38 茶実のサポゲニンTheasapogenol A及びBの構造

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概要

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• The sanogenol mixture obtained by the successive treatment with acid and alkaline of the title saponin has been found consisting mainly of four triterpenic alcohols, designated as theasapogenol A (major)(Ia), C_<30>H_<50>O_6, mp.301-3°;[α]_D+14°(c: 0.5, in pyridine), theasapogenol B (second major)(Ib), C_<30>H_<50>O_5, mp.278-284°;[α]_D+23°(c: 0.5, in pyridine), C, and D, respectively, according to their Rf values from the bottom on TLC. In this report, the chemical studies on theasapogenol A and B leading to the structures: 3β,16α,21β,22α,-23,28-hexahydroxy-olean-12-ene and 3β,16α,21β,22α,28-pentahydroxy-olean-12-ene, are presented. The structure of theasapogenol A was determined by converting it to theasapogenol B through reductive elimination of the 23-hydroxylic function. However, it has been found that anhydro-theasapogenol B (VIb) (3β,22α,28-trihydroxy-16α,21α-epoxy-olean-12-ene) is identical with barringtogenol D, whose structure (XX) has already been proposed as having 22β-OH by Barua et al. The inconsistency of the observation lies on the different configuration of the 22-hydroxyl function. In addition, the identity of theasapogenol B with barringtogenol C (proposed as having 21α,22β-glycol (XXI) by Barua et al.) presents another discrepancy concerning to α-glycolic hydroxyls in ring E. Although the present study favors the 21β,22α-glycol (trans diequatorial) configuration in theasapogenol B and 22α-OH in its anhydro derivative mostly based on the NMR analyses, the further chemical studies on these subjects are important requisite and in progress in this laboratory.

• 天然有機化合物討論会の論文
• 1966-09-15

著者

• 西村 正

  Faculty Of Pharmaceutical Sciences Osaka University

• 松田 明子

  Faculty Of Pharmaceutical Sciences Osaka University

• 吉岡 一郎

  阪大薬学部

• 西村 正

  阪大薬学部

• 松田 明子

  阪大薬学部

• 北川 勲

  阪大薬学部

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