Lupinine

Lupinine
Names
IUPAC name
[(1R,9aR)-2,3,4,6,7,8,9,9a- Octahydro-1H-quinolizin-1-yl]methanol
Identifiers
486-70-4 N
3D model (Jmol) Interactive image
ChEBI CHEBI:28012 YesY
ChEMBL ChEMBL459397 YesY
ChemSpider 82587 YesY
ECHA InfoCard 100.006.944
PubChem 91461
Properties
C10H19NO
Molar mass 169.26 g/mol
Melting point 68 to 69 °C (154 to 156 °F; 341 to 342 K)
Boiling point 269 to 270 °C (516 to 518 °F; 542 to 543 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lupinine is a bitter tasting quinolizidine alkaloid present in Lupinus species (lupins), plants of the family Fabaceae. The scientific literature contains many reports on the isolation and synthesis of this compound. The characteristically bitter taste of lupin beans, attributable to the alkaloids which they contain,[1] renders them unsuitable for human and animal consumption. However, because lupin beans have potential nutritional value due to their high protein content,[2] efforts have been made to reduce their alkaloid content,[1][3] as well as to develop "sweet" varieties of Lupinus.

Isolation

One of the earliest isolations of lupinine, from Lupinus palmeri collected in Utah, USA, is that reported by Couch, who was able to obtain crystalline lupinine without the use of chromatographic techniques.[4]

Synthesis

There are numerous syntheses of lupinine in the literature. A recent synthesis, notable because it describes the preparation of all four stereoisomers of lupinine, and containing many references to earlier work in this field, was published by Ma and Ni.[5]

References

  1. 1 2 R. Bleitgen, et al. (1979). "Lupins - a new source of food for Andean countries. 5. Traditional methods of debittering of lupins by water". Z. Ernahrungswiss. 18 (2): 104–111. doi:10.1007/BF02023724. PMID 556411.
  2. ↑ E. Yanez, et al. (1983). "Chemical and nutritional evaluation of sweet lupines". Ann. Nutr. Metab. 27 (6): 513–520. doi:10.1159/000176728. PMID 6651228.
  3. ↑ F. T. Torres, et al. (1980). "Methods of eliminating alkaloids from the seeds of Lupinus mutabilis Sweet". Arch. Latinoam. Nutr. 30 (2): 200–209. PMID 7212919.
  4. ↑ J. F. Couch (1934). "Lupine Studies. VIII. The Alkaloids of Lupinus Palmeri, S. Wats". J. Am. Chem. Soc. 56 (11): 2434–2436. doi:10.1021/ja01326a067.
  5. ↑ S. Ma and B. Ni (2004). "Double ring-closing metathesis reaction of nitrogen-containing tetraenes: Efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives". Chem. Eur. J. 10 (13): 3286–3300. doi:10.1002/chem.200305581. PMID 15224338.

See also

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