Biologically Active Cannabinoids from High-Potency Cannabis sativa
Nine new cannabinoids were isolated from a high-potency variety of Cannabis sativa. Their structures were identified as (±)-4-acetoxycannabichromene, (±)-3′′-hydroxy-Δ(4′′,5′′)-cannabichromene, (−)-7-hydroxycannabichromane, (−)-7R-cannabicoumarononic acid A, 5-acetyl-4-hydroxycannabigerol , 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol, 8-hydroxycannabinol, 8-hydroxycannabinolic acid A, and 2-geranyl-5-hydroxy-3-n-pentyl-1,4-benzoquinone through 1D and 2D NMR spectroscopy, GC-MS, and HRESIMS. The known sterol β-sitosterol-3-O-β-d-glucopyranosyl-6′-acetate was isolated for the first time from cannabis.
Compounds 6 and 7 displayed significant antibacterial and antifungal activities, respectively, while 5 displayed strong antileishmanial activity.
As part of our program aimed at the discovery of new cannabinoids and other metabolites with significant biological activity from highpotency cannabis (!9-THC > 10%, w/w), we have reported 25 new metabolites.2-5 In this paper, we report the isolation and identification of nine additional new cannabinoids (1-9), including three cannabichromene derivatives (1-3), (-)-7R-cannabicoumarononic acid A (4), two cannabigerol derivatives (5 and 6), two cannabinol derivatives (7 and 8), and a C21 benzoquinone derivative.
Results and Discussion
Compound 1 was isolated...read full pdf