Biliary bile acids in birds of the Cotingidae family: Taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy-5β-cholestan-27-oic acid

Lee R. Hagey, Takashi Iida, Shoujiro Ogawa, Yuuki Adachi, Mizuho Une, Kumiko Mushiake, Masamitsu Maekawa, Miki Shimada, Nariyasu Mano, Alan F. Hofmann

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Three C27 bile acids were found to be major biliary bile acids in the capuchinbird (Perissocephalus tricolor) and bare-throated bellbird (Procnias nudicollis), both members of the Cotingidae family of the order Passeriformes. The individual bile acids were isolated by preparative RP-HPLC, and their structures were established by RP-HPLC, LC/ESI-MS/MS and NMR as well as by a comparison of their chromatographic properties with those of authentic reference standards of their 12α-hydroxy derivatives. The most abundant bile acid present in the capuchinbird bile was the taurine conjugate of C 27 (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid, a diastereomer not previously identified as a natural bile acid. The four diastereomers of taurine-conjugated (24ξ,25ξ)-3α,7α,24- trihydroxy-5β-cholestan-27-oic acid could be distinguished by NMR and were resolved by RP-HPLC. The RRT of the diastereomers (with taurocholic acid as 1.0) were found to be increased in the following order: (24R,25R) < (24S,25R) < (24S,25S) < (24R,25S). Two epimers (25R and 25S) of C27 3α,7α-dihydroxy-5β-cholestan-27-oic acid were also present (as the taurine conjugates) in both bird species. Epimers of the two compounds could be distinguished by their NMR spectra and resolved by RP-HPLC with the (25S)-epimer eluting before the (25R)-epimer. Characterization of the taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan- 27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy- 5β-cholestan-27-oic acid should facilitate their detection in peroxisomal disease and inborn errors of bile acid biosynthesis.

Original languageEnglish
Pages (from-to)1126-1135
Number of pages10
JournalSteroids
Volume76
Issue number10-11
DOIs
Publication statusPublished - 2011 Sep

Keywords

  • 24-Hydroxylation
  • 3α,7α,12α,24-Tetrahydroxy-5β-cholestan-27-oic acid
  • 3α,7α,24-Trihydroxy-5β-cholestan- 27-oic acid
  • 3α,7α-Dihydroxy- 5β-cholestan-27-oic acid
  • Bile acid metabolism
  • C bile acids
  • H and C NMR
  • LC/ESI-MS/MS
  • Taurine conjugate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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