Chemistry of Natural Compounds

, Volume 8, Issue 3, pp 306–312 | Cite as

A comparison of the mass-spectrometric properties of compounds of the pregnane series with the properties of substances similar to cardenolides

  • Ya. V. Rashkes
  • M. B. Gorovits
  • F. S. Khristulas
  • N. K. Abubakirov


1. The mass spectra of several intermediates in the synthesis of uzarigenin from 5α-pregn-16-enolone have been characterized. Their general features and the differences between the spectra of 14α-H and 14β-OH compounds have been discussed.

2. It has been established that all the main processes of the decomposition of the molecular ions of the compounds studied take place close to ring D, and the contribution of ring A is small. The sequences of ejection of the 3β and 20α substituents and also the characteristics of their fragmentation in dependence on their volume have been investigated.

3. Schemes are proposed which explain the fragmentation pathways of 14β, 15β-epoxy compounds.

4. It has been shown that the introduction of a double bond into the 20(22) position of 14β-hydroxy steroids leads to the appearance in the mass spectra of fragments due to the decomposition that is typical for the cardenolides.


Epoxide Diacetate Fragmentation Pathway Cardenolides Triol 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    L. Tökes, R. T. Lalonde, and C. Djerasii, J. Org. Chem.,32, 1020 (1967).CrossRefGoogle Scholar
  2. 2.
    L. Peterson, Anal. Chem.,34, 1781 (1962).CrossRefGoogle Scholar
  3. 3.
    H. Egger and G. Spiteller, Monatsh. Chem.,97, 579 (1966).CrossRefGoogle Scholar
  4. 4.
    M. Ardenne, R. Tümmler, E. Weiss, and T. Reichstein, Helv. Chim. Acta,47, 1032 (1964).CrossRefGoogle Scholar
  5. 5.
    H. H. Sauer, E. Weiss, and T. Reichstein, Helv. Chim. Acta,48, 857 (1965); A. Sauer, C. Zerlentis, W. Stöcklin, and T. Reichstein, Helv. Chim. Acta,53, 221 (1969).CrossRefGoogle Scholar
  6. 6.
    M. Fukuoka, K. Hayashi, and H. Mitsuhashi, Chem. Pharm. Bull.,19, 1469 (1971).CrossRefGoogle Scholar
  7. 7.
    G. Spiteller, Z. Anal. Chem.,197, 1 (1963).CrossRefGoogle Scholar
  8. 8.
    M. B. E. Fayez and S. A. R. Negm, Chem. Ind. (London),40, 1361 (1968).Google Scholar
  9. 9.
    P. Brown, F. Brüschweiler, G. R. Pettit, and T. Reichstein, Org. Mass. Spectr.,5, 573 (1971).CrossRefGoogle Scholar
  10. 10.
    Ya. V. Rashkes, M. B. Gorovits, G. K. Makarichev, and N. K. Abubakirov, Khim. Prirodn. Soedin., 747 (1971).Google Scholar
  11. 11.
    F. S. Khristulas, M. B. Gorovits, and N. K. Abubakirov, Dokl. Akad. Nauk SSSR,193, 1083 (1970).Google Scholar
  12. 12.
    J. Caillet and B. Pullmann, Theoret. Chim. Acta,17, 377 (1970).CrossRefGoogle Scholar
  13. 13.
    R. Tschesche, P. Weizel, and H. W. Fehlhaber, Tetrahedron,21, 1797 (1965).CrossRefGoogle Scholar
  14. 14.
    G. Unruh and G. Spiteller, Tetrahedron,26, 3039; 3289; 3303; 3329 (1970).CrossRefGoogle Scholar
  15. 15.
    E. Caspit, J. Wicha, and A. Mandelbaum, Chem. Commun.,1967, 1161.Google Scholar
  16. 16.
    I. A. Bessonova, Z. Sh. Faizutdinova, Ya. V. Rashkes, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 446 (1970).Google Scholar
  17. 17.
    M. K. Strong, P. Brown, and C. Djerassi, Org. Mass. Spectr.,2, 1201 (1969).CrossRefGoogle Scholar
  18. 18.
    A. I. Kalinovsky, E. P. Serebryakov, B. M. Zolotarev, A. V. Shimolin, V. F. Kucherov, and O. S. Chizhov, Org. Mass Spectrom.,3, 1393 (1970).CrossRefGoogle Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • Ya. V. Rashkes
  • M. B. Gorovits
  • F. S. Khristulas
  • N. K. Abubakirov

There are no affiliations available

Personalised recommendations