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Biologically active cannabinoids from high-potency Cannabis sativa.
J Nat Prod 2009; 72(5):906-11JN

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.

Authors+Show Affiliations

Department of Pharmaceutics, National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, Mississippi 38677, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

19344127

Citation

Radwan, Mohamed M., et al. "Biologically Active Cannabinoids From High-potency Cannabis Sativa." Journal of Natural Products, vol. 72, no. 5, 2009, pp. 906-11.
Radwan MM, Elsohly MA, Slade D, et al. Biologically active cannabinoids from high-potency Cannabis sativa. J Nat Prod. 2009;72(5):906-11.
Radwan, M. M., Elsohly, M. A., Slade, D., Ahmed, S. A., Khan, I. A., & Ross, S. A. (2009). Biologically active cannabinoids from high-potency Cannabis sativa. Journal of Natural Products, 72(5), pp. 906-11. doi:10.1021/np900067k.
Radwan MM, et al. Biologically Active Cannabinoids From High-potency Cannabis Sativa. J Nat Prod. 2009 May 22;72(5):906-11. PubMed PMID: 19344127.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biologically active cannabinoids from high-potency Cannabis sativa. AU - Radwan,Mohamed M, AU - Elsohly,Mahmoud A, AU - Slade,Desmond, AU - Ahmed,Safwat A, AU - Khan,Ikhlas A, AU - Ross,Samir A, PY - 2009/4/7/entrez PY - 2009/4/7/pubmed PY - 2010/7/21/medline SP - 906 EP - 11 JF - Journal of natural products JO - J. Nat. Prod. VL - 72 IS - 5 N2 - 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. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/19344127/abstract/Biologically_Active_Cannabinoids_from_High_Potency_Cannabis_sativa_ L2 - https://dx.doi.org/10.1021/np900067k DB - PRIME DP - Unbound Medicine ER -