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Lupine alkaloids have been studied from the viewpoints of biosynthesis, biotechnology, chemotaxonomy, and biological activity, on the basis of the chemical investigation of the leguminous plants of the 28 species belonging to the 9 genera, which mainly grow in Japan. The results obtained have been comprehensively reviewed by authors. This review describes the stereochemistry of lupine alkaloids and focuses on the conformational flexibility of nitrogen-fused systems such as quinolizidine and indolizidine, syntheses of new unusual types of alkaloids from known lupine alkaloids, and pharmacological activity of lupine alkaloids, especially kappa-opioid receptor-mediated antinociceptive effects of matrine-type lupine alkaloids.

Stereochemistry, Syntheses and Biological Activity of Lupine Alkaloids-from Studies on the Leguminous Plants Growing Mainly in Japan