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Chemical defense of common antarctic shallow-water nudibranchTritoniella belli eliot (Mollusca: Tritonidae) and its prey,Clavularia frankliniana rouel (Cnidaria: Octocorallia)

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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.

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References

  • Anderson, R.J., andSum, F.W. 1980. Farnesic acid glycerides from the nudibranchArchidoris alheri.Tetrahedron Lett. 21:979–800.

    Article  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    CAS  Google Scholar 

  • Davies-Coleman, M.T., andFaulkner, D.J. 1991. New diterpenoic acid glycerides from the antarctic nudibranchAustrodoris mcmurdensis.Tetrahedron 47:9732–9750.

    Article  Google Scholar 

  • 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.

    PubMed  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • Eastman, J.T. 1993. Antarctic Fish Biology. Academic Press, New York, 322 pp.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • Faulkner, D.J. 1991. Marine natural products.Nat. Prod. Rep. 7:97–147.

    Article  Google Scholar 

  • Gustafson, K., andAnderson, R.J. 1985. Chemical studies of British Columbia nudibranchs.Tetrahedron 41:1101–1108.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • Karuso, P. 1987. Chemical ecology of the nudibranchs. pp. 31–60,in P.J. Scheuer (ed.). Bioorganic Marine Chemistry. Springer-Verlag, New York.

    Google Scholar 

  • Kong, F., Harper, M.K., andFaulkner, D.J. 1992. Fuscusine, a tetrahydroisoquinoline alkaloid from the seastarPerknaster fuscus antarcticus.Nat. Prod. Lett. 1:71–74.

    CAS  Google Scholar 

  • McClintock, J.B. 1994. Trophic biology of antarctic echinoderms.Mar. Ecol. Prog. Ser. 111:191–202.

    Google Scholar 

  • McClintock, J.B., andJanssen, J. 1990. Pteropod abduction as a chemical defense in a pelagic antarctic amphipod.Nature 346:424–426.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Molinski, T.F., andFaulkner, D.J. 1987. Metabolites of the antarctic spongeDendrilla membranosa.J. Org. Chem. 52:298–300.

    Article  Google Scholar 

  • Molinski, T.F., andFaulkner, D.J. 1988. An antibacterial pigment from the spongeDendrilla membranosa.Tetrahedron Lett. 29:2137–2138.

    Article  CAS  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • Peckham, V. 1964. Year-round SCUBA diving in the Antarctic.Polar Rec. 12:143–146.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Google Scholar 

  • Sloan, N.A. 1980. Aspects of feeding biology of asteroids.Oceanogr. Mar. Biol. Ann. Rev. 18:57–124.

    Google Scholar 

  • Sokal, R.R., andRohlf, F.J. 1981. Biometry, 2nd Ed. W.H. Freeman, San Francisco, 859 pp.

    Google Scholar 

  • Still, W.C., Kahn, M., andMitra, A. 1978. Rapid chromatographic technique for preparative separations with moderate resolution.J. Org. Chem. 43:2923–2925.

    Article  CAS  Google Scholar 

  • Thompson, G.A., Jr., andLee, P. 1965. Studies of the alpha-glycerol ether lipids occurring in molluscan tissues.Biochem. Biophys. Acta 98:151–159.

    PubMed  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

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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

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