テイカカズラのリグナン(第7報)Trachelosideの糖結合位置の化学的証明ならびにTrachelogeninの各種誘導体について

概要

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D-Glucose linkage in tracheloside (Ia) was chemically proved to be the 4'-position by converting acetylethyltrachelogenin (II) to ethylarctigenic acid (V) of the established structure. The "methyltrachelogenin" reported by Takano and others was not the titled compound but identical with methylarctigenin (VIII). Therefore, the trachelogenin derivatives reported by Takano and others were re-examined. As a result, the compounds reported by them as "isotrachelogenic acid, " "methyltrachelogenin, " "isomethyltrachelogenic acid, " "methyl methyltrachelogenate diacetate, " and "isomethyltrachelogenin" are assumed to be identical with trachelogenic acid (X), methylarctigenin (IX), methylarctigenic acid (XVI), methyl methyltrachelogenate monoacetate (XIII), and 3-(hydroxymethyl)-6,7-dimethoxy-4-(3', 4'-dimethoxyphenyl)-2-naphthoic acid lactone (XIX), respectively, judging from the properties. Therefore, the "trachelogenin derivatives" should be correctly revised to the compounds as follows ; trachelogenin (VI), methyltrachelogenin (VII), trachelogenic acid (X), methyltrachelogenic Acid (XI), methyl methyltrachelogenate (XII), methyl methyltrachelogenate monoacetate (XIII), and methyl methyltrachelogenate diacetate (XIV), respectively. Also it is concluded that the isotrachelogenin derivatives do not exist.
1973-04-25