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Microbial transformation of cannabinoids. Part 3 : Major metabolites of (3 R , 4 R )‐Δ 1 ‐tetrahydrocannabinol
Author(s) -
Binder Michael,
Popp Astrid
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630846
Subject(s) - chemistry , cannabinoid , gibberella fujikuroi , biotransformation , chromatography , stereochemistry , tetrahydrocannabinol , mass spectrometry , fusarium , biochemistry , enzyme , botany , receptor , biology
The metabolic transformations of the psychotropic cannabinoid (3 R , 4 R )‐Δ 1 ‐tetrahydrocannabinol (5) (=Δ 1 ‐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‐Δ 1 ‐THC (4) 2″‐hydroxy‐β 1 ‐THC (1) 6Δ‐hydroxy‐ζ 1 ‐THC (8) and 2″,6Δ‐dihydroxy‐Δ 1 ‐THC (9) so far have not been reported as microbial transformation products of 5 .