69 Cage型lupin alkaloidの存在についてツクシムレスズメ(Sophora franchetiana)の塩基性成分

概要

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A novel cage-type lupin alkaloid, named tsukushinamine(I), was newly isolated from the epigeal parts and roots of Sophora franchetiana (Leguminosae), together with (-)-cytisine(V), (-)-rhombifoline (VI), (-)-N-formylcytisine, (-)-anagyrine(VII), (-)-baptifoline(VIII) and (±)-ammodendrine. Its structure has been proposed to be shown as I' from spectroscopic data. The proposed structure of I' has also been confirmed by X-ray analysis, including the absolute configuration at the positions 6, 7, 9 and 14 as shown by the structure I. From the same source, we have further isolated two other tsukushinamine isomers, isomer-A(II) and isomer-B(III), in 0.45 and 0.05% yields/total base, respectively. However, the isomer-B (III) seems to be an artificial product arising from tsukushinamine (I) since I is transformed into III by a heat-treatment in N_2-gas. The biosynthetic pathway leading to the synthesis of tsukushinamine skeleton is assumed to be formed from (-)-baptifoline(VIII), coexisting in the same plant, or from baptifoline-type alkaloid, as shown in fig.1.
天然有機化合物討論会の論文
1979-09-20