Open AccessHydroxylation and Further Oxidation of Δ 9 -Tetrahydrocannabinol by Alkane-Degrading Bacteria
Author(s) -
Hassan Rashidi,
M Akhtar,
Frank van der Kooy,
Robert Verpoorte,
Wouter A. Duetz
Publication year - 2009
Publication title -
applied and environmental microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.552
H-Index - 324
eISSN - 1070-6291
pISSN - 0099-2240
DOI - 10.1128/aem.01277-09
Subject(s) - biotransformation , chemistry , heteronuclear molecule , rhodococcus , nuclear magnetic resonance spectroscopy , hydroxylation , alkane , methylene , organic chemistry , bacteria , mass spectrometry , stereochemistry , chromatography , biology , hydrocarbon , enzyme , genetics
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 generaRhodococcus ,Mycobacterium ,Gordonia , andDietzia , 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,1 H-nuclear magnetic resonance (1 H-NMR), and two-dimensional NMR (1 H-1 H 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.