Cannabis, 21. Biotransformation of cannabinol to its glycosides by in vitro plant tissue.

A marijuana compound, cannabinol [1], was converted to two metabolites using in vitro tissue of Pinellia ternata. The structures of the metabolites were determined to be cannabinol-O-beta-D-glucopyranoside [2] and 9'-hydroxycannabinol-O-beta-D-glucopyranoside [3] by 1H nmr and 13C nmr. From the time course experiments, 1 was absorbed rapidly in the tissues and glycosylated. Hydroxylation at the pentyl group occurred, and its metabolite was secreted in the medium.