2 いわなんてん(Leucothoe Keiskei Mig.)の成分研究

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概要

• 論文の詳細を見る

• Finding toxicity in a methanolic extract of Leucothoe Keiskei Miq. (Ericaceae) led to the isolation of the principles, designated as poriolide (1) and isoporiolide (2). The structural elucidation and the synthesis of the aglycone of the two toxic substances, having a novel structure of the macrocyclic biphenyl-type flavanoid glycoside, will be discussed. The structure of poriolide (1) was determined by the spectral data, degradation works, and finally the X-ray crystallographic analysis of a bromide (25). The structure of isoporiolide (2), an isomer of poriolide, was derived from a comparison of the degradation products of poriolide, isoporiolide and their derivatives. On hydrolysis with barium hydroxide, both poriolide and isoporiolide gave the identical propiophenone glycoside (11a), but isoporiolide yielded an isomer (27a) of the carboxylic acid (12a) obtained from poriolide. The structure of the carboxylic acids (12a and 27a) was confirmed by an unambiguous synthesis. A key point of the synthesis of the aglyconeis the construction of the unsymmetric biphenyl compounds, this point was effected by application of the rearrangement reaction of suitable phenyltropone derivatives to biphenyl compounds.

• 天然有機化合物討論会の論文
• 1972-10-01

著者

• 佐藤 定男

  Analytical And Metabolic Research Laboratories Sankyo Co. Ltd.

• 田村 千尋

  三共中研

• 小木曽 彰

  Central Research Laboratories Sankyo Co. Ltd.

• 佐藤 定男

  三共中研

• 小木曽 彰

  三共中研

• 佐藤 藹也

  三共中研

• 樫田 育子

  三共中研

• 佐藤 藹也

  Central Research Laboratories Sankyo Co. Ltd.

• 田村 千尋

  Analytical And Metabolic Research Laboratories : Sankyo Company Ltd.

• 樫田 育子

  Central Research Laboratories Sankyo Co. Ltd.

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