Lupine alkaloids

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

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

## Contents

* 1 Occurrence
* 2 Representatives
* 3 Properties
* 4 References

## 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. ↑ 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. ↑ 2.0 2.1 2.2 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 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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