Paper
Deuterium-Labeling Studies Reveal the Mechanism of Cytochrome P450-Catalyzed Formation of 2-Aminoacetophenone from 3-Methylindole (Skatole) in Porcine Liver Microsomes.
Published Nov 29, 2017 · Christopher P. Gerlach, M. Wüst
Journal of agricultural and food chemistry
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Abstract
2-Aminoacetophenone, a product of the hepatic 3-methylindole (skatole) clearance in pigs, contributes to the specific aroma of fat from tainted boar meat. Surprisingly, high formation rates for 2-aminoacetophenone from skatole in microsomal preparations from Pietrain × Baden-Württemberg hybrid type boars have been previously demonstrated, but the mechanism of this cytochrome P450-mediated reaction remained unknown. Therefore, microsomal fractions from boars were incubated with deuterium-labeled skatole and with possible reaction intermediates. 3-Methyloxindole and 3-hydroxy-3-methyloxindole were identified as degradation products of skatole en route to 2-aminoacetophenone. Additionally, the labeling studies provided further evidence for a cytochrome P450-mediated lyase reaction that leads to the cleavage of the indole heterocyclic ring system in 3-hydroxy-3-methyloxindole and demonstrated the involvement of several cytochrome P450-isoforms by employing isotopically sensitive branching experiments.
In Vitro StudyCytochrome P450-mediated lyase reaction in porcine liver microsomes leads to the formation of 2-aminoacetophenone, contributing to the specific aroma of tainted boar meat.
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