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 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 neuroblastomaxglioma 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 CBI 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 microM. To our knowledge, this is the first report showing the occurrence of a cannabimimetic monoacylglycerol in higher plants.
Nakane
S
S
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa, Japan.
Tanaka
T
T
Satouchi
K
K
Kobayashi
Y
Y
Waku
K
K
Sugiura
T
T
D016718:Arachidonic Acid / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001095:Arachidonic Acids; D002188:Cannabis / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D005989:Glycerides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018716:Molecular Mimicry; D012639:Seeds / Q000737:chemistry; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
C414322:2-sciadonoylglycerol; D001095:Arachidonic Acids; D005989:Glycerides; D016718:Arachidonic Acid