Skip to main content
Log in

Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid

  • Published:
Experientia Aims and scope Submit manuscript

Abstract

A polyenoic fatty-acid isomerase (PFI) from a red marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethanolamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide isomer. This novel eicosanoid, termed conjugated triene anandamide (CTA), was assessed for its ability to bind to the cannabinoid receptor in rat brain membrane preparations. CTA is a high affinity cannabimimetic substance whose novel structure provides new insight into structure-activity relationships of cannabinoid receptor ligands. These experiments illustrate the utility of enzymes isolated from marine organisms in the development of pharmacological probes.

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.

Institutional subscriptions

Similar content being viewed by others

Literatur

  1. Devane, D. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R., Science258 (1992) 1946.

    Article  CAS  PubMed  Google Scholar 

  2. Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., and Bonner, T. I., Nature346 (1990) 561.

    Article  CAS  PubMed  Google Scholar 

  3. Wise, M. L., Hamberg, M., and Gerwick, W. H., Biochemistry33 (1994) 15223.

    Article  CAS  PubMed  Google Scholar 

  4. Evershed, R. P. in: Handbook of Derivatives for Chromatography, 2nd edn p. 59. Eds K. Blau and J. Halket, John Wiley & Sons, Chichester (England) 1993.

    Google Scholar 

  5. Melvin, L. S., Milne, G. M., Johnson, M. R., Subramaniam, B., Wilken, G. H., and Howlett, A. C., Molec. Pharm.44 (1993) 1008.

    CAS  PubMed  Google Scholar 

  6. Lowry, O. H., Rosenbrough, N. J., Farr, A. L., and Randall, R. J., J. biol. Chem.193 (1951) 265.

    Article  CAS  PubMed  Google Scholar 

  7. Lopez, A., and Gerwick, W. H., Lipids22 (1987) 190.

    Article  CAS  PubMed  Google Scholar 

  8. Wolff, I. A., and Miwa, T. K., J. Am. Oil chem. Soc.42 (1965) 208.

    Article  CAS  Google Scholar 

  9. Deutsch, D. G., and Chin, S. A., Biochem. Pharmac.46 (1993) 791.

    Article  CAS  Google Scholar 

  10. Childers, S. R., Sexton, T., and Roy, M. B., Biochem. Pharmac.47 (1994) 711.

    Article  CAS  Google Scholar 

  11. Pinto, J. C., Potie, F., Rice, K. C., Boring, D., Johnson, M. R., Evans, D. M., Wilken, G. H., Cantrell, C. H., and Howlett, A. C., Molec. Pharmac.46 (1994) 516.

    CAS  Google Scholar 

  12. Felder, C. C., Briley, E. M., Axelrod, J., Simpson, J. T., Mackie, K., and Devane, W. A., Proc. natl Acad. Sci.90 (1993) 7656.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Hanus, L., Gopher, A., Almog, S., and Mechoulam, R., J. med. Chem.36 (1993) 3032.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wise, M.L., Soderstrom, K., Murray, T.F. et al. Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid. Experientia 52, 88–92 (1996). https://doi.org/10.1007/BF01922423

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01922423

Key words

Navigation