Abstract
In an earlier work, examinations were made on the alkaloids contained in Magnolia kachirachirai DANDY (=Michelia kachirachirai DANDY) (Japanese name “Kachirachirainoki”). Glaucine and two kinds of bases showing m. p. 130-131° in minute quantity were isolated as the tertiary non-phenolic bases and magnoflorine as the watersol-uble quaternary base. In the present series of work, the phenolic bases were purified by alumina chromatography and separated into crystalline Base-I, m. p. 157-158°, and Base-II, m. p. 191-192°.
Base-I, formed colorless needles, m. p. 157-158°, [α]D+31.49° (CHCl3), is a new base with the composition of C18H21O3N⋅C16H13(OH)(OCH3) (NH). The N-methylated compounds, N-methyl methiodide, and N, O-dimethyl methiodide of this base were compared with the corresponding derivatives of L-(-)-N-norarmepavine, obtained from Machilus kusanoi HAYATA and, as shown in Table I, all the data were in complete agreement, except for the reversed direction of the optical rotation, suggesting that the two are antipodes. Mixed fusion and comparison of the infrared spectrum (in Nujol) of the N-methylated compound of Base-I with D-(-)-armepavine, whose structure had already been established, showed that the two are identical substances. This has proved that Base-I is D-(+)-N-norarmepavine (I). No detailed examination has yet been made on Base-II due to the minute amount available.
