On the Metabolism of Prostaglandin F2α in Female Subjects

Abstract

Abstract Metabolites of prostaglandin F2α administered intravenously to female subjects were isolated. The structures of the two main compounds were 5α,7α-dihydroxy-11-ketotetranorprosta-1,16-dioic acid and its δ-lactone. The elucidation of their structures was based on gas chromatography and mass spectrometry of several derivatives and on infrared and nuclear magnetic resonance spectrometry. The structure of the δ-lactone was further established by its conversion into 5α,7α-dihydroxy-11-ketotetranor-prosta-1,16-dioic acid by alkaline hydrolysis and by mass spectrometry of a derivative obtained by borodeuteride reduction. A pathway for the formation of 5α,7α-dihydroxy-11-keto-tetranor-prosta-1,16-dioic acid from prostaglandin F2α is proposed.