Abstract
Extracts of the dorid nudibranchTritoniella belli and stoloniferan coralClavularia frankliniana were chromatographed and analyzed by1H NMR and thin-layer chromatography. Three glycerol ethers were detected inT. belli, primarily 1-O-hexadecyl glycerol (chimyl alcohol). Chimyl alcohol was also detected after gradient flash chromatography and reverse-phase HPLC purification in the tissues ofC. frankliniana. The common omnivorous predatory Antarctic sea starOdontaster validus, a likely predator of benthic invertebrates, showed feeding deterrence to small cubes ofT. belli mantle tissue placed on the tube feet along the ambulacral feeding groove, while always extruding the cardiac stomach when presented with cubes of shrimp tissue of similar size. Filter-paper disks soaked in an aqueous shrimp solution and then dried were found to elicit a broad range of feeding behaviors inO. validus, including movement of the shrimp disk to the mouth, extrusion of the cardiac stomach, and the assumption of a humped feeding posture. Chimyl alcohol-treated shrimp disks caused significant feeding deterrence in sea stars when compared with control disks (solvent plus shrimp treated disks alone).T. belli andC. frankliniana appear to employ a defensive compound that has been found in a variety of temperate and tropical mollusks, where it has been demonstrated to deter fish predators. We provide evidence for further deterrent capabilities of chimyl alcohol and of its trophic relationship in the polar ecosystem of McMurdo Sound, Antarctica.
Similar content being viewed by others
References
Anderson, R.J., andSum, F.W. 1980. Farnesic acid glycerides from the nudibranchArchidoris alheri.Tetrahedron Lett. 21:979–800.
Avila, C., Ballesteros, M., Cimino, G., Crispino, A., Bavignin, M., andSodano, G. 1990. Biosynthetic origin and anatomical distribution of the main secondary metabolites in the nudibranch molluskDoris verrucosa.Comp. Biochem. Physiol. 97B:363–368.
Baker, B.J., andScheuer, P.J. 1994. The punaglandins: 10-Chloroprostanoids from the octocoralTelesto riisei. J. Nat. Prod. In press.
Baker, B.J., Kopitzke, R.W., Hamann, M., McClintock, J.B. 1994. Chemical ecology of antarctic sponges from McMurdo Sound, Antarctica: chemical aspects.Antarct. J. U.S. 28:132–133.
Baker, B.J., Yoshida, W., Kopitzke, B.W., andMcClintock, J.B. 1995. Norditerpenes from the antarctic spongeDendrilla membranosa. In preparation.
Bakus, G.J., Targett, N.M., andSchulte, B. 1986. Chemical ecology of marine organisms: An overview.J. Chem. Ecol. 12:951–987.
Blunt, J.W., Munro, M.H.G., Battershill, C.N., Copp, B.R., McCombs, J.D., Perry, N.B., Prinsep, M., andThompson, A.M. 1990. From the antarctic to the antipodes; 45° of marine chemistry.New J. Chem. 14:751–775.
Bryan, P.J., Yoshida, W.Y., McClintock, J.B., andBaker, B.J. 1994. An ecological role for pteroenone, a novel antifeedant produced by the conspicuous antarctic pteropodClione antarctica (Gymnosomata: Gastropoda).Mar. Biol. In press.
Cimino, G., De Rosa, S., andSodano, G. 1982. The chemical defense of four Mediterranean nudibranchs.Comp. Biochem. Physiol. 73B:471–474.
Davies-Coleman, M.T., andFaulkner, D.J. 1991. New diterpenoic acid glycerides from the antarctic nudibranchAustrodoris mcmurdensis.Tetrahedron 47:9732–9750.
Dayton, P.K., Robilliard, G.A., andDeVries, A.L. 1969. Anchor ice formation in McMurdo Sound, Antarctica, and its biological effects.Science 163:273–274.
Dayton, P.K., Robilliard, G.A., andPaine, R.T. 1970. Benthic faunal zonation as a result of anchor ice at McMurdo Sound, Antarctica, pp. 244–258,in M. Holgate (ed.) Antarctic Ecology, Vol. 1. Academic Press, London.
Dayton, P.K., Robilliard, G.A., Paine, R.T., andDayton, L.B. 1974. Biological accommodation in the benthic community at McMurdo Sound, Antarctica.Ecol. Monogr. 44:105–128.
Dearborn, J.H. 1977. Food and feeding characteristics of antarctic asteroids and ophiuroids, pp. 293–326,in G.A. Llano (ed.). Adaptations within Antarctic Ecosystems, Gulf Publ. Co., Houston, Texas.
Eastman, J.T. 1993. Antarctic Fish Biology. Academic Press, New York, 322 pp.
Eggersdorfer, M., Kokke, W.C.M.C., Crandell, C.W., Hochlowski, J.E., andDjerassi, C. 1982. Sterols in marine invertebrates. 32. Isolation of 3-beta-(hydroxymethyl)A-nor-5-alpha-cholest-15-ene, the first naturally occurring sterol with a 15,16-double bond.J. Org. Chem. 47:5304–5309.
Faulkner, D.J. 1988. Feeding deterrents in mollusks, pp. 29–36,in D.G. Fautin (ed.). Biomedical Importance of Marine Organisms, Memoir 13. California Academy of Science, San Francisco.
Faulkner, D.J. 1991. Marine natural products.Nat. Prod. Rep. 7:97–147.
Gustafson, K., andAnderson, R.J. 1985. Chemical studies of British Columbia nudibranchs.Tetrahedron 41:1101–1108.
Heine, J., McClintock, J.B., Slattery, M., andWeston, J. 1991. Energetic composition, biomass, and chemical defense in the common antarctic nemerteanParborlasia corrugatus.J. Exp. Mar. Biol. Ecol. 153:15–25.
Karuso, P. 1987. Chemical ecology of the nudibranchs. pp. 31–60,in P.J. Scheuer (ed.). Bioorganic Marine Chemistry. Springer-Verlag, New York.
Kong, F., Harper, M.K., andFaulkner, D.J. 1992. Fuscusine, a tetrahydroisoquinoline alkaloid from the seastarPerknaster fuscus antarcticus.Nat. Prod. Lett. 1:71–74.
McClintock, J.B. 1994. Trophic biology of antarctic echinoderms.Mar. Ecol. Prog. Ser. 111:191–202.
McClintock, J.B., andJanssen, J. 1990. Pteropod abduction as a chemical defense in a pelagic antarctic amphipod.Nature 346:424–426.
McClintock, J.B., Pearse, J.S., andBosch, I. 1988. Population structure and energetics of the common antarctic sea starOdontaster validus.Mar. Biol. 99:235–246.
McClintock, J.B., Heine, J., Slattery, M., andWeston, J. 1990. Chemical bioactivity in shallow-water antarctic marine invertebrates.Antarct. J. U.S 25:204–206.
McClintock, J.B., Heine, J., Slattery, M., andWeston, J. 1992a. Biochemical and energetic composition, population biology, and chemical defense of the antarctic ascidianCnemidocarpa verrucosa Lesson.J. Exp. Mar. Biol. Ecol. 147:163–175.
McClintock, J.B., Slattery, M., Heine, J., andWeston, J. 1992b. Chemical defense, biochemical composition and energy content of three shallow-water antarctic gastropods.Polar Biol. 11:623–629.
McClintock, J.B., Baker, B.J., Hamann, M., Slattery, M., Kopitzke, R.W., andHeine, J. 1994a. Chemotactic tube-foot responses of the spongivorous sea starPerknaster fuscus to organic extracts of antarctic sponges.J. Chem. Ecol. 20:859–870.
McClintock, J.B., Slattery, M., Baker, B.J., andHeine, J. 1994b. Chemical ecology of antarctic sponges from McMurdo Sound: ecological aspects.Ant. J. U.S. 28:134–135.
McClintock, J.B., Baker, B.J., Hamann, M.T., Yoshida, W., Slattery, M., Heine, J., Bryan, P.J., Jayatilaka, G., andMoon, B. 1994c. Homarine as a feeding deterrent in the common shallow-water antarctic lamellarian gastropodMarseniopsis mollis: A rare example of chemical defense in a marine prosobranch.J. Chem. Ecol. 20:2539–2549.
Molinski, T.F., andFaulkner, D.J. 1987. Metabolites of the antarctic spongeDendrilla membranosa.J. Org. Chem. 52:298–300.
Molinski, T.F., andFaulkner, D.J. 1988. An antibacterial pigment from the spongeDendrilla membranosa.Tetrahedron Lett. 29:2137–2138.
Paul, V.J., Lindquist, N., andFenical, W. 1990. Chemical defense of the tropical ascidianAtapozoa sp. and its nudibranch predatorsNembrotha spp.Mar. Ecol. Prog. Ser. 59:109–118.
Pawlik, J.R., Kernan, M.R., Molinski, T.F., Harper, M.K., andFaulkner, D.J. 1988. Defensive chemicals of the spanish dancer nudibranchHexabranchus sanguineus and its egg ribbons: macrolides derived from a sponge diet.J. Exp. Mar. Biol. Ecol. 119:99–109.
Pearse, J.S. 1965. Reproductive periodicities in several contrasting populations ofOdontaster validus Koehler, a common antarctic asteroid. pp. 39–85,in G.A. Llano (ed). Biology of the Antarctic Seas, Vol. 2 Antarctic Research Series 5.
Pearse, J.S. 1969. Antarctic sea-star.Aust. Nat. Hist. 16:234–238.
Peckham, V. 1964. Year-round SCUBA diving in the Antarctic.Polar Rec. 12:143–146.
Perry, B.B., Ettouati, L., Litaudon, M., Blunt, J.W., Munro, M.H.G., Parkin, S., andHope, H. 1994. Alkaloids from the antarctic spongeKirkpatrickia variolosa. Part 1: Variolin B, a new antitumour and antiviral compound.Tetrahedron 50:3987–3992.
Rudman, W.B. 1981. The anatomy and biology of alcyonarian-feeding aeolid opisthobranch mollusks and their development of symbiosis with zooxanthellae.Zool. J. Linn. Soc. 72:219–262.
Seldes, A.M., Rovirosa, J., San Martin, A., andGros, E.G. 1986. Steroids from aquatic organisms; XII. Sterols from the antarctic spongeHomaxinella balfourensis (Ridley and Dendy).Comp. Biochem. Physiol. 83B:841–842.
Slattery, M. 1994. A comparative study of population structure and chemical defenses in the soft coralsAlcyonium paessleri May,Clavularia frankliniana Rouel, andGersemia antarctica Kukenthal in McMurdo Sound, Antarctica. PhD dissertation. University of Alabama at Birmingham, 109 pp.
Slattery, M., McClintock, J.B., Heine, J., andWeston, J. 1990. The chemical ecology of the antarctic soft coralAlcyonium paessleri.Am. Zool. 30:130.
Sloan, N.A. 1980. Aspects of feeding biology of asteroids.Oceanogr. Mar. Biol. Ann. Rev. 18:57–124.
Sokal, R.R., andRohlf, F.J. 1981. Biometry, 2nd Ed. W.H. Freeman, San Francisco, 859 pp.
Still, W.C., Kahn, M., andMitra, A. 1978. Rapid chromatographic technique for preparative separations with moderate resolution.J. Org. Chem. 43:2923–2925.
Thompson, G.A., Jr., andLee, P. 1965. Studies of the alpha-glycerol ether lipids occurring in molluscan tissues.Biochem. Biophys. Acta 98:151–159.
Thompson, J.E., Walker, R.P., Wratten, S.J., andFaulkner, D.J. 1982. A chemical defense mechanism for the nudibranchCadlina luteomarginata.Tetrahedron 38:1865–1873.
Trimurtulu, G., Faulkner, D.J., Perry, N.B., Ettouati, L., Litaudon, M., Blunt, J.W., Munro, M.H.G., andJamieson, G.B. 1994. Alkaloids from the antarctic spongeKirkpatrickia variolosa. Part 2: variolin A andN(3′)-methyl tetrahydrovariolin B.Tetrahedron 50:3993–4000.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
McClintock, J.B., Baker, B.J., Slattery, M. et al. Chemical defense of common antarctic shallow-water nudibranchTritoniella belli eliot (Mollusca: Tritonidae) and its prey,Clavularia frankliniana rouel (Cnidaria: Octocorallia). J Chem Ecol 20, 3361–3372 (1994). https://doi.org/10.1007/BF02033732
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02033732