Quinolizidine alkaloids lupins

Quinolizidine alkaloids (lupine alkaloids) occur in the family Leguminosae, especially the subfamily Papilionaceae. They are also found in some species of other families such as Chenopodiaceae, Berberidaceae, Papaveraceae, Nymphaeaceae, Ranunculaceae, Scrophulariaceae, Solanaceae, Compositae, Rubiaceae, Monimiaceae, Ericaceae, and Adociidae. 

The quinolizidine alkaloids (lupine alkaloids) occur in the Leguminosae family, subfamily Faboideae, where they are restricted to the Sophoreae, Podalyrieae, and Genisteae tribes (1). They have been previously reviewed by Leonard (2) in these volumes. The present review is complete to the end of 1965. 

Carey, D.B. and Wink, M. (1994). Elevational variation of quinolizidine alkaloid contents in a lupine Lupinus argenteus) of the Rocky Mountains, J. Chem. EcoL, 20, 849-857. 

Keeler, R.F. 1989. Quinolizidine alkaloids in range and grain lupins, in Cheeke, P.R., Ed., Toxicants of plant origin, Vol. I Alkaloids, CRC Press, Boca Raton, pp. 133-168. 

The biochemistry and physiology of quinolizidine alkaloids is reviewed with respect to their role in lupin meteibolism. Minor roles of the alkaloids may be nitrogen transport and nitrogen storage, but their main function is that of chemical defense. 

Figure 7. The raw extraction of quinolizidine alkaloids from different lupine species in the Research and Teaching Laboratory of Applied Botany of the University of Joensuu (Photo T. Aniszewski). Observe the different colours of the raw extracts, which signifies different concentrations of alkaloids in different species.

This is a non-chemical, and probably the first biological, method of determining the presence of alkaloids. It was first used particularly with quinolizidine alkaloids in lupine plants. The tasters were men or animals, even in ancient times. It is based on the fact that quinolizidine alkaloid has a bitter taste. This method is qualitative. Taste is a subjective and individual category, especially in the... 

The idea of calorimetry is based on the chemical reaction characteristic of molecules. The calorimetry method does not allow absolute measurements, as is the case, for example, with volumetric methods. The results given by unknown compounds must be compared with the calibration curve prepared from known amounts of pure standard compounds under the same conditions. In practical laboratory work there are very different applications of this method, because there is no general rule for reporting results of calorimetric determinations. A conventional spectrophotometry is used with a calorimeter. The limitations of many calometric procedures lie in the chemical reactions upon which these procedures are based rather than upon the instruments available . This method was first adapted for quinolizidine alkaloid analysis in 1940 by Prudhomme, and subsequently used and developed by many authors. In particular, a calorimetric microdetermination of lupine and sparteine was developed in 1957. The micromethod depends upon the reaction between the alkaloid bases and methyl range in chloroform. 

Yovo et al. stated that these alkaloids act via inhibition of ganglionic impulse transmissions of the sympathetic nervous system. It is evident that each alkaloid has its own effect. Anagyrine caused skeletal deformity in foetuses when pregnant cows consumed toxic lupines . On the other hand, some quinolizidine alkaloids are used as a drug in folk medicine". They probably have chronic toxicity. However, adequate knowledge about the chronic toxicity of these alkaloids and especially of chronic toxication across generations is not available. The premise that quinolizidine alkaloids have not produced hereditary symptoms has not been checked with total reliability. 

Alkaloids are used as fertilizers for some crops. Mittex AG in Germany has developed a natural product, Lupinex, which contains quinolizidine alkaloids, minerals and carbohydrates. Lupinex has more than 9% N, 1% P and 2% K. The raw material for this natural product is a waste received from the lupin alkaloid remowing process, when the edible and non-edible components of food... 

Quinolizidine alkaloids, pure or in mixtures of plant extract, can be used to protect plants against noxious insects. Scientific data has shown that quinolizidine alkaloids play a role in the resistance of some lupine varieties to the pea... 

Hartmann, T. 1988. Secondary metabolism of lupins Biosynthesis, translocation and accumulation of the quinolizidine alkaloids. In Proceedings of the 5th International Lupin Conference. (Twardowski, T., ed.) pp. 64-78. Poznari, Polish Academy of Sciences, Institute of Bioorganic Chemistry. 

Reinhard, H., Rupp, H., Sager, F., Streule, M. and Zoller, O. 2006. Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food. Journal of Chromatography A, 1112(1-2) 353-360. 

Aniszewski, T. 1998. Perennial stability of total quinolizidine alkaloid content in alkaloid-poor Washington lupin Lupinus polyphyllus Lindl). Journal of the Science of Foof and Agriculture, 76 195-199. 

Aniszewski, T. 1995. Lupin adaptative factor quinolizidine alkaloids. In Adaptation in Plant Breeding. XIV EUCARPIA congress. Abstracts. (Raatikainen, M., ed.), pp. 31-32. University of Jyvaskyla, Jyvaskyla. 

Aniszewski, T. 1993. Lupine A Potential Crop in Finland. Studies on the Ecology, Productivity and Quality of Lupinus spp. PhD thesis. University of Joensuu, Joensuu and, Aniszewski, T. 1994. The biological basis of quinolizidine alkaloids. Science of Legumes, 1 1-24. 

Biosynthesis, transport and storage of quinolizidine alkaloids in lupins. Alkaloid concentrations are given as % dry weight. 

Wink, M. 1983. Wounding-induced increase of quinolizidine alkaloid accumulation in lupin leaves. Z. Naturforsch. 38c, 905-909... 

Wink, M. 1984. Chemical defence of Leguminosae. Are quinolizidine alkaloids part of the antimicrobial defence system of lupins Z. Naturforsch. 39c, 548-552... 

Wink, M. and Witte, L. 1985. Quinolizidine alkaloids as nitrogen source for lupin seedlings and cell suspension cultures. Z. Naturforsch. 40c,767-775. 

Lupines are known as rich leguminosae in lipids and proteins. This makes them very interesting if they were produced in a large industrial scale. However the presence of bitter and poisonous quinolizidine alkaloids is the main obstacle to overcome for a broader utilisation. 

Fig. 1.1 Relationships between plants, their secondary metabolites, and potential enemies (herbivores, microorganisms, and viruses). Example Lupins produce quinolizidine alkaloids, isoflavonoids, and saponins as main defense compounds.

Fig. 1.3 Importance of quinolizidine alkaloids for lupins against herbivores.ln this experiment, lupins with or without alkaloids were grown in the field. When rabbits got into the field, they preferentially consumed the sweet, alkaloid-free lupins. Also larvae of mining flies preferred sweet lupins.

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