Hydroxylation and Further Oxidation of Δ⁹-Tetrahydrocannabinol by Alkane-Degrading Bacteria

The microbial biotransformation of Δ⁹-tetrahydrocannabinol was investigated using a collection of 206 alkane-degrading strains. Fifteen percent of these strains, mainly gram-positive strains from the genera Rhodococcus, Mycobacterium, Gordonia, and Dietzia, yielded more-polar derivatives. Eight deri...

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Bibliographic Details
Published in:Applied and Environmental Microbiology 2009-11, Vol.75 (22), p.7135-7141
Main Authors: Rashidi, Hassan, Akhtar, Muhammad T, van der Kooy, Frank, Verpoorte, Robert, Duetz, Wouter A
Format: Article
Language:English
Subjects:
Biological and medical sciences
Biotechnology
Fundamental and applied biological sciences. Psychology
Microbiology
Online Access:Get full text
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Summary:The microbial biotransformation of Δ⁹-tetrahydrocannabinol was investigated using a collection of 206 alkane-degrading strains. Fifteen percent of these strains, mainly gram-positive strains from the genera Rhodococcus, Mycobacterium, Gordonia, and Dietzia, yielded more-polar derivatives. Eight derivatives were produced on a mg scale, isolated, and purified, and their chemical structures were elucidated with the use of liquid chromatography-mass spectrometry, ¹H-nuclear magnetic resonance (¹H-NMR), and two-dimensional NMR (¹H-¹H correlation spectroscopy and heteronuclear multiple bond coherence). All eight biotransformation products possessed modified alkyl chains, with hydroxy, carboxy, and ester functionalities. In a number of strains, β-oxidation of the initially formed C₅ carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.
ISSN:0099-2240
1098-5336
DOI:10.1128/AEM.01277-09