著者

崎谷 陽子 赤田 良信 河野 貞子 宮内 芳子

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.27, no.5, pp.1125-1129, 1979-05-25

被引用文献数

9

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A method was established by which glycyrrhizin and glycyrrhetinic acid present in plasma can be extracted with methanol and then separated and determined quantitatively within 10 min by means of high-speed liquid chromatography. Using this method, glycyrrhizin and glycyrrhetinic acid added to the plasma were recovered to satisfactory extents. An in situ recirculating perfusion technique showed that G is absorbed in rat small intestine in an apparent first-order process. There was no detectable amount of glycyrrhetinic acid in the blood after bolus injection of glycyrrhizin into the portal vein, althouth glycyrrhetinic acid was present in a detectable amount in the blood after oral administration. Since it is water-soluble and has a high molecular weight, glycyrrhizin is probably absorbed in the small intestine in the form of glycyrrhetinic acid. With the decline of glycyrrhetinic acid in the blood, there was a rise in the blood level of a substance which exhibited the same chromatographic behavior as glycyrrhizin. This substance appears to be a glucuronic acid conjugate formed as a metabolite of glycyrrhetinic acid, although it is not clear whether it is a mono-or diglucuronic acid conjugate or a mixture of the two. Glycyrrhizin injected into the portal vein was eliminated from the blood only slowly.

著者

Jiang Liu Seikou Nakamura Yan Zhuang Masayuki Yoshikawa Ghazi Mohamed Eisa Hussein Kyohei Matsuo Hisashi Matsuda

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.61, no.6, pp.655-661, 2013-06-01 (Released:2013-06-01)

参考文献数

50

被引用文献数

7 22

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Six dihydroisocoumarin glycosides, florahydrosides I and II, thunberginol G 8-O-β-d-glucopyranoside, thunberginol C 8-O-β-d-glucopyranoside, 4-hydroxythunberginol G 3′-O-β-d-glucopyranoside, and thunberginol D 3′-O-β-d-glucopyranoside, have been isolated from the flowers of Hydrangea macrophylla Seringe var. thunbergii Makino (Saxifragaceae) together with 20 known compounds. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, acylated quinic acid analog, neochlorogenic acid, was shown to substantially inhibit aldose reductase [IC50=5.6 µm]. In addition, the inhibitory effects on aldose reductase of several caffeoylquinic acid analogs were examined for structure–activity relationship study. As the results, 4,5-O-trans-p-dicaffeoyl-d-quinic acid was found to exhibit a potent inhibitory effect [IC50=0.29 µm].

著者

Rina Miyake Tomohiro Uchimura Xu Li Totaro Imasaka

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.61, no.1, pp.82-84, 2013-01-01 (Released:2013-01-08)

参考文献数

13

被引用文献数

2

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Fluorescence lifetime imaging microscopy (FLIM) was used to monitor the interaction between androgen receptor (AR) tagging of a green fluorescent protein (GFP) and the ligands in living cells. The fluorescence lifetime of the AR-GFP without ligands was ca. 3.1 ns, which was reduced to ca. 2.5 ns after treatment with agonist 5α-dihydrotestosterone. On the other hand, the fluorescence lifetime of AR-GFP was not changed after treatment with antagonist hydroxyflutamide. The reaction kinetics was simulated in the present study, and the obtained results indicated the possibility of the presence of an intermediate complex during the reaction. FLIM can be used to record the ratio of the AR as it reacts with an agonist, and, therefore, it is useful for acquiring information concerning the interaction between AR and ligands in living cells.

著者

森田 岩男 国本 克俊 津田 正己 但田 信一 黄瀬 正博 木村 喜代史

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.10, pp.4144-4154, 1987-10-25

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A series of 1,4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1,4-dihydropyridine-3,5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2,6-dimethyl-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-4(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

著者

森田 岩男 津田 正己 黄瀬 正博 杉山 信

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.36, no.3, pp.1139-1142, 1988-03-25

---

Attempts were made to improve the synthesis of methyl 2,6-dimethyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate (DHP-218), a new calcium antagonist. 2-Acetonyl-2-oxo-1,3,2-dioxaphosphosphorinane (5a), the key intermediate, was prepared from the allenylphosphonate (2) via the enaminophosphonate (4) in a good yield. Subsequently, the Knoevenagel condensation using 5a and the imine (6a) gave the benzylideneacetonylphosphonate (7a) in a good yield without the use of the Horner-Emons reaction. This condensation also gave good results for other acetonylphopshonates. The final step gave DHP-218 in a good yield through a modified Hantzsch synthesis with the use of a dehydrating agent. The overall yield was increased from 1.7% to 22%.

著者

瀬川 純 数野 憲二 松岡 正人 白波瀬 一朗 尾崎 正邦 松田 真人 冨井 由文 北野 正彦 黄瀬 正博

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.43, no.1, pp.63-70, 1995-01-15

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A seried of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives was prepared and evaluated for antibacterial activity. In the 7-piperazinyl series, addition of a fluorine at C-8,which increased the in vitro activity for the 1-hydrogen and 1-methyl analogues and decreased it for the 1-phenyl analogue, improved the in vivo activity of all the analogues. Introduction of a methoxy group at C-8 of the 1-methyl-7-piperazinyl analogue also improved its in vivo antibacterial activity. The effect of 8-substituents on the in vitro and in vivo antibacterial activity of the 1-methyl-7-(4-methyl-1-piperazinyl) series is also discussed.

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

Wei He Li-Fang Fan Qing Du Bai Xiang Chun-Lei Li Min Bai Yong-Zhen Chang De-Ying Cao

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.57, no.2, pp.122-128, 2009-02-01 (Released:2009-02-01)

参考文献数

31

被引用文献数

7 17 9

---

The purpose of the study is to perform the in vitro and in vivo evaluation of multi-layer film coatings for omeprazole. The system consists of drug-layered or drug-containing core pellets coated with salt (sodium chloride and disodium hydrogen phosphate), hydroxypropyl methyl cellulose (HPMC), and enteric film-coating layer, respectively. The drug-layered core pellets were prepared by a coating layer of omeprazole on inert pellet cores in fluidized bed coater. An in vitro/in vivo gastro-resistance study was conducted, and a dissolution study was performed in pH 7.4 phosphate buffer for omeprazole release. The multi-layer coated pellets were stable in gastric pH conditions and upper gastrointestinal (GI) tract in rats. Salt layer improved the drug stability, and its coating levels had little influence on the dissolution profiles of omeprazole. The rate of drug release was significantly delayed by HPMC layer. The salt layer could function as a separated layer, and substitute part of the HPMC layer and decrease the coating levels of HPMC. The bioavailability (AUC) of the multi-layer coated drug-layered and drug-containing pellets was 3.48±0.86 and 2.97±0.57 μg·h/ml, respectively. The drug-layered pellets with multi-layer film coatings not only provided delayed and rapid release of omeprazole, but also could provide a good stable property for omeprazole. It was confirmed that rapid in vitro drug release rate resulted in better absorption.

著者

小湊 潔

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.17, no.11, pp.2198-2200, 1969-11-25

被引用文献数

1

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In the previous paper, scordinin A_1 was isolated from boiled garlic, and it was seemed as the biological active component in garlic. In this paper the constituents of scordinin A_1 were described from the hydrolysis products of scordinin A_1. By acid hydrolysis of scordinin A_1,fructuronic acid was detected, and by garlic enzyme allyl mercaptan was proved. And by hydrolysis with barium hydroxide, one kind of peptide, scormin, was isolated. From the above results, the author presumed that allyl thiofructuronic acid combined with scormin to form scordinin A_1,and on the chemical structure of scormin will be discussed in Part III in this series.

著者

Hiroyuki Tsutsumi Yoshifumi Kinoshita Takashi Sato Takashi Ishizu

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.59, no.8, pp.1008-1015, 2011-08-01 (Released:2011-08-01)

参考文献数

28

被引用文献数

12 13 5

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Crystals of the complexes of (+)-catechin (CA) of non-galloylated catechin and (−)-catechin-3-O-gallate (Cg) of galloylated catechin with caffeine were prepared, and their stereochemical structures and intermolecular interactions were determined by X-ray crystallographic analysis. CA formed a 1 : 1 complex with caffeine by intermolecular hydrogen bonds, whereas Cg formed a 1 : 2 complex with caffeine, which was formed by face-to-face and offset π–π interactions and intermolecular hydrogen bonds. A solution of two kinds of non-galloylated catechin, CA and (−)-epicatechin (EC), and caffeine (molar ratio 1 : 1 : 2) in water afforded a 1 : 1 : 2 complex, the crystal structure of which had two layers, one layer in which CA and caffeine formed alternate lines and an other layer in which EC and caffeine formed alternate lines. The 1 : 1 : 2 complex was formed by offset π–π and CH–π interactions and intermolecular hydrogen bonds.

著者

和田 啓爾 石垣 静香 上田 かおり 阪田 正勝 羽賀 正信

出版者

公益社団法人日本薬学会

雑誌

Chem Pharm Bull. (ISSN:00092363)

巻号頁・発行日

vol.33, pp.3555-3557, 1985

被引用文献数

2

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An antivitamin B_6,4'-methoxypyridoxine (1) was isolated from the seed of Ginkgo biloba L. (Ginkgoaceae). The albumen of the seed of G. biloba L., which is called "Gin-nan or Ginkyo", is used as a crude drug in China and as food in Japan. However, in Japan, there have been about 70 reports of "Gin-nan sitotoxism." In this paper, we report that the substance responsible for this sitotoxism is 4'-methoxypyridoxine (1), which is known to have antivitamin B_6 activities. This compound (1) is reported for the first time from natural products.

著者

西部 三省 木下 英弘 武田 秀勝 岡野 五郎

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.6, pp.1763-1765, 1990-06-25

被引用文献数

16

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Ten phenolic compounds, isofraxidin (1), (+)-syringaresinol-di-O-β-D-glucoside (2), syringin (3), chlorogenic acid (4), isofraxidin-7-O-β-D-glucoside (5), 2,6-dimethoxy-p-benzoquinone (6), (+)-pinoresinol-O-β-D-glucoside (7), (+)-syringaresinol-O-β-D-glucoside (8), (+)-pinoresinol-di-O-β-D-glucoside (9), and (+)-medioresinol-di-O-β-D-glucoside (10), were isolated from the stem bark of Acanthopanax senticosus HARMS and identified, respectively.The aquenous extract of the stem bark exhibited a prolonging effect on the exercise time to exhaustion in chronic swimming stressed rats. The effect on the exercise time in the chronic swimming stressed rats was respectively tested for compounds 2 and 4,which are major constituents of the stem bark. As a result, it was indicated that compound 2 is the compound responsible for part of the pharmacological effect which the aqueous extract of the stem bark showed.

著者

Harinantenaina Liva Tanaka Michi Takaoka Shigeru ODA Munehiro MOGAMI Orie UCHIDA Masayuki ASAKAWA Yoshinori

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.54, no.7, pp.1017-1021, 2006-07-01

被引用文献数

4 150

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Bioguided fractionation of the methanol extract of Momordica charantia dried gourds led to the isolation of three new cucurbitane triterpenoids (1-3), together with eight known compounds (4-11). The aglycone of momordicoside I was isolated from the ether soluble fraction in a high amount. The structures of the metabolites were established on the basis of one and two dimensional NMR spectroscopic evidence, X-ray analysis, and comparison with the reported data in the literature. A number of phytochemicals have been isolated from Momordica charantia but the constituents responsible for the hypoglycaemic/antihyperglycaemic activities have not been determined. Therefore, in order to evaluate the contribution of the cucurbitane triterpenoids of the ether fraction of M. charantia methanol extract to in vivo anti-diabetic effects, the major compounds, 5β,19-epoxy-3β,25-dihydroxycucurbita-6,23(E)-diene (4), and 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al(5) have been tested and have shown blood hypoglycaemic effects in the diabetes-induced male ddY mice strain at 400 mg/kg. The two aglycones of charantin did not show any hypoglycaemic effects. Our finding is the first demonstration that major pure cucurbutanoid compounds of M. charantia have in vivo hypoglycaemic effects.

著者

Chih-Yang Chiu Chia-Ying Li Chao-Chen Chiu Masatake Niwa Susumu Kitanaka Amooru Gangaiah Damu E-Jian Lee Tian-Shung Wu

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.53, no.9, pp.1118-1121, 2005 (Released:2005-09-01)

参考文献数

31

被引用文献数

11 20

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Three new flavonoid derivatives, 6′′′-O-acetyl amurensin (1), 6′′′-O-acetyl phellamurin (3) and (2R)-phellodensin-F (5), together with thirty known compounds have been isolated from the leaves of Phellodendron japonicum MAXIM. Their structures were established by means of spectroscopic analysis, including extensive 2D NMR and Mass spectra. The known compounds were identified by comparison with published physical and spectral data. The isolated compounds were screened for their in vitro antioxidant activity through DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. Compounds quercetin and phellodenin-A demonstrated significant radical scavenging activity.

著者

MINH DUC Nguyen THOI NHAM Nguyen 笠井 良次 伊藤 優子 山崎 和男 田中 治

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.41, no.11, pp.2010-2014, 1993-11-15

被引用文献数

6

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From rhizomes and roots of Panax vietnamensis HA et GRUSHV., Araliaceae, commonly known as Vietnamese Ginseng, two new acetylated saponins named vina-ginsenoside-R1 (13) and vina-ginsenoside-R2 (15) were isolated. On the basis of chemical and spectral data, 13 was formulated as monoacetyl 24(S)-pseudo-ginsenoside-F_<11> and 15 was proved to be monoacetyl majonoside-R2.Besides the two new saponins and β-sitosteryl-3-O-β-D-glucopyranoside, sixteen known saponins were also isolated and identified. Dammarane saponins : ginsenoside-Rh_1 and 20(R)-ginsenoside-Rh_1 (1), ginsenosides-Rg_1 (2), -Re (3), -Rd(6), -Rb_3 (7), -Rb_2 (8), -Rb_1 (9), pseudo-ginsenoside-RS_1 (=monoacetyl ginsenoside-Re, 4), notoginsenosides-R1 (5) and -Fa (10). Ocotillol-type saponins : pseudo-ginsenoside-RT_4 (11), 24(S)-pseudo-ginsenoside-F_<11> (12), majonosides-R1 (16) and -R2 (14). Oleanolic acid saponins : ginsenoside-Ro (=chikusetsusaponin V, 17) and hemsloside-Ma3 (18), a saponin previously isolated from a cucurbitaceous plant, Hemsleya macrosperma C. Y. WU.Despite having large horizontally elongated rhizomes, the underground part of this plant contains mainly dammarane saponins and a small amount of oleanolic acid saponins. In addition, the yield of ocotillol-type saponins, especially majonoside-R2,is surprisingly very high (more than 5% and ca. half of the total yield of saponin). This characteristic saponin composition has made Vietnamese Ginseng an interesting species among Panax spp.

著者

西出 喜代治 山村 真理子 小堀 武夫 常本 大英 近藤 聖 佐藤 清

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.36, no.7, pp.2354-2361, 1988-07-25

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The syntheses and the antibacterial activities of new 3-dimethoxyphosphinylmethyl and 3-dihydroxyphosphinylmethyl cephalosporins I-(Z), II-(Z), III-(Z) and III-(E), possessing the chloromethylene or methoxyimino substituent at the α-position to the 7-(2-aminothiazol-4-yl)acetamido or 7-(thiazol-4-yl)acetamido moiety of the cephem nucleus, are described. The key steps of these syntheses were the Michaelis-Arbusov reaction of the 3-halomethylcephem 1 with trimethyl phosphite and the dealkylation reactions of both the dimethoxyphosphinyl group and the p-methoxybenzyl ester of 7a, b-(Z) by treatment with bromotrimethylsilane to afford 9a, b-(Z).

著者

坂田 紳二 米井 清志郎 吉野 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.30, no.7, pp.2583-2585, 1982-07-25

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A new method for the synthesis of 2-substituted 6-methylpurine ribosides from guanosine is described. Reaction of N (2), O (2'), O (3'), O (5')-tetraacetyl-O (6)-p-toluenesulfonylguanosine with carbanion from ethylacetoacetate gave the 6-ethoxycarbonylmethyl derivative, which was further converted to 2-amino-6-methylpurine riboside by deacetylation and decarboxylation. Replacement of the amino group of the compound by the fluoro group was achieved by the Schiemann reaction. The fluoro group could easily be replaced by several nucleophiles. As a result, 2-methylthio-, and 2-dimethylamino-6-methyl-9-β-D-ribofuranosylpurines could be effectively prepared.

著者

Kazusa Nishiyama Atsushi Yamada Miki Takahashi Tomoharu Takeuchi Ken-ichi Kasai Susumu Kobayashi Hideaki Natsugari Hideyo Takahashi

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.58, no.4, pp.495-500, 2010-04-01 (Released:2010-04-10)

参考文献数

29

被引用文献数

15 17

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To search for the endogenous glyco-epitope in Caenorhabditis elegans, we synthesized labeled Galβ1-3Fuc and Galβ1-4Fuc and examined their binding affinity for C. elegans galectin LEC-6 using frontal affinity chromatography analysis. We developed a new strategy for synthesizing the labeled saccharides, in which the labeling unit, the 2-aminopyridine moiety, is coupled with a spacer unit derived from D-mannitol. Our results indicate that Galβ1-4Fuc is the endogenous glyco-epitope present in C. elegans N-glycans.

著者

Gao Jiang-Jing Min Byung-Sun Ahn Eun-Mi NAKAMURA Norio LEE Hyeong-Kyu HATTORI Masao

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.50, no.6, pp.837-840, 2002-06-01

被引用文献数

6 119

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Three new lanostante-type triterpene aldehydes, named lucialdehydes A-C (1-3), were isolated from the fruiting bodies of Ganoderma lucidum, together with ganodermanonol (4), ganodermadiol (5), ganodermanondiol (6), ganodermanontriol (7), ganoderic acid A (8), ganoderic acid B8 (9), and ganoderic acid C1 (10). The structures of the new triterpenes were determined as (24E)-3β-hydroxy-5α-lanosta-7,9(11),24-trien-26-al (1), (24E)-3,7-dioxo-5α-lanosta-8,24-dien-26-al (2), and (24E)-3β-hydroxy-7-oxo-5α-lanosta-8,24-dien-26-al (3), respectively, by spectroscopic means. The cytotoxicity of the compounds isolated from the ganoderma mushroom was tested in vitro against Lewis lung carcinoma (LLC), T-47D, Sarcoma 180, and Meth-A tumor cell lines. Lucialdehydes B, C (2, 3), ganodermanonol (4) and ganodermanondiol (6) showed cytotoxic effects on tested tumor cells. Of the compounds, lucialdehyde C (3) exhibited the most potent cytotoxicity against LLC, T-47D, Sarcoma 180, and Meth-A tumor cells with ED_<50> values of 10.7, 4.7, 7.1, and 3.8 /μg/ml, respectively.

著者

Maeda Takuya Manabe Yuki Yamamoto Masashi YOSHIDA Munehiro OKAZAKI Kiyo NAGAMUNE Hideaki KOURAI Hiroki

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.47, no.7, pp.1020-1023, 1999-07-15

被引用文献数

18

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Potent new biocides against both bacteria and fungi, 4,4'-(1,6-hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s (4DOCBP-6,n) (alkyl chain length, n=8,10,12,14,16 and 18) were synthesized. 4DOCBP-6,n is bis-quaternary ammonium compound (bis-QAC) and has a symmetrical dimeric structure which is composed of two alkylpyridinium iodides connected with a hexamethylenedioxydicarbonyl chain. 4DOCBP-6,10 and 4DOCBP-6,12 exhibited wide and effective antimicrobial spectra, compared with those of typical bactericides, N-dodecylpyridinium iodides (P-12) and benzyldimethyldodecylammonium chloride (BAC), or a popularly-used fungicide, 2-(4-thiazolyl)benzimidazole (TBZ). Their superior properties would be due to the unique dimeric structure which contains two active moieties in a molecule.