Document Detail


Microbiological transformations of nabilone, a synthetic cannabinoid.
MedLine Citation:
PMID:  114111     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A screening program was conducted to find microorganisms that modify the synthetic cannabinoid nabilone. After purification, the products from three cultures were analyzed by spectral methods to determine their chemical structures. An optically active 9S-hydroxy-6aR,10aR-trans cannabinoid was isolated from a culture of an unidentified soil bacterium designated A24007. From Bacillus cereus cultures were isolated a 9S,6'-dihydroxy-6aR,10aR-trans cannabinoid, a 9S-hydroxy-6'-keto-6aR,10aR-trans cannabinoid, a 9-keto-6'-hydroxy-6aS,10aS-trans cannabinoid, and a 6',9-diketo-6aS,10aS-trans cannabinoid. All of these products were optically active, as was a 9S-hydroxy-6aS,10AS-trans cannabinoid also isolated from B. cereus cultures. A series of acidic products were isolated from cultures of Nocardia salmonicolor. All of these products contained a carboxylic acid group at the terminal end of three-position alkyl side chains having varying numbers of carbon atoms. Two of the acidic products contained a 9-keto group, whereas all other carboxylic acid products were 9-hydroxy cannabinoids. The array of products obtained from incubation of nabilone indicates the usefulness of microbial transformations in the preparation of new cannabinoids.
Authors:
R A Archer; D S Fukuda; A D Kossoy; B J Abbott
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Applied and environmental microbiology     Volume:  37     ISSN:  0099-2240     ISO Abbreviation:  Appl. Environ. Microbiol.     Publication Date:  1979 May 
Date Detail:
Created Date:  1979-11-21     Completed Date:  1979-11-21     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  7605801     Medline TA:  Appl Environ Microbiol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  965-71     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Actinomycetales / metabolism
Bacillus cereus / metabolism
Bacteria / metabolism*
Biodegradation, Environmental
Cannabinoids / biosynthesis
Chemical Phenomena
Chemistry
Fungi / metabolism*
Nocardia / metabolism
Tetrahydrocannabinol / analogs & derivatives*,  metabolism
Chemical
Reg. No./Substance:
0/Cannabinoids; 1972-08-3/Tetrahydrocannabinol
Comments/Corrections

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