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19-Hydroxylation ofΔ4-androstene-3,17-dione and dehydroepiandrosterone by bovine adrenals

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Zusammenfassung

Die Aufklärung der Struktur von 19-Oxy-Δ4-androsten-3,17-dion (VI), einer Substanz, isoliert nach Inkubation von Δ4-Androsten-3,17-dion und von Dehydroepiandrosteron mit einem Rinder-Nebennieren-Homogenat, ist beschrieben. Dies ist unseres Wissens die erste Beobachtung der Hydroxylierungin vitro einer angulären Methylgruppe eines Steroids. Mehrere Folgerungen sind erörtert.

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References

  1. A. S. Meyer, M. Hayano, M. C. Lindberg, M. Gut, andO. G. Rodgers, Acta Endocrin.18, 148 (1955).

    Article  CAS  Google Scholar 

  2. A. S. Meyer, H. Rosenkrantz, andG. Pincus, Amer. Chem. Soc. 126th Meeting, Abstract p. 53–0, New York, 1954.

  3. The absence of an isolated olefinic bond in compound VI has been kindly confirmed by Dr.R. Norman Jones who examined the infrared absorption of the compound in chloroform solution with a Perkin-Elmer double-beam spectrophotometer with a sodium chloride prism (R. N. Jones, P. Humphries, E. Packard, andK. Dobriner, J. Amer. Chem. Soc.72, 86 [1950]), and was unable to detect any evidence of an unsaturation other than theΔ 4-bond.

    Article  CAS  Google Scholar 

  4. TheR-values indicate the mobilities of the substances in the ligroin- and toluene-propylene glycol paper chromatographic system respectively as defined previously (A. S. Meyer, M. Hayano, M. C. Lindberg, M. Gut, andO. G. Rodgers, Acta Endocrin. [l. c.]). For compound II for instance aR lig 2·2 cm/h and for compound IV aR tol 4·0 cm/b have been determined.

  5. S. H. Eppstein, P. D. Meister, H. M. Leigh, D. H. Peterson, M. C. Murray, L. M. Reineke, andA. Weintraub, J. Amer. Chem. Soc.76, 3174 (1954).

    Article  CAS  Google Scholar 

  6. Ch. Meystre andA. Wettstein, Helv. chim. Acta32, 1978 (1949).

    Article  CAS  Google Scholar 

  7. Dr.Josef Fried, private communication.

  8. G. I. Poos, G. E. Arth, R. E. Beyler, andL. H. Sarett, J. Amer. Chem. Soc.75, 422 (1953).

    Article  CAS  Google Scholar 

  9. L. Dorfman, Chem. Revs.53, 82 (1953).

    Article  Google Scholar 

  10. A. S. Meyer, manuscript in preparation.

  11. A. S. Meyer et al., Acta Endocrin. l. c.

  12. A. S. Meyer, manuscript in preparation.

  13. Cf. P. Stiebel andCh. Tamm, Helv. chim. Acta37, 1094 (1954); see also1 for a vinylogous instance.

    Article  Google Scholar 

  14. G. W. Barber andM. Ehrenstein, J. Org. Chem.19, 1758 (1954).

    Article  CAS  Google Scholar 

  15. D. H. R. Barton andP. deMayo, J. Chem. Soc.1954, 887.

  16. We are grateful to Dr.Derek H. R. Barton for having brought to our attention the formaldehyde elimination reaction and for the specimens of the triterpenes employed in this study.

  17. W. A. Jacobs, J. Biol. Chem.63, 631 (1925).

    Article  CAS  Google Scholar 

  18. G. W. Barber andM. Ehrenstein, J. Org. Chem.19, 1758 (1954).

    Article  CAS  Google Scholar 

  19. P. Th. Herzig andM. Ehrenstein, J. Org. Chem.17, 713 (1952).

    Article  CAS  Google Scholar 

  20. A. L. Wilds andN. A. Nelson, J. Amer. Chem. Soc.75, 5366 (1953).

    Article  CAS  Google Scholar 

  21. A. J. Birch, J. Chem. Soc.367 (1950).

  22. A. S. Meyer andM. C. Lindberg, Anal. Chem. (in press).

  23. A. S. Meyer, manuscript in preparation.

  24. These data would thus confirm that 19-hydroxyprogesterone and 19-hydroxydesoxycorticosterone, prepared byEhrenstein and co-workers from strophanthidin, have the normal steroid configuration. (G. W. Barber, M. Ehrenstein, J. Org. Chem.19, 1758 [1954]).

    Article  CAS  Google Scholar 

  25. E. Eisenberg andG. S. Gordan, J. Pharmacol. Exper. Therapy99, 38 (1950).

    CAS  Google Scholar 

  26. R. I. Dorfman, Endocr.42, 1 (1948).

    Article  CAS  Google Scholar 

  27. M. R. Cook, Jr. andF. Elmadjian, J. Amer. Pharm. Assoc.42, 329 (1953).

    Article  CAS  Google Scholar 

  28. V. Schenker, Endocr.53, 345 (1953).

    CAS  Google Scholar 

  29. Cf. reviews byL. F. Fieser andM. Fieser,Natural Products Related to Phenanthrene, 3rd ed. (New York, 1949);H. Heusser, Progr. Chem. Organic Natural Products7, 87 (1950);T. Reichstein, Angew. Chemie63, 412 (1951);A. Stoll, Exper.10, 282 (1954).

  30. G. W. Barber andM. Ehrenstein, J. Org. Chem.19, 1758 (1954).

    Article  CAS  Google Scholar 

  31. W. W. Tullner andR. Hertz, Endocr.52, 359 (1953).

    Article  CAS  Google Scholar 

  32. L. G. Hershberger, E. G. Shipley, andR. K. Meyer, Proc. Exptl. Biol. Med.83, 175 (1953).

    Article  CAS  Google Scholar 

  33. A. Sandoval, L. Miramontes, G. Rosenkranz, C. Djerassi, andF. Sondheimer, J. Amer. Chem. Soc.75, 4117 (1953).

    Article  CAS  Google Scholar 

  34. Cf., inter al.,M. Ehrenstein,A. R. Johnson,P. C. Olmsted,V. I. Vivian, andM. A. Wagner, J. Org. Chem.15, 264 (1950).

    Article  CAS  Google Scholar 

  35. G. W. Barber andM. Ehrenstein, J. Org. Chem.19, 363 (1954).

    Google Scholar 

  36. E. B. Hershberg, M. Rubin, andE. Schwenk, J. Org. Chem.15, 292 (1950).

    Article  CAS  Google Scholar 

  37. D. Beall, J. Endocr.2, 81 (1940).

    Article  CAS  Google Scholar 

  38. M. Hayano andR. I. Dorfmann, J. Biol. Chem.211, 227 (1954).

    CAS  Google Scholar 

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  1. Worcester Foundation for Experimental Biology, Shrewsbury, Mass.

    A. S. Meyer

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Meyer, A.S. 19-Hydroxylation ofΔ4-androstene-3,17-dione and dehydroepiandrosterone by bovine adrenals. Experientia 11, 99–102 (1955). https://doi.org/10.1007/BF02161690

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