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Veralkamine, a novel type of steroidal alkaloid with a 17β-methyl-18-nor-17-isocholestane carbon skeleton

✍ Scribed by J. Tomko; A. Vassová; G. Adam; K. Schreiber; E. Höhne


Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
267 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis


Some years ago, Tomko et al. (I) isolated a secondary alkaloid, veralkamine, from Veratrum album ssp. lobelianum (Bernh.) Suessenguth. In alteration of a formerly proposed provisional constitution (2) its complete structure has been established by recent chemical and physical reinvestigations including an X-ray structural analysis of veralkamine hydroiodide. According to these studies briefly described in this paper veralkamine was shown to be (22~:2~~)-22.26-epimino-l7B-methyl-l8-nor-cholesta-~.l2-diene-jB.lGB-diol [(17~:22~:2~~)-22.26-epimino-l8(1~~l7)-~-cholesta-~.12-d~ene-3B.l6B-diol, I]. Elemental analysis and mass spectroscopy indicated that veraikamine (I) has the empirical formula C2?Hh3N02. Selenium debydrogenation afforded in addition to 2-ethyl-5-methylpyridine y-methylcyclopentenophenantbrene (Diels' hydrocarbon) demonstrating the steroidal nature of the alkaloid as well as the absence of a C-nor-D-homo steroidal skeleton characteristical for many other Veratrum bases. The mass spectra (negative and positive * Alkaloids from Veratrum album ssp. lobelianum (Bernh.) Suessenguth, Part XIV. -Part XIII of this series of. G. Adam, K. Schreiber, and J. Tomko, LiebiR's Ann., in press.


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