Minor oxygenated cannabinoids from high potency Cannabis sativa L.

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 9 alpha-hydroxyhexahydrocannabinol, 7-oxo-9 alpha-hydroxyhexa-hydrocannabinol, 10 alpha-hydroxyhexahydrocannabinol, 10aR-hydroxyhexahydrocannabinol, Delta(9)-THC aldehyde A, 8-oxo-Delta(9)-THC, 10a alpha-hydroxy-10-oxo-Delta(9)-THC, 9 alpha-hydroxy-10-oxo-Delta(6a,10a)-THC, and 1'S-hydroxycannabinol, respectively. The latter compound showed moderate anti-MRSa (IC50 10.0 mu g/mL), moderate antileishmanial (IC50 14.0 mu g/mL) and mild antimalarial activity against Plasmodium falciparum (D6 clone) and P. falciparum (W2 clone) with IC50 values of 3.4 and 2.3 mu g/mL, respectively. (C) 2015 Elsevier Ltd. All rights reserved.