.
47. NISHIDA, K, A. KOBAYASHI, AND T. NAGAHAMA. 1955. Studies on cycasin, a new toxic glycoside of Cycas revouta Thunb. Agri. Chem. Soc. Bull. 19: 77-83.
48. NORSTOG, K. J., AND P. K. S. FAWCETT. 1989. Insect-cycad symbiosis and its relation to the pollination of Zamia furfuracea (Zamiaceae) by Rophalotria mollis (Curculionidae). Am. J. Bot. 76: 1380-1394.
49. NORSTOG K. J., AND T. J. NICHOLLS. 1997. The Biology of the Cycads. Cornell University Press, New York.
50. ORNELAS, J. F. 1998. Filogenias y método comparativo: identificación y evaluación de hipótesis evolutivas y establecimiento de criterios para conservar especies en riesgo. Acta Zool. Mex. 74: 5-42.
51. PRICE, N., T. P. COB, G. W. CRAIG, J. K. FERNANDES, S. ITAMI, R. MOPPER, AND R. W. PRESZLER. 1990. Insect herbivore population dynamics on trees and shurbs: New approaches relevant to latent and eruptive species an life table development, pages 1-38. In Insect-plant interactions. E. Bernays (ed.). CRC Press.
52. PRICE, P. W., C. E. BOUTON, P. GROSS., B. A. McPHERON, J. N. THOMPSON, AND A. E. WEIS. 1991. Interactions among three trophic levels: Influence of plants on interactions between insect herbivores and natural enemies. Ann. Rev. Ecol. Syst. 11: 41-65.
53. PURVIS, A., AND A. RAMBAUT. 1995. Comparative analysis by independent contrasts (CAIC): an Apple Macintosh application for analysing comparative data. Computer Appl. Biosciences 11: 247-251.
54. RAWSON, G. W. 1961. The recent rediscovery of Eumaeus atala (Lycaenidae) in Southern Florida. Especially for field collectors. J. Lep. Soc. 15: 237-245.
55. ROSS, G. N. 1964. Ann annoted list of buterflies collected in British Honduras in 1961. J. Lep. Soc. 18: 11-26.
56. ROTHSCHILD, M., R. J. NASH, AND E. A. BELL. 1986. Cycasin in the endangered butterfly Eumaeus atala florida. Phytochem. 25: 1853-1854.
57. SCHOENTAL, R. 1969. Carcinogenic action of elaiomycin in rats. Nature 221: 765-766.
58. SCHUTZMAN, B, AND B. DEHGAN. 1993. Computer assisted systematics in the Cycadales. In D. W. Stevenson, and K. J. Norstog, (eds.) Proceedings of CYCAD 90, The second International Conference on Cycad Biology. Palm & Cycad Societies of Australia, Ltd.
59. SCOTT, J. A. 1986. The butterflies of North America. Stanford University Press, California.
60. SHIRMAL, S. K. AND K. PRASAD. 1977. Effects of root and ovule extracts of Cycas circinalis on seed germination and seedling growth of Crotalaria juncea (Papilionaceae). Zeitschhhrift fur Pflanzenphysiologie 81: 80-84.
61. SINISCALCO, G. G. 1990. Chemotaxonomic significance of MAM glycosides and mucilages in cycads. Mem. New York Bot. Gar. 57: 123-131.
62. STEVENSON, D. W. 1990. Morphology and systematics of the Cycadales. Mem. New York Bot. Gar. 57: 8-55.
63. STEVENSON, D. W. 1992. A formal classification of the extant cycads. Brittonia 44: 220-223.
64. TEAS, H. J. 1967. Cycasin synthesis in Seirarctia echo (Lepidoptera) larvae fed methylazoxymethanol. Biochem. Biophys. Res. Comm. 26: 686-690.
65. THOMPSON, J. N. 1982. Interaction and coevolution. John Wiley & Sons, New York.
66. THOMPSON, J. N. 1994. The coevolutionary process. The University of Chicago Press, Chicago.
67. TREUTLEIN, J., AND M. WINK. 2002. Molecular phylogeny of cycads inferred from rbcL sequences. Naturwissenschaften 89: 221-225.
68. TRIGO, J. R. 2000. The chemistry of antipredator defence by secondary compounds in Neotropical lepidoptera: facts, perspectives and caveats. J. Braz. Chem. Soc. 6: 551-561.
69. VOVIDES, A. P. 1991. Insect symbionts of some Mexican cycads in their natural habitat. Biotropica 23: 102-104.
70. VOVIDES, A. P, J. D. REES, AND M. VÁZQUEZ-TORRES. 1983. Zamiaceae, pages 3-31. In A. Gómez-Pompa, V. Sosa (eds.), Flora de Veracruz, Fascículo 26. Institute Nacional de Investigaciones sobre Recursos Bióticos, México.
71. VOVIDES, A. P., K. J. NORSTOG, P. K. S. FAWCETT, M. W. DUNCAN, R. J. NASH, AND D. V. MOLSEN. 1993. Histological changes during maturation in male and female cones of Zamia furfuracea L. fil. (Zamiaceae, Cycadales) and their significance in relation to pollination biology. Bot. J. Linn. Soc. 111: 241-252.
72. VOVIDES, A. P., N. OGATA, AND V. SOSA. 1997. Pollination of endangered Cuban cycad Microcycas calocoma (Miq.) A.D.C. Bot. J. Linn. Soc. 125: 201-210.
73. WHITING, G. M. 1963. Toxicity of cycads. Econ. Bot. 17: 270-302.
74. WINDSOR, D., J. NESS, L. D. GOMEZ, AND P. H. JOLIVET. 1999. Species of Aulacosceles Duponchel and Chevrolat (Chrysomelidae) and Nomotus Gorham (Languriidae) feed on fronds of Central American cycads. Coleop. Bull. 53: 217-231.
75. YAGI, F., AND K. TADERA. 1996. Substrate specific and transglucosylation catalyzed by cycad beta-glucosidase. Biochem. Biophys. Acta. 1289: 315-321.
76. YAGI, F., K. TADERA, AND A. KOBAYASHI. 1980. Simultaneous determination of cycasin, methylazoxymethanol and formaldehyde by high per formance liquid chromatography. Agr. Biol. Chem. 44: 1423-1425.
77. YAGI, F., K. TADERA, AND A. KOBAYASI. 1985. A new azoxyglycoside containing simaltose-neosicasyn- β -alpha. Agr. Biol. Chem. 49: 1531-1532.
78. ZAR, J. H. 1999. Biostatistical Analysis. Prentice-Hall, New Jersey.