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Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative

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Lipids

Abstract

Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes Buceros bicornis (great hornbill) and Penelopides panini (Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24R,25S)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to B. bicornis and P. panini. The previous stereochemical assignment for (24R,25S)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24S,25S)-configuration.

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Abbreviations

VA:

Varanic acid (3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid)

DVA:

12-Deoxy varanic acid (3α,7α,24-trihydroxy-5β-cholestan-27-oic acid)

RP-TLC:

Reversed-phase thin-layer chromatography

RP-HPLC:

Reversed-phase high performance liquid chromatography

HR-LC:

High-resolution liquid chromatography

RI:

Refractive index

ELSD:

Evaporative light-scattering detector

ESI:

Electrospray ionization

MS/MS:

Tandem mass spectrometry

NMR:

Nuclear magnetic resonance

DEPT:

Distortionless enhancement by polarization transfer

HMBC:

Heteronuclear multiple bond connectivity

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Acknowledgments

This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Sciences, and Technology of Japan (to T.I., 15K01809) for 2015–2017. Work at the University of California, San Diego was also supported in part by a grant from the American Physiological Society.

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Authors and Affiliations

  1. Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan

    Rika Satoh, Hiroaki Ogata, Tetsuya Saito, Biao Zhou, Kaoru Omura & Takashi Iida

  2. Faculty of Pharmaceutical Sciences, Kinki University, Kowakae, Higashi-Osaka, 577-8502, Japan

    Satoshi Kurabuchi, Kuniko Mitamura & Shigeo Ikegawa

  3. Department of Medicine, University of California at San Diego, La Jolla, San Diego, CA, 92093-063, USA

    Lee R. Hagey & Alan F. Hofmann

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  1. Rika Satoh
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  2. Hiroaki Ogata
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  3. Tetsuya Saito
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  4. Biao Zhou
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  5. Kaoru Omura
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  6. Satoshi Kurabuchi
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  8. Shigeo Ikegawa
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  9. Lee R. Hagey
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  10. Alan F. Hofmann
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  11. Takashi Iida
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Correspondence to Takashi Iida.

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Satoh, R., Ogata, H., Saito, T. et al. Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative. Lipids 51, 757–768 (2016). https://doi.org/10.1007/s11745-016-4150-0

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  • DOI: https://doi.org/10.1007/s11745-016-4150-0

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