Sparteine-Synonyms l-Sparteine; Lupinidine-obtained from yellow and black lupin beans Lupinus luteus L., and Lupinus niger

C. Sparteine


Synonyms l-Sparteine; Lupinidine.
Biological Sources It is obtained from yellow and black lupin beans Lupinus luteus L., and Lupinus niger Hort.; and also found in Cytisus scoparius (L.) Link. (Fabaceae) (Scotch Broom); Anagyris foetida L., belonging to natural order Leguminosae. Besides, it is also obtained from the roots of Aconitum napellus L. (Ranunculaceae) (Aconite, Monkshood, Blue Rocket); from the herbs of Chelidonium majus L. (Papaveraceae) (Celandine, Great Celandine, Nipplewort); from leaves of Peumus boldus Molina (Monimiaceae) (Boldo).
Chemical Structure

Sparteine
[7S-(7α, 7aα, 14α, 14a β]-Dodecahydro-7, 14-methano-2H, 6H-dipyrido [1, 2-a: 1’, 2’-e] [1, 5] diazocine, (C15H26N2).
Isolation It is isolated from yellow and black lupin beans by the method put forward by Clemo* (1949).
Characteristic Features
1. It is a viscous oily liquid having bp8 173°C.
2. It is volatile with steam.
3. Its physical parameters are: [α ]D21  -16.4o (C = 10 in absolute ethanol); nD20 1.5312; d420 1.020; pK1 at 20°C : 2.24; pK2:9.46; pH of 0.01 molar solution is 11.6.
4. Solubility profile: It is freely soluble in ethanol, ether and chloroform; and 1 g dissolves in 325 ml of water.
Identification Test
Sparteine Sulphate Pentahydrate (C15H26N2.H2SO4.5H2O): (Synonyms: Depasan;
Tocosamine) It is obtained as columnar crystals which loses water of crystallization at 100°C turning brown and ultimately gets decomposed at 136°C. The pH of a 0.05 molar solution is 3.3. It is practically insoluble in ether and chloroform, and 1 g dissolves in 1.1 ml of water, 3 ml of ethanol.
Uses
1. It is used mostly as an oxytocic.
2. It is employed as a cardiac depresant, cathartic, diuretic and for stimulating uterine contractions.
3. Sparteine is used occasionally as a quinidine substitute in stubborn cases of atrial fibrillation.
Biosynthesis of Lupinine, Lupanine and Sparteine Experimental evidence reveals lysine to be incorporated into lupinine via cadaverine; however, the intermediate related to homospermidine is excluded. It has been observed that ∆1-piperideine happens to be an important intermediate after
cadaverine. Thus, the proposed pathway given below suggests coupling of two such molecules. In fact, the two tautomers of ∆1-piperideine, as N-analogues of corresponding carbonyl compounds, are in a position to couple by an aldol-type mechanism. In reality, this coupling takes place in solution at physiological pHs, although the stereospecific coupling as shown in the proposed pathway shall evidently require the participation of suitable enzymes. After coupling, the imine system gets hydrolyzed, the resulting primary amine function undergoes oxidation, and ultimately the formation of the quinolizidine nucleus is accomplished by Schiff base formation. Thus, lupinine is then synthesized by two further reductive steps. Hence, the pathway to sparteine and lupanine eventually requires participation of another molecule of cadaverine or ∆1-piperideine.

Biosynthesis of Lupinine, Lupanine and Sparteine
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* Clemo et al. J. Chem. Soc. 6.63, (1949)

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