著者

北川 勲 石津 隆 大橋 一慶 澁谷 博孝

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.120, no.10, pp.1017-1023, 2000-10-01 (Released:2008-05-30)

参考文献数

20

被引用文献数

6 9

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Monthly changes of the content-ratio between S-(-)-and R-(+)-hyoscyamine as well as those between S-(-)-and R-(+)-scopolamine in the leaves of Datura metel L. cultivated in the field, were quantitatively analyzed by the use of HPLC with a chiral adsorbent. It was found that S-(-)-isomer was predominant for hyoscyamine and the ratio of R-(+)-isomer gradually increased during the growth, whereas in the case of scopolamine, S-(-)-isomer was the sole one found throughout the cultivation period. The 1H-NMR study in the CD3OD solution has suggested that S-(-)-hyoscyamine (1) and S-(-)-scopolamine (2) take a "face-to-face"conformation between their tropane skeletons and the benzene rings of the tropic acid moieties. In the presence of an equimolar NaOD in the CD3OD solution, the racemization at C-2' of 1 and 2 proceeded more rapidly than the hydrolysis at the tropic acid ester bond, presumably due to the steric hindrance caused by their"face-to-face"conformations. In the D2O and H2O solutions, on the other hand, the racemization and the hydrolysis of 1 proceeded smoothly, while those of 2 did not occur. It has been supposed that these individual reaction manners are ascribable in considerable extent to the different basicity of N atom in each tropane skeleton of 1 and 2 and to stronger intramolecular hydrogen bond occurring between the carbonyl oxygen at C-1' and the hydroxyl group at C-3' in the tropic acid moiety of 1.

著者

北川 勲 陳 兆隆 吉原 実 小林 勝也 吉川 雅之 小野 尚彦 吉村 祐次

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.104, no.8, pp.858-866, 1984-08-25 (Released:2008-05-30)

参考文献数

17

被引用文献数

10 16

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The alkaloidal constituents of two types of "pao-fuzi ( ?? ?? ?? )", the processed tuber of Aconitum carmichaeli DEBX., were investigated. Aconitine (1), hypaconitine (2), mesaconitine (3), talatizamine (5), 14-acetyltalatizamine (6), isotalatizidine (7), karakoline (8), neoline (9), lipoaconitine (10), lipohypaconitine (11), lipomesaconitine (12), and lipodeoxyaconitine (13) were identified from"banshu-fuzi ( ?? ?? ?? ?? )", while benzoylaconine (1a), benzoylhypaconine (2a), and benzoylmesaconine (3a) together with 1-3, 5-9 were identified from"fupian ( ?? ?? )". By use of a dual-wavelength thin layer chromatography scanner, lipo-alkaloids (10-13) were shown to be distributed as major alkaloids in thirteen out of fifteen kinds of "fuzi"and wutou". It was also found that these lipo-alkaloids were less toxic as compared with the corresponding fatally toxic alkaloids such as 1 and 3. However, lipomesaconitine (12) was found to exhibit antiinflammatory and analgesic activities. It was suggested that the substitutions of the acetyl residues attached to the C-8 hydroxyls of 1-4 for the fatty acid residues were the other possible chemical modifications in the decrease of toxicities of Aconiti Tuber.

著者

小林 資正 田中 淳一 香取 岳人 北川 勲

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.11, pp.2960-2966, 1990-11-25

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Following the characterization of swinholide A (1), the major cytotoxic dimeric macrolide, three new congeneric dimeric macrolides, named swinholide B (2), swinholide C (3), and isoswinholide A (10), have been isolated from the Okinawa marine sponge Theonella swinhoei. The structures of these dimeric macrolides have been elucidated on the basis of chemical and physiocochemical evidence. These dimeric macrolides were shown to exhiit potent cytotoxicities toward KB cell lines.

著者

北川 勲

出版者

公益社団法人日本薬学会

雑誌

ファルマシア (ISSN:00148601)

巻号頁・発行日

vol.37, no.7, 2001-07-01