Journal of Chemical Ecology

, Volume 25, Issue 10, pp 2255–2265 | Cite as

Chemical Defenses Against Fish Predation in Three Brazilian Octocorals: 11β,12β-Epoxypukalide as a Feeding Deterrent in Phyllogorgia dilatata

  • Rosângela De A. Epifanio
  • Danielle L. Martins
  • Roberto Villaça
  • Rebecca Gabriel
Article

Abstract

The feeding-deterrence properties of crude extracts of three Brazilian octocoral species, Neospongodes atlantica Kükenthal (Alcyonacea, Nephtheidae), Plexaurella regia Castro (Gorgonacea, Plexauridae), and Phyllogorgia dilatata Esper (Gorgonacea, Gorgoniidae), were investigated. All the extracts were incorporated into food strips at the concentrations occurring in the living organisms. Crude extract and its ethyl acetate fraction obtained from P. dilatata collected in Armação dos Búzios (Rio de Janeiro State), when incorporated into artificial diets and tested in the habitat of origin, reduced consumption of food strips by fishes, relative to controls. Crude extracts from two octocoral species collected at the National Marine Park of Abrolhos (Bahia State), N. atlantica and P. regia, had no apparent feeding-deterrence properties; in fact, they seemed to stimulate feeding. Bioassay-guided fractionation of the bioactive P. dilatata crude extract revealed that the deterrent property was restricted to a medium polarity fraction. Field palatability experiments with two pure compounds isolated from this fraction revealed that the furanocembranolide 11β,12β-epoxypukalide is a potent feeding deterrent produced by P. dilatata against fish. Apparently, furanocembranolides are a particular class of compounds with feeding deterrent properties, protecting some octocorals from potential fish predator species in both tropical and temperate environments.

Phyllogorgia dilatata Neospongodes atlantica Plexaurella regia Octocorallia chemical ecology feeding deterrent field palatability assay epoxypukalide southwest Atlantic Brazil 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. Castro, C. B. 1989. A new species of Plexaurella Valenciennes, 1855 (Coelenterata, Octocorallia), from the Abrolhos Reefs, Bahia, Brazil. Rev. Bras. Biol. 49(2):597-603.Google Scholar
  2. Castro, C. B. 1990. Revisão taxonômica dos Octocorallia (Cnidaria, Anthozoa) do Litoral Sul-Americano: Da foz do Rio Amazonas à foz do Rio da Prata. DSc thesis. Universidade de São Paulo, São Paulo, Brazil.Google Scholar
  3. Chan, W. R., Tinto, W. F., Richard, S. L., Manchand, P. S., Reynolds, W. F., and McLean, S. 1991. Cembrane and pseudopterane diterpenoids of the octocoral Pseudopterogorgia acerosa. J. Org. Chem. 56:1773-1776.Google Scholar
  4. Cronin, G., Hay, M. E., Fenical, W., and Lindquist, N. 1995. Distribution, density, and sequestration of host chemical defenses by the specialist nudibranch Tritonia hamnerorum found at high densities on the sea fan Gorgonia ventalina. Mar. Ecol. Prog. Ser. 119:177-189.Google Scholar
  5. Epifanio, R. de A., Maia, L. F., Pinto, A. C., Hardt, I., and Fenical, W. 1998. Natural products from the gorgonian Lophogorgia punicea: Isolation and structure elucidation of an unusual 17-hydroxy sterol. J. Braz. Chem. Soc. 9:187-192.Google Scholar
  6. Epifanio, R. de A., Gabriel, R., Martins, D. L., and Muricy, G. 1999. The sesterterpene variabilin as a fish-predation deterrent in the western Atlantic sponge Ircinia strobilina J. Chem. Ecol. 25:2247-2254.Google Scholar
  7. Faulkner, D. J. 1998. Marine natural products. Nat. Prod. Rep. 2:113-159.Google Scholar
  8. Fenical, W., and Pawlik, J. R. 1991. Defensive properties of secondary metabolites from the Caribbean gorgonian coral Erythropodium caribaeorum. Mar. Ecol. Prog. Ser. 75:1-8.Google Scholar
  9. Fenical, W., Okuda, R. K., Bandurraga, M. M., Culver, P., and Jacobs, R. 1981. Lophotoxin: a novel neuromuscular toxin from Pacific sea whips of the genus Lophogorgia. Science 212:1512-1514.Google Scholar
  10. Fernandes, L., and Kelecom, A. 1995. A further nardosinane sesquiterpene from the gorgonian Phyllogorgia dilatata (Octocorallia, Gorgonacea). An. Acad. Brac. Ci. 67:171-173.Google Scholar
  11. Gerhart, D. J. 1984. Prostaglandin A2: An agent of chemical defense in the Caribbean gorgonian Plexaura homomalla. Mar. Ecol. Prog. Ser. 19:181-187.Google Scholar
  12. Gerhart, D. J., and Coll, J. C. 1993. Pukalide, a widely distributed octocoral diterpenoid, induces vomiting in fish. J. Chem. Ecol. 19:2697-2704.Google Scholar
  13. Harvell, C. D., Fenical, W., and Greene, C. H. 1988. Chemical and structural defenses of Caribbean gorgonians (Pseudopterogorgia spp.). I. Development of an in situ feeding assay. Mar. Ecol. Prog. Ser. 49:287-294.Google Scholar
  14. Hay, M. E., and Fenical, W. 1997. Chemical ecology and marine biodiversity: insights and products from the sea. Oceanography 9:10-19.Google Scholar
  15. Hay, M. E., Satchowicz, J. J., Cruz-Rivera, E., Bullard, S., Deal, M. S., and Lindquist, N. 1998. Bioassays with marine and freshwater macroorganisms, pp. 39-141, in K. F. Haynes and J. C. Millar (eds.). Methods in Chemical Ecology, Volume 2, Bioassay Methods. Chapman and Hall, New York.Google Scholar
  16. Kelecom, A., SolÉ-Cava, A. M., and Kannengieser, G. J. 1980. Occurrence of 23, 24ζ-dimethylcholesta-5,22-dien-3β-ol in the Brazilian gorgonian Phyllogorgia dilatata (Octocorallia, Gorgonacea) and its associated zooxanthella. Bull. Soc. Chim. Belg. 89:1013-1014.Google Scholar
  17. Kelecom, A., Peres, M. B., and Fernandes, L. 1990. A new nardosinane sesquiterpene from the Brazilian endemic gorgonian Phyllogorgia dilatata. J. Nat. Prod. 53:750-752.Google Scholar
  18. Lasker, H. R. 1985. Prey preferences and browsing pressure of the butterflyfish Chaetodon capistratus on Caribbean gorgonians. Mar. Ecol. Prog. Ser. 21:213-220.Google Scholar
  19. Martins, D. L. 1997. Produção de metabólitos secundários contra predadores naturais em octocorais brasileiros: Isolamento, elucidação estrutural e atividade fagorrepelente de produtos naturais da gorgônia Phyllogorgia dilatata. MS thesis. Universidade Federal Fluminense, Rio de Janeiro, Brazil.Google Scholar
  20. Martins, D. L., and Epifanio, R. de A. 1998. A new germacrane sesquiterpene from the Brazilian endemic gorgonian Phyllogorgia dilatata Esper. J. Braz. Chem. Soc. 9:586-591.Google Scholar
  21. Nunan, G. W. 1992. Composition, species distribution and zoogeographical affinities of the Brazilian reef-fishes fauna. PhD thesis. University of Newcastle upon Tyne, Newcastle upon Tyne, England.Google Scholar
  22. Paul, V. J. 1992. Ecological Roles of Marine Natural Products. Comstock Publishing Associates, Ithaca, New York, pp. 164-188.Google Scholar
  23. Pawlik, J. R. 1993. Marine invertebrate chemical defenses. Chem. Rev. 93:1911-1922.Google Scholar
  24. Pawlik, J. R., and Fenical, W. 1989. A re-evaluation of the ichthyodeterrent role of prostaglandins in the Caribbean gorgonian coral Plexaura homomalla. Mar. Ecol. Prog. Ser. 52:95-98.Google Scholar
  25. Pawlik, J. R., and Fenical, W. 1992. Chemical defense of Pterogorgia anceps, a Caribbean gorgonian coral. Mar. Ecol. Prog. Ser. 87:183-188.Google Scholar
  26. Pawlik, J. R., Burch, M. T., and Fenical, W. 1987. Patterns of chemical defense among Caribbean gorgonian corals: a preliminary survey. J. Exp. Mar. Biol. Ecol. 108:55-66.Google Scholar
  27. Schmitz, F. J., Ksebati, M. B., and Ciereszko, L. S. 1984. 11β, 12β-Epoxypukalide, a furanocembranolide from the gorgonian Leptogorgia setacea. J. Nat. Prod. 47:1009-1012.Google Scholar
  28. Van Alstyne, K. L., Wylie, C. R., and Paul, V. J. 1994. Antipredator defenses in tropical Pacific corals (Coelenterata: Alcyonacea) II. The relative importance of chemical and structural defenses in three species of Sinularia. J. Exp. Mar. Biol. Ecol. 178:17-34.Google Scholar
  29. Vreeland, H. V., and Lasker, H. R. 1989. Selective feeding of the polychaete Hermodice carunculata Pallas on Caribbean gorgonians. J. Exp. Mar. Biol. Ecol. 129:265-277.Google Scholar
  30. Wright, A. E., Burres, N. S., and Schulte, G. K. 1989. Cytotoxic cembranoids from the gorgonian Pseudopterogorgia bipinnata. Tetrahedron Lett. 30:3491-3494.Google Scholar
  31. Wylie, C. R., and Paul, V. J. 1989. Chemical defenses in three species of Sinularia (Coelenterata, Alcyonacea): effects against generalist predators and the butterflyfish Chaetodon unimaculatus Bloch. J. Exp. Mar. Biol. Ecol. 129:141-160.Google Scholar
  32. Zar, J. H. 1984. Biostatistical Analysis, 2nd ed. Prentice-Hall, Englewood Cliffs, New Jersey.Google Scholar

Copyright information

© Plenum Publishing Corporation 1999

Authors and Affiliations

  • Rosângela De A. Epifanio
    • 1
  • Danielle L. Martins
    • 1
    • 4
  • Roberto Villaça
    • 2
  • Rebecca Gabriel
    • 3
  1. 1.Departamento de Química OrgânicaInstituto de Química, Universidade Federal FluminenseNiterói, RJBrazil
  2. 2.Departamento de Biologia MarinhaInstituto de Biologia, Universidade Federal FluminenseNiterói, RJBrazil
  3. 3.Núcleo de Pesquisas de Produtos NaturaisUniversidade Federal do Rio de JaneiroRio de Janeiro, RJBrazil
  4. 4.This work is part of D. L. M. MS thesis at Organic Chemistry DepartmentUFF

Personalised recommendations