Cannabis 25, biotransformation of cannabidiol and cannabidiolic acid by Pinellia ternata tissue segments

Two marihuana constituents, cannabidiol (1) and cannabidiolic acid (4) were each converted mainly to two metabolites using tissue segments of Pinellia ternata tuber. The structures of the metabolites formed from 1 were determined to be 1-0-β-D-glucopyranoside and 1-0-β-D- diglucopyranoside by ¹H nmr, ¹³C nmr and fabms. Those from 4 were determined as 4- 0- β-D- glucopyranoside and 10'-hydroxyl 4-0- βD-glucopyranoside. In time course experiments, 1 was absorbed rapidly by the tissues and glucosylated. Hydroxylation subsequent to the glucosylation occurred at the pentyl group in 4.