防已科植物アルカロイド研究 (第196報)
ホウザンツヅラフジ (鉄牛入石) Cocculus sarmentosus DIELSのアルカロイド その4 水溶性第4級Aporphine型塩基Cocsarrnineの構造
1963 年 83 巻 2 号 p. 190-194
詳細
1963 年 83 巻 2 号 p. 190-194
Tomita has previously isolated such a tertiary biscoclaurine-type base as trilobine, isotrilobine and menisarine from the root-stock of Cocculus sarmentosus DIELS (Japanese name “Hozan-tsuzurafuji”) produced in Formosa.
From the residual mother liquior, from which the crystals mentioned above had already separated, a little amount of crystal, m. p. 155-157° was obtained and it was certified to be a bimorphism of tetrandrine (I). On the other hand, an investigation of new water-soluble quaternary base was made on this plant and a new aporphine-type base, which was named cocsarmine, was obtained. The picrate, C21H26O4N⋅C6H2-O7N3, m. p. 226-227° (decomp.), iodide, C21H26O4NI⋅3H2O-C16H10(OCH3)3(OH)NCH3CH3I⋅3H2O, m. p. 205-207° (decomp.) (185° sint.), [α]D+27.9°(EtOH). Its O-methyl derivative, C22H28O4NI, m. p. 219-221° was identical with O, O-dimethyllaurifoline (II) iodide by the mixed m. p. determination and IR analysis (CHCl3, Nujol). The O-ethyl derivative was also identical with the authentic sample of 1, 2, 9-trimethoxy-10-ethoxyapor-phine methiodide (VIII) by IR analysis (CHCl3). Thus cocsarmine has been certified to be d-N-methyl-10-hydroxy-1, 2, 9-trimethoxyaporphine (IV).
