Mass spectrometry in the elucidation of shikimate biotransformation products in the rat

Abstract

The biotransformation products of shikimate in the rat have been identified by electron impact mass spectrometry. Analysis of the metabolites produced after oral administration of shikimate resulted in the identification of hippurate, 3,4,5,6-tetrahydrohippurate, hexahydrohippurate, benzoyl and cyclohexylcarbonyl-beta-D-glucuronides and two isomeric 3,4-dihydroxycyclohexanecarboxylates. Results showed that shikimate itself is not metabolized by rat tissues and that all metabolites produced were dependent upon initial metabolic transformations by gastrointestinal microrganisms. The various hippurate derivatives and glucuronide conjugates appear to arise via a conversion of shikimate to cyclohexanecarboxylate, which is then further metabolized by the rat tissues.