Microbial models of mammalian metabolism: production of novel alpha-diketone metabolites of warfarin and phenprocoumon using Aspergillus niger.
1. The coumarin anticoagulants warfarin and phenprocoumon were metabolized by Aspergillus niger via oxidative ring cleavage to yield the corresponding alpha-diketone metabolites. 2. Structural identification was based upon physical, spectral, and chromatographic comparisons of isolated metabolites and synthetic standards generated by the oxidative cleavage of warfarin or phenprocoumon with pyridinium chlorochromate. 3. This pathway of metabolism has been previously observed for coumarin anticoagulants in mammalian systems.
Rizzo
J D
JD
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Texas, Austin 78712.
Davis
P J
PJ
D015110:4-Hydroxycoumarins / Q000378:metabolism*; D000818:Animals; D001234:Aspergillus niger / Q000378:metabolism*; D001711:Biotransformation; D007659:Ketones / Q000378:metabolism; D008322:Mammals; D008954:Models, Biological; D015394:Molecular Structure; D010644:Phenprocoumon / Q000378:metabolism* / Q000493:pharmacokinetics; D014859:Warfarin / Q000378:metabolism* / Q000493:pharmacokinetics
D015110:4-Hydroxycoumarins; D007659:Ketones; D014859:Warfarin; D010644:Phenprocoumon