Quinolizidine alkaloids

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Quinolizidine, basic structure of the quinolizidine alkaloids
Dyer's gorse ( Genista tinctoria )
Common laburnum ( Laburnum anagyroides )

Quinolizidine alkaloids are natural substances that have a quinolizidine basic structure, including the lupine alkaloids .

Occurrence

Quinolizidine alkaloids are found in the legume family , especially in the butterflies . While the lupine alkaloids are found in lupins , as is their name , tinctorine was isolated from the dyer's gorse .

Representative

More than 200 quinolizidine alkaloids are known. The alkaloids can be classified into 6 structural types:

  • the lupinine type with 34 known structures, u. a. Lupine and its derivatives
  • the camoensin type with 6 known structures, u. a. Camoensidin
  • the Sparteine ​​type with 66 structures, etc. a. Sparteine , Lupanine , Angustifolin
  • the α-pyridone type with 25 structures, u. a. Anagyrin and cytisine
  • the Matrin-type with 31 structures, u. a. Matrin
  • and the ormosanine type with 19 structures, u. a. Ormosanine

  • (-) - Lupine

  • (-) - Sparteine

  • (-) - lupanine

  • (-) - anagyrin

  • (+) - matrine

properties

Cytisine is the main toxic alkaloid in golden rain . Similar to nicotine, it has a stimulating to hallucinogenic effect in low doses, and paralyzes in higher doses. Cytisine and matrine are active ingredients in Sophora beans in Mexico and the cow seng and shinkyogan drugs in China and Japan.

The quinolizidine alkaloids serve to protect the plants against chemicals. They show a variety of effects on warm-blooded animals and lead to poisoning of grazing cattle (sheep and cattle). Cytisine and anagyrine are particularly responsible for this. The effects of poisoning are agitation, incoordination, shortness of breath, convulsions and ultimately death from respiratory paralysis. Anagyrin is teratogenic . The only therapeutically used quinolizidine alkaloid is sparteine, which has an anti-arrhythmic effect and promotes labor.

Individual evidence

  1. ↑ a b c d E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 45 ff .
  2. ↑ a b c Entry on quinolizidine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on April 28, 2020.
  3. ↑ D. Knöfel, H. Schütte: Quinolizidine alkaloids: constitution and configuration of tinctorin from Genista tinctoria . In: Journal for practical chemistry . tape 312 , no. 5 , 1970, p. 887-888 , doi : 10.1002 / prac.19703120521 .

Web links

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