Lupine alkaloids biological activity

Wysocki, W., Gulewicz, P., Aniszewski, T., Ciesiolka, D. and Gulewicz, K. 2001. Bioactive preparations from alkaloid-rich lupin. Relation between chemical composition and biological activity. Bulletin of the Polish Academy of Sciences. Biological Sciences, 49 9-17. 

The cyclic ammonium ylide/[l,2]-shift approach has been successfully applied by West and Naidu to a key step in the total synthesis of (—)-epilupinine, one of the biologically active lupin alkaloids. Cu(acac)2-catalyzed diazo decomposition of enantiomeric pure diazoketone 160 in refluxing toluene generates a spiro ammonium ylide 161 and 162, which then undergoes [l,2]-shift to give rise to a quinolizidine skeleton as a mixture of diastereomers (95 5) (Scheme Major diastereomer 164 has enantiomeric purity of 75% ee. The partial retention of stereo-... 

In general, plants do very well in their environments, notwithstanding the omnipresence of a multitude of potential insect herbivores and a number of vertebrate herbivores as well. Some plant species are very insecticidal, as a consequence of their producing a variety of alkaloids including nicotine, piperine, lupine alkaloids, steroidal alkaloids, ephedrine, berberine, strychnine, gramine, and caffeine.37 These biologically active alkaloids also function as deterrents. In terms of families, caffeine is the the most widely distributed alkaloid, a fact that may be... 

During 1993, Daly and co-workers reviewed the alkaloids found in amphibians [5] and Takahata et al. focused on structural assignments and the synthesis of amphibian and polyhydroxylated indolizidines [6]. Wink reviewed the characterisation, natural distribution and biological activity of lupine alkaloids [7] and systematic updates on indolizidine and quinolizidine alkaloids are annually summarized by Michael [8-14]. 

The conformational study of sparteine derivatives has been of great interest due to their use as synthetic chiral auxiliaries and a brief account of the progress made in this area will be presented. A description of the newly isolated and characterised lupine alkaloids, as well as an updated review of the biological activity of these metabolites will be given. 

Table V Example of recently examined biological activities of lupin alkaloids.

Stereochemistry, syntheses, and biological activity of lupine alkaloids 07YZ1557. 

Wink, M. 1994. Biological activities and potential application of lupin alkaloids. In Neves-Martins, J.M., and M.L. Beirao da Costa, eds. Advances in lupin research. Lisboa ISA Press. 

Heteroatom nucleophiles were described less often. Ye and coworkers published a phospha-Michael addition catalysed by prolinol silyl ether catalyst. Another method for constructing a new C-N bond is the aza-Michael addition, that is the addition of nitrogen-based nucleophiles to a,(3-unsaturated aldehydes. Several groups published these type of reactions using diatylprolinol silyl ether as catalyst. " Fustero and coworkers used this reaction as a key step in the synthesis of biologically active chiral heterocycles. Recently, the authors showed the synthesis of quinolizidine alkaloids, such as (-l-)-myrtine, (-)-lupine and (-l-)-epiquinamide. Vicario applied 5-mercaptotetrazoles as nucleophiles towards a range of unsaturated aldehydes. The reaction proceeded via the iminium activation. The... 

An extract taken from the composted straw of the alkaloid-rich lupin plants has produced very promising results in the development of biological control agents. The fungistatic activity of straw compost extracts increased markedly when the lupin straw used for composting was enriched with alkaloid extract. 

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