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Occurrence of a Novel Cannabimimetic Molecule 2-Sciadonoylglycerol(2-Eicosa-5', 11', 14'-trienoylgly

Occurrence of a Novel Cannabimimetic Molecule 2-Sciadonoylglycerol(2-Eicosa-5', 11', 14'-trienoylgly

  1. ThirdEyeFloond
    Biological & pharmaceutical bulletin 23(6), 758-761, 2000-06-01

    Nakane S, Tanaka T, Satouchi K, Kobayashi Y, Waku K, Sugiura T.

    Abstract
    The umbrella pine Sciadopitys verticillata seeds were found to contain a substantial amount (16.7 nmol/g) of sciadonic acid (all-cis-5,11,14-eicosatrienoic acid)-containing 2-monoacylglycerol, i.e., 2-sciadonoylglycerol (2-eicosa-5', 11', 14'-trienoylglycerol). Because the structure of 2-sciadonoylglycerol closely resembles that of 2-arachidonoylglycerol, the endogenous natural ligand for the cannabinoid receptor, we examined whether or not 2-sciadonoylglycerol exhibits cannabimimetic activity using NG108-15 neuroblastoma├Śglioma hybrid cells which express the cannabinoid CB1 receptor. We found that 2-sciadonoylglycerole induces rapid transient elevation of intracellular free Ca^ concentration in NG108-15 cells through a cannabinoid CB1 receptor-dependent mechanism similar to the case of 2-arachidonoylglycerol, yet the activity of 2-sciadonoylglycerol was apparently lower than that of 2-arachidonoylglycerol. The activity of 2-sciadonoylglycerol was detectable from 3-10 nM, reaching a maximum at around 10 ╬╝M. To our knowledge, this is the first report showing the occurrence of a cannabimimetic monoacylglycerol in higher plants.