著者

小倉 治夫 伊藤 常男 岡本 孝 大村 智

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.4, pp.844-846, 1969-04-25

著者

秦 藤樹 大村 智 片桐 通子 小倉 治夫 納谷 恵三 阿部 仁之助 渡辺 哲夫

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.15, no.3, pp.358-359, 1967

被引用文献数

8

著者

大村 智 中川 彰 関川 賢二 小谷 勝 秦 藤樹

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.2361-2363, 1969

被引用文献数

14

著者

木村 善行 奥田 拓道 奥田 拓男 吉田 隆志 波多野 力 有地 滋

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.31, no.7, pp.2501-2506, 1983-07-25

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The effects of various tannins and related compounds on the actions of adrenocorticotropic hormone (ACTH) and insulin in fat cells isolated from rats were investigated. Hydrolyzable tannins such as geraniin, mallotusinic acid, chebulinic acid and chebulagic acid enhanced the ACTH-induced lipolysis at the concentration of 20 μg/ml or 5 μg/ml. On the other hand, these hydrolyzable tannins had no effect on the insulin-stimulated lipogenesis from glucose. Condensed tannins such as Ss-tannin 1 and RSF-tannin H showed weak inhibitory effects on the ACTH-induced lipolysis, while they enhanced the insulin-stimulated lipogenesis from glucose. Based on these results, the relationship between the structures and physiological actions of these tannins is discussed.

著者

木村 善行 久保 道徳 草加 君代 谿 忠人 東野 正行 有地 滋 奥田 拓道

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.1, pp.219-222, 1982-01-25

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The effects of oral administration of flavonoid components of Scutellariae Radix on serum and liver lipid levels of rats treated with ethanol were investigated. It was found that wogonin reduced serum triglyceride level, and that baicalein and baicalin, the major components of the drug, decreased total cholesterol, free cholesterol and triglyceride contents in the liver. Baicalein increased high density lipoprotein-cholesterol (HDL-ch) in the serum of the ethanol-treated rats. In addition to these in vivo experiments, the actions of wogonin, baicalein and baicalin on catecholamine-induced lipolysis in isolated fat cells were investigated. It was found that the three flavones inhibited noradrenaline-induced lipolysis in isolated fat cells. The relationship between these in vivo and in vitro experiments is discussed.

著者

Hong Seong Su Lee Seon A Han Xiang Hua LEE Min Hee HWANG Ji Sang PARK Jeong Sook OH Ki-Wan HAN Kun LEE Myung Koo LEE Heesoon KIM Wook LEE Dongho HWANG Bang Yeon

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.56, no.2, pp.199-202, 2008-02-01

被引用文献数

1 27

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Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.

著者

河島 進 井上 陽子 示野 哲也 藤原 洋

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.2, pp.498-505, 1990-02-25

被引用文献数

2

---

Rectal absorption of morphine from various kinds of suppository bases was investigated. The extent of bioavailability of morphine by rectal administration varied with the bases used (30.5-97.5%), but every value was higher than that in the case of oral administration (13.5%). Witepsol bases were preferable to macrogol base for the rectal absorption of morphine. In particular, Witepsol S-55 or W-35 gave a higher plasma peak level than H-15 or E-75,whereas the difference in the mean residence times obtained from these bases could not be regarded as significant. Sustained-release suppositories of morphine could be prepared simply by mixing alginic acid (Alg) with morphine in a suppository base. Further, prolonged rectal absorption could be obtained by using these sustained-release suppositories, and the absorption rate was controlled by the amount of Alg added. It seems likely that the sustained release was due to the binding of morphine to Alg from the results of partition coefficient and binding ratio measurements in aqueous solution. The rapid initial absorption and the subsequent prolonged absorption of morphine simultaneously obtained from the morphine-Alg suppository may be useful in the clinical context.

著者

増田 克忠 神谷 高明 今城 芳夫 金児 龍彦

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.19, no.1, pp.72-79, 1971

被引用文献数

25

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A number of N-acyl and N-nitroso-3-dialkylaminosydnonimines (II) were synthesized by various acylating methods. In some cases, the acylation with activated esters, mixed anhydrides or dicyclohexylcarbodiimide was found to be more favorable. The reactivities of these derivatives towards acids and alkalis were investigated. Trifluoroacetyl (II-6) and formyl (II-1) compounds were easily deacylated in varuous conditions. Methylation took place at the acylated imino nitrogen of N-ethoxycarbonyl compound to give the quaternary salt (II-18). N-Acetyl compound (II-2) was compared with its 3-alkyl analog in the physicochemical properties ; its pK<SUB>a</SUB> values reveals that the morpholino group has little effect on the basicity of the compound.

著者

樫原 宏 末宗 洋 常広 菜穂美 酒井 浄

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.9, pp.2581-2582, 1990-09-25

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The enones (II), which were obtained from dimethyl 4,5-isopropylidenedioxy-2-oxopentylphosphonate (Ia) and various aldehydes, were easily converted to 2-alkenylfurans (III) by treatment with p-TsOH in MeOH. In a similar manner, the furfuryl phosphonate (IVa) and the 3-methylfurfuryl phosphonate (IVb) were obtained from Ia and its 3-methylated analogue (Ib), respectively.

著者

Fortin Helene Tomasi Sophie Jaccard Philippe ROBIN Valerie BOUSTIE Joel

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.49, no.5, pp.619-621, 2001-05-01

参考文献数

18

被引用文献数

19

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A new coumarin identified as 5-hydroxy-6-methoxy-7-(3-methyl-but-2-enyloxy)-2H-1-benzopyran-2-one (isoobtusitin) was isolated from Psiadia dentata. This compound showed, in vitro, a moderate inhibitory activity against poliovirus and a very weak activity against (HIV), whereas it was inactive against (HSV1), (VSV), and murine tumoral cell lines (3LL, L1210).

著者

梅澤 勲 野澤 雅子 南雲 紳史 秋田 弘幸

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.7, pp.1111-1118, 1995

被引用文献数

5

---

Three kinds of oudemansin X, (-)-1, (+)-1 and (&plusmn;)-1, were totally synthesized. The key point in the present chiral synthesis was the enantioselective acetylation of the racemic alcohols, (&plusmn;)-5 and (&plusmn;)-8, using lipase in an organic solvent. The synthetic (-)-1 was found to exhibit strong antifungal activity against several molds and yeasts.

著者

宮内 正雄 笹原 邦宏 藤本 光一 川本 勲 井手 純也 中尾 英雄

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.37, no.9, pp.2369-2374, 1989

被引用文献数

9

---

The degradation kinetics of pivaloyloxymethyl (POM) esters of cephalosporins in phosphate buffer solution (pH6-8) were investigated. The degradation of the starting &Delta;<SUP>3</SUP> cephalosporin ester proceeded mainly via isomerization to the &Delta;<SUP>2</SUP> ester and subsequent hydrolysis to the &Delta;<SUP>2</SUP> acid. Hydrolysis to the &Delta;<SUP>3</SUP> acid (the parent acid) was very slow. Analysis of the rate constants indicated that the isomerization rate k<SUB>12</SUB> was approximately equal to the apparent degradation rate of the &Delta;<SUP>3</SUP> ester k<SUB>deg</SUB>, and slower than the hydrolysis rate of the &Delta;<SUP>2</SUP> ester k<SUB>24</SUB>. The isomerization process to the &Delta;<SUP>2</SUP> ester was found to be the rate-determining step in the degradation of cephalosporin esters. The substituent at the C-3 position of the cephalosporins affected the degradation kinetics. The degradation was accelerated by increase of pH, buffer concentartion and added protein.

著者

宮内 正雄 栗原 英志 藤本 光一 川本 勲 井手 純也 中尾 英雄

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.37, no.9, pp.2375-2378, 1989

被引用文献数

2

---

The effect of substituents at the C-3 position on the degradation kinetics of the pivaloyloxymethyl (POM) ester of &Delta;<SUP>3</SUP> cephalosporin in phosphate buffer solution (pH6-8) was investigated. In the degradation, the isomerization process to the &Delta;<SUP>2</SUP> ester was the rate-determining step. In this study, the logarithm of the isomerization rate to the &Delta;<SUP>2</SUP> ester (log k<SUB>12</SUB>) correlated with the carbon-13 unclear magnetic resonance chemical shift difference value at C-3 and C-4 of the &Delta;<SUP>3</SUP> ester (&Delta;&delta;(4-3)). The energy level of the lowest unoccupied molecular orbital (LUMO) of the &Delta;<SUP>3</SUP> esters also correlated with log k<SUB>12</SUB>. The electronic properties at the C-2 position had no effect on the isomerization reaction. On the other hand, the logarithm of the isomerization rate back to the &Delta;<SUP>3</SUP> ester (log k<SUB>21</SUB>) correlated with the van der Waals volume (MV) of the 3-substituent. These results show that the substituent at the C-3 position influences mainly the electronic structure of the conjugated &pi;-bond system (C<SUB>3</SUB>=C<SUB>4</SUB>-C<SUB>4</SUB>=O) and consequently affects the feasibility of isomerization to the &Delta;<SUP>2</SUP> ester, i.e., the stability to degradation.

著者

Kwon Hak Cheol Jung Chil Mann Shin Cha Gyun LEE Jong Kyo CHOI Sang Un KIM Sun Yeou LEE Kang Ro

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.48, no.11, pp.1796-1798, 2000-11-01

参考文献数

17

被引用文献数

5

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The phytochemical study of the aerial parts of Aster scaber THUNB. (Asteraceae) yielded a new caffeoyl quinic acid, (-) 3,5-dicaffeoyl-muco-quinic acid (2) and three known compounds, (-) 3,5-dicaffeoyl quinic acid (1), (-) 4,5-dicaffeoyl quinic acid (3), (-) 5-caffeoyl quinic acid (4). The structures were established by high resolution spectroscopic methods. The antiviral effects against HIV-1 integrase of the compounds was evaluated. (-) 3,5-Dicaffeoyl-muco-quinic acid (2) exhibited potent antiviral activity with an IC_<50> value of 7.0±1.3 μg/ml.

著者

伊藤 豊 矢野 真吾 渡辺 和夫 山中 悦二 相見 則郎 坂井 進一郎

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.1702-1706, 1990

被引用文献数

19

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We investigated the selectivities and structure requirements for alpha-1 and alpha-2 adrenoceptor blocking activities of yohimbine (YO) and its 12 related analogs, such as &beta;-yohimbine (&beta;-YO), dihydrocorynantheine (DHC) and (-)indoloquinolizidine ((-)IQ). The affinity of YO analogs to alpha-adrenoceptor was assessed by measuring their blockade of pressor responses to epinephrine in pithed rats. Among YO structure groups, the potency order was YO>DHC=&beta;-YO>geissoschizine methylether>14&beta;-hydroxy YO>14&beta;-benzoyloxy YO (inactive). (-)IQ was slightly less potent than YO, but much stronger than (+)IQ. Among (&plusmn;)IQ structure groups, the potency order was (&plusmn;)IQ>(&plusmn;)1, 12b-trans-1-hydroxy IQ&raquo;(&plusmn;)1, 12b-cis-1-hydroxy IQ (imactive). (&plusmn;)Borrerine was active, but (&plusmn;)desmethylborrerine was inactive. The alpha-1 blocking activities of the four compounds YO, &beta;-YO, DHC and (-)IQ, were assessed in experiments of pressor responses to methoxamine in pithed rats and contractile responses to methoxamine in the rat vas deferens. The potency order was (-)IQ>YO>DHC>&beta;-YO. Furthermore, the alpha-2 blocking activities of the four analogs were assessed in experiments of pressor responses to clonidine and inhibition of electrically driven cardioacceleration by clonidine, in pithed rats. The potency order was YO>&beta;-YO>(-)IQ>DHC. Based on the potency ratio between alpha-1 and alpha-2 blocking activities, DHC or YO was most selective for alpha-1 or alpha-2 subtype, respectively, among the four YO analogs. These results suggest that the A, B, C and D rings of YO analogs and their planarity are necessary for the affinity to alpha-adrenoceptors and that the predominant conformation of the carboxymethyl or hydroxy group on the E ring of YO structure determines the selectivity for alpha-1 and alpha-2 blocking activities.

著者

狐塚 寛 小山 又次郎 興津 知明

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.29, no.2, pp.433-437, 1981

被引用文献数

7

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The murexide reaction was investigated to clarify the mechanism of the coloration, with caffeine as a model compound. From the reaction mixture of caffeine with hydrogen peroxide and hydrochloric acid, 1-hydroxy-5, 7-dimethyl-2, 4, 6-trioxo-1H, 5H, 7H-oxazolo-[4, 5-d] pyrimidine (yellow oil) (I) and 1, 3, 7-trimethyl-2, 6, 8-trioxo-9-hydroxy-1H, 3H, 7H-xanthine (red powder) (II) were isolated, and these two compounds were shown to be responsible for the murexide reaction of caffeine. Compound I was regarded as a key intermediate, since its purple coloration with dil. ammonia was similar to that of caffeine developed by the murexide reaction. The absorption maximum of II corresponds to that of the red-colored solution obtained from the reaction of caffeine with hydrogen peroxide and hydrochloric acid.

著者

瀬沼 勝 藤井 武彦 瀬戸 正彦 岡村 公生 伊達 忠正 絹巻 明生

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.4, pp.882-887, 1990-04-25

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The direct resolution of (3aRS, 6SR, 6aSR)-1,3-dibenzyl-6-hydroxy-3,3a, 6,6a-tetrahydro-1H-furo[3,4-d]imidazole-2,4-dione [(±)-9], a key intermediate for biotin, with optically active amines was examined. Reaction of (±)-9 with cinchonidine readili gave the cinchonidine salt of the (4S, 5R)-aldehyde-carboxylic acid (12), acidification of which gave (3aS.6R, 6aR)-9,convertible to biothin. N-alkyl-D-glucamines (14) were also found to be effective resolving agents for (±)-9 applicable for industrial use. Reutilizatin of the unwanted epimer [(3aR, 6S, 6aS)-9] was effected by facile oxidation to the meso-diacid (3) with sodium chlorite.

著者

吉岡 龍藏 大槻 理 瀬沼 勝 土佐 哲也

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.37, no.4, pp.883-886, 1989-04-25

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A practical preparation of D-aspartic acid β-methyl ester [D-Asp(OMe)], a raw material for the antibiotic aspoxicillin, has been developed by the use of a second-order asymmetric transformation. The diastereomeric resolution of DL-Asp(OMe) with (-)-1-phenylethanesulfonic acid (PES) resulted in salt formation of less soluble D-・(-) and more soluble L-・(-) in acetonitrile. The soluble L-・(-) was easily epimerized into DL-・(-) by heating it in acetonitrile in the presence of catalysts. Attempted fractional crystallization of DL-・(-) or L-・(-) under such epimerizing conditions led to the desired D-・(-) in 90% yield via equilibrium asymmetric transformation in a solid-liquid heterogeneous system. Details of optimum techniques for the asymmetric transformation are presented.From these results, unique preparation processes of both D-Asp(OMe) and D-p-hydroxyphenylglycine, important intermediate materials for aspoxicillin, have been achieved by asymmetric transformation using chiral PES as the resolving agent.

著者

三橋 博 金子 光 佐々木 希吉

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.10, no.11, pp.1119-1122, 1962-11-25

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It was shown that DL-phenylalanine [2-^<14>C] was incorporated into C-3 of two kinds of isoflavone, formononetin and genistein, by Trifolium pratense sp., in vivo. These results indicate that the aryl group undergoes a migration within the C_6-C-C-C fragment, and this observation agrees with Grisebach's experimental data.

著者

室伏 良信 木村 美佐子 桑野 晴光 飯島 康輝 山崎 光郎 金子 正勝

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.10, pp.3760-3769, 1988-10-25

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Addition reactions of the C^<4′>-C^<5′> double bond of griseolic acid were investigated. C^<4′>-C^<5′>Dihydrogrisiolic acid was obtained by reduction of the adduct having halogen at the 4′-position.The ring juncture of the two five-membered rings of the C^<4′>-C^<5′> dihydro derivaticves was of all-"cis"configuration. Acetolysis of the protected dihydrogriseolic acid gave the corresponding 1′-acetoxy sugar derivative. Reaction of this sugar derivative with silylated bases gave guanine and uracil derivatives of the dihydrogriseolic acid. The cyclic nucleotide phosphodiesterase (PDE)-inhibitory activity of the C^<4′>-C^<5′> cis dihydrogriseolic acid derivative was weaker than that of griseolic acid.The uracil derivative of C^<4′>-C^<5′> cis dihydrogriseolic acid completely lost the inhibitory activity against both adenosine 3′, 5′-cyclic monophosphate (cAMP) and guanosine 3′, 5′-cyclic monophosphate (cGMP) PDE, whereas the guanine derivative showed reduced inhibitory activity against cAMP PDE, but retained its activity against cGMP PDE. It was also apparent that the C^<4′>-C^<5′>trans dihydro derivative which was obtained as a minor product from the same culture broth of griseolic acid had almost the same inhibitory activity as griseolic acid.