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. 2009 May 22;72(5):906-11.
doi: 10.1021/np900067k.

Biologically active cannabinoids from high-potency Cannabis sativa

Mohamed M Radwan  1 , Mahmoud A Elsohly, Desmond Slade, Safwat A Ahmed, Ikhlas A Khan, Samir A Ross
Affiliations

Biologically active cannabinoids from high-potency Cannabis sativa

Mohamed M Radwan et al. J Nat Prod. .

Abstract

Nine new cannabinoids (1-9) were isolated from a high-potency variety of Cannabis sativa. Their structures were identified as (+/-)-4-acetoxycannabichromene (1), (+/-)-3''-hydroxy-Delta((4'',5''))-cannabichromene (2), (-)-7-hydroxycannabichromane (3), (-)-7R-cannabicoumarononic acid A (4), 5-acetyl-4-hydroxycannabigerol (5), 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol (6), 8-hydroxycannabinol (7), 8-hydroxycannabinolic acid A (8), and 2-geranyl-5-hydroxy-3-n-pentyl-1,4-benzoquinone (9) through 1D and 2D NMR spectroscopy, GC-MS, and HRESIMS. The known sterol beta-sitosterol-3-O-beta-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.

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Figures

Figure 1
Figure 1
Key HMBC correlations for 2, 3, 5, 6, 7, and 9.
Figure 2
Figure 2
Key ROESY correlation between H-7 and pseudoequatorial H3-10 of 4.
Chart 1
Chart 1
See this image and copyright information in PMC

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