- 著者
- 田之口 真理子 加島 竜彦 雑賀 英之 井上 大志 有本 正生 山口 秀夫
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.37, no.1, pp.68-72, 1989-01-25 (Released:2008-03-31)
- 参考文献数
- 31
- 被引用文献数
- 11 16
Two new lignans, hernolactone (1) and fernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in recemic forms. Firstly, (±)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups. Synthesis of 2 was pursued using the corresponding 4-phenyl-1, 2-dihydronaphthalene lactone(18). The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22). Subsequent hydrogenation of 22 followed by acidification with concetrated hydrochloric acid gave isopicrobernanadin (21), leaving the 2, 3-trans, 3, 4-cis hydroxy acid (23), which was lactonized by means of N, N-dicyclohexylcarbodiimide to afford (±)-2.
- 著者
- 田之口 真理子 細野 江津子 北岡 真由子 有本 正生 山口 秀夫
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.39, no.7, pp.1873-1876, 1991-07-25 (Released:2008-03-31)
- 参考文献数
- 10
- 被引用文献数
- 8 11
Two kinds of lignans were isolated from the seeds of Hernandia ovigera L. in addition to the nine lignans previously reported. One was confirmed as (-)-dimethylmatairesinol (11) and the other was identified as 5'-methoxypodorhizol (14) by comparison with the anthentic sample. An attempt at the cyclization of 14 afforded two compounds which were determined to be isohernandin (15) and an isomer of 15, 2-hydroxymethy 1-5, 6-methylenedioxy-7-methoxy-4-(3', 4', 5'-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthoic acid lactone (16).
- 著者
- 山口 秀夫 中島 淳二 有本 正生 田之口 真理子 石田 寿昌 井上 正敏
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.32, no.5, pp.1754-1760, 1984-05-25 (Released:2008-03-31)
- 参考文献数
- 18
- 被引用文献数
- 2 5
Two kinds of 4-aryltetralin type lignans, β-peltatin-A methyl ether (I-A) and β-peltatin-B methyl ether (I-B), were synthesized from desoxypodophyllotoxin (DPT), which is available in large quantities from the seeds of Hernandia ovigera L. (Hernandiaceae). The syntheses were achieved via demethylene-DPT (IV), 8-bromo-demethylene-DPT (V) and 8-bromo-DPT (VI). Methylenation of V was carried out successfully by using cesium fluoride and methylene iodide in DMF. Compound I-B was readily obtained by the reaction of VI with cuprous iodide and sodium methoxide in the presence of pyridine. Synthesis of I-A was only achieved by the reaction of lithiated VI with nitrobenzene at-100°C in the presence of tetramethylethylene diamine, and I-A was obtained in low yield, together with I-B.
- 著者
- 山口 秀夫 有本 正生 田之口 真理子 沼田 敦
- 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.101, no.5, pp.485-488, 1981-05-25 (Released:2008-05-30)
- 参考文献数
- 12
- 被引用文献数
- 5 7
Two kinds of reactions were carried out on the components of the seeds of Hernandia ovigera L. The reaction of lead tetraacetate on desoxypodophyllotoxin (I) and its analogous compounds caused the cleavage of methylenedioxyl group, affording the corresponding diphenols. In the case of 3, 4-methylenedioxypropylbenzene (XII), an intermediate acetoxyl compound (XIII) was isolated. The reactions of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) on I and its analogous compounds afforded smoothly aromatized compounds. By the same reaction on bursehernin (III), cyclization and aromatization occurred simultaneously affording chinensin (XVIII) which was confirmed by direct comparison with authentic speciemen. The results of the cleavage reaction on I and XII by use of borontrichloride were also described.
- 著者
- 山口 秀夫 有本 正生 田之口 真理子 沼田 敦
- 出版者
- 公益社団法人日本薬学会
- 雑誌
- 藥學雜誌 (ISSN:00316903)
- 巻号頁・発行日
- vol.101, no.5, pp.485-488, 1981
- 被引用文献数
- 7
Two kinds of reactions were carried out on the components of the seeds of Hernandia ovigera L. The reaction of lead tetraacetate on desoxypodophyllotoxin (I) and its analogous compounds caused the cleavage of methylenedioxyl group, affording the corresponding diphenols. In the case of 3, 4-methylenedioxypropylbenzene (XII), an intermediate acetoxyl compound (XIII) was isolated. The reactions of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) on I and its analogous compounds afforded smoothly aromatized compounds. By the same reaction on bursehernin (III), cyclization and aromatization occurred simultaneously affording chinensin (XVIII) which was confirmed by direct comparison with authentic speciemen. The results of the cleavage reaction on I and XII by use of borontrichloride were also described.