Metabolism of perhydroanthracenes in the rabbit

1. The metabolism in rabbits of several perhydroanthracenes was investigated. All compounds were to different degrees excreted in the urine as glucuronides. 2. The aglycones of the glucuronides were found to be racemic secondary alcohols, having the hydroxyl group at a beta-methylene carbon. Where determinable, the hydroxyl group was shown to have an equatorial configuration. 3. These results suggested that hydroxylation was enzyme mediated, and, when compared with the results from studies on other alicyclic hydrocarbons, that the same enzyme system participated generally in the hydroxylation of such hydrocarbons. 4. A model for the enzyme active site is proposed to accord with the pattern of hydroxylation observed.