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

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• 作者：Mohamed M. Radwan ; Mahmoud A. ElSohly ; Abir T. El-Alfy ; Safwat A. Ahmed ; Desmond Slade ; Afeef S. Husni ; Susan P. Manly ; Lisa Wilson ; Suzanne Seale ; Stephen J. Cutler ; Samir A. Ross
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：June 26, 2015
• 年：2015
• 卷：78
• 期：6
• 页码：1271-1276
• 全文大小：302K
• ISSN：1520-6025

文摘

Seven new naturally occurring hydroxylated cannabinoids (1鈥?b>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伪-hydroxy-螖⁹-tetrahydrocannabinol (1), 8尾-hydroxy-螖⁹-tetrahydrocannabinol (2), 10伪-hydroxy-螖⁸-tetrahydrocannabinol (3), 10尾-hydroxy-螖⁸-tetrahydrocannabinol (4), 10伪-hydroxy-螖^9,11-hexahydrocannabinol (5), 9尾,10尾-epoxyhexahydrocannabinol (6), and 11-acetoxy-螖⁹-tetrahydrocannabinolic acid A (7). The binding affinity of isolated compounds 1鈥?b>8, 螖⁹-tetrahydrocannabinol, and 螖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.