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Biologically Active Cannabinoids from High-Potency Cannabis sativa

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National Center for Natural Products Research, Department of Pharmaceutics, and Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677
* To whom correspondence should be addressed. Tel: +1-662-915-1031. Fax: +1-662-915-7989. E-mail: [email protected] (S.A.R.). Tel: +1-662-915-5928. Fax: +1-662-915-5587. E-mail: [email protected] (M.A.E.).
†National Center for Natural Products Research.
‡Department of Pharmaceutics.
§Current address: Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt.
⊥Department of Pharmacognosy.
Cite this: J. Nat. Prod. 2009, 72, 5, 906–911
Publication Date (Web):April 3, 2009
https://doi.org/10.1021/np900067k
Copyright © 2009 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    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-Δ(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 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.

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    1H and 13C NMR spectroscopic data for compounds 1−9. This material is available free of charge via the Internet at http://pubs.acs.org.

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