Sparteine – another Alkaloid in luteus family – University of Copenhagen

NaToxAq > Toxin of the week > Sparteine

09 April 2018

Sparteine – another Alkaloid in luteus family

Natural toxin

Sparteine is one of the quinolizidine alkaloids that show acute oral toxicity due to neurological effect leading to the loss of motor co-ordination and muscular control.

From left to right: narrow-leaved lupin, seeds of narrow-leaved lupin, yellow-lupin, and scotch broom.

Sparteine is one of the basic, tetracyclic alkaloids with a quinolizidine nucleus.  It is a quinolizidine alkaloid (QA) containing a tetracyclic bis-quinolizidine ring system derived from three C5 chains of lysine. It is isolated from several Fabaceae Including Lupinus; Spartium and Cytisus, also reported in scotch broom (Cytisus scoparius). In lupinidine (Luteus sparteine L.), Sparteine is a major alkaloid. It occurs in all lupine species, although in different concentrations.

Structure of Sparteine. Click image for interactive 3D model

QAs and sparteine are strong selective ecological impact. Sparteine is one of the QAs that show acute oral toxicity due to neurological effect leading to the loss of motor co-ordination and muscular control. The oral LD50 value of sparteine is 220 mg kg-1, its more toxic compare to other QA.

Many species of lupins are used in agriculture. Lupins are increasingly grown for their seeds, which can be used as an alternative to soybeans, because of their nutritional value, also they can serve as fix nitrogen. All lupin species can have 200 – 550 mgs of QAs per one tone of plant material, this 10 – 25% of the QA amount could be sparteine. The fate of sparteine in environment is unknown. Using EPI Suite - environmental fate estimation program, predicted half-life (days) and log Koc for sparteine is 90 and 2.304, respectively. Thus, it may leach to soil and water. However, research need to conduct to find the fate of QA and sparteine in environment.

Smiles: C1CCN2CC3CC(C2C1)CN4C3CCCC4

CAS Number: 90-39-1 

References:

  • Isamu Murakoshi, Yoshiaki Yamashita, Shigeru Ohmiya, Hirotaka Otomasu, (−)-3β-13α-dihydroxylupanine from cytisus scoparius, Phytochemistry, 25, (2), 1986, 521-524, https://doi.org/10.1016/S0031-9422(00)85514-4.
  • Musco, N. , Cutrignelli, M. I., Calabrò, S. , Tudisco, R. , Infascelli, F. , Grazioli, R. , Lo Presti, V. , Gresta, F. and Chiofalo, B. (2017), Comparison of nutritional and antinutritional traits among different species (Lupinus albus L., Lupinus luteus L., Lupinus angustifolius L.) and varieties of lupin seeds. J Anim Physiol Anim Nutr, 101: 1227-1241. doi:10.1111/jpn.12643
  • Pothier, J. , Cheav, S. , Galand, N. , Dormeau, C. and Viel, C. (1998), A Comparative Study of the Effects of Sparteine, Lupanine and Lupin Extract on the Central Nervous System of the Mouse. Journal of Pharmacy and Pharmacology, 50: 949-954. doi:10.1111/j.2042-7158.1998.tb04013.x
  • Silva MR, Alvarez CM, García PM, Ruiz MA. Assessing the genotoxicities of sparteine and compounds isolated from Lupinus mexicanus and L. montanus seeds by  using comet assay. Genet Mol Res. 2014 Dec 12;13(4):10510-7. doi: 10.4238/2014.December.12.12.
  • Tadeusz Aniszewski, Chapter 3 - Biology of alkaloids, In Alkaloids (Second Edition), Elsevier, Boston, 2015, Pages 222142, ISBN 9780444594334, https://doi.org/10.1016/B978-0-444-59433-4.00003-1.
  • Tadeusz Aniszewski, Chapter 2 - Alkaloid chemistry, In Alkaloids (Second Edition), Elsevier, Boston, 2015, Pages 1, ISBN 9780444594334, https://doi.org/10.1016/B978-0-444-59433-4.00002-X.

Figures/photos: