Three new glycosides from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO.

Abstract:

:Three new glycosides, 7-deoxyloganic acid beta-D-glucopyranosyl ester (1), (3R)-hydrangenol 8,4'-di-O-beta-D-glucopyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-beta-D-glucopyranoside (3), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO (Saxifragaceae). The structures of 1-3 were elucidated on the basis of spectral data and chemical evidence.

authors

Kikuchi M,Kakuda R,Kikuchi M,Yaoita Y

doi

10.1248/cpb.56.610

subject

Has Abstract

pub_date

2008-04-01 00:00:00

pages

610-1

issue

4

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/56.610

journal_volume

56

pub_type

杂志文章
  • Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica.

    abstract::The CHCl3 extract of the root of Angelica japonica showed high inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth. From this extract, a new furanocoumarin named japoangelone and four furanocoumarin ethers of falcarindiol, named japoangelols A-D, were isolated together with caffeic acid methyl ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.96

    authors: Fujioka T,Furumi K,Fujii H,Okabe H,Mihashi K,Nakano Y,Matsunaga H,Katano M,Mori M

    更新日期:1999-01-01 00:00:00

  • Studies on agents with vasodilator and beta-blocking activities. V. Synthesis and pharmacological activity of the optical isomers of TZC-5665.

    abstract::Synthesis of the four optical isomers of TZC-5665 (1), a candidate for the treatment of congestive heart failure, was achieved by the reaction of chiral diaminopyridazinone (2) with chiral glycidyl ether. (3). The hypotensive and beta-blocking activities of 1 and its optical isomers were examined when given intravenou...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.84

    authors: Seki T,Kanada A,Nakao T,Shiraiwa M,Asano H,Miyazawa K,Ishimori T,Minami N,Shibata K,Yasuda K

    更新日期:1998-01-01 00:00:00

  • A new method to modify the C-4 position of 10-deacetylbaccatin III.

    abstract::We have developed a new method to modify the C-4 position of 10-deacetylbaccatin III (5) using the C-4 acetoxy anion of the 13-keto derivative (7) and various alkyl halides. The method developed herein should be very useful for the preparation of C-4 modified taxoid analogs. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.2093

    authors: Uoto K,Takenoshita H,Ishiyama T,Terasawa H,Soga T

    更新日期:1997-12-01 00:00:00

  • A novel antivirally active fucan sulfate derived from an edible brown alga, Sargassum horneri.

    abstract::A novel fucan sulfate (Hor-1) was isolated from the hot water extract of an edible brown alga, Sargassum horneri (Turner) C. Agardh. The fucan sulfate was revealed to have sugar linkage types, sulfate content and uronic acid content different from those of sodium hornan (Na-HOR), another fucan sulfate isolated from th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.484

    authors: Preeprame S,Hayashi K,Lee JB,Sankawa U,Hayashi T

    更新日期:2001-04-01 00:00:00

  • Syntheses of taxuspine C derivatives as functional inhibitors of P-glycoprotein, an ATP-associated cell-membrane transporter.

    abstract::UV-Irradiation of taxinine and related compounds in acetonitrile induced a smooth transannulation between the C-3 and C-11 positions without any influence from the C-2, C-9 and C-10 substituents to give tetracyclic taxuspine C derivatives in almost quantitative yields. Photochemical transannular reaction of taxoids po...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1135

    authors: Sako M,Suzuki H,Hirota K

    更新日期:1998-07-01 00:00:00

  • Synthetic studies on (+)-biotin, part 15: A chiral squaramide-mediated enantioselective alcoholysis approach toward the total synthesis of (+)-biotin.

    abstract::An efficient stereocontrolled total synthesis of (+)-biotin (1) has been achieved via the intermediacy of Roche's lactone 5 starting from cis-1,3-dibenzyl-2-imidazole-4,5-dicarboxylic acid (2). The bifunctional cinchona alkaloid-derived squaramide-promoted enantioselective alcoholysis was utilizing as a tool for the c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.488

    authors: Chen XX,Xiong F,Fu H,Liu ZQ,Chen FE

    更新日期:2011-01-01 00:00:00

  • An approach for decontamination of beta-lactam antibiotic residues or contaminants in the pharmaceutical manufacturing environment.

    abstract::An effective procedure for decontamination of beta-lactam antibiotic residues or contaminants in the pharmaceutical manufacturing environment was investigated. Decontamination with solutions of hydrochloric acid, sodium hydroxide, hydrogen peroxide and hydroxylamine as agents for degradation was assessed. According to...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1340

    authors: Fukutsu N,Kawasaki T,Saito K,Nakazawa H

    更新日期:2006-09-01 00:00:00

  • Four new cycloartane glycosides from Thalictrum fortunei.

    abstract::Four new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these new glycosides were elucidated as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-beta-D-glucopyranoside, 3-O-beta-D-glucop...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.107

    authors: Zhang XT,Zhang LH,Ye WC,Zhang XL,Yin ZQ,Zhao SX,Yao XS

    更新日期:2006-01-01 00:00:00

  • Evaluation of new pasty-type implantable devices consisting of poly(epsilon-caprolactone/delta-valerolactone) and Estracyt or estramustine.

    abstract::Biodegradable pasty-type copolyesters with a relatively low molecular weight of 4500 were synthesized by direct copolycondensation of epsilon-caprolactone (CL) and delta-valerolactone (VL) in the absence of catalysts to evaluate in vivo capabilities of the polymer for implantable controlled release devices in drug del...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2096

    authors: Imasaka K,Yoshida M,Fukuzaki H,Asano M,Kumakura M,Mashimo T,Yamanaka H,Nagai T

    更新日期:1991-08-01 00:00:00

  • Studies on topical antiinflammatory agents. II. Synthesis and vasoconstrictive activity of 21-substituted corticosteroids with sulfur-containing moieties.

    abstract::As part of the search for new topical antiinflammatory agents, various 21-substituted corticosteroids having sulfur-containing moieties were prepared and tested for vasoconstrictive activity in humans. A structure-activity relationship study revealed that substitution of the 21-hydroxy group with a lower alkyl-thio gr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1795

    authors: Mitsukuchi M,Ikemoto T,Taguchi M,Higuchi S,Abe S,Yasui H,Hatayama K,Sota K

    更新日期:1989-07-01 00:00:00

  • Deoxymanoalides from the nudibranch Chromodoris willani.

    abstract::Two sesterterpenes, deoxymanoalide (1) and deoxysecomanoalide (2), were isolated from the nudibranch Chromodoris willani collected in Okinawa and their structures determined on the basis of spectroscopic data and chemical conversions. The mollusk feeds on a sponge containing manoalide (3) and secomanoalide (4) and is ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.885

    authors: Uddin MH,Otsuka M,Muroi T,Ono A,Hanif N,Matsuda S,Higa T,Tanaka J

    更新日期:2009-08-01 00:00:00

  • Miscibility of nifedipine and hydrophilic polymers as measured by (1)H-NMR spin-lattice relaxation.

    abstract::The miscibility of a drug with excipients in solid dispersions is considered to be one of the most important factors for preparation of stable amorphous solid dispersions. The purpose of the present study was to elucidate the feasibility of (1)H-NMR spin-lattice relaxation measurements to assess the miscibility of a d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1227

    authors: Aso Y,Yoshioka S,Miyazaki T,Kawanishi T,Tanaka K,Kitamura S,Takakura A,Hayashi T,Muranushi N

    更新日期:2007-08-01 00:00:00

  • Synthesis and antioxidant activity of styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles.

    abstract::A new class of mono and bis heterocycles-styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles were prepared and studied their antioxidant activity. The compound methyl substituted 2-(p-methylphenylamino-sulfonylmethyl)-5-[Z-(p-methylstyrylsulfonylmethyl)]-1,3,4-oxadiazole displayed slightly h...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00652

    authors: Mallikarjuna Reddy G,Muralikrishna A,Padmavathi V,Padmaja A,Krishna Tilak T,Appa Rao C

    更新日期:2013-01-01 00:00:00

  • Formal (3+3) cycloaddition of silyl enol ethers catalyzed by trifric imide: domino Michael addition-claisen condensation accompanied with isomerization of silyl enol ethers.

    abstract::We describe here a Tf₂NH-catalyzed formal (3+3) cycloaddition of silyl enol ethers with acrylates as a new domino reaction. In the domino sequence, the catalyst activates Michael addition, deprotonation of the resulting silyloxonium cation and intramolecular Claisen condensation. It was found that reaction modes signi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1190

    authors: Azuma T,Takemoto Y,Takasu K

    更新日期:2011-01-01 00:00:00

  • Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. II. Optimization of the phenylpiperazine moiety of 1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-phenylpiperazinyl-1-trans-propenes.

    abstract::A series of novel 3-substituted-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes in order to improve the in vitro and in vivo activity of our prototype 3-[4-(3-chlorophenyl)-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propene (2) were synthesized and evaluated by assays of growth inhib...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.453

    authors: Naito H,Ohsuki S,Sugimori M,Atsumi R,Minami M,Nakamura Y,Ishii M,Hirotani K,Kumazawa E,Ejima A

    更新日期:2002-04-01 00:00:00

  • Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method.

    abstract::The hydrolysis of protopanaxadiol-type saponin mixture by various glycoside hydrolases was examined. Among these enzymes, crude preparations of lactase from Aspergillus oryzae, beta-galactosidase from A. oryzae, and cellulase from Trichoderma viride were found to produce ginsenoside F(2) [3-O-(beta-D-glucopyranosyl)-2...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1522

    authors: Ko SR,Suzuki Y,Suzuki K,Choi KJ,Cho BG

    更新日期:2007-10-01 00:00:00

  • Effect of Drug Combination on Omeprazole Metabolism by Cytochrome P450 2C19 in Helicobacter pylori Eradication Therapy.

    abstract::Helicobacter pylori (H. pylori) infection is common and can result in gastric and duodenal ulcers, and in some cases, gastric lymphoma and cancer. Omeprazole (OMP)-in combination with clarithromycin (CLR), amoxicillin (AMX), tinidazole (TND), or metronidazole (MET)-is used in double or triple combination therapy for e...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00084

    authors: Attia TZ,Yamashita T,Tsujino H,Derayea SM,Tsutsumi Y,Uno T

    更新日期:2019-01-01 00:00:00

  • Two new acyclic diterpene glycosides from fruits of Habanero, Capsicum chinense.

    abstract::Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyran...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.730

    authors: Lee JH,El-Aasr M,Ikeda T,Oda K,Miyashita H,Yoshimitsu H,Okawa M,Kinjo J,Nohara T

    更新日期:2009-07-01 00:00:00

  • Taste-masking effect of physical and organoleptic methods on peppermint-scented orally disintegrating tablet of famotidine based on suspension spray-coating method.

    abstract::Orally disintegrating tablets (ODTs) are useful for improving benefits for patients of various ages. Masking the unpleasant taste of a drug is an important factor in the compliance of patients who take ODTs. We evaluated the taste acceptability effects of various taste-masking methods on bitter famotidine ODTs as a cl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,随机对照试验

    doi:10.1248/cpb.60.315

    authors: Sugiura T,Uchida S,Namiki N

    更新日期:2012-01-01 00:00:00

  • Interaction of microcrystalline cellulose and water in granules prepared by a high-shear mixer.

    abstract::Microcrystalline cellulose (MCC) granules were prepared by wet granulation using a high-shear mixer. Physical characteristics of the granules were investigated using near IR spectrometry, thermogravimetry and isothermal water vapor adsorption. Near IR spectra of dried MCC granules prepared for various granulation time...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.373

    authors: Suzuki T,Kikuchi H,Yonemochi E,Terada K,Yamamoto K

    更新日期:2001-04-01 00:00:00

  • Modulating the cyclic guanosine monophosphate substrate selectivity of the phosphodiesterase 3 inhibitors by pyridine, pyrido[2,3-d]pyrimidine derivatives and their effects upon the growth of HT-29 cancer cell line.

    abstract::Analogues with the scaffolds of 3-cyano-4-alkoxyphenyl-6-bromoaryl-2-pyridone and 2-amino-3-cyano-4-alkoxyphenyl-6-bromoarylpyridine were synthesized. Cyclization of the 2-amino derivatives with formic acid and formamide gave the corresponding pyrido[2,3-d]pyrimidin-4(3H)-one and the pyrido[2,3-d]-pyrimidin-4-amine de...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00993

    authors: Abadi AH,Hany MS,Elsharif SA,Eissa AA,Gary BD,Tinsley HN,Piazza GA

    更新日期:2013-01-01 00:00:00

  • Synthesis and evaluation of antioxidant, anti-inflammatory and antiulcer activity of conjugates of amino acids with nifedipine.

    abstract::A new series of novel (2S)-2-({2-[1,4-dihydro-3,5-bis(methoxycarbonyl)-2,6-dimethyl-4-(2-nitrophenyl)pyridin-1-yl]-2-oxoethyl}amino)-3-(4-hydroxyphenyl) propanoic acid (3a) and its analogues 3b-j has been synthesized. These compounds were evaluated for their in vitro antioxidant activity, anti-inflammatory activity an...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1153

    authors: Subudhi BB,Sahoo SP

    更新日期:2011-01-01 00:00:00

  • Proton nuclear magnetic resonance study on the aromatic amino acid-guanine nucleotide system: effect of base methylation on the stacking interaction with tyrosine and phenylalanine.

    abstract::The stacking interactions of tyrosine methylester (TyrOMe)-guanosine-5'-monophosphate (GMP), TyrOMe-7-methylguanosine-5'-monophosphate (m7GMP), phenylalanine methylester (PheOMe)-GMP and PheOMe-m7GMP pairs in neutral buffer solution have been studied by proton nuclear magnetic resonance (1H-NMR). The H8 proton signal ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1

    authors: Ishida T,Ohnishi K,Doi M,Inoue M

    更新日期:1989-01-01 00:00:00

  • Properties of gastroretentive sustained release tablets prepared by combination of melt/sublimation actions of L-menthol and penetration of molten polymers into tablets.

    abstract::A novel floating sustained release tablet having a cavity in the center was developed by utilizing the physicochemical properties of L-menthol and the penetration of molten hydrophobic polymer into tablets. A dry-coated tablet containing famotidine as a model drug in outer layer was prepared with a L-menthol core by d...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1221

    authors: Fukuda M,Goto A

    更新日期:2011-01-01 00:00:00

  • Characterization of binding sites for sulfadimethoxine and its major metabolite, N4-acetylsulfadimethoxine, on human and rabbit serum albumin.

    abstract::In order to gain an understanding of protein binding of sulfadimethoxine (SDM) and its major metabolite, N4-acetylsulfadimethoxine (N4-AcSDM), the binding of SDM and N4-AcSDM to human and rabbit serum albumin (HSA and RSA) was investigated using circular dichroism (CD), fluorescence and dialysis techniques. The CD spe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.498

    authors: Otagiri M,Nakamura H,Maruyama T,Imamura Y,Takadate A

    更新日期:1989-02-01 00:00:00

  • Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis Fischer from northeastern China. (1). Licorice-saponins A3, B2, and C2.

    abstract::From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.43

    authors: Kitagawa I,Hori K,Taniyama T,Zhou JL,Yoshikawa M

    更新日期:1993-01-01 00:00:00

  • New cyclopropyl-triterpenoids from the aerial roots of Ficus microcarpa.

    abstract::Four new cyclopropyl-triterpenes, 27-nor-3beta-hydroxy-25-oxocycloartane (1), (22E)-25,26,27-trinor-3beta-hydroxycycloart-22-en-24-al (2), 3beta-acetoxy-15alpha-hydroxy-13,27-cyclours-11-ene (3), 3beta-acetoxy-12alpha-formyloxy-13,27-cycloursan-11alpha-ol (4), together with (23E)-27-nor-3beta-hydroxycycloart-23-en-25-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.581

    authors: Chiang YM,Su JK,Liu YH,Kuo YH

    更新日期:2001-05-01 00:00:00

  • New green synthesis and formulations of acyclovir prodrugs.

    abstract::Different green synthesis of alkyl esters of acyclovir (acyclovir prodrugs) is described. Hexanoic, decanoic, dodecanoic and tetradecanoic acyclovir esters were synthesized reacting acyclovir and the respective acid anhydride in dimethyl sulfoxide (DMSO), in solvents from renewable sources and without solvent (T=30 °C...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1089

    authors: de Regil-Hernández R,Martínez-Lagos F,Rodríguez-Bayón A,Sinisterra JV

    更新日期:2011-01-01 00:00:00

  • Bio-active Natural Products with TRAIL-Resistance Overcoming Activity.

    abstract::Tumor necrosis factor related apoptosis-inducing ligand (TRAIL) has emerged as a promising anticancer agent as it selectively kills cancer cells. However, TRAIL resistance limits its use as a therapeutic agent. An understanding the mechanisms responsible for TRAIL resistance and strategies to overcome it are important...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c15-00732

    authors: Ahmed F,Ishibashi M

    更新日期:2016-01-01 00:00:00

  • Drug Discovery Researches on Modulators of Lysine-Modifying Enzymes Based on Strategic Chemistry Approaches.

    abstract::Enzymatic and post-translational modifications (PTMs) such as ubiquitination, acetylation, and methylation occur at lysine residues. The PTMs play critical roles in the regulation of the protein functions, and thus, various cellular processes. In addition, aberrations of the PTMs are associated with various diseases, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c19-00741

    authors: Itoh Y

    更新日期:2020-01-01 00:00:00