Abstract
Chemical analysis of the eggs spawned by fiveSinularia soft corals (Octocorallia, Alcyoniidae) collected in the central region of the Great Barrier Reef, Australia, revealed the presence of the known cembranoid diterpenes epoxypukalide and/or pukalide in all cases. Examination of the colonies from which the eggs were released one month before spawning and also some time after spawning failed to detect either diterpene in the coral tissue. The three dimensional structures of pukalide and epoxypukalide, as determined by the single-crystal X-ray technique, are reported for the first time. The wide distribution of pukalide and epoxypukalide and of related compounds within the octocorallia is discussed.
Similar content being viewed by others
References
Alino, P.M., Heaton, A., andWillis, R. 1987. Aspects of the reproductive activity and postlarval settlement behavior of several octocorals from the central region of the Great Barrier Reef.Proc. A.M.S.A. Conf., Townsville 1:1. Australian Marine Sciences Association, Inc., Sydney.
Bakus, G.J. 1981. Chemical defence mechanisms on the Great Barrier Reef, Australia.Science 211:497–499.
Bayer, P.M. 1973. Colonial organisation in octocorals, pp. 69–93,in R.S. Boardman, A.H. Cheetham, and W.A. Oliver, (eds.). Animal Colonies: Development and Function through Time. Dowden, Hutchinson and Ross, Stroudsberg, Pennsylvania.
Benayahu, Y., andLoya, Y. 1983. Surface brooding in the Red Sea soft coralParerythropodium fitlvum fulvum (Forskal, 1775).Biol Bull. 165:353–369.
Benayahu, Y., andLoya, Y. 1984. Life history studies on the Red Sea soft coralXenia macros- piculata Gohar, 1940. II. Planulae shedding and post larval development.Biol. Bull. 166:44–53.
Benayahu, Y., andLoya, Y. 1985. Settlement and recruitment of soft coral: WhyXenia macro-spiculata is a successful colonizer?Bull. Mar. Sci. 36:177–178.
Benayahu, Y., andLoya, Y. 1986. Sexual reproduction of a soft coral: Synchronous and brief annual spawning ofSarcophyton glaucum (Quoy and Gaimard, 1833).Biol. Bull. 170:32–42.
Bowden, B.F., andColl, J.C. 1986. The application of vacuum liquid chromatography to the separation of terpene mixtures.J. Nat. Prod. 49:934–936.
Bowden, B.F., Coll, J., Tapiolas, D., andWillis, R. 1985. Some chemical aspects of spawning in alcyonacean corals.Proc. 5th Intl. Coral ReefSymp. 4:325–329.
Coll, J.C., andSammarco, P.W. 1983. Terpenoid toxins of soft corals (Cnidaria, Octocorallia): Their nature, toxicity and ecological significance.Toxicon 3 (Suppl.):69–72.
Coll, J.C., Bowden, B.F., Tapiolas, D.M., andDunlap, W.C. 1982a.In situ isolation of allelochemicals released from soft corals (Coelenterata: Octocorallia): A totally submersible sampling apparatus.J. Exp. Mar. Biol. Ecol. 60:293–299.
Coll, J.C., La Barre, S., Sammarco, P.W., Williams, W.T., Bakus, G.J. 1982b. Chemical defenses in soft corals (Coelenterata: Octocorallia) of the Great Barrier Reef: A study of comparative toxicities.Mar. Ecol. Prog. Ser. 8:271–278.
Coll, J.C., Bowden, B.F., Konig, G.M., Braslau, R., andPrice, I.R. 1986. Studies of Australian soft corals. The natural products chemistry of Alcyonacean soft corals with special reference to the genusLobophytum.Bull. Soc. Chim. Belg. 95:815–834.
Coll, J.C., Bowden, B.F., Heaton, A., andClayton, M.E. 1987. Chemotaxis in tropical Alcyonacean corals.Proc. A.M.S.A. Conf., Townsville, 1:12. Australian Marine Sciences Association, Inc., Sydney.
Dinesen, Z.D. 1985. Aspects of the life history of a stolon-bearing species ofEfflatounaria (Octocorallia: Xeniidae).Proc. 5th Intl. Coral Reef Symp., Tahiti 6:89–94.
Farrant, P. 1985. Reproduction in the temperate Australian soft coralCapnella gaboensis.Proc. 5th Intl. Coral Reef Symp., Tahiti 2:129.
Faulkner, D.J. 1984. Marine natural products: Metabolites of marine invertebrates.Nat. Prod. Rep. 1:551–598.
Faulkner, D.J. 1986. Marine natural products.Nat. Prod. Rep. 3:1–33.
Faulkner, D.J. 1987. Marine natural products.Nat. Prod. Rep. 5:539–576.
Fenical, W., Okuda, R.K., Bandurraga, M.M., Culver, P., andJacobs, R.S. 1981. Lophotoxin: A novel neuromuscular toxin from Pacific sea whips of the genusLophogorgia.Science 212:1512–1514.
Gohar, H.A.F., 1940. Studies of the Xeniidae of the Red Sea, their ecology, physiology, taxonomy and phylogeny.Mar. Biol. Stn., Ghardaqa (Red Sea) Publn. 2:25–118.
Harrison, P.L., Babcock, R.C., Bull, G.D., Oliver, J.K., Wallace, C.C., andWillis, B. 1984. Mass spawning in tropical reef corals.Science 223:1186–1189.
Hartnoll, R.G. 1975. The annual cycle ofAlcyonium digitatum.Estuarine Coastal Mar. Sci. 3:71–75.
Heaton, A. 1988. PhD thesis. James Cook University of North Queensland, Townsville, Queensland, Australia.
Hirotsu, K., andArnold, E. 1980. BLS78A, An Anisotropie Block Diagonal Least Squares Refinement. Cornell University, Ithaca, New York.
Hirotsu, K., andVan Duyne, G. 1985. BOND, A Program to Calculate Molecular Parameters and Prepare Tables. Cornell University, Ithaca, New York.
Klein, D.M. 1986. Secondary metabolites of several marine invertebrates. PhD dissertation. University of Hawaii at Manoa (Department of Chemistry), Honolulu, Hawaii.
Ksebati, M.B., Ciereszko, L.S., andSchmitz, F.J. 1984. 11β,12β-Epoxypukalide, afuranocem-branolide from the gorgonianLeptogorgia setacea.J. Nat. Prod. 47:1009–1012.
La Barre, S.C. 1984. Studies in the chemical ecology of Alcyonarians (Coelenterata: Octocorallia). PhD dissertation. James Cook University of North Queensland, Townsville, Queensland, Australia, pp. 1–348.
La Barre, S.C., Coll, J.C., andSammarco, P.W. 1986. Defensive strategies of soft corals (Coelenterata: Octocorallia) of the Great Barrier Reef. II. The relationship between toxicity and feeding deterrence.Biol. Bull. 171:625–636.
Leonowicz, M.E. 1978. REDUCE and UNIQUE. Data Reduction Programs. Cornell University, Ithaca, New York.
Li, M.K.W. 1986. PhD dissertation. University of Hawaii at Manoa (Department of Chemistry), Honolulu, Hawaii.
Main, P., Hull, S.E., Lessinger, L., Germain, G., De Clerco, J.P., andWoolfson, M.M. 1980. MULTAN-80, RANTAN-80. Systems of computer programs for the automatic solution of crystal structures from X-ray diffraction data. University of York, England.
Missakian, M.G., Burreson, B.J., andScheuer, P.J. 1975. Pukalide, A furanocembranolide from the soft coralSimdaria abrupto.Tetrahedron 31:2513–2515.
Moore, R.E. 1977. Volatile compounds from marine algae.Acc. Chem. Res. 10:40–47.
Motherwell, W.D.S. 1978. PLUTO 78, A Crystallographic Illustration Program. Cambridge Crystallographic Data Centre, Cambridge, UK.
Sammarco, P.W., Coll, J.C., La Barre, S.C., andWillis, B. 1983. Competitive strategies of soft corals (Coelenterata: Octocorallia). Allelopathic effects on selected scleractinian corals.Coral Reef s 1:173–178.
Tursch, B. 1982. Chemical protection of a fish (Abudefduf leucogaster (Blaeker) by a soft coral (Litophyton viridis May).J. Ghent. Ecol. 8:1421–1428.
Tursch, B., Braekman, J.C., Daloze, D., andKaisin, M. 1978. Terpenoids from coelenterates, pp. 247–291,in P.J. Scheuer (ed.). Marine Natural Products, Vol. II. Academic Press, New York.
Yamasato, K., Sato, M., andYamashiro, H. 1981. Reproductive biology of an alcyonium coralLobophytum crassum Marenzeller.Proc. 4th Intl. Coral Reef Symp., Manila, Philippines 2:671–678.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Coll, J.C., Bowden, B.F., Heaton, A. et al. Structures and possible functions of epoxypukalide and pukalide. J Chem Ecol 15, 1177–1191 (1989). https://doi.org/10.1007/BF01014821
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01014821