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

Experientia. 1996 Jan 16;52(1):88-92. doi: 10.1007/BF01922423.

Abstract

A polyenoic fatty-acid isomerase (PFI) from a red marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethan olamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanol amide 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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Arachidonic Acids / chemical synthesis*
  • Arachidonic Acids / metabolism
  • Brain / metabolism*
  • Cannabinoids / metabolism
  • Cell Membrane / metabolism
  • Eicosanoids / chemical synthesis*
  • Eicosanoids / metabolism
  • Endocannabinoids
  • Eukaryota / metabolism
  • Polyunsaturated Alkamides
  • Radioligand Assay
  • Rats
  • Receptors, Cannabinoid
  • Receptors, Drug / metabolism*

Substances

  • Arachidonic Acids
  • Cannabinoids
  • Eicosanoids
  • Endocannabinoids
  • Polyunsaturated Alkamides
  • Receptors, Cannabinoid
  • Receptors, Drug
  • anandamide