Minor oxygenated cannabinoids from high potency Cannabis sativa L

  • Phytochemistry. 2015 Sep:117:194-199. doi: 10.1016/j.phytochem.2015.04.007.
Safwat A Ahmed  1 ,  Samir A Ross  2 ,  Desmond Slade  3 ,  Mohamed M Radwan  4 ,  Ikhlas A Khan  5 ,  Mahmoud A ElSohly  6
Affiliations
  • 1. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt.
  • 2. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, United States. Electronic address: [email protected].
  • 3. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States.
  • 4. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Department of Pharmacognosy, Faculty of Pharmacy, Alexandria University, Alexendria, Egypt.
  • 5. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, United States.
  • 6. National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, MS 38677, United States. Electronic address: [email protected].
PMID: 26093324 DOI: 10.1016/j.phytochem.2015.04.007
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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