Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver

Abstract

Incubation of [3H]retinoic acid in the presence of hamster liver 10,000 g supernatant produces several metabolites that are more polar than the parent compound. Two of these metabolites are identical with synthetic all-trans-4-hydroxyretinoic acid and all-trans-4-oxoretinoic acid both in UV absorption and mass spectral characteristics and in migration rates on 2 different reverse-phase, high-pressure liquid chromatographic (HPLC) systems. The metabolites produced in a cell-free liver incubation reaction also migrate on a HPLC column together with metabolites isolated from a tracheal organ culture system. Both the metabolites and the synthetic standards show less biological activity than the parent all-trans-retinoic acid in a tracheal organ culture assay.