著者

金井 貞 小嶋 孝志 丸山 修 市野 元信

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.18, no.12, pp.2569-2571, 1970-12-25 (Released:2008-03-31)

被引用文献数

10 17

著者

小菅 卓夫 辻 邦郎 平井 孝一 福山 俊典

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.7, pp.3059-3061, 1985-07-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

20 35

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A Coryneform bacterium, isolated from the digestive gland of the Japanese ivory shell, Babylonia japonica, was shown to produce neosurugatoxin and prosurugatoxin, the causative toxins of a food poisoning outbreak in 1965 following ingestion of the shellfish. This is the first evidence that marine toxins may be produced by bacteria.

著者

山口 秀夫 有本 正生 中島 淳二 田之口 眞理子 深田 能成

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.34, no.5, pp.2056-2060, 1986-05-25

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Epipodophyllotoxin (EPT) and podophyllotoxin (PT) were prepared from desoxypodophyllotoxin (DPT), obtained from the seeds of Hernandia ovigera L. (Hernandiaceae) EPT was obtaind together with dehydrodesoxypodophyllotoxin (I) by a radical bromination of DPT with N-bromosuccinimide (NBS) followed by hydrolysis of the resultant 1-bromo-DPT, which was confirmed to be a mixture of 1α- and 1β-bromo compounds (7 : 3). EPT was oxidized with pyridinium chlorochromate to give podophyllotoxone (IV). The stereoselective reduction of IV to afford PT was examined with a variety of reagents, and borane-tert-butylamine complex was found to be effective.

著者

落合 正仁 藤田 榮一 有本 正生 山口 秀夫

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.33, no.3, pp.989-997, 1985-03-25

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Oxidative cyclization of hydroxy allylsilanes utilizing the combination of a hypervalent organoiodine compound and a Lewis acid was studied. The allylsilanes 4,prepared from the γ-lactones 1 via conversion to the bis (trimethylsilylmethyl) carbinols 3,on treatment with iodosyl-benzene in the presence of boron trifluoride-etherate in an ethereal solution, afforded the 6-membered β-methylene cyclic ethers 13a and 13b in good yields. Similar treatment of the allylsilanes 8a and 8b gave the 5-membered cyclic ethers 13a and 13b. On the other hand, oxidative cyclization of the carboxylic acid 12 gave a poor yield of the lactone 21 and the major product was found to be the rearranged γ-keto acid 22. Regioselectivity in the iodine (III)-mediated cyclization of 8a is discussed.

著者

加島 竜彦 田ノ口 真理子 有本 正生 山口 秀夫

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.39, no.1, pp.192-194, 1991-01-25

---

(±)-Desoxypodophyllotoxin (2), a chief component of the seeds of Hernandia ovigera L., and (±)-β-peltatin-A methyl ether (3), an analogous phenyltetralin lignan, which have 2,3-trans, 3,4-cis configuration were synthesized according to the method developed for the synthesis of hernandin (1). The syntheses were pursued using the corresponding 4-phenyl-1,2-dihydronaphthalene lactones (9 and 10) followed by cleavage of the lactone moiety to give the unsaturated hydroxy acids (11 and 12). Subsequent hydrogenation and ring closure by means of p-toluenesulfonic acid afforded both 2,3-trans, 3,4-cis and 2,3-cis, 3,4-cis ligans (2 and 13 or 3 and 14), which were isolated by preparative thin layer chromatography.

著者

枡井 雅一郎 原 晴次郎 上嶋 孝博 川口 哲央 尾崎 茂子

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.11, pp.4209-4211, 1983-11-25 (Released:2008-03-31)

参考文献数

9

被引用文献数

12 61

---

Benzylic, allylic carbons and the carbon α to hetero atoms are electrochemically oxidized to the corresponding carbonyl group in the presence of N-hydroxyphthalimide under mild conditions.

著者

枡井 雅一郎 細見 克子 土田 圭一 尾崎 茂子

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.11, pp.4798-4802, 1985-11-25 (Released:2008-03-31)

参考文献数

32

被引用文献数

15 46

---

Electrochemical oxidation of olefins using N-hydroxyphthalimide as a mediator was studied. Allylic methylene and allylic methine groups were oxidized to give the corresponding enones, while allylic methyl groups were not readily oxidized except for those of 2, 3-dimethyl-2-butene. The product distribution was similar to that observed in free radical autoxidation of olefins. A possible mechanism of the oxidation is proposed.

著者

Masateru Ono Chikako Masuoka Mihoko Koto Michiko Tateishi Haruki Komatsu Hiromasa Kobayashi Keiji Igoshi Yasuyuki Ito Masafumi Okawa Toshihiro Nohara

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.50, no.10, pp.1416-1417, 2002 (Released:2002-10-01)

参考文献数

6

被引用文献数

5 10

---

A new ortho-benzoyloxyphenyl acetic acid ester, called vaccihein A (1), was isolated from the fruit of rabbiteye blueberry (Vaccinium ashei). The chemical structure was determined on the basis of spectroscopic data. Compound 1 had antioxidative activity using the ferric thiocyanate method. In addition, 1 showed a scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl.

著者

SHOHGO ATARASHI SHUICHI YOKOHAMA KEN-ICHI YAMAZAKI KATSU-ICHI SAKANO MASAZUMI IMAMURA ISAO HAYAKAWA

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.5, pp.1896-1902, 1987-05-25 (Released:2009-10-19)

参考文献数

14

被引用文献数

46 99

---

Two optically active (100% enantiomeric excess) isomers (13a and 13b) of ofloxacin (1) [(±) -ofloxacin; DL-8280; (±) -9-fluoro-2, 3-dihydro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-7H-pyrido [1, 2, 3-de] [1, 4] benzoxazine-6-carboxylic acid] and their fluoromethyl derivatives (14a and 14b) were prepared via their optically active intermediates resolved by use of high-performance liquid chromatography (HPLC). The isomers (13a and 13b) were also obtained efficiently by an alternative route via separation of the diastereoisomers (18, 19) prepared in the reaction of benzoxazine (17) with L-prolinyl chloride.The (-) -isomers of 1 and its fluoromethyl derivative (2) were approximately twice as active as the corresponding racemates, while the (+) -isomers were considerably less active than the racemates.The absolute configuration at the C3 position in the oxazine ring in a series of (-) -compounds (b) was confirmed by X-ray analysis of the hydrochloride of the (-) -benzoxazine derivative (15b) to be S.

著者

平島 昭司 堀越 正美 中西 義信 平井 洋 関水 和久 水野 伝一 名取 俊二

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.35, no.2, pp.877-881, 1987-02-25

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We previously reported the purification of eukaryotic transcription factor S-II and its phosphorylated form S-H' from Ehrlich ascites tumor cells. In this work, we modified the previous purification procedure to make it quicker and simpler. By this improved procedure, involving a different solubilization method, and improved buffer solutions and centrifugation processes, S-II could be purified to homogeneity from 1 kg of frozen cells in about 10 d instead of 1 month. The purity, specific activity and total yield of S-II purified by the new method were comparable to those obtained by using the previous method.

著者

Thi Hong Van Le Gwang Jin Lee Huynh Kim Long Vu Sung Won Kwon Ngoc Khoi Nguyen Jeong Hill Park Minh Duc Nguyen

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.63, no.11, pp.950-954, 2015-11-01 (Released:2015-11-01)

参考文献数

20

被引用文献数

22

---

Chemical and pharmacological studies of Panax vietnamensis (Vietnamese ginseng; VG) have been reported since its discovery in 1973. However, the content of each saponin in different parts of VG has not been reported. In this study, 17 ginsenosides in the different underground parts of P. vietnamensis were analyzed by HPLC/evaporative light scattering detector (ELSD). Their contents in the dried rhizome, radix, and fine roots were 195, 156, and 139 mg/g, respectively, which were extremely high compared to other Panax species. The content of protopanaxatriol (PPT)-type saponins were not much different among underground parts; however, the content of protopanaxadiol (PPD)- and ocotillol (OCT)-type saponins were greatly different. It is noteworthy that the ginsenoside pattern in the fine roots is different from other underground parts. In particular, despite the content of PPD-type saponins being the highest in the fine roots, which is similar to other Panax species, the total content of saponins was the lowest in the fine roots, which is different from other Panax species. The ratios of PPT : PPD : OCT-type saponins were 1 : 1.7 : 7.8, 1 : 1.6 : 5.5, and 1 : 4.8 : 3.3 for the rhizome, radix, and fine roots, respectively. OCT-type saponins accounted for 36–75% of total saponins and contributed mostly to the difference in the total saponin content of each part.

著者

Toshimasa Toyo’oka Ruri Kikura-Hanajiri

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.63, no.10, pp.762-769, 2015-10-01 (Released:2015-10-01)

参考文献数

27

被引用文献数

2 22

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A reliable method using supercritical fluid chromatography with mass spectrometry (SFC-MS) was developed for cannabinoids using compressed carbon dioxide (CO2) and methanol as the mobile-phase. The cannabinoids, i.e., cannabicyclohexanol (CCH: cis-isomer), trans-CCH, 5-(1,1-dimethylheptyl)-2-[(1R,3S)-3-hydroxycyclohexyl]-phenol (CP-47497), 5-(1,1-dimethylheptyl)-2-[(1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]-phenol (CP-55940), 3-(1,1′-dimethylheptyl)-6aR,7,10,10aR-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol (HU-210), 2-[1R-3-methyl-6R-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol (CBD), (1-pentyl-1H-indol-3-yl)-1-naphthalenyl-methanone (JWH-018), (1-butyl-1H-indol-3-yl)-1-naphthalenyl-methanone (JWH-073) and 1-(1-pentyl-1H-indol-3-yl)-2-(2-methoxyphenyl)-ethanone (JWH-250), were determined within 12 min using a conventional column (2-EP) for SFC. Furthermore, two optical isomers of CCH and trans-CCH were completely and rapidly separated by a chiral stationary phase column (AMY1). A highly sensitive detection (0.002–3.75 ppb) was also obtained by these methods using 2-EP and AMY1 columns. These methods were applied to the qualitative and quantitative determination of cannabinoids in dried plant products. Although the concentration and species were different in the products, JWH-018, JWH-073 and CCH, including the cis-isomer, trans-isomer and the optical isomers, were detected in the products. Therefore, the proposed SFC-MS method seems to be useful as an alternative method to GC-MS and LC-MS for illegal drugs, such as cannabinoids.

著者

松山 賢治 山下 親正 野田 敦子 後藤 茂 野田 浩司 市丸 保幸 五味田 裕

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.10, pp.4089-4095, 1984-10-25 (Released:2008-03-31)

参考文献数

29

被引用文献数

16 26 23

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Isonicotinoyl-γ-aminobutyric acid (GABA) (IG) and nicotinoyl-GABA (NG), candidate prodrugs of GABA, were assessed by measuring various pharmacological responses such as anticonvulsant effect, prolongation of pentobarbital sleeping time and depressive effect on rearing or ambulation in general behavior, in relation to the GABA level in the mouse brain. The GABA level after the intraperitoneal administration of IG at a dose of 1000 mg/kg increased significantly from 2.30±0.02μmol/g wet wt. in the control to 2.93±0.05μmol/g wet wt., while NG caused only a slight increase in GABA level. IG showed a stronger anticonvulsant effect, greater prolongation of pentobarbital sleeping time and greater depressive effect on rearing in general behavior than NG did. The pharmacological effect of IG or NG corresponded well to the GABA level in the brain.

著者

三橋 博 佐々木 希吉 清水 譲

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.11, no.11, pp.1452-1455, 1963-11-25

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The whole plant of Perugularia extensa N. E. Br. was proved to contain a glycoside mixture which showed strong Keller-Kiliani reaction, suggesting the presence of a 2-deoxy-sugars in the sugar part. The sugar fraction obtained by acid hydrolysis was found to contain D-cymarose, D-sarmentose, L-oleandrose, and D-glucose by a paper chromatographic comparison with authentic specimens. Uzarigenin and a new glycoside (m.p. 244〜248°) were found.

著者

ATTA-UR-RAHMAN Muhammad Iqbal CHOUDHARY Safdar HAYAT Abdul Majeed KHAN Aftab AHMED

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.49, no.1, pp.105-107, 2001 (Released:2002-03-29)

参考文献数

9

被引用文献数

41 55

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Two new aurones, 4'-chloro-2-hydroxyaurone (1) and 4'-chloroaurone (2) were isolated from Spatoglossum variabile. The structures of these compounds were elucidated by modern spectroscopic techniques.

著者

Genki Terashi Yuuki Nakamura Hiromitsu Shimoyama Mayuko Takeda-Shitaka

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.62, no.8, pp.744-753, 2014-08-01 (Released:2014-08-01)

参考文献数

23

被引用文献数

6

---

In the absence of experimentally determined three dimensional (3D) structures of proteins, the prediction of protein structures using computational methods is a standard alternative approach in bioinformatics. When using the predicted protein models to compute the native structure of an unknown target protein, estimating the actual quality of the protein models is important for selecting the best or near-best model. Moreover, estimates of the differences between the protein models and the native protein structure are obviously useful to end users who can then decide on the utility of the models for their specific problems. This article describes two new single-model quality assessment (QA) programs, pure single-model QA method (psQA) and a template based QA method (tbQA), that we developed. psQA is a pure single-model QA program that uses a neural network method to predict residue–residue distance matrices of the native protein structures. tbQA is a quasi-single-model QA program that mainly uses target-template sequence alignments and template structures. The performance of these two model QA programs was analyzed in a data set of 24022 models for 94 targets from the 10th critical assessment of protein structure prediction (CASP10) experiment.

著者

渡辺 正純 豊田 満里子 今田 伊助 森本 浩

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.22, no.1, pp.176-182, 1974-01-25

被引用文献数

1

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Urinary metabolites from rabbits dosed with phylloquinone and dl-α-tocopheryl acetate were examined. We found that phylloquinone was excreted as conjugate forms of 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-naphthoquinone and 2-methyl-3-(3'-carboxybutyl)-1,4-naphthoquinone, and dl-α-tocopheryl acetate was excreted mainly as the conjugate form of 2,3,5-trimethyl-6-(5'-carboxy-3'-hydroxy-3'-methylpentyl)-1,4-benzoquinone lactone and in small amounts, as the conjugate form of 2,3,5-trimethyl-6-(3'-carboxybutyl)-1,4-benzoquinone.

著者

三浦 俊明 村岡 早苗 小木曾 健人

出版者

公益社団法人日本薬学会

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.3, pp.709-712, 1992-03-25

被引用文献数

6

---

Semiquinone radicals of menadione were generated during the reaction of menadione with reduced glutathione (GSH), dependent upon the pH. Under aerobic conditions, cytochrome c was reduced during the reaction, and superoxide dismutase (SOD) inhibited the cytochrome c reduction. The inhibitory effect of SOD was greater at a high pH than at a low pH. In the presence of Fe^<3+> or ethylenediaminetetraacetic acid (EDTA)-Fe^<3+>, deoxyribose was degraded during the reaction of menadione with GSH, dependent upon the pH. Greater amounts of deoxyribose were degraded at a low pH than at a high pH. The reduction of Fe^<3+> of EDTA-Fe^<3+> also depended on the pH, and SOD strongly inhibited the Fe^<3+> reduction, indicating that Fe^<3+> or Fe^<3+>-EDTA was reduced by superoxide. SOD, catalase, mennitol and benzoate inhibited the deoxyribose degradation at various pH values. These results indicate that the menadione semiquinone radical is readily formed at an alkali pH but a hydroxyl radical is predominantly produced near a neutral pH. A hydroxyl radical may be generated via an iron-catalyzed Haber-Weiss reaction.

著者

関屋 実 鈴木 次郎 柿谷 芳宏

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.18, no.6, pp.1233-1238, 1970-06-25

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Reaction for preparation of a new series of 5-acylaminooxazole-4-carboxamides has been found. 5-Acetamidooxazole-4-carboxamides were obtained by heating 2-acylamino-2-cyanoacetamides with acetic anhydride in the presence of perchloric acid. Analogous 5-form-amido derivatives were also obtained by heating the same substrates with a mixture of formic acid and acetic anhydride in the presence of hydrochloric acid. Trials for synthesis of oxazolo [5,4-d] pyrimidine-7-ol from the 5-acylaminooxazole-4-carboxamide obtained were also successful in some cases by means of heating with potassium bicarbonate solution.

著者

中島 恵美 横川 弘一 市村 藤雄 倉田 孝一 木戸 日出喜 山口 成良 山名 月中

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.35, no.2, pp.718-725, 1987-02-25

被引用文献数

4

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The disposition characteristics of biperiden were investigated in rats, rabbits, beagles, and humans, and a physiologically based pharmacokinetic model was established by using the hepatic intrinsic clearance of unbound drug concentration and the tissue-to-plasma unbound concentration ratios. Protein-binding parameters and blood-to-plasma concentration ratios were determined, and linear parameters were obtained in beagles and humans over a wide concentration range. The hepatic intrinsic clearance of humans was predicted from the animal data. The coincidence of each tissue-to-plasma Unbound concentration ratio between rats and rabbits was confirmed in the steady state, and the mean tissue-to-plasma unbound concentration ratios were used for the prediction of the plasma concentration-time courses of beagles and humans. The predicted lines fitted the observed plasma concentrations of beagles and a patient well after a single intravenous injection and repeated intramuscular administrations, respectively.