The aromatization of cyclohexanecarboxylic acid to hippuric acid: substrate specificity and species differences |
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Authors: | Asbjørn M Svardal Ronald R Scheline |
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Institution: | (1) Department of Pharmacology, School of Medicine, University of Bergen, 5016 Haukeland Sykehus, Bergen, Norway |
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Abstract: | Summary The ability to convert cyclohexanecarboxylic acid to hippuric acid has been studied in liver from guinea pigs, rabbits, rats
and mice using a gas chromatographic- mass spectrometric method employing selected ion monitoring. Guinea pig liver showed
the highest activity, giving values double of those found in rabbit liver and five times those in rat liver. Only very weak
activity was found in mouse liver.
(Hydroxymethyl)cyclohexane, cyclohexanealdehyde and a-hydroxyethylcyclohexane, which are structurally related to cyclohexanecarboxylic
acid but lack the carboxyl group, were not aromatized by guinea pig liver mitochondria. This finding indicates that the carboxyl
group is essential for aromatization. Absence of aromatization was also found with the homologs cyclohexaneacetic acid and
cyclohexanepropionic acid and with the di-acidstrans-1,2- andtrans-1,4-cyclohexanedicarboxylic acid.
The effect of a methyl group in cyclohexanecarboxylic acid depended on its position. 2-Methyl-1-cyclohexanecarboxylic acid
was not aromatized, however the 3- and 4-methyl derivatives underwent aromatization and subsequent conjugation with glycine.
The rates of formation ofm-methyl- andp-methylhippuric acid were 16% and 9%, respectively, of that found for hippuric acid from cyclohexanecarboxylic acid (8.0 nmol/min/mg
protein). |
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Keywords: | aromatization of cyclohexanecarboxylic acid guinea pig liver hippuric acid formation mitochondria |
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