Skip to main content
SpringerLink
Log in

Diasteroisomeric ichthyotoxic acylglycerols from the dorsum of two geographically distinct populations ofArchidoris nudibranchs

  • Research Articles
  • Published:
Experientia Aims and scope Submit manuscript

Abstract

Two marine opisthobranchs,Archidoris tuberculata from Asturias (N. Spain) andArchidoris carvi from Patagonia (S. Argentina), contain in their dorsum diasteroisomeric ichthyotoxic acylglycerols esterified in position 1-sn by antipodal diterpenoid acids.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Karuso, P., in: Biorganic Marine Chemistry, vol. 1, p. 31. Ed. P. J. Scheuer. Springer-Verlag, Berlin-Heidelberg 1987.

    Chapter  Google Scholar 

  2. Faulkner, D. J., Nat. Prod. Rep.9 (1992) 323, and previous reports.

  3. Cimino, G., and Sodano, G., Chem. Scripta29 (1989) 389.

    CAS  Google Scholar 

  4. Avila, C., Cimino, G., Crispino, A., and Spinella, A., Experientia47 (1991) 306.

    Article  CAS  Google Scholar 

  5. Cimino, G., Crispino, A., Di Marzo, V., Spinella, A., and Sodano, G., J. org. Chem.56 (1991) 2907.

    Article  CAS  Google Scholar 

  6. Cimino, G., Gavagnin, M., Sodano, G., Puliti, R., Mattia, C. A., and Mazzarella, L., Tetrahedron44 (1988) 2301.

    Article  CAS  Google Scholar 

  7. Coll, J. C., La Barre, S., Sammarco, P. W., Williams, T. W., and Bakus, G. J., Mar. Ecol. Prog. Ser.8 (1982) 271.

    Article  Google Scholar 

  8. Gunthorpe, L., and Cameron A. M., Mar. Biol.94 (1987) 39.

    Article  CAS  Google Scholar 

  9. De Petrocellis, L., Di Marzo, V., Arca, B., Gavagnin, M., Minei, R., and Cimino, G., Comp. Biochem. Physiol.100C (1991) 603.

    Google Scholar 

  10. Gavagnin, M., Spinella, A., Cimino, G., and Sodano, G., Tetrahedron Lett.31 (1990) 6093.

    Article  CAS  Google Scholar 

  11. Previously reported11, absolute stereochemistry of the terpenoid part is wrong (see ref. 20).

  12. Gustafson, K., Andersen, R. J., Chen, M. H. M., Clardy, J., and Hochlowski, J. E., Tetrahedron Lett.25 (1984) 11.

    Article  CAS  Google Scholar 

  13. Gustafson, K., and Andersen, R. J., Tetrahedron41 (1985) 1101.

    Article  CAS  Google Scholar 

  14. Davies-Coleman, M. T., and Faulkner, D. J., Tetrahedron47 (1991) 9743.

    Article  CAS  Google Scholar 

  15. Imamura, P. M., and Ruveda, E. A., J. org. Chem.45, (1980) 510.

    Article  CAS  Google Scholar 

  16. Muniain, C., Ortea, J., and Rodriguez, G., Iberus10 (1992) 105.

    Google Scholar 

  17. Spectral data for8: IR (film) 3450, 1738 cm−1 1H-NMR and13C-NMR in table, MS,m/z 420(0.5), 402(2), 347(2), 286(100), 192(67), 177(67), 117(47). Spectral data for 9: IR (film) 3400, 1738 cm−1;1H-NMR in table. MS,m/z 420(1), 402(2), 347(2), 286(100), 192(61), 177(71), 117(70).

  18. Cimino, G., De Rosa, S., De Stefano, S., and Minale, L., Tetrahedron30 (1974) 645.

    Article  CAS  Google Scholar 

  19. Surprisingly, recording CD spectra of verrucosin-A and-B (1 and 2) positive, curves, analogous with those of 8 and 9, were obtained. An erroneous observation of the X-ray model of 2 led to assign11 a rearrangedent-isocopalane skeleton to the diterpenoid residue whereas, correctly, verrucosins should derive from an isocopalane precursor as shown by formulas 1 and 2.

  20. Fraga, B. M., Nat. Prod. Rep.7 (1990) 515. and references cited therein.

    Article  CAS  Google Scholar 

  21. Hanson, J. R., Nat. Prod. Rep.9 (1992) 1, and references cited therein.

    Article  CAS  PubMed  Google Scholar 

  22. De Giulio, A., De Rosa, S., and Di Vicenzo, G., J. nat. Prod.52 (1989) 1258.

    Article  Google Scholar 

Download references

Author information

Author notes

  1. E. Zubía

    Present address: I.C.M.I.B. from Universidad de Cádiz, Cádiz, Spain

Authors and Affiliations

  1. Istituto per la Chimica di Molecole di Interesse Biologico del C.N.R., Via Toiano 6, I-80072, Arco Felice, Napoli, Italy

    E. Zubía, M. Gavagnin, A. Crispino & G. Cimino

  2. Departmento de Biologia de Organismos y Sistemas, Universidad de Oviedo, C/J. Arias de Velasco, Oviedo, Spain

    E. Martinez & J. Ortea

Authors
  1. E. Zubía
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Gavagnin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Crispino
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Martinez
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. Ortea
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. Cimino
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zubía, E., Gavagnin, M., Crispino, A. et al. Diasteroisomeric ichthyotoxic acylglycerols from the dorsum of two geographically distinct populations ofArchidoris nudibranchs. Experientia 49, 268–271 (1993). https://doi.org/10.1007/BF01923538

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01923538

Key words

Search

Navigation