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. 2015 Sep:117:194-199.
doi: 10.1016/j.phytochem.2015.04.007. Epub 2015 Jun 17.

Minor oxygenated cannabinoids from high potency Cannabis sativa L

Safwat A Ahmed  1 , Samir A Ross  2 , Desmond Slade  3 , Mohamed M Radwan  4 , Ikhlas A Khan  5 , Mahmoud A ElSohly  6
Affiliations

Minor oxygenated cannabinoids from high potency Cannabis sativa L

Safwat A Ahmed et al. Phytochemistry. 2015 Sep.

Abstract

Nine oxygenated cannabinoids were isolated from a high potency Cannabis sativa L. variety. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR, HRMS and GC-MS. These minor compounds include four hexahydrocannabinols, four tetrahydrocannabinols, and one hydroxylated cannabinol, namely 9α-hydroxyhexahydrocannabinol, 7-oxo-9α-hydroxyhexa-hydrocannabinol, 10α-hydroxyhexahydrocannabinol, 10aR-hydroxyhexahydrocannabinol, Δ(9)-THC aldehyde A, 8-oxo-Δ(9)-THC, 10aα-hydroxy-10-oxo-Δ(8)-THC, 9α-hydroxy-10-oxo-Δ(6a,10a)-THC, and 1'S-hydroxycannabinol, respectively. The latter compound showed moderate anti-MRSa (IC50 10.0 μg/mL), moderate antileishmanial (IC50 14.0 μg/mL) and mild antimalarial activity against Plasmodium falciparum (D6 clone) and P. falciparum (W2 clone) with IC50 values of 3.4 and 2.3 μg/mL, respectively.

Keywords: Anti-bacterial; Anti-leishmanial; Anti-malarial; Cananbis; Cannabaceae; Cannabis sativa; High potency; Oxygenated cannabinoids.

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Figures

Fig. 1
Fig. 1
Important HMBC (blue), COSY (red) and ROESY (violet) correlations for 1–9. (For interpretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
Fig. 2
Fig. 2
Selective oxidation of cannabiripsol (PCC).
Fig. 3
Fig. 3
Mosher ester analysis of 9.
See this image and copyright information in PMC

References

    1. Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, ElSohly MA. Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod. 2008a;71:536–542. - PMC - PubMed
    1. Ahmed SA, Ross SA, Slade D, Radwan MM, Ikhlas AK, ElSohly MA. Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa. Tetrahedron Lett. 2008b;49:6050–6053. - PMC - PubMed
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    1. ElSohly MA, Gul W. Constituents of Cannabis Sativa. In: Pertwee RG, editor. Handbook of Cannabis. Oxford University Press; 2014. pp. 3–22.

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