ON THE TOXIN OF ILLICIUM ANISATUM .1. THE ISOLATION AND CHARACTERIZATION OF A CONVULSANT PRINCIPLE - ANISATIN
ON THE TOXIN OF ILLICIUM ANISATUM .1. THE ISOLATION AND CHARACTERIZATION OF A CONVULSANT PRINCIPLE - ANISATIN
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DOI：
10.1021/ja01133a002
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发表时间：
1952-01-01
影响因子：
15
通讯作者：
GORIN, G
中科院分区：
文献类型：
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作者：
LANE, JF;KOCH, WT;GORIN, G
从日本星星茴香的干燥粉末状种子和心皮中分离出一种纯的、结晶状的激动剂成分，茴香苷，顺式。对该化合物的反应和红外吸收光谱的研究表明，它是一种五羟基二羧酸的酸酐。与茴香红有关的是两种生理学上不活跃的物质：共同茴香红和茴香红，它们的暂定分子式分别为C12 H32 O 8和C21 H32 O 8。几个世纪以来，人们一直知道日本星星茴香的果实具有惊厥活性，但试图分离这种活性成分却收效甚微。1881年，Eykman 4报告说，他分离出了几毫克不纯的、结晶状的有毒物质（“sikimin”或“shikimin”），这些物质在“大约175”时熔化，但他没有进一步描述。最近Siersch 5报道了Eykman的工作的重复，其中给出了微量的“shikimin”，再次没有进一步的特点。其他工人只得到了剧毒的浓缩物。本文介绍了一种纯净的，明确的，晶体物质的高毒性的名称茴香红的建议的分离。通过实验部分中描述的方法，惊厥原理首先被分离为2-
From the dried, powdered seeds and carpels of the Japanese star anise there has been isolated a pure, crystalline con-vulsant principle, anisatin, CisHíoOs. A study of the reactions of this compound and ofits infrared absorption spectrum indicates that it is the anhydride of a pentahydroxydicarboxylic acid. Associated with anisatin are two physiologically inactive substances: co-anisatin and-anisatin to which the tentative formulas CiaH^ Os and C21H32O8, respectively, have been assigned.The convulsant activity of the fruit of the Japa-nese star anise2 has beenknown3 for several centuries, but attempts to isolate the active principle have met with little success. In 1881, Eykman4 re-ported isolating a few milligrams of impure, crystal-line, toxic material (“sikimin” or“shikimin”) which melted “at about 175” but which he did not further characterize. More recently Siersch5 re-ported a repetition of Eykman’s work, which gave minute quantities of “shikimin,” again not further characterized. Other workers6· 7 obtained only highly toxic concentrates. The present paper describes the isolation of a pure, well-defined, crystalline substance of high toxicity for which the name anisatin is proposed. By methods described in the Experimental part the convulsant principle was first isolated as the 2-