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Research ArticleArticle

Metabolism of (2S)-Pterosin A: Identification of the Phase I and Phase II Metabolites in Rat Urine

Yung-Ping Lee, Feng-Lin Hsu, Jaw-Jou Kang, Chien-Kuang Chen and Shoei-Sheng Lee
Drug Metabolism and Disposition August 2012, 40 (8) 1566-1574; DOI: https://doi.org/10.1124/dmd.112.045039
Yung-Ping Lee
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Feng-Lin Hsu
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Jaw-Jou Kang
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Chien-Kuang Chen
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Shoei-Sheng Lee
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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.

Footnotes

  • This work was supported by the National Science Council, Taiwan [Grants NSC98-2323-B-002-001, NSC99-2323-B-002-010].

  • Article, publication date, and citation information can be found at http://dmd.aspetjournals.org.

    http://dx.doi.org/10.1124/dmd.112.045039.

  • ↵Embedded Image The online version of this article (available at http://dmd.aspetjournals.org) contains supplemental material.

  • ABBREVIATIONS:

    HPLC
    high-performance liquid chromatography
    SPE
    solid-phase extraction
    TT
    tube transfer
    RP
    reverse-phase
    DAD
    diode array detector
    HRESIMS
    high-resolution electrospray ionization mass spectrometry
    MS
    mass spectrometry
    NOEDS
    nuclear Overhauser effect difference spectrum
    HSQC
    heteronuclear single quantum correlation
    HMBC
    heteronuclear multiple bond coherence
    FA
    formic acid
    GlcUA
    glucuronyl
    LC15-0133
    1-[2-(5-tert-butyl-[1,3,4]oxadiazole-2-carbonyl)-4-fluoro-pyrrolidin-1-yl]-2-(2-hydroxy-1,1-dimethylethylamino)-ethanone.

  • Received February 10, 2012.
  • Accepted May 15, 2012.
  • Copyright © 2012 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 40 (8)
Drug Metabolism and Disposition
Vol. 40, Issue 8
1 Aug 2012
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Research ArticleArticle

(2S)-PTEROSIN, A METABOLITES IN RAT URINE

Yung-Ping Lee, Feng-Lin Hsu, Jaw-Jou Kang, Chien-Kuang Chen and Shoei-Sheng Lee
Drug Metabolism and Disposition August 1, 2012, 40 (8) 1566-1574; DOI: https://doi.org/10.1124/dmd.112.045039

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Research ArticleArticle

(2S)-PTEROSIN, A METABOLITES IN RAT URINE

Yung-Ping Lee, Feng-Lin Hsu, Jaw-Jou Kang, Chien-Kuang Chen and Shoei-Sheng Lee
Drug Metabolism and Disposition August 1, 2012, 40 (8) 1566-1574; DOI: https://doi.org/10.1124/dmd.112.045039
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