防巳科植物アルカロイド研究(第218報) : ハスノハカズラStephania japonica MIERSのアルカロイド(補遺15) : Dehydroepistephanineとその水素化について

概要

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Dehydrogenation of epistephanine (I), isolated from Stephania japonica MIERS (Japanese name "Hasunoha-kazura"), with mercury acetate and ethylenediaminetetraacetic acid (EDTA) was examined. Epistephanine is converted by this reagent into dehydroepiste-phanine (X)(Table I). Catalytic reduction of X over palladium-carbon in sodium hydroxide alkalinity converts it to dl-epistephanine (XI) whose reduction with sodium borohydride in methanol results in stereospecific hydrogenation, giving optically inactive dl-dihydroepistephanine-B (XII-B). Reduction of XI with zinc dust in dil. sulfuric acid results in progress of the reaction in two directions, yielding dl-dihydroepistephanine-A (XII-A) and XII-B. These facts agree well with reduction of optically active epistephanine (I) by sodium borohydride in methanol and by zinc dust in dil. sulfuric acid. Treatment of X with sodium borohydride in methanol directly produces optically inactive dl-dihydroepistephanine-B (XII-B).
公益社団法人日本薬学会の論文
1966-04-25