Skip to main content
SpringerLink
Log in

The metabolic fate of cholesterol-5α,6α-epoxide in vivo

  • Published:
Lipids

Abstract

[14C] Cholesterol-5α,6α-epoxide, administered to mice by either gastric intubation or skin painting, was rapidly and primarily excreted in the feces. Residual amounts of the epoxide and its metabolites were found in a wide variety of organs, and persisted for at least 72 hr. At some sites (principally the liver, the small intestinal contents and the combined stomach/duodenum and their contents), the labeled compound existed in a water-soluble form which could not be extracted with chloroform/methanol. Treatment of the small intestinal contents with a preparation of β-glucuronidase/sulfatase produced a marked increase in the amount of organic-solvent-extractable cholesterol-α-epoxide and other polar metabolites. Unchanged epoxide was found mainly in the feces and the skin at the site of application. On the basis of these results, stool specimens, and not blood samples, should be analyzed to detect the presence of this compound and/or its metabolites in vivo.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Black, H.S., and D.R. Douglas, Cancer Res. 32:2630 (1972).

    PubMed  CAS  Google Scholar 

  2. Black, H.S., and D.R. Douglas, Cancer Res. 33:2094 (1973).

    PubMed  CAS  Google Scholar 

  3. Chan, J.T., and H.S. Black, Science 186:1216 (1974).

    Article  PubMed  CAS  Google Scholar 

  4. Chan, J.T., and H.S. Black, J. Invest. Dermatol. 66:112 (1976).

    Article  PubMed  CAS  Google Scholar 

  5. Bischoff, F., in “Progr. Exp. Tumor Res.,” Vol. 3, Karger, Basle, New York, 1963, pp. 412–444.

    Google Scholar 

  6. Aringer, L., and P. Eneroth, J. Lipid Res. 15:389 (1974).

    PubMed  CAS  Google Scholar 

  7. Martin, C.M., and H.J. Nicholas, J. Lipid Res. 14:618 (1973).

    PubMed  CAS  Google Scholar 

  8. Bischoff, F., and G. Bryson, AACR Abstracts No. 23:6 (1974).

    Google Scholar 

  9. Fioriti, J.A., N. Buide, and R.J. Sims, Lipids 4:142 (1967).

    Article  Google Scholar 

  10. Fioriti, J.A., M.J. Kanuk, M. George, and R.J. Sims, Lipids 5:71 (1970).

    Article  PubMed  CAS  Google Scholar 

  11. Roscoe, H.G., R. Goldstein, and M.J. Fahrenbach, Biochem. Pharmacol. 17:1189 (1968).

    Article  PubMed  CAS  Google Scholar 

  12. Roscoe, H.G., and M.J. Fahrenbach, J. Lipid Res. 12:71 (1971).

    Google Scholar 

  13. Kikuchi, S., Y. Imai, S. Ziro, T. Matsuo, and S. Noguichi, J. Pharmacol. Exp. Ther. 159:399 (1968).

    PubMed  CAS  Google Scholar 

  14. Fieser, L.F., and M. Fieser, in “Reagents for Organic Synthesis,” Vol. 1, John Wiley and Sons, Inc., New York, 1967, p. 136.

    Google Scholar 

  15. Sakaguchi, N., and E.C. Horning, Anal. Lett. 4:41 (1971).

    Google Scholar 

  16. Black, H.S., and J.L. Laseter, Comp. Biochem. Physiol. 53C:29 (1976).

    Google Scholar 

  17. Gray, M.F., T.D.V. Lawrie, and C.J.W. Brooks, Lipids 6:836 (1971).

    Article  PubMed  CAS  Google Scholar 

  18. Assman, G., D.S. Frederickson, H.r. Sloan, H.M. Fales, and R.J. Highet, J. Lipid Res. 16:28 (1975).

    Google Scholar 

  19. Black, H.S., and J.T. Chan, Oncology 33:119 (1976).

    Article  PubMed  CAS  Google Scholar 

  20. Smith, L.L., and M.J. Kulig, Cancer Biochem. Biophys. 1:79 (1975).

    CAS  Google Scholar 

  21. Imai, H., V. Subramanyam, P.W. LeQuesne, and N.T. Werthessen, Fed. Proc. 37:934 (1978).

    Google Scholar 

  22. Chen, H.W., A.A. Kandutsch, and C. Waysmouth, Nature 251:419 (1974).

    Article  PubMed  CAS  Google Scholar 

  23. Peng, S.K., C.B. Taylor, P. Tham, N.T. Werthessen, and B. Mikkelson, Arch. Path. Lab. Med. 102:57 (1978).

    PubMed  CAS  Google Scholar 

  24. Kelsey, M.I., and R.J. Pienta, Cancer Lett. 6:143 (1979).

    Article  PubMed  CAS  Google Scholar 

  25. Teng, J.I., and L.L. Smith, J. Am. Chem. Soc. 95:4060 (1973).

    Article  PubMed  CAS  Google Scholar 

  26. Smith, L.L., J.I. Teng, M.J. Kulig, and F.L. Hill, J. Org. Chem. 38:1763 (1973).

    Article  PubMed  CAS  Google Scholar 

  27. Mitton, J.R., N.A. Scholan, and G.S. Boyd, Eur. J. Biochem. 20:569 (1971).

    Article  PubMed  CAS  Google Scholar 

  28. Reddy, B.S., C.W. Martin, and E.L. Wynder, Cancer Res. 37:1697 (1977).

    PubMed  CAS  Google Scholar 

  29. Reddy, B.S., and E.L. Wynder, Cancer 39:2533 (1977).

    Article  PubMed  CAS  Google Scholar 

  30. Hwang, K.K., and M.I. Kelsey, Cancer Biochem. Biophys. 3:31 (1978).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Carcinogenesis Program, NCI Frederick Cancer Research Center, 21701, Frederick, MD

    J. P. Bowden, G. M. Muschik & J. C. Kawalek

Authors
  1. J. P. Bowden
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. M. Muschik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. C. Kawalek
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Bowden, J.P., Muschik, G.M. & Kawalek, J.C. The metabolic fate of cholesterol-5α,6α-epoxide in vivo. Lipids 14, 623–629 (1979). https://doi.org/10.1007/BF02533447

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02533447

Keywords

Search

Navigation