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.