Lupine Alkaloids

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

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]

(−)-Lupinin
(+)-Lupanin
(−)-Lupanine
(+)-Sparteine
(−)-Spartein
(−)-Cytisin

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

↑ ^1.0 ^1.1 ^1.2 Rudolf Hänsel, Otto Sticher (2007), Pharmakognosie Phytopharmazie (8 ed.), Heidelberg: Springer Medizin Verlag, pp. 1338, ISBN 978-3-540-26508-5
↑ ^2.0 ^2.1 ^2.2 Entry on Lupinen-Alkaloide. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
↑ Eberhard Breitmaier (1997), Alkaloide, Wiesbaden: Springer Fachmedien, pp. 45f., ISBN 3-519-03542-1
↑ 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 52 (5): 1032, doi:10.1021/np50065a019
↑ 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 28 (3): 958-959, doi:10.1016/0031-9422(89)80158-X
↑ 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 57 (1): 223-226, doi:10.1002/anie.201710261
↑ 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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[Pharm-1] 1.0 ^1.1 ^1.2 Rudolf Hänsel, Otto Sticher (2007), Pharmakognosie Phytopharmazie (8 ed.), Heidelberg: Springer Medizin Verlag, pp. 1338, ISBN 978-3-540-26508-5

[Römpp-2] 2.0 ^2.1 ^2.2 Entry on Lupinen-Alkaloide. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

[Alkaloide-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 52 (5): 1032, doi:10.1021/np50065a019

[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 28 (3): 958-959, doi:10.1016/0031-9422(89)80158-X

[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 57 (1): 223-226, doi:10.1002/anie.201710261

[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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