Chelidonin

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Structural formula
Structure of chelidonin
General
Surname Chelidonin
other names
  • Stylophorine
  • Diphylline
  • CHELIDONINE ( INCI )
Molecular formula C 20 H 19 NO 5
External identifiers / databases
CAS number 476-32-4
EC number 207-504-1
ECHA InfoCard 100.006.823
PubChem 197810
ChemSpider 171216
Wikidata Q1069066
properties
Molar mass 353.36 g mol −1
Physical state

firmly

Melting point

approx. 135 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-312-332
P: 280
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chelidonine , also called stylophorine or diphylline , is a heterocyclic compound containing oxygen and nitrogen .

Occurrence

Celandine flowers

The alkaloid , which occurs together with the similar substances coptisine and berberine in the milky sap of celandine ( Chelidonium majus ), belongs to the group of benzophenanthridine or. Isoquinoline derivatives.

history

In 1825 the Parisian chemist JP Godefroy noticed an alkaloid while examining the celandine, which he called "chélidonine". When Leo Meier repeated the analysis steps given by Godefroy in Königsberg in 1827, however, he did not find an alkaloid. So the discovery of Chelidonins was Johann Maximilian Alexander Probst awarded it purely represented. 1839 The pharmacist Reuling in Umstadt found after a self-experiment in 1839: “Chelidonin has little or no narcotic effect. Five grains [approx. 0.3 g] sulfuric acid chelidonin ingested only produces a bitter, salty, scratchy, pungent taste ”.

Properties and use

Chelidonine is a mitotic poison, but has a weaker effect than colchicine . Chelidonin can therefore also be used as a cytostatic agent and as an agent against gram-positive bacteria . Chelidonin, which has less analgesic and spasmolytic effects than morphine and papaverine , was used as a medicinal substance for stomach and intestinal pain and for cramps in asthma . In the Middle Ages, the caustic sap of celandine was also used as a remedy for warts .

Individual evidence

  1. ↑ Entry on CHELIDONINE in the CosIng database of the EU Commission, accessed on July 11, 2020.
  2. ↑ a b data sheet chelidonine (PDF) from Carl Roth , accessed on December 14, 2010.
  3. ↑ a b Chelidonine data sheet from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
  4. ^ Federation Proceedings, Federation of American Societies for Experimental Biology. 5 (1946) p. 163.
  5. ↑ a b Arzneimittel-Forschung / Drug Research . 10 (1960) p. 135.
  6. ^ JP Godefroy. Sur les plantes nommées Chelidonium Majus et Chelidonium Glaucium . In: Journal de Pharmacie et des Sciences Accessoires . Volume X (1824), pp. 635-644 (digitized) .
  7. ↑ Godefroy. Observations and experiments on Chelidonium majus and Chelidonium Glaucium . (Excerpt from the Journal de Pharmacie, December 1824.) In: Magazin für Pharmacie and the sciences involved. 3rd year, Volume 9, pp. 274–279 (digitized version ) .
  8. ^ Leo Meier (Königsberg). Chemical analysis of the leaves of the greater celandine . In: Berlinisches Jahrbuch für die Pharmacie , F. Oehmicke, Berlin, Volume XXIX (1827), Issue 1, pp. 169–232 (digitized version ) .
  9. ↑ Gustav Polex. About chelidonine and pyrrhopine . In: Archiv der Pharmacie , 2nd series, Volume XVI (1838), pp. 77-83 (digitized version ) .
  10. ↑ Dr. Probst. Description and method of representation of some of the substances newly discovered during the analysis of Chelidonium majus . In: Annalen der Pharmacie , Volume XXIX (1839), pp. 113-131 (digitized version ) .
  11. ↑ Heinrich Will . Composition of chelidonin and jervin . In: Annals of Chemistry and Pharmacy , Volume XXXV (1840), pp. 113-119 (digitized version ) .
  12. ^ GLW Reuling, pharmacist in Umstadt. Chelidonin . In: Annals of Pharmacy , Volume XXIX (1839), pp 131-135: chelidonine (digitized) .
  13. ↑ L. Roth, M. Daunderer, K. Kormann: Poison plants, plant poisons . 4th edition. ecomed, Landsberg 1994, ISBN 3-933203-31-7 , pp. 777-778 (reprint).
  14. ^ Wissenschaft-Online-Lexika: Entry on Chelidonin in the Lexikon der Biologie. Retrieved August 14, 2008.