Bisbenzylisoquinoline alkaloids

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Bisbenzylisoquinoline alkaloids are natural products found primarily in the plant families of the barberry family, the Menispermaceae, the Monimiaceae, and the buttercup family. [1]

Contents

Occurrence

More than 225 different bisbenzylisoquinoline alkaloids are known and have been isolated. [1]

Representative

The bisbenzylisoquinoline alkaloids are considered the largest group within the isoquinoline alkaloids. [2] The best-known representative of this group is tubocurarine chloride. Other representatives include dauricin, oxyacanthin, tetrandrine, and tiliacorin. [3]

Structure

Bisbenzylisoquinoline alkaloids are characterized by their structure. Typically, they consist of two benzyl-tetrahydroquinoline units linked by ether groups, and occasionally by C-C bonds. Multiple ether bridges are often present. [1] [4] These alkaloids can be categorized into three groups, using the nomenclature head for the 1,2,3,4-tetrahydroisoquinoline unit and tail for the 1-benzyl residue:

Dauricine is the simplest representative with a tail-to-tail linkage. Oxyacanthine and Tetrandrin contain both head-head and tail-tail linkages, while Tiliacorine features one tail-tail linkage and two head-head linkages linking to a dibenzodioxin moiety. Tubocurarine chloride is characterized by two head-tail linkages of the tetrahydroisoquinoline units. [3] In the following structural formulae, the tail linkages are marked red and the head linkages are marked blue:

Uses

The alkaloids belonging to the bisbenzylisoquinoline group are generally toxic and exhibit curarizing effects. Oxyacanthine serves as a sympatholytic agent, an antagonist to epinephrine, and a vasodilator. Tubocurarine, a potent curarizing poison, stands as the oldest known muscle relaxant. South American indigenous populations have traditionally employed it as an arrow poison (see curare). [1]

Tetrandine, found as an ingredient in the Chinese medicine "han-fang-shi," possesses analgesic and antipyretic properties. [3]

References

  1. 1 2 3 4 Entry on Bisbenzylisoquinoline alkaloids . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  2. ↑ Peter Nuhn (2006), Naturstoffchemie (4 ed.), Stuttgart: S.Hirzel Verlag, pp. 603f, ISBN   9783777613635
  3. 1 2 3 4 Eberhard Breitmaier (1997), Alkaloide, Wiesbaden: Springer Fachmedien, pp. 63f, ISBN   9783519035428
  4. ↑ H. Latscha, U. Kazmaier (2016), Chemie für Biologen (4 ed.), Berlin Heidelberg: Springer Spektrum, p. 691, ISBN   9783662477830
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