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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 9?-hydroxyhexahydrocannabinol, 7-oxo-9?-hydroxyhexa-hydrocannabinol, 10?-hydroxyhexahydrocannabinol, 10aR-hydroxyhexahydrocannabinol, ?(9)-THC aldehyde A, 8-oxo-?(9)-THC, 10a?-hydroxy-10-oxo-?(8)-THC, 9?-hydroxy-10-oxo-?(6a,10a)-THC, and 1'S-hydroxycannabinol, respectively. The latter compound showed moderate anti-MRSa (IC50 10.0 ?g/mL), moderate antileishmanial (IC50 14.0 ?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 ?g/mL, respectively.

SUBMITTER: Ahmed SA

PROVIDER: S-EPMC4883105 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Minor oxygenated cannabinoids from high potency Cannabis sativa L.

Ahmed Safwat A SA Ross Samir A SA Slade Desmond D Radwan Mohamed M MM Khan Ikhlas A IA ElSohly Mahmoud A MA

Phytochemistry 20150617

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- ...[more]

PMID: 26093324

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