title: Hydroxylation and further oxidation of delta9-tetrahydrocannabinol by alkane-degrading bacteria.
abstract: The microbial biotransformation of Delta(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 (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, beta-oxidation of the initially formed C5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.
authors.affiliation: Department of Pharmacognosy, IBL Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Hassan
authors.initials: H
authors.lastname: Rashidi
authors.forename: Muhammad T
authors.initials: MT
authors.lastname: Akhtar
authors.forename: Frank
authors.initials: F
authors.lastname: van der Kooy
authors.forename: Robert
authors.initials: R
authors.lastname: Verpoorte
authors.forename: Wouter A
authors.initials: WA
authors.lastname: Duetz
mesh_terms: D000473:Alkanes / Q000378:metabolism*; D001419:Bacteria / Q000378:metabolism*; D001711:Biotransformation; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D013058:Mass Spectrometry; D008956:Models, Chemical; D010084:Oxidation-Reduction
chemical_list: D000473:Alkanes; D013759:Dronabinol