TY - JOUR
T1 - Hydroxylation and further oxidation of Δ9-tetrahydrocannabinol by alkane-degrading bacteria
AU - Rashidi, Hassan
AU - Akhtar, Muhammad T.
AU - Van der Kooy, Frank
AU - Verpoorte, Robert
AU - Duetz, Wouter A.
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
UR - http://handle.uws.edu.au:8081/1959.7/528453
U2 - 10.1128/AEM.01277-09
DO - 10.1128/AEM.01277-09
M3 - Article
SN - 0099-2240
VL - 75
SP - 7135
EP - 7141
JO - Applied and Environmental Microbiology
JF - Applied and Environmental Microbiology
IS - 22
ER -