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

被引：90

作者：

Radwan, Mohamed M. ^{[1
]}

ElSohly, Mahmoud A. ^{[1
,2
]}

El-Alfy, Abir T. ^{[3
]}

Ahmed, Safwat A. ^{[1
]}

Slade, Desmond ^{[1
]}

Husni, Afeef S. ^{[3
]}

Manly, Susan P. ^{[3
]}

Wilson, Lisa ^{[3
]}

Seale, Suzanne ^{[3
]}

Cutler, Stephen J. ^{[1
,3
]}

Ross, Samir A. ^{[1
,3
]}

机构：

[1] Univ Mississippi, Sch Pharm, Natl Ctr Nat Prod Res, University, MS 38677 USA

[2] Univ Mississippi, Sch Pharm, Dept Pharmaceut & Drug Delivery, University, MS 38677 USA

[3] Univ Mississippi, Sch Pharm, Dept BioMol Sci, University, MS 38677 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 06期

关键词：

RECEPTOR; CONSTITUENTS; DELTA-9-TETRAHYDROCANNABINOL; DELTA(9)-TETRAHYDROCANNABINOL; METABOLITES; MARIJUANA;

D O I：

10.1021/acs.jnatprod.5b00065

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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 alpha-hydroxy-Delta(9)-tetrahydrocannabinol (1), 8 beta-hydroxy-Delta(9)-tetrahydrocannabinol (2), 10 alpha-hydroxy-Delta(8)-tetrahydrocannabinol (3), 10 beta-hydroxy-Delta(8)-tetrahydrocannabinol (4), 10 alpha-hydroxy-Delta(9,11)-hexahydrocannabinol (5), 9 beta,10 beta-epoxyhexahydrocannabinol (6), and 11-acetoxy-Delta(9)-tetrahydrocannabinolic acid A (7). The binding affinity of isolated compounds 1-8, Delta(9)-tetrahydrocannabinol, and Delta(8)-tetrahydrocannabino1 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.

引用

页码：1271 / 1276

页数：6

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