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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Die Bildung von 1-Methyl-4-iminochinolin aus Echinorin durch Einwirkung von Ammonia

  • P. Schröder and M. Luckner

The alkaloid echinorine (I) is the only alkaloid occurring in the fruits of Echinops ritro L. and Echinops sphaerocephalus L. The previously reported echinopsine (III) was found to have been formed from echinorine (I) during the isolation procedures or during storage of the plant material. In addition to echinopsine (III) a further alkaloid echinopsidine (II) is found under certain conditions. Our experiments show that this compound is formed if extracts of the fruits are treated with ammonia.

When 15N labelled ammonia is used, the isotope is found in the echinopsidine formed. By degradation of the labelled compound to echinopsine and ammonia it is shown that the isotope 15N is located in the imino group only. This result shows conclusively that echinopsidine can be formed by ammonolysis of echinopsine.

A small amount of echinopsidine is also found in the extract of fruits on addition of sodium carbonate. No free ammonia could be detected in the extract adjusted to pH 8.4 following extractions of the fruits with methanol or a mixture of methanol and acetic acid. The addition of sodium carbonate, however, liberated small quantities of ammonia, possibly from arginine or other N containing substances and this could explain the formation of small amounts of echinopsidine without the addition of ammonia to the extracts under these conditions.

Other products are obtained from echinorine in the presence of amino acids (e.g. glycine, alanine or phenylalanine) and sodium carbonate. Here the complete degradation of the alkaloid and the formation of new compounds (and echinopsine) was observed.

Received: 1967-12-5
Published Online: 2014-6-2
Published in Print: 1968-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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