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