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

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.

著者

山口 秀夫 有本 正生 山本 起巳子 沼田 敦

出版者

公益社団法人日本薬学会

雑誌

薬学雑誌 (ISSN:00316903)

巻号頁・発行日

vol.99, no.6, pp.p674-677, 1979-06

被引用文献数

1

---

Four kinds of lignans were isolated from the seeds of Hernandia ovigera L. collected in Okinawa besides the previously reported desoxypodophyllotoxin (I). Oily substance II, named bursehernin, C_<21>H_<22>O_6,was confirmed to be lignan-2 isolated from Bursera schlechtendalii. III, mp 171-173°, and IV, mp 125-126°, were determined as desoxypicropodophyllin and podorhizol obtained from Podophyllum emodi WALL. respectively. V, mp 270-275°, could not be clarified due to its small amount.

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

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(±)-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

Masashi Kitamura Masako Aragane Kou Nakamura Kazuhito Watanabe Yohei Sasaki

出版者

公益社団法人日本薬学会

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

pp.b16-00090, (Released:2016-04-27)

参考文献数

31

被引用文献数

1 23

---

In many parts of the world, the possession and cultivation of Cannabis sativa L. are restricted by law. As chemical or morphological analyses cannot identify the plant in some cases, a simple yet accurate DNA-based method for identifying C. sativa is desired. We have developed a loop-mediated isothermal amplification (LAMP) assay for the rapid identification of C. sativa. By optimizing the conditions for the LAMP reaction that targets a highly conserved region of tetrahydrocannabinolic acid (THCA) synthase gene, C. sativa was identified within 50 min at 60-66 °C. The detection limit was the same as or higher than that of conventional PCR. The LAMP assay detected all 21 specimens of C. sativa, showing high specificity. Using a simple protocol, the identification of C. sativa could be accomplished within 90 min from sample treatment to detection without use of special equipment. A rapid, sensitive, highly specific, and convenient method for detecting and identifying C. sativa has been developed and is applicable to forensic investigations and industrial quality control.

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

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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

望月 昭典

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.46, no.2, 2010-02-01

著者

東 壮平

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.38, no.4, pp.345-346, 2002-04-01

著者

千葉 剛

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.47, no.7, pp.666-667, 2011-07-01

著者

生塩 孝則 遠藤 寛二 山本 恵司

出版者

公益社団法人日本薬学会

雑誌

藥學雜誌 = Journal of the Pharmaceutical Society of Japan (ISSN:00316903)

巻号頁・発行日

vol.116, no.11, pp.866-875, 1996-11-25

参考文献数

20

被引用文献数

4

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The physicochemical properties of the enantiomer and racemates of suplatast tosilate (ST) were investigated by means of infrared spectroscopy, solid-state <SUP>13</SUP>C CP/MAS NMR spectroscopy, thermal analysis, and X-ray diffraction analysis, and by measuring the solubility and hygroscopy. The infrared and NMR spectra and X-ray diffraction pattern of the enantiomer were distinctly different from those of the racemate. The melting point of the enantiomer was lower than that of the racemate by 5&deg;C, while the solubility of the enantiomer was 1.3 times higher than that of the racemate. The hygroscopic rate of the enantiomer was greater than that of the racemate. These results suggested that ST was classified into a racemic compound crystal. Furthermore, by comparing the relative peak intensity ratios on X-ray diffraction patterns of crystals with various optical purities prepared by recrystallization, it was found that a mixture of racemic compound crystals and either of racemic mixture crystals or racemic solid solutions was obtained by recrystallization of ST in the content of 0 to 64%ee, while the recrystallization of ST in the content of more than 64%ee led to the formation of racemic mixture crystals or racemic solid solutions.

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

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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

Ji Yin Zhou Shi Wen Zhou Ke Bin Zhang Jian Lin Tang Li Xia Guang Yi Ying Ying Xu Le Zhang Dan Dan Li

出版者

公益社団法人日本薬学会

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.31, no.6, pp.1169-1176, 2008-06-01 (Released:2008-06-01)

参考文献数

37

被引用文献数

61 114

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Berberine is one of the main alkaloids of Rhizoma coptidis which has been used as a folk medicine to treat diabetes mellitus for more than 1400 years in China. To investigate the chronic effect of berberine on diabetic hyperlipidemic rats, fasted rats were intraperitoneally injected 35 mg/kg streptozotocin. Diabetic rats were admitted after 2 weeks and given a high-carbohydrate/high-fat diet to induce hyperlipidemia. The rats were divided into 7 groups at the end of week 16: normal and diabetic rats received no drug, 5 treatment groups were administered with either 75, 150, 300 mg/kg berberine, 100 mg/kg fenofibrate or 4 mg/kg rosiglitazone per day for 16 weeks, respectively. The blood glucose, hemoglobin A1c, lipid metabolic parameters and hepatic glycogen and triglyceride were measured, and histopathology and peroxisome proliferator-activated receptors (PPARs) α/δ/γ expression of liver were determined by hematoxylin eosin and immunohistochemical staining. Berberine reduced diabetic rats' body weight, liver weight and liver to body weight ratio. Berberine restored the increased blood glucose, hemoglobin A1c, total cholesterol, triglyceride, low density lipoprotein-cholesterol, apolipoprotein B and the decreased high density lipoprotein-cholesterol, apolipoprotein AI levels in diabetic rats to near the control ones. Berberine alleviated the pathological progression of liver and reverted the increased hepatic glycogen and triglyceride to near the control levels. Berberine increased PPARα/δ expression and reduced PPARγ expression in liver of diabetic rat to near the control ones. Berberine improved glucolipid metabolism both in blood and liver in diabetic rats possibly through modulating the metabolic related PPARα/δ/γ protein expression in liver.

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

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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

Guo-Sheng Li Xu-Han Liu Hua Zhu Lan Huang Ya-Li Liu Chun-Mei Ma Chuan Qin

出版者

公益社団法人日本薬学会

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.34, no.5, pp.644-654, 2011-05-01 (Released:2011-05-01)

参考文献数

41

被引用文献数

10 28

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The diabetic “lipotoxicity” hypothesis presents that fat-induced visceral white adipose tissue insulin resistance plays a central role in the pathogenesis of type 2 diabetes. Berberine, a hypolipidemic agent, has been reported to have antidiabetic activities. The molecular mechanisms for this property are, however, not well clarified. Therefore in this study type 2 diabetic hamsters were induced by high-fat diet with low-dose streptozotocin. Then, we investigated the gene expression alterations and explored the molecular mechanisms underlying the therapeutic effect of berberine on fat-induced visceral white adipose tissue insulin resistance in diabetic hamsters by microarray analysis followed by real-time reverse transcription-polymerase chain reaction (RT-PCR) confirmation. Type 2 diabetic hamsters exhibited hyperglycemia and relative hyperinsulinemia, glucose intolerance, insulin resistance, intra-adipocyte lipid accumulation, significant increase in body weight and visceral white adipose tissue weight, abnormal serum adipokines levels, and deleterious dyslipidemia. Furthermore, they had increased sterol regulatory element-binding proteins (SREBPs) expression and decreased liver X receptors (LXRs) and peroxisome proliferator-activated receptors (PPARs) expression in visceral white adipose tissue. After 9-week berberine treatment, fat-induced insulin resistance and diabetic phenotype in type 2 diabetic hamsters were significantly improved. Compared with diabetic hamsters, expression of LXRs and PPARs significantly increased and SREBPs significantly decreased in visceral white adipose tissue from berberine-treated diabetic hamsters. These results suggest that altered visceral white adipose tissue LXRs, PPARs, and SREBPs transcriptional programs are involved in the therapeutic mechanisms of berberine on fat-induced visceral white adipose tissue insulin resistance in type 2 diabetic hamsters.

著者

Yong-Qiang Shan Yan-Ping Zhu Jing Pang Yan-Xiang Wang Dan-Qing Song Wei-Jia Kong Jian-Dong Jiang

出版者

公益社団法人日本薬学会

雑誌

Biological and Pharmaceutical Bulletin (ISSN:09186158)

巻号頁・発行日

vol.36, no.10, pp.1562-1569, 2013-10-01 (Released:2013-10-01)

参考文献数

41

被引用文献数

11 40

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This study was designed to improve the absorption and hypoglycemic efficacy of berberine (BBR), which is a substrate of P-glycoprotein (P-gp), by combination with a P-gp inhibitor tetrandrine (Tet). Flow cytometry and LC-MS/MS were used to determine the cellular efflux or retention of chemicals. Pharmacokinetic study was performed in ICR mice following oral administration of the study compounds. The hypoglycemic efficacies of the compounds were evaluated in diabetic KK-Ay mice. In the in vitro experiments, Tet significantly inhibited the efflux and increased the uptake of P-gp substrates rhodamine-123 as well as BBR in MCF7/DOX cells and Caco-2 intestinal cells. Meanwhile, Tet greatly reduced the expression of P-gp in Caco-2 cells. The inhibition of BBR efflux by Tet was translated into improved pharmacokinetics in vivo. When co-administered, Tet dose-dependently increased the average maximum concentration (Cmax) and area under concentration–time curve (AUC0–24) of BBR in mice. Tet itself had no impact on glucose metabolism. However, it greatly potentiated the hypoglycemic efficacy of BBR in diabetic KK-Ay mice. In addition, we found that Tet had moderate inhibitory effect on the catalytic activity of CYP3A4, which played a role in the bio-transformation of BBR, and this may also take part in the improvement of the pharmacokinetics of BBR. In summary, combination with P-gp inhibitors such as Tet can improve the pharmacokinetics and hypoglycemic efficacy of BBR greatly; this implicates a feasible strategy for exploring the therapeutic effects of BBR and other pharmaceuticals which are substrates of P-gp.

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

丸山 節子

出版者

公益社団法人日本薬学会

雑誌

衛生化学 (ISSN:0013273X)

巻号頁・発行日

vol.44, no.1, pp.17-24, 1998-02-28

被引用文献数

1

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In Nagano Prefecture, in the period of January to March, 1997,sudden deaths of Bombycilla spp. birds happened in many places, amounting to 13 places with the total death of 187 birds. Of the places, Shimosuwa Town, Komoro City, and Iida City were selected to be inquired into the cause of the sudden deaths. In the case of Shimosuwa Town, the esophagus was choked with nuts of Pyracantha, and cyanide was detected in the content from the esophagus at 10.0 μg/g (average) and in the content from the stomach at 17.0 μg/g (average), suggesting that cyanide or nitrile glycoside would be one of the causes of the deaths. In the case of Komoro City, EPN, an organophosphorus pesticide, was detected from the content in the stomach at 5960 μg/g (average) and from the liver at 11.4 μg/g (average), suggesting that EPN would be a many cause of the death. In the case of Iida City no cause of the death has been known.

著者

窪田 正彦 新井 清 頼光 彰子 島岡 真佐子 星野 響 林 一之 伊田 泰康 南 典昭 山本 博文 田中 恵一 高田 三千人 西原 正勝 藤谷 幸治 神田 博史

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.113, no.11, pp.810-817, 1993-11-25

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The cultivation of Papaver bracteatum, having thebaine as a major alkaloid, needs permission by the law of the narcotic regulation in Japan. Therefore, the flowergrowing of P. bracteatum as garden plants is prohibited by law. Chemical, morphological and cytological analyses of gardening 18 plants of the section Oxytona of the genus Papaver collected in western Hiroshima prefecture were carried out as a preliminary study. On inquiry, thebaine was identified as an only alkaloid from one of the gardening plants. The amounts of thebaine contained in this sample was 0.68%. Petals of this plant are scarlet with black spots at their bases which are surrounded by bracts. These results indicated that one of the investigated plants was identified to be P. bracteatum.