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

The umbrella pine Sciadopitys verticillata seeds were found to contain a su bstantial amount (16.7 nmol/g) of sciadonic acid (all-cis-5,11,14-eicosatri enoic acid)-containing 2-monoglycerol, i.e., 2-sciadonoylglycerol (2-eicosa -5',11',14'-trienoglycerol). Because the structure of 2-sciadonoylglycerol closely resembles that of 2-arachidonoylglycerol, the endogenous natural li gand for the cannabinoid receptor; we examined whether or not 2-sciadonoylg lycerol exhibits cannabimimetic activity using NG108-15 neuroblastoma x gli oma hybrid cells which express the cannabinoid CB1 receptor. We found that 2-sciadonoylglycerol induces rapid transient elevation of intracellular fre e Ca2+ concentration in NG108-15 cells through a cannabinoid CB1 receptor-d ependent mechanism similar to the case of 2-arachidonoylglycerol, yet the a ctivity of 2-sciadonoylglycerol was apparently lower than that of 2-arachid onoylglycerol. The activity of 2-sciadonoylglycerol was detectable from 3-1 0 nM, reaching a maximum at around 10 mu M. To our knowledge, this is the f irst report showing the occurrence of a cannabimimetric monoacylglycerol in higher plants.