Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Xenobiotic conjugation: a novel role for bile acids

Abstract

The conjugation of foreign compounds with hydrophilic natural products (for example, amino acids, glucuronic acid) represents an important biochemical mechanism of attenuating xenobiotic toxicity and of facilitating excretion of hydrophobic chemicals. Although several conjugation reactions are known1, bile acids have not been implicated previously in the conjugation of xenobiotics. The physiological importance of natural bile acids is based partly on their propensity to conjugate through their carboxyl groups with several amino acids (especially glycine and taurine), thereby creating effective emulsifying agents to aid the digestion of lipids. However, we now report that in several animal species, bile acids form metabolic conjugates through a hydroxyl group with an acidic metabolite of fluvalinate, a pyrethroid insecticide. Conjugates of this acidic metabolite with cholic, taurochenodeoxycholic and taurocholic acids are major secondary metabolites found in excreta of the cow, chicken and rat, respectively, and represent 5–12% of the faecal 14C-labelled residue.

This is a preview of subscription content, access via your institution

Access options

Rent or buy this article

Prices vary by article type

from$1.95

to$39.95

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Caldwell, J. in Concepts in Drug Metabolism (eds Jenner, P. & Testa, B.) 211–250 (Dekker, New York, 1980).

    Google Scholar 

  2. Henrick, C. A. et al. Pestic. Sci. 11, 224–241 (1980).

    Article  CAS  Google Scholar 

  3. Staiger, L. E., Quistad, G. B. & Schooley, D. A. 2nd. chem. Congr. of the North American Continent, Las Vegas, Nevada, PEST-116 (Am. chem. Soc., 1980).

    Google Scholar 

  4. Quistad, G. B., Staiger, L. E., Jamieson, G. C. & Schooley, D. A. J. agric. Fd Chem. (submitted).

  5. Fieser, L. F. & Fieser, M. Steroids, 421–443 (Reinhold, New York, 1959).

  6. Haslewood, G. A. D. The Biological Importance of Bile Salts, 102–108 (North Holland, Amsterdam, 1978).

    Google Scholar 

  7. Plaa, G. L. Handbk exp. Pharmac. 28, 130–149 (1975).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Quistad, G., Staiger, L. & Schooley, D. Xenobiotic conjugation: a novel role for bile acids. Nature 296, 462–464 (1982). https://doi.org/10.1038/296462a0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/296462a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing