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Chemistry of Natural Compounds

, Volume 22, Issue 5, pp 566–571 | Cite as

Influence of spatial effects on the oxidation of cardenolides and bufadienolides containing aldehyde groups

  • M. A. Kazarinov
  • N. F. Komissarenko
  • L. B. Nel'zeva
  • N. S. Solodun
Article

Abstract

The reactivity of a number of aglycones and glycosides with a cardiac action containing a carbonyl group at C10 is considered. The study was based on the use of the oxidation reaction in the presence of diethylamine, the excess of which after the binding of the hydrochloric acid liberated in the reaction was backtitrated with percholoric acid in methanol. The rate constants of 15 compounds have been determined and it has been established that their reactivity depends on their structure: the nature of the linkage of the A/B rings of the steroid skeleton, the position of a double bond in it, the introduction of a sugar or acetyl group in position 3 of the aglycon, and the nature of the sugar.

Keywords

Glycoside Aldehyde Group Cardenolides Triterpene Glycoside Sugar Component 

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Literature cited

  1. 1.
    N. A. Kazarinov and N. P. Dzyuba, in: Proceedings of the IIIrd All-Union Conference on the Analytical Chemistry of Nonaqueous Solutions and Their Physicochemical Properties. Part 1. The Analytical Chemistry of Nonaqueous Solutions [in Russian], Gor'kii (1974), p. 104.Google Scholar
  2. 2.
    N. A. Kazarinov, N. F. Komissarenko, L. B. Nel'zeva, and N. S. Solodun, An Investigation of Drugs and Their Provision for the Population. Interdepartmental Collection of Scientific Papers [in Russian], Sverdlovsk (1983), p. 7.Google Scholar
  3. 3.
    I. P. Kovalev, E. V. Titov, V. T. Chernobai, and N. F. Komissarenko, Ukr. Khim Zh., 513 (1965).Google Scholar
  4. 4.
    V. T. Chernobai, Khim. Prir. Soedin., 229 (1965).Google Scholar
  5. 5.
    I. P. Kovalev and V. T. Chernobai, Khim. Prir. Soedin., 179 (1966).Google Scholar
  6. 6.
    L. Nover, G. Baumgarten, and M. Luckner, J. Chromatogr., 39, 450 (1969).CrossRefGoogle Scholar
  7. 7.
    N. F. Komissarenko, Khim. Prir. Soedin., 141 (1969).Google Scholar
  8. 8.
    I. L. Shamovskii, G. M. Barenboim, and A. A. Ovhinnikov, Bioorg. Khim.,11, 113 (1985).PubMedGoogle Scholar
  9. 9.
    J. F. Stoddart, Stereochemistry of Carbohydrates, Interscience, New York (1971) [Russian translation, Moscow (1975), p. 304].Google Scholar
  10. 10.
    R. Tschesche, S. Goenechea, and G. Snatzke, Ann. Chem.,674, 176 (1964).CrossRefGoogle Scholar
  11. 11.
    V. P. Georgievs'kii, M. O. Kazarinov, and E. I. Puchkova, Farmats. Zh.,3, 54 (1971).Google Scholar
  12. 12.
    K. B. Yatsimirskii, Kinetic Methods of Analysis [in Russian], Moscow (1967), p. 17.Google Scholar

Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • M. A. Kazarinov
  • N. F. Komissarenko
  • L. B. Nel'zeva
  • N. S. Solodun

There are no affiliations available

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