Hydroxylation and Further Oxidation of Δ 9 -Tetrahydrocannabinol by Alkane-Degrading Bacteria

Abstract

ABSTRACT The microbial biotransformation of Δ 9 -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, 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 C 5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.