Collect. Czech. Chem. Commun. 2009, 74, 1179-1193
Published online 2009-08-11 16:51:29

Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions

Vigi Chaudharya, Hannes Leischa, Alena Moudraa, Blake Allena, Vincenzo De Lucaa, D. Phillip Coxb and Tomáš Hudlickýa,*

a Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON L2S 3A1, Canada
b Noramco Inc., 503 Carr Road, Suite 200, Wilmington, DE 19809, USA


Morphine alkaloids and some of its derivatives (morphine, codeine, thebaine, oripavine, hydrocodone, and oxycodone) were subjected to fermentations with six fungal strains. The alkaloids were transformed to a variety of products via biological oxidations, reductions, and oxidative demethylations. The strain Cunninghamella echinulata proved to be the most effective for demethylations of all of the above compounds, except for morphine. The time profile of the conversion of 3-[14CH3]thebaine to 3-[14CH3]northebaine by C. echinulata cultures was also determined.

Keywords: Morphine alkaloids; Fungal biotransformations; Demethylation; Oxidation; Reduction.

References: 59 live references.