Metabolism of polycyclic compounds. 21. The metabolism of phenanthrene in rabbits and rats: dihydrodihydroxy compounds and related glucosiduronic acids

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Abstract
Phenanthrene is converted by rabbits and rats into the (+)- and ([long dash])-isomers of trans-9,10-dihydro-9,10-dihydroxyphenanthrene and trans-l,2-dihydro-l,2-dihydroxyphenanthrene. The glucuronic acid conjugates of these compounds were isolated together with a conjugate of trans-3,4-dihydro-3,4-dihydroxyphenanthrene. The glucuronic acid conjugate of 2-hydroxy-phenanthrene was isolated from these urines, and evidence was obtained for the presence of similar conjugates of 1-, 3-and 4-hydroxyphenanthrene. The glucuronic acid conjugate of 9-hydroxy-phenanthrene was not detected. The presence of 1,2-dihydroxyphen-anthrene and small amounts of 3,4-dihydroxyphenanthrene in conjugation with glucuronic acid was demonstrated. A substance, present as a glucuronic acid conjugate, which yielded phenanthrene on acidification with mineral acid, was detected in the urine of rabbits dosed with phenanthrene. A possible mechanism for the formation of the known phenanthrene metabolites in the body is discussed.