- 著者
- 古森 徹哉 瀬戸口 信郎 川崎 敏男
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集 10 (ISSN:24331856)
- 巻号頁・発行日
- pp.216-223, 1966-09-15 (Released:2017-08-18)
The unknown, nonsteroidal, nonglycosidal and N-free substance, which had been obtained as crystals from the root tubers of Dioscorea bulbifera L. forma spontanea Makino et Nemoto, was found to be a mixture of at least three compounds. One of them, named bulbiferin C, m.p.255°, (α)_D +17.3°, was isolated only in trace and the structures of major component, bulbiferin B, m.p. 285°, (α)_D+103.0° and minor, bulbiferin A, m.p. 283°, (α)_D +16.2°, were investigated. Bulbiferin B, C_<19>H_<20>O_6, m.w. 344 (mass) has γ-lactone, β-substituted furane and no hydroxyl groups (positive Ehrlich reaction, I.R., U.V. and mass spectra). B is converted to A by hydrolysis with NaOH in pyridine followed by neutralisation and methylation with diazometane. Bulbiferin A,C_<20>H_<24>O_7, m.w. 376 (mass), has hydroxyl, ester, γ-lactone and β-substituted furane functions (Ehrlich reaction, I.R., U.V. and mass spectra). On treatment with NaBH_4 B is unchanged but by catalytic hydrogenation over PtO_2 it gives a hexahydro-compound having tertiary hydroxyl group indicating B (and also A) has an ether oxygen. The hydrogenated B is reduced with LiAlH_4 and the product is subjected to the Se-dehydrogenation to give 1,2,5-trimethyl naphthalene. The N.M.R. spectra of tetrahydro-B and -A indicate the presence of one tertiary methyl group. From these and other experimental data B and A are respectively assigned the partial formulae (a) and (b) of furano-norditerpene type. The results of a further investigation on the location of the functional groups which lead to the tentative structures of B and A are presented.
- 著者
- 古森 徹哉 瀬戸口 信郎 川崎 敏男
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.10, pp.216-223, 1966
The unknown, nonsteroidal, nonglycosidal and N-free substance, which had been obtained as crystals from the root tubers of Dioscorea bulbifera L. forma spontanea Makino et Nemoto, was found to be a mixture of at least three compounds. One of them, named bulbiferin C, m.p.255°, (α)_D +17.3°, was isolated only in trace and the structures of major component, bulbiferin B, m.p. 285°, (α)_D+103.0° and minor, bulbiferin A, m.p. 283°, (α)_D +16.2°, were investigated. Bulbiferin B, C_<19>H_<20>O_6, m.w. 344 (mass) has γ-lactone, β-substituted furane and no hydroxyl groups (positive Ehrlich reaction, I.R., U.V. and mass spectra). B is converted to A by hydrolysis with NaOH in pyridine followed by neutralisation and methylation with diazometane. Bulbiferin A,C_<20>H_<24>O_7, m.w. 376 (mass), has hydroxyl, ester, γ-lactone and β-substituted furane functions (Ehrlich reaction, I.R., U.V. and mass spectra). On treatment with NaBH_4 B is unchanged but by catalytic hydrogenation over PtO_2 it gives a hexahydro-compound having tertiary hydroxyl group indicating B (and also A) has an ether oxygen. The hydrogenated B is reduced with LiAlH_4 and the product is subjected to the Se-dehydrogenation to give 1,2,5-trimethyl naphthalene. The N.M.R. spectra of tetrahydro-B and -A indicate the presence of one tertiary methyl group. From these and other experimental data B and A are respectively assigned the partial formulae (a) and (b) of furano-norditerpene type. The results of a further investigation on the location of the functional groups which lead to the tentative structures of B and A are presented.
- 著者
- 鶴田 峯生 三ケ島 浩 大江 孝範 川崎 和幸 瀬戸口 信郎 中 洋一 田原 哲治
- 出版者
- 公益社団法人 日本薬学会
- 雑誌
- YAKUGAKU ZASSHI (ISSN:00316903)
- 巻号頁・発行日
- vol.109, no.1, pp.33-45, 1989-01-25 (Released:2008-05-30)
- 参考文献数
- 28
- 被引用文献数
- 7 5
Several imidazolylpyridinemethanols and imidazolylbenzenemethanols were prepared and evaluated for an inhibitory activity against arachidonic acid-induced platelet aggregation. The result shows that the arylmethanol moiety is essential for the activity and may correspond to the 15-OH group of prostagrandin H2 (PGH2). Among the compounds tested, 4-[α-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3, 5-dimethylbenzoic acid (XV) was found to have a potent inhibitory activity and a long duration of action. Structureactivity relationships are also discussed briefly.