Occurrence of a novel cannabimimetic molecule 2-sciadonoylglycerol (2- eicosa-5',11',14'-trienoylglycerol) in the umbrella pine Sciadopitys verticillata seeds

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 x glioma hybrid cells which express the cannabinoid CB1 receptor. We found that 2- sciadonoylglycerol induces rapid transient elevation of intracellular free Ca2+ 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.