Lupine alkaloids

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White lupine ( Lupinus albus )
Blue Lupine ( Lupinus angustifolius )

Lupine alkaloids are natural products of the quinolizidine alkaloid type . They were named after their occurrence in lupins .

Occurrence

Depending on the variety, lupins contain between 0.6 and 4.3% lupine alkaloids.

Representative

In total, more than 170 lupine alkaloids are known. The main alkaloid is lupinine . Further representatives are u. a. Lupanine , Lupanolin and sparteine . (-) - Lupanine occurs in the white lupine , while (+) - Lupanine occurs in the blue lupine . Both (+) - sparteine ​​and (-) - sparteine ​​occur in nature. (-) - Cytisine , the main alkaloid of the golden rain , is a representative of the lupine alkaloids.

  • (-) - Lupine

  • (+) - lupanine

  • (-) - lupanine

  • (+) - Sparteine

  • (-) - Sparteine

  • (-) - cytisine

properties

The lupine alkaloids are considered poisonous. Grazing animals should not consume more than 60 g / kg. The effects of poisoning include: a. Liver and kidney degeneration, miscarriages or deformities. Sheep are particularly sensitive.

Individual evidence

  1. ↑ a b c R. Hansel, O. Sticher: Pharmakognosie Phytopharmazie . 8th edition. Springer Medizin Verlag, Heidelberg 2007, ISBN 978-3-540-26508-5 , p. 1338 .
  2. ↑ a b c Entry on lupine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on April 27, 2020.
  3. ↑ E. Breitmaier: Alkaloids . Springer Fachmedien, Wiesbaden 1997, ISBN 978-3-519-03542-8 , pp. 45 f .
  4. ↑ K. Saito, S. Takamastsu, I. Murakoshi, S. Ohmiya, H. Otomasu: Isolation of a New Alkaloid (-) - 0- Acetylbaptifoline and the Absolute Stereochemical Relationships of Lupine Alkaloids in Thermopsis chinensis . In: Journal of Natural Products . tape 52 , no. 5 , 1989, pp. 1032 , doi : 10.1021 / np50065a019 .
  5. ↑ K. Saito, S. Takamastsu, T. Sekine, F. Ikegami, H. Kubo, I. Murakoshi, S. Ohmiya, H. Otomasu: Absolute configuration of (+) - 5,6-dehydrolupanine, a key intermediate in biosynthesis of lupine alkaloid . In: Phytochemistry . tape 28 , no. 3 , 1989, pp. 958-959 , doi : 10.1016 / 0031-9422 (89) 80158-X .
  6. ↑ James D. Firth, Steven J. Canipa, Leigh Ferris, Peter O'Brien: Gram-Scale Synthesis of the (-) - Sparteine ​​Surrogate and (-) - Sparteine . In: Journal of the German Chemical Society . tape 57 , no. 1 , 2017, p. 223–226 , doi : 10.1002 / anie.201710261 .
  7. ↑ T. Dingermann, K. Hiller, G. Schneider, I. Zündorf: Schneider drug drugs. 5th edition. Elsevier 2004, ISBN 3-8274-1481-4 , pp. 339 f.