Hydroxylation and Further Oxidation of Delta(9)-Tetrahydrocannabinol by Alkane-Degrading Bacteria

Hassan Rashidi, Muhammad T. Akhtar, Frank van der Kooy, Robert Verpoorte, Wouter A. Duetz*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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, H-1-nuclear magnetic resonance (H-1-NMR), and two-dimensional NMR (H-1-H-1 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 C-5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups.

Original languageEnglish
Pages (from-to)7135-7141
Number of pages7
JournalApplied and Environmental Microbiology
Volume75
Issue number22
DOIs
Publication statusPublished - 15 Nov 2009

Keywords

  • MICROBIAL TRANSFORMATION
  • MICROBIOLOGICAL TRANSFORMATIONS
  • SIDE-CHAIN
  • CANNABIS-SATIVA
  • METABOLITES
  • DELTA-6-TETRAHYDROCANNABINOL
  • BIOTRANSFORMATION
  • LIMONENE

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