Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.

ABSTRACT: Seven new naturally occurring hydroxylated cannabinoids (1-7), along with the known cannabiripsol (8), have been isolated from the aerial parts of high-potency Cannabis sativa. The structures of the new compounds were determined by 1D and 2D NMR spectroscopic analysis, GC-MS, and HRESIMS as 8?-hydroxy-?(9)-tetrahydrocannabinol (1), 8?-hydroxy-?(9)-tetrahydrocannabinol (2), 10?-hydroxy-?(8)-tetrahydrocannabinol (3), 10?-hydroxy-?(8)-tetrahydrocannabinol (4), 10?-hydroxy-?(9,11)-hexahydrocannabinol (5), 9?,10?-epoxyhexahydrocannabinol (6), and 11-acetoxy-?(9)-tetrahydrocannabinolic acid A (7). The binding affinity of isolated compounds 1-8, ?(9)-tetrahydrocannabinol, and ?(8)-tetrahydrocannabinol toward CB1 and CB2 receptors as well as their behavioral effects in a mouse tetrad assay were studied. The results indicated that compound 3, with the highest affinity to the CB1 receptors, exerted the most potent cannabimimetic-like actions in the tetrad assay, while compound 4 showed partial cannabimimetic actions. Compound 2, on the other hand, displayed a dose-dependent hypolocomotive effect only.

SUBMITTER: Radwan MM 

PROVIDER: S-EPMC4880513 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature