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Lupine alkaloids

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White lupine (Lupinus albus) Lupinus albus 000 223 259 O.jpg
White lupine (Lupinus albus)
Blue lupine (Lupinus angustifolius) Lupinus angustifolius1.jpg
Blue lupine (Lupinus angustifolius)

Lupine alkaloids are natural substances classified as quinolizidine alkaloids. They are named after their presence in lupins. [1]

Contents

Occurrence

Depending on the variety, lupins contain between 0.6% and 4.3% lupine alkaloids. [2]

Representatives

More than 170 lupine alkaloids have been identified. [1] The primary alkaloid is lupinin. Other notable compounds include lupanine, lupinine, lupanolin [2] and sparteine. [1] (-)-Lupanine is found in the white lupin, while (+)-lupanine is present in the blue lupin. [3] [4] [5] Both (+)-sparteine and (-)-sparteine occur naturally. [6] (-)-cytisine, the primary alkaloid of the laburnum, is also classified as a lupine alkaloid. [7]

Properties

Lupine alkaloids are considered toxic. Grazing animals should not ingest more than 60 g/kg. Symptoms of poisoning include liver and kidney degeneration, miscarriages, and congenital deformities. Sheep are particularly sensitive to these toxins. [2]

References

  1. 1 2 3 Rudolf Hänsel, Otto Sticher (2007), Pharmakognosie Phytopharmazie (8 ed.), Heidelberg: Springer Medizin Verlag, p. 1338, ISBN   978-3-540-26508-5
  2. 1 2 3 Entry on Lupinen-Alkaloide . at: Römpp Online . Georg Thieme Verlag, retrieved {{{Datum}}}.
  3. ↑ Eberhard Breitmaier (1997), Alkaloide, Wiesbaden: Springer Fachmedien, pp. 45f., ISBN   3-519-03542-1
  4. ↑ K. Saito, S. Takamastsu, I. Murakoshi, S. Ohmiya, H. Otomasu (1989), "Isolation of a New Alkaloid (−)-O- Acetylbaptifoline and the Absolute Stereochemical Relationships of Lupine Alkaloids in Thermopsis chinensis", Journal of Natural Products, vol. 52, no. 5, p. 1032, doi:10.1021/np50065a019 {{citation}}: CS1 maint: multiple names: authors list (link)
  5. ↑ K. Saito, S. Takamastsu, T. Sekine, F. Ikegami, H. Kubo, I. Murakoshi, S. Ohmiya, H. Otomasu (1989), "Absolute configuration of (+)-5,6-dehydrolupanine, a key intermediate in biosynthesis of lupin alkaloids", Phytochemistry, vol. 28, no. 3, pp. 958–959, doi:10.1016/0031-9422(89)80158-X {{citation}}: CS1 maint: multiple names: authors list (link)
  6. ↑ James D. Firth, Steven J. Canipa, Leigh Ferris, Peter O’Brien (2017), "Gram-Scale Synthesis of the (−)-Sparteine Surrogate and (−)-Sparteine", Journal of the German Chemical Society, vol. 57, no. 1, pp. 223–226, doi:10.1002/anie.201710261 {{citation}}: CS1 maint: multiple names: authors list (link)
  7. ↑ T. Dingermann, K. Hiller, G. Schneider, I. Zündorf: Schneider Arzneidrogen. 5. Auflage. Elsevier 2004, ISBN 3-8274-1481-4, S. 339 f.
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