Microbial transformation of cannabinoids. Part 3: Major metabolites of (3R, 4R)-Δ1-tetrahydrocannabinol

The metabolic transformations of the psychotropic cannabinoid (3R, 4R)-Δ¹-tetrahydrocannabinol (5) (=Δ¹-THC) by cultures of Fusarium Nivale, Gibberella fujikuroi (both Ascomycetes) and Thamnidium elegans (Phycomycetes) were investigated. A number of metaboilites, 1–4 and 6–9 were isolated from the incubations, partly purified and their structures elucidated by combined gas chromatography/mass spectrometry. Four of these metabolites, 1″-hydroxy-Δ¹-THC (4) 2″-hydroxy-β¹-THC (1) 6Δ-hydroxy-ζ¹-THC (8) and 2″,6Δ-dihydroxy-Δ¹-THC (9) so far have not been reported as microbial transformation products of 5 .