Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa. J Nat Prod 2015 Jun 26;78(6):1271-6
Date
05/23/2015Pubmed ID
26000707Pubmed Central ID
PMC4880513DOI
10.1021/acs.jnatprod.5b00065Scopus ID
2-s2.0-84933055128 (requires institutional sign-in at Scopus site) 102 CitationsAbstract
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 8α-hydroxy-Δ(9)-tetrahydrocannabinol (1), 8β-hydroxy-Δ(9)-tetrahydrocannabinol (2), 10α-hydroxy-Δ(8)-tetrahydrocannabinol (3), 10β-hydroxy-Δ(8)-tetrahydrocannabinol (4), 10α-hydroxy-Δ(9,11)-hexahydrocannabinol (5), 9β,10β-epoxyhexahydrocannabinol (6), and 11-acetoxy-Δ(9)-tetrahydrocannabinolic acid A (7). The binding affinity of isolated compounds 1-8, Δ(9)-tetrahydrocannabinol, and Δ(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.
Author List
Radwan MM, ElSohly MA, El-Alfy AT, Ahmed SA, Slade D, Husni AS, Manly SP, Wilson L, Seale S, Cutler SJ, Ross SAAuthor
Abir El-Alfy PhD Assistant Dean, Professor in the School of Pharmacy Administration department at Medical College of WisconsinMESH terms used to index this publication - Major topics in bold
AnalgesicsAnimals
Cannabinoids
Cannabis
Dose-Response Relationship, Drug
Dronabinol
Gas Chromatography-Mass Spectrometry
Mice
Mississippi
Molecular Structure
Motor Activity
Nuclear Magnetic Resonance, Biomolecular
Receptor, Cannabinoid, CB1
Receptor, Cannabinoid, CB2
