Metabolism of (2S)-pterosin A: identification of the phase I and phase II metabolites in rat urine

Drug Metabolism and Disposition : the Biological Fate of Chemicals
Yung-Ping LeeShoei-Sheng Lee

Abstract

The metabolic profile of the potent hypoglycemic agent, (2S)-pterosin A (1), in rat urine via intragastrical oral administration was investigated. In total, 19 metabolites (M1-M19) were identified. Among these, 16 metabolites were characterized by high-performance liquid chromatography solid-phase extraction-tube transfer-NMR, and seven metabolites were further isolated from the treated urine to enable further structural determination. Twelve of these are new compounds. The phase I metabolites of 1 were formed via various oxidations at positions C-3, C-10, C-12, C-13, or C-1 followed by decarboxylation of C-10 or C-14, and lactonization at C-12/C-14 or C-14/C-12. The phase II metabolites were glucuronide conjugates from the parent compound or phase I metabolites. The major metabolites were found to be (2S)-14-O-glucuronylpterosin A (M9), (2S)-2-hydroxymethylpterosin E (M14), and (±)-pterosin B (M19). Quantitative HPLC analysis of metabolites, based on similar UV absorption and use of the regression equation of 1, indicated that ∼71% 1 was excreted as metabolites in rat urine.

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Jul 14, 2010·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Yi-Chun LaiShoei-Sheng Lee

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Citations

Mar 7, 2014·Journal of Natural Products·Chien-Kuang ChenShoei-Sheng Lee
May 2, 2015·Journal of Pharmaceutical and Biomedical Analysis·Yung-Ping LeeShoei-Sheng Lee
Oct 17, 2013·Chemistry & Biodiversity·Jih-Jung ChenJinn-Fen Chen

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