Studies on the Steroidal Components of Domestic Plants. XLVII. Constituents of the Stem of Smilax sieboldi MIQ. (1). The Structure of Laxogenin

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From the aerial parts of Smilax sieboldi MIQ. a new steroidal sapogenin, laxogenin (I), was isolated together with tigogenin and neotigogenin. The analytical values of I corresponded to formula C_<27>H_<42>O_4 for sapogenin and C_<29>H_<44>O_5 for the acetate. On Huang-Minlon reduction I afforded tigogenin (II), and on sodium borohydride reduction of I, β-chlorogenin (III) and chlorogenin (IV) were obtained in ratio about 85 : 15. The chromic acid oxidation of I afforded a diketone (V), m.p. 229〜231°, which was proved to be identical with 25_D-allospirostane-3,6-dione. From these results the structure of laxogenin was assumed to be 3β-hydroxy-25_D, 5α-spirostan-6-one and this assumption was confirmed by the synthesis of this compound from 5,6-epoxydiosgenin (XI).
公益社団法人日本薬学会の論文
1965-05-25