Bisbenzylisoquinoline alkaloids

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Shiny meadow rue ( Thalictrum lucidum )

Bisbenzylisoquinoline alkaloids are natural substances that occur primarily in the plant families of the barberry family , the moon seed family , the monimia family and the buttercup family .

Occurrence

More than 225 different bisbenzylisoquinoline alkaloids are known and have already been isolated.

Representative

The bisbenzylisoquinoline alkaloids are considered to be the largest group within the isoquinoline alkaloids . The best-known representative of this group is tubocurarine chloride. Further representatives are u. a. Dauricin, Oxyacanthin, Tetrandrine and Tiliacorin.

  • Dauricin

  • Oxyacanthin

  • Tiliacorin

  • Tubocurarine

structure

The bisbenzylisoquinoline alkaloids are characterized by their structure. As a rule, two benzyl-tetrahydroquinoline units are linked to one another via ether groups , but often also via C − C bonds. Often two or more ether bridges can be found. With the designation head for the 1,2,3,4-tetrahydroisoquinoline unit and tail for the 1- benzyl residue, the alkaloids can be divided into three groups:

  • Head to head
  • Tail tail
  • Head-to-tail linked bisbenzylisoquinoline alkaloids.

The simplest representative with a tail-tail linkage is Dauricin . Oxyacanthin and tetrandrine contain both a head-to-head and a tail-to-tail connection. Tiliacorin contains a tail-to-tail link and two head-to-head links which link to form a dibenzodioxin unit. Tubocurarine chloride is characterized by two head-to-tail linkages of the tetrahydroisoquinoline units. In the following structural formulas, the tail links are marked red and the head links are marked blue :

  • Dauricin

  • Oxyacanthin

  • Tiliacorin

  • Tubocurarine

use

The alkaloids of the bisbenzylisoquinoline group are generally poisonous and have a curarizing effect. Oxyacanthin is a sympatholytic agent, an adrenaline antagonist, and a vasodilator. Tubocurarine is a powerful curarizing poison and the oldest known muscle relaxant. It is used by the South American Indians as an arrow poison (see curare ).

Tetrandin is an ingredient of the Chinese drug han-fang-shi with an analgesic and antipyretic effect .

Individual evidence

  1. ↑ a b c d Entry on bisbenzylisoquinoline alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on April 19, 2020.
  2. ^ P. Nuhn: Naturstoffchemie . 4th edition. S. Hirzel Verlag, Stuttgart 2006, ISBN 978-3-7776-1363-5 , p. 603 f .
  3. ↑ a b c d E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 63 f .
  4. ↑ H. Latscha, U. Kazmaier: Chemistry for Biologists . 4th edition. Springer Spectrum, Berlin Heidelberg 2016, ISBN 978-3-662-47783-0 , p. 691 .