Microbiological transformations of delta6a10a-tetrahydrocannabinol

Appl Environ Microbiol. 1977 May;33(5):1134-40. doi: 10.1128/aem.33.5.1134-1140.1977.

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

MeSH terms

  • Actinomycetales / metabolism
  • Bacillus cereus / metabolism*
  • Bacteria / metabolism
  • Cannabinoids / biosynthesis
  • Chemical Phenomena
  • Chemistry
  • Dronabinol / metabolism*
  • Fungi / metabolism
  • Mycobacterium / metabolism*
  • Nontuberculous Mycobacteria / metabolism*
  • Oxidation-Reduction
  • Streptomyces / metabolism*

Substances

  • Cannabinoids
  • Dronabinol