YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
アキカラマツThalictrum Thunbergii DC.のアルカロイド研究 (第5報)
葉茎部第三級塩基ThalicberineおよびO-Methylthalicberineの構造 その1
藤田 栄一富松 利明
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1959 年 79 巻 10 号 p. 1256-1260

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A new tertiary phenolic base, thalicberine, was isolated from the leaf base of Thalictrum Thunbergii DC. as colorless needles of m.p. 161° (sint. 155°), [α]D+231.2° (CHCl3), and a new tertiary non-phenolic base, O-methylthalicberine, as colorless needles, m.p. 186-187°, [α]D+265.9° (CHCl3). This latter base was also isolated from the leaf base of commercial crude drug, “Takatogusa.” On the other hand, thalicberine was O-methylated to form O-methylthalicberine and this was proved to be identical with natural O-methylthalicberine from elementary analytical values, optical rotation, mixed fusion, and by comparison of infrared spectra in Nujol. The composition and empirical formula of thalicberine are represented as C37H40O6N2⋅H2O=C32H24O2(OCH3)3(OH)(N-CH3)2⋅H2O, and those of O-methylthalicberine as C38H42O6N2=C32O24O2(OCH3)4(N-CH3)2. O-Methylthalicberine dimethochloride was submitted to the Hofmann degradation to be derived to the methylmethine which was oxidized with potassium permanganate to form 2-methoxydiphenyl ether-5, 4′-dicarboxylic acid (I). The experimental evidences, ultraviolet spectra (Fig. 1, A and B), and optical rotation suggest that both these are new bases closely related to the oxyacanthineberbamine series of the biscoclaurine-type bases.

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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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