Abstract
Alkaloids contained in Michelia compressa MAXIM. var. formosana KANEHIRA (Japanes name “Taiwan-Ogatamanoki”), a plant of the Magnoliaceae family indigenous to Formosa, were examined. From the heartwood of this tree, tertiary non-phenolic beses were isolated as colorless prisms, m.p. 180-181°, and pale yellow needles, m.p. 279-281°(decomp.). The main alkaloid of m.p. 180-181° was named “ushinsunine.” This base corresponds to the molcular formula of C18H17O3N, [α]D -113.6° (EtOH), it is positive to the Gaebel and Labat's color reaction for methylenedioxy group, and does not contain methoxyl group. It easily forms a basic monoacetate of colorless prisms, m.p. 202-203°, C18H16O2N(OCOCH3). Infrared spectrum of ushinsunine revealed the presence of alcoholic hydroxyl and methylenedioxy groups (Chart 1) and its ultraviolet spectrum suggested the structure of an aporphine-type base (Fig. 1). It was thereby assumed that ushinsunine is an aporphine-type base represented by the experimental formula of C18H17O3N=C16H11(OH)(O2CH2)(NCH3).The other base of m.p. 279-281° (decomp.) was proved to be the identical with oxoushinsunine, m.p. 280-281°(decomp.), obtained by oxidation of ushinsunine with pyridine and chromium trioxide, as will be described in a later report.Water-soluble quaternary bases were obtained in the form of magnoflorine (I) and a minute amount of a new base as a picrate.
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