This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Reprints and Permissions Copyright Information Books from ASM Press MicrobeWorld Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Fukuda, D. Articles by Abbott, B. J. Search for Related Content PubMed PubMed Citation Articles by Fukuda, D. Articles by Abbott, B. J. Agricola Articles by Fukuda, D. Articles by Abbott, B. J.

 Previous Article  |  Next Article 

Appl Environ Microbiol. 1977 May; 33(5): 1134-1140
Copyright © 1977 American Society for Microbiology. All Rights Reserved.

Microbiological Transformations of ^6a,10a-Tetrahydrocannabinol

The Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46206

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 ^6a,10a-tetrahydrocannabinol (^6a,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 ^6a,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 ^6a,10a-THC to cannabinol and a diastereomeric pair of 6a-hydroxy-^10,10a-THC isomers; a Streptomyces sp. and a Bacillus sp. oxidized ^6a,10a-THC to 7-keto-^6a,10a-THC and 4'-hydroxy-^6a,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.