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. 1977 May;33(5):1134–1140. doi: 10.1128/aem.33.5.1134-1140.1977

Microbiological Transformations of Δ6a,10a-Tetrahydrocannabinol

David Fukuda 1, Robert A Archer 1, Bernard J Abbott 1
PMCID: PMC170839  PMID: 406841

Abstract

A screening program was conducted to find microorganisms that catalyze transformation reactions with cannabinoids. Three hundred fifty-eight cultures, consisting of 97 bacteria, 175 actinomycetes, and 86 molds, were incubated in media containing 0.5 mg of Δ6a,10a-tetrahydrocannabinol (Δ6a,10a-THC) per ml. After 120 h of cultivation, ethyl acetate extracts of the cultures were examined by thin-layer chromatography (TLC) for transformation products. About 18% of the cultures modified Δ6a,10a-THC. The ability to modify the substrate did not predominate among any particular group of microorganisms. After purification, the products from three cultures were analyzed by high-resolution mass spectrometry, 100-mHz proton magnetic resonance spectrometry, ultraviolet spectrometry, and infrared spectrometry. These spectral data indicated that a Mycobacterium sp. oxidized Δ6a,10a-THC to cannabinol and a diastereomeric pair of 6a-hydroxy-Δ10,10a-THC isomers; a Streptomyces sp. and a Bacillus sp. oxidized Δ6a,10a-THC to 7-keto-Δ6a,10a-THC and 4′-hydroxy-Δ6a,10a-THC, respectively. The occurrence of these products and the presence of others that have not yet been isolated or identified indicate that microbial transformation may be a useful tool for the preparation of new cannabinoids that have desirable pharmacological properties.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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