title: Minor oxygenated cannabinoids from high potency Cannabis sativa L.
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.
authors.affiliation: 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.
authors.forename: Safwat A
authors.initials: SA
authors.lastname: Ahmed
authors.affiliation: 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: sross@olemiss.edu.
authors.forename: Samir A
authors.initials: SA
authors.lastname: Ross
authors.affiliation: National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States.
authors.forename: Desmond
authors.initials: D
authors.lastname: Slade
authors.affiliation: 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.
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Radwan
authors.affiliation: 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.
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
authors.affiliation: 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: melsohly@olemiss.edu.
authors.forename: Mahmoud A
authors.initials: MA
authors.lastname: ElSohly
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000494:pharmacology; D002186:Cannabinoids / Q000737:chemistry* / Q000494:pharmacology*; D002188:Cannabis / Q000737:chemistry*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D010084:Oxidation-Reduction; D010963:Plasmodium falciparum / Q000187:drug effects
chemical_list: D000890:Anti-Infective Agents; D000962:Antimalarials; D000981:Antiprotozoal Agents; D002186:Cannabinoids
keywords: Anti-bacterial; Anti-leishmanial; Anti-malarial; Cananbis; Cannabaceae; Cannabis sativa; High potency; Oxygenated cannabinoids