Skip to main content
Log in

Aplysia sea hare assimilation of secondary metabolites from brown seaweed,Stypopodium zonale

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

JuvenileAplysia dactylomela were found feeding in abundance on the tropical brown algaStypopodium zonale, a seaweed previously shown to contain numerous unique terpene-quinone natural products. Lipid extracts of these herbivorous mollusks were shown by TLC and HPLC-NMR analyses to contain appreciable quantities of twoS. zonale metabolites as well as one new but closely related compound. Spectroscopic analyses of the new compound in concert with functional group modifications identified this new compound as 3-keto epitaondiol. A careful analysis of the seaweed extract failed to locate this ketone, and thus, it most likely represents anAplysia-biotransformed compound. This is the first clear reported observation of metabolite transfer between an alga of the phylum Phaeophyta and a sea hare.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Amico, A., Oriente, G., Piatelli, M., Tringali, C., Fattorusso, E., Magno, S., andMayol, L. 1980. Diterpenes based on the dolabellane skeleton fromDictyota dichotoma.Tetrahedron 36:1409–1414.

    Google Scholar 

  • Ballantine, D.L., Gerwick, W.H., Velez, S.M., Alexander, E., andGuevara, P. 1987. Antibiotic activity of lipid-soluble extracts from Caribbean marine algae.Hydrobiologia 151/ 152:463–469.

    Google Scholar 

  • Coll, J.C., andBowden, B.F. 1986. The application of vacuum liquid chromatography to the separation of terpene mixtures.J. Nat. Prod. 49:934–936.

    Google Scholar 

  • Erickson, K.L. 1983. Constituents ofLaurencia, pp. 131–257,in P.J. Scheuer (ed.). Marine Natural Products, Vol. 5. Academic Press, New York.

    Google Scholar 

  • Faulkner, D.J. 1984. Marine natural products: Metabolites of marine algae and herbivorous marine molluscs.Nat. Prod. Rep. 1:251–280.

    Google Scholar 

  • Gerwick, W.H., andFenical, W. 1981. Ichthyotoxic and cytotoxic compounds from the tropical brown algaStypopodium zonale.J. Org. Chem. 46:22–27.

    Google Scholar 

  • Gerwick, W.H., Fenical, W., van Eagen, D., andClardy, J. 1979. Stypotriol and stypoldione: Ichthyotoxins of mixed biogenesis from the marine algaStypopodium zonale.Tetrahedron Lett. 20:145–148.

    Google Scholar 

  • Gonzalez, A.G., Martin, J.D., Norte, M., Perez, R., Weyler, V., Rafu, S., andClardy, J. 1983. A new diterpene fromAplysia dactylomela.Tetrahedron Lett. 24:1075–1076.

    Google Scholar 

  • Ireland, C., Faulkner, D.J., Finer, J., andClardy, J. 1976. A new diterpene fromDolabella californien.J. Am. Chem. Soc. 98:4664–4665.

    Google Scholar 

  • Midland, S.L., Wing, R.M., andSims, J.J. 1983. New crenulides from the sea hareAplysia vaccaria.J. Org. Chem. 48:1906–1909.

    Google Scholar 

  • Rose, A.F., Scheuer, P.J., Springer, J.P., andClardy, J. 1978. Stylocheilamide, an unusual constituent of the sea hareStylocheilus longicauda.J. Am. Chem. Soc. 100:7665–7670.

    Google Scholar 

  • Sun, H.H., andFenical, W. 1979. Diterpenoids of the brown seaweedGlossophora galapagensis.Phytochemistry 18:340–341.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gerwick, W.H., Whatley, G. Aplysia sea hare assimilation of secondary metabolites from brown seaweed,Stypopodium zonale . J Chem Ecol 15, 677–683 (1989). https://doi.org/10.1007/BF01014710

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01014710

Key words

Navigation