Occurrence of a Novel Cannabimimetic Molecule 2-Sciadonoylglycerol(2-Eicosa-5', 11', 14'-trienoylglycerol) in the Umbrella Pine Sciadopitys verticillata Seeds

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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×glioma hybrid cells which express the cannabinoid CB1 receptor. We found that 2-sciadonoylglycerole induces rapid transient elevation of intracellular free Ca^<2+> 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 μM. To our knowledge, this is the first report showing the occurrence of a cannabimimetic monoacylglycerol in higher plants.
公益社団法人日本薬学会の論文
2000-06-01