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Synthesis and Hepatic Metabolism of Xanthobilirubinic Acid Regioisomers

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Summary.

A set of four regioisomeric dipyrrinone propionic acids has been synthesized and their hepatic metabolism examined in rats: xanthobilirubinic acid and pseudo-xanthobilirubinic acid each with a propionic acid on a pyrrole ring; exo-ψ-xanthobilirubinic acid and endo-ψ-xanthobilirubinic acid, each with a propionic acid transposed to a lactam ring. After intravenous injection all four isomers were excreted to some degree in unchanged form in bile in normal rats. Xanthobilirubinic acid, the structurally closest dipyrrinone to bilirubin, and exo-ψ-xanthobilirubinic acid were excreted almost entirely in unchanged form. However, a small fraction of xanthobilirubinic acid acyl glucuronide was also detected. More extensive acyl glucuronidation was observed for pseudo-xanthobilirubinic acid, and endo-ψ-xanthobilirubinic acid underwent slow metabolism to unidentified more polar products that did not seem to be glucuronides.

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Authors and Affiliations

  1. Department of Chemistry, University of Nevada, Reno, Nevada, USA

    Stefan E. Boiadjiev, Brian A. Conley, Justin O. Brower & David A. Lightner

  2. Division of Gastroenterology and the Liver Center, University of California, San Francisco, California, USA

    Antony F. McDonagh

Authors
  1. Stefan E. Boiadjiev
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  2. Brian A. Conley
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  3. Justin O. Brower
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  4. Antony F. McDonagh
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  5. David A. Lightner
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Correspondence to David A. Lightner.

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Boiadjiev, S., Conley, B., Brower, J. et al. Synthesis and Hepatic Metabolism of Xanthobilirubinic Acid Regioisomers. Monatsh. Chem. 137, 1463–1476 (2006). https://doi.org/10.1007/s00706-006-0543-8

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  • DOI: https://doi.org/10.1007/s00706-006-0543-8

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