Furostanol Bisglycosides Corresponding to Dioscin and Gracillin

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概要

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• Two compounds, positive (red) to the Ehrlich reagent and predominant in the methanol extracts of the fresh rhizomes of Dioscorea gracillima MIQ., were isolated. Their structures were established as 26-O-β-D-glucopyranosyl 22-methoxyfurost-5-ene-3β, 26-diol 3-O-β-chacotrioside (I), mp 187-191°(decomp.), [α]_D-95.6°, and its 22-hydroxy analog (I'), mp 190-196°(decomp.), [α]_D-79.8°, the furostanol bisglycosides corresponding to 25D-spirost-5-en-3β-ol (diosgenin) 3-O-β-chacotrioside (dioscin) (III), the major component of the stored materials. I is regarded as an artifact formed from I', and I'and I are named proto-dioscin and methyl proto-dioscin, respectively. Smilax-saponin B, which had been assigned a structure, diosgenin hexaglycoside, was identical with I and the structure is revised. Among the Ehrlich positive compounds in the methanol extracts of the fresh rhizomes of D. septemloba THUNB., the major, mp 249-251°(decomp.), [α]_D-76.9°, was isolated and characterized as the analog (II) of I, chacotriose being replaced by gracillimtriose, corresponding to gracillin (IV). One of the minor components was identified with the 22-hydroxy compound (II') of II, mp 235-238°(decomp.), [α]D-57.8°. II'and II are named proto-gracillin and methyl proto-gracillin, respectively. Kikuba-saponin, which had been assigned the structure, IV monoglucoside, was identical with II and the structure is revised.

• 社団法人日本薬学会の論文
• 1974-09-25

著者

• 古森 徹哉

  九大薬

• 野原 稔弘

  Faculty Of Pharmaceutical Sciences Kyushu University

• 細川 一郎

  Faculty of Pharmaceutical Sciences, Kyushu University

• 三橋 国英

  Faculty of Pharmaceutical Sciences, Fukuoka University

• 細川 一郎

  Faculty Of Pharmaceutical Sciences Kyushu University

• 三橋 国英

  Faculty Of Pharmaceutical Sciences Fukuoka University

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