Microbiological transformations of delta6a10a-tetrahydrocannabinol

Area of Science:

• Microbiology
• Biotechnology
• Medicinal Chemistry

Background:

• Cannabinoids, such as Delta(6a,10a)-tetrahydrocannabinol (Delta(6a,10a)-THC), are compounds with potential pharmacological properties.
• Microbial transformation offers a pathway for modifying complex organic molecules.
• Exploring microbial capabilities for cannabinoid modification is crucial for discovering new therapeutic agents.

Purpose of the Study:

• To screen for microorganisms capable of catalyzing transformation reactions with Delta(6a,10a)-THC.
• To identify the specific transformation products generated by these microorganisms.
• To assess the potential of microbial transformation in synthesizing novel cannabinoids.

Main Methods:

• Incubation of 358 microbial cultures (bacteria, actinomycetes, molds) with Delta(6a,10a)-THC.
• Analysis of culture extracts using thin-layer chromatography (TLC) to detect transformation products.
• Purification and characterization of products using high-resolution mass spectrometry, NMR, UV, and IR spectroscopy.

Main Results:

• Approximately 18% of the screened cultures demonstrated the ability to modify Delta(6a,10a)-THC.
• Specific microorganisms, including a Mycobacterium sp., Streptomyces sp., and Bacillus sp., were identified as producers of distinct cannabinoid metabolites.
• Identified products included cannabinol, 6a-hydroxy-Delta(10,10a)-THC isomers, 7-keto-Delta(6a,10a)-THC, and 4'-hydroxy-Delta(6a,10a)-THC.

Conclusions:

• Microbial transformation is a viable strategy for modifying cannabinoids.
• This approach can yield novel cannabinoid derivatives with potentially desirable pharmacological activities.
• Further research into microbial transformation can expand the library of pharmacologically relevant cannabinoids.