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Volume 58, Issue 5
Displaying 1-34 of 34 articles from this issue
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Review
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Yoshiji TakemotoArticle type: Review
2010 Volume 58 Issue 5 Pages 593-601
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSWe have developed several multifunctional thiourea catalysts bearing a tertiary amine or an 1,2-amino alcohol in expectation of their synchronous activation of a nucleophile and an electrophile through both acid-base and hydrogen-bonding interactions. From these studies, it was revealed that the weak acidity of thioureas compared with metallic Lewis acids could be overcome by this modification. The bifunctional aminothiourea could be used efficiently for a wide range of diastereoselective and enantioselective nucleophilic reactions such as Michael addition of 1,3-dicarbonyl compounds to nitroolefines, aza-Henry reaction of nitroalkanes to N-Boc imines, and hydrazination of cyclic β-keto esters. We also discovered that multifunctional thiourea catalyst, bearing an 1,2-amino alcohol moiety, significantly accelerated the Petasis-type reaction of alkenylboronic acids to N-phenoxycarbonyl quinolinium salts, prepared from quinolines and phenyl chloroformate, to afford 1,2-addition products with high enantioselectivity (up to 97% ee). Furthermore, to expand the synthetic applicability of the thiourea-catalyzed asymmetric reactions, tandem organocatalyzed reactions were explored to establish the concise one-pot synthesis of chiral densely functionalized three-, five-, and six-membered compounds.View full abstractDownload PDF (1371K)
Regular Articles
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Suresh Kumar Raju, Michael Rajesh Stephen, Perumal Subbu, Banerjee Deb ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 602-610
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe four-component reaction of ethyl-3-oxo-4-(arylsulfanyl)butanoate, substituted aromatic aldehydes and ammonium acetate afforded novel ethyl 4-hydroxy-2,6-diaryl-5-(arylsulfanyl)-1,2,5,6-tetrahydro-3-pyridinecarboxylates. These tetrahydro-pyridine esters upon dehydrogenation with dichlorodicyanobenzoquinone (DDQ) afforded highly functionalized pyridines in excellent yields. These novel heterocycles were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv using agar dilution method. Among the compounds screened, ethyl 2,6-di(2-bromophenyl)-4-hydroxy-5-(phenylsulfanyl)-3-pyridinecarboxylate was found to be the most active with a minimum inhibitory concentration of 1.33 μM against Mycobacterium tuberculosis and is 5.74 and 38.17 times more potent than the first line anti-tuberculosis (TB) drugs, ethambutol and pyrazinamide respectively.View full abstractDownload PDF (734K) -
Yaw-Bin Huang, Ko-Feng Lee, Chi-Te Huang, Yi-Hung Tsai, Pao-Chu WuArticle type: Regular Article
2010 Volume 58 Issue 5 Pages 611-614
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe aim of this study was to optimize hesperetin cream formulations by in vitro permeation study and evaluate topical whitening active effect and skin irritation by in vivo study. The results showed that the solubility of lipophilic compound of hesperetin was increased by short-chain alcohol including ethanol, glycerin, propylene glycol and polyethylene glycols 400 (PEG 400). PEG 400 showed strongest solubilized effect by increased 3400-fold. With the addition of 5% enhancers, it was found that menthol showed the most potent enhancing effect, followed by azone and depigmentation agents (linoleic acid and lecithin). Moreover, enhancers could shorten the lag time from 3.7 to 1 h. Combination of menthol, linoleic acid and lecithin of 2.5% had a higher permeation rate of 9.8 μg/cm2/h and lower lag time 1 h, therefore the formulation was selected to process the skin whitening and irritation test. The results showed that a significantly topical photoprotective effect with acceptable skin irritation was obtained after hesperetin cream topical application when compared with that of the non-treatment group, indicating that the hesperetin cream may be used as an effective whitening agent.View full abstractDownload PDF (240K) -
Nagahisa Yamaoka, Yasuhiko Kawano, Yuko Izuhara, Toshio Miyata, Kanji ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 615-619
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSSmall molecule inhibitors of plasminogen activator inhibitor (PAI)-1 have been reported to date but their clinical effects still remain unknown. The present study was undertaken to investigate the structure–activity relationships (SAR) of newly synthesized 2-acylamino-3-thiophenecarboxylic acid dimers based upon a core structure of TM5001 (1) and TM5007 (2) that we have previously identified as orally effective PAI-1 inhibitors. In general, compounds possessing bulky or/and hydrophobic substituents (e.g. phenyl, isobutyl group) on the both thiophene rings showed potent PAI-1 inhibitory activities irrespective of the positions of the substitution. The mono-carboxyl derivative (10) exhibited PAI-1 inhibition comparable to the corresponding dicarboxyl compound (9f).View full abstractDownload PDF (314K) -
Shigeki Kobayashi, Makoto Watanabe, Toshiyuki ChikumaArticle type: Regular Article
2010 Volume 58 Issue 5 Pages 620-627
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSWe examined the interaction between several ligands and alkaline (M+) or lanthanide (Ln3+) ions using η–χ diagrams. η and χ represent absolute hardness and absolute electronegativity, respectively. Based on the diagrams, new double-stranded amino acid chelators (1) conjugated to Cat (catechol) were synthesized. They had two cavities coordinating hard metal ions, such as Li+ and K+, and soft metal ions, such as Lu3+ and Eu3+. 1 formed a solvated molecular complex, 1–Ln3+, with a molar ratio of 1 : 1 at a binding constant (Kb) of 104—106 with Y3+, La3+, Eu3+, and Lu3+, respectively. With a chemical hard ion, Li+, we found that the Kb of the 1–Eu3+ complex increased. The optimized geometries of 1–Lu3+ and 1–La3+ complexes were obtained from B3LYP correlation functions using Stuttgart-Dresden-Bonn (SDD) Effective Core Potential (ECP) basis sets for Lu3+ and La3+ ions. The double-stranded chelator may prove useful for studying the selective separation of lanthanide ions, and the development of functional peptides.View full abstractDownload PDF (923K) -
Masanobu Ito, Keiichi Matsuzaki, Jue Wang, Akihiro Daikonya, Nai-Li Wa ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 628-633
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSNew phenanthrenes, loddigesiinols A (1) and B (7), and stilbenes, loddigesiinols C (8) and D (9), were isolated from 80% ethanol extract of Dendrobium loddigesii ROLFE (Orcharedceae) along with known compounds, including five phenanthrenes, three stilbenes, two lignans, and three sterols. Their structures were determined by spectroscopic studies. These compounds were evaluated for their inhibitory activities against nitric oxide (NO) production and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging. Phenanthrenes (1—3, 7) and dihydrophenanthrenes (4—6) showed significant inhibitory activity against NO production. In particular, 2 showed stronger inhibitory activity against NO production than 5 and 6. This suggested that this phenanthrene is a stronger inhibitor of NO production than dihydrophenanthrene. The new phenanthrenes, loddigesiinols A (1) and B (7), significantly inhibited NO production with IC50 values of 2.6 and 10.9 μM, respectively. One new dihydrostilbene, loddigesiinol D (9), showed weak inhibitory activity against NO production with an IC50 value of 69.7 μM, but the other new dihydrostilbene, loddigesiinol C (8), did not show this activity at 100 μM.View full abstractDownload PDF (371K) -
Ashish Kumar Tewari, Priyanka Srivastava, Ved Prakash Singh, Amit Sing ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 634-638
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSSeries of pyrazole ester prodrugs analogues have been synthesized and found to contain highly potent inhibitors of the cyclooxygenase-2 (COX-2) enzyme. The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-, 13C-NMR mass spectroscopy (MS) and their purity were ascertained by TLC and elemental analyses. The biological in vivo evaluation of these compounds in experimental models (carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Docking studies into the catalytic site of COX-2 were used to identify potential anti-inflammatory lead compounds. One lead derivative was chosen endowed with good binding energies.View full abstractDownload PDF (721K) -
Qi Shen, Xi Li, Dan Yuan, Wei JiaArticle type: Regular Article
2010 Volume 58 Issue 5 Pages 639-643
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSTo enhance oral absorption of poorly water-soluble daidzein, self-microemulsifying drug delivery system (SMEDDS) composed of oil, surfactant and cosurfactant for oral administration of daidzein was formulated, and its physicochemical properties and pharmacokinetic parameters were evaluated. Solubility of daidzein was determined in various vehicles. Pseudo-ternary phase diagrams were constructed to identify the efficient self-microemulsification region and particle size distributions of the resultant microemulsions were determined using a laser diffraction sizer. From these studies, an optimized formulation consisting of Ethyl oleate (10%), Cremophor RH 40 (60%), and polyethylene glycol 400 (PEG400) (30%) was selected. The dissolution rate of daidzein from SMEDDS was significantly higher than the conventional tablet. Relative bioavailability of SMEDDS was enhanced about 2.5-fold compared with that of the control group. The data suggest that the use of SMEDDS provide a potential way of daidzein administered orally.View full abstractDownload PDF (831K) -
Pilar Bustamante, Susana Muela, Begoña Escalera, Ángeles ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 644-649
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSA model based on solubility parameters is proposed to predict the solubility curves of antihelmintic drugs at several temperatures, including aqueous and non-aqueous mixtures. The solubility of the drugs was measured in ethanol–water and ethanol–ethyl acetate mixtures at 15—35 °C (mebendazole) and at 25 °C (thiabendazole and metronidazole). The solid phases were analyzed by differential scanning calorimerty. The polymorphic form A of mebendazole was also characterized from infrared spectroscopy. Markedly different solubility profile shapes were obtained against the solubility parameter of the mixtures: two symmetrical peaks (metronidazole), two maxima of different height (mebendazole) and a single peak (thiabendazole). The solubility parameter of the drugs was related to the co-solvent action of both mixtures and to the solubility peaks. The single equation proposed was able to predict solubility profiles of different shape, including both mixtures and all temperatures, providing reasonable physical meaning for the regression coefficients. The model was successfully tested for its predictive capability using a limited number of experimental data. More than 100 solubilities were predicted at several temperatures using 20 data point for each drug.View full abstractDownload PDF (459K) -
Sanjay Singh, Ajay Kumar Dobhal, Achint Jain, Jayant Kumar Pandit, Sub ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 650-655
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe present investigation was undertaken to develop solid lipid nanoparticles (SLN) of a hydrophilic drug Zidovudine (an anti-human immunodeficiency viral agent) and improve the entrapment efficiency of the drug in SLN. The SLN were prepared with stearic acid by process of w/o/w double-emulsion solvent-evaporation method using 32 factorial design. Different triglycerides alone and in different combinations, with/without stearic acid were used to prepare SLN using similar procedure. Two operating variables, polyvinyl alcohol concentration and amount of lipid were found to have significant effect on the particle size and entrapment efficiency (EE) of the SLN. The maximum EE was found to be ca. 27% with particle size of 621 nm which was significantly higher than that reported earlier. The optimized batch was also analyzed for its morphological, physiochemical and drug release properties. EE of batches with triglycerides were significantly less than that achieved with stearic acid alone. This work indicates the possible advantage of fatty acids over triglycerides in the entrapment of hydrophilic drugs in SLN.View full abstractDownload PDF (1691K) -
Chun-Rong Yang, Xiu-Li Zhao, Hai-Yang Hu, Ke-Xin Li, Xin Sun, Lei Li, ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 656-661
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe objective of the present work was to study the preparation, optimization and characteristics of Huperzine A (Hup A), an effective Traditional Chinese Medicine treatment of Alzheimer's disease (AD), loaded nanostructured lipid carriers (NLC). NLC were successfully prepared by a modified method of melt ultrasonication followed by high pressure homogenization using Cetyl Palmitate (CP) as the solid lipid, Miglyol®812 as the liquid lipid, Soybean phosphatidylcholine (Spc) and Solutol HS15® as the emulsifiers. The best formulation was optimized with a three-factor, three-level Box–Behnken design. Independent variables studied were the amount of the mixed lipid, the amount of the emulsifier mixture and lipid/drug ratio in the formulation. The dependent variables were the particle size, entrapment efficiency (EE) and drug loading (DL). Properties of NLC such as the morphology, particle size, zeta potential, EE, DL and drug release behavior were investigated, respectively. As a result, the designed nanoparticles showed nearly spherical particles with a mean particle size of 120 nm and −22.93±0.91 mV. The EE (%) and DL (%) could reach up to 89.18±0.28% and 1.46±0.05%, respectively. Differential scanning calorimetry (DSC) of Hup A loaded NLC indicated no tendency of recrystallisation. In vitro release studies showed a burst release at the initial stage and followed by a prolonged release of Hup A from NLC up to 96 h. The results suggest that the presented Hup A loaded NLC system is a potential delivery system for improving drug loading capacity and controlled drug release.View full abstractDownload PDF (1054K) -
Excavatoids L—N, New 12-Hydroxybriaranes from the Cultured Octocoral Briareum excavatum (Briareidae)Jui-Hsin Su, Bo-Yuan Chen, Tsong-Long Hwang, Yung-Husan Chen, I-Chu Hu ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 662-665
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThree new 12-hydroxybriarane diterpenoids, excavatoids L—N (1—3), have been isolated from the cultured octocoral Briareum excavatum. The structures of new briaranes 1—3 were elucidated by the interpretations of spectroscopic methods. Excavatoid L (1) displayed moderate inhibitory effects on superoxide anion generation and elastase release by human neutrophils.View full abstractDownload PDF (203K) -
Masateru Ono, Yoko Takagi-Taki, Fumiko Honda-Yamada, Naoki Noda, Kazum ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 666-672
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSAlkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the seeds of Quamoclit pennata BOJER (Convolvulaceae) provided five new glycosidic acids, quamoclinic acids B, C, D, E, and F, along with six organic acids, isobutyric, 2S-methylbutyric, tiglic, 2R,3R-nilic, 7S-hydroxydecanoic, and 7S-hydroxydodecanoic acids. These new compounds were characterized on the basis of spectroscopic data as well as chemical evidence. Quamoclinic acids E and F are the first examples of heptaglycosides of glycosidic acid.View full abstractDownload PDF (269K) -
Yoshihisa Nakada, Masaki Ogino, Kouhei Asano, Kazuko Aoki, Hiroshi Mik ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 673-679
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSIn a program to discover new small molecule diacylglycerol acyltransferase (DGAT)-1 inhibitors, screening of our in-house chemical library was carried out using recombinant human DGAT-1 enzyme. From this library, the lead compound 1a was identified as a new class of DGAT-1 inhibitor. A series of novel N-(substituted heteroaryl)-4-(substituted phenyl)-4-oxobutanamides 2 was designed from 1a, synthesized and evaluated for inhibitory activity against DGAT-1 enzyme. Among these compounds, N-(5-benzyl-4-phenyl-1,3-thiazol-2-yl)-4-(4,5-diethoxy-2-methylphenyl)-4-oxobutanamide 9 was found to exhibit potent inhibitory activity and good enzyme selectivities. Following administration in KKAy mice with 3 mg/kg high fat diet admixture for four weeks, 9 reduced body weight gain and white adipose tissue weight without affecting total food intake. These results suggested that the small molecule DGAT-1 inhibitor might have potential in the treatment of obesity and metabolic syndrome.View full abstractDownload PDF (564K) -
Eriko Azuma, Kouji Kuramochi, Kazunori TsubakiArticle type: Regular Article
2010 Volume 58 Issue 5 Pages 680-684
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSBoc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.View full abstractDownload PDF (855K) -
Kensuke Okuda, Hiroshi Deguchi, Setsuo Kashino, Takashi Hirota, Kenji ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 685-689
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSReaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines via a Truce–Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.View full abstractDownload PDF (340K) -
Seikou Nakamura, Gang Chen, Souichi Nakashima, Hisashi Matsuda, Yuehu ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 690-695
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe ethyl acetate and 1-butanol soluble fractions of the roots of Pfaffia glomerata were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the ethyl acetate and 1-butanol soluble fractions, we isolated a new noroleanane-type triterpene, pfaffianol A, its glycosides, pfaffiaglycosides A and B, and ecdysterone-type sterol glycosides, pfaffiaglycosides C, D, and E, together with eight known constituents. The structures of new constituents were determined on the basis of physicochemical and chemical evidence. Among them, pfaffianol A (IC50=44 μM) and pfaffoside C (IC50=92 μM) substantially inhibited melanogenesis without cytotoxic effects. The inhibitory effects were stronger than that of reference compound, arbutin (IC50=174 μM).View full abstractDownload PDF (364K) -
Toshihiro Murata, Toshio Miyase, Fumihiko YoshizakiArticle type: Regular Article
2010 Volume 58 Issue 5 Pages 696-702
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe dried whole plant of Meehania fargesii (H. LéV.) C. Y. WU is utilized as an antipyretic and antidote for poison in China. Water soluble fractions, obtained from an 80% acetone extract of the whole plant, showed hyaluronidase inhibitory activity. From these fractions, hyaluronidase inhibitors were isolated along with two new spermidine alkaloids (meefarnines A and B), four new flavone glycosides (fargenins A—D), and 10 known compounds. The structure of each was elucidated by spectroscopic methods.View full abstractDownload PDF (386K) -
Rilka M. Taskova, Tetsuo Kokubun, Ken G. Ryan, Phil John Garnock-Jones ...Article type: Regular Article
2010 Volume 58 Issue 5 Pages 703-711
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSSnow hebes are the alpine cushion-forming plants of New Zealand Veronica, formerly classified as Chionohebe. The chemical compositions of Veronica pulvinaris and Veronica thomsonii were studied and 33 water-soluble compounds were isolated. The structures of 14 previously unknown esters of phenylethanoid glycosides were elucidated by spectroscopic analyses. Further, eight known phenylethanoids, nine iridoids, 6′-feruloyl-sucrose and mannitol are also reported. It was found that the iridoid profile of the snow hebes was different from the other species of Veronica in New Zealand but similar to the alpine Northern Hemisphere representatives of the genus.View full abstractDownload PDF (341K)
Notes
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Rekha Shankar Hunoor, Basavaraj Rudragouda Patil, Dayananda Shivappa B ...Article type: Note
2010 Volume 58 Issue 5 Pages 712-716
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSA new 2,3-disubstituted 1,2-dihydroquinazolin-4(3H)-one derivative namely 2-hydroxy-2-ethyl-(3-carboxylideneamino)-3-(2-(4-methyl-phenyl))-1,2-dihydroquinazolin-4(3H)-one (HECMDQ) is synthesized employing a modified method in higher yield and is complexed with Co(II), Ni(II), Cu(II) and Zn(II) metal ions in order to study its coordinating behavior. All the complexes were characterized by various physicochemical (analytical, IR, NMR, Electron Paramagnetic Resonance (EPR), mass, Thermogravimetric Analysis Differential Thermogravimetric Analysis (TGA-DTA)) methods. The molar conductivity measurements in N,N-dimethylformamide (DMF) solution indicate the non-electrolytic nature of complexes. IR spectral analysis reveal that coordination takes place through the deprotonated hydroxyl group, azomethine nitrogen and carbonyl oxygen. Four coordinated geometry was assigned to all the complexes on the basis of spectral studies. The anti-inflammatory activities of compounds are moderate. Co(II) complex exhibited highest activity among all the complexes. At lower dose level activity of Ni(II) and Cu(II) complexes is more compared to that of ligand. The analgesic activity of ligand has enhanced on complexation with Co(II), Ni(II) and Zn(II) metal ions. Among the compounds studied Co(II) complex has shown highest activity and is comparable with standard used.View full abstractDownload PDF (295K) -
Kazuki Ishikawa, Tomoo Hosoe, Takeshi Itabashi, Daigo Wakana, Kayoko T ...Article type: Note
2010 Volume 58 Issue 5 Pages 717-719
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSTwo new diketopiperazine metabolites, novoamauromine (1) and ent-cycloechinulin (2) have been isolated from Aspergillus novofumigatus CBS117520. The structures of 1 and 2 were established on the basis of spectroscopic and chemical investigation, including a detailed comparison of the spectroscopic and physico-chemical data of amauromine (3) and cycloechinulin (4).View full abstractDownload PDF (238K) -
Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Ninh Khac Ban, Nguyen ...Article type: Note
2010 Volume 58 Issue 5 Pages 720-724
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSFourteen cucurbitane-type triterpene glycosides (1—14) were isolated from a methanol extract of Momordica charantia fruits, including three new compounds, charantosides A—C (1, 5, 6). Their structures were elucidated by chemical and spectroscopic methods. All isolated compounds were evaluated for α-glucosidase inhibitory effect. Of which, 12 and 13 showed moderate inhibitory activity against α-glucosidase. Whereas, 2, 3, 6—11, and 14 showed weak inhibitory activity, and 1, 4, and 5 were inactive.View full abstractDownload PDF (252K) -
Chonticha Seeka, Somyote SutthivaiyakitArticle type: Note
2010 Volume 58 Issue 5 Pages 725-728
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSTwo 15β-hydroxycardenolides (1,2) and a 16α-hydroxycalactinic acid methyl ester (3) along with eleven known compounds including 16α-hydroxycalotropagenin, coroglaucigenin, 16α-hydroxycalotropin, calactinic acid, calotoxin, 6′-O-(E-4-hydroxycinnamoyl)desglucouzarin, 12β-hydroxycoroglaucigenin, frugoside, calotropagenin, 9,12,13-trihydroxyoctadeca-10(E),15(Z)-dienoic acid and R-(−)-mevalonolactone were isolated from the polar fraction of the CH2Cl2 extract, and n-BuOH extract of the leaves of this plant. The isolated compounds were evaluated for their inhibitory activities against a panel of cell lines.View full abstractDownload PDF (176K) -
Lu Lu, Jian-Chao Chen, He-Jiao Song, Yan Li, Yin Nian, Ming-Hua QiuArticle type: Note
2010 Volume 58 Issue 5 Pages 729-733
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSFive new triterpene bisglycosides, foetidinosides A (1), B (2), C (3), D (4) and E (5), including three of the cycloartane type, one of its derivative, and one of the lanostane type were isolated from the rhizomes of Cimicifuga foetida. Their structures were elucidated on the basis of spectroscopic data and chemical evidence. They were the first bisglycosides with acyclic side chains which were different from the typical triterpenes with side chains epoxidized with ring D in Cimicifuga species.View full abstractDownload PDF (388K) -
Guang-Yu Yang, Peng Fan, Rui-Rui Wang, Jing-Li Cao, Wei-Lie Xiao, Liu- ...Article type: Note
2010 Volume 58 Issue 5 Pages 734-737
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThree new dibenzocyclooctadiene lignans, schilancifolignans A—C (1—3), together with thirteen known ones, were isolated from the leaves and stems of Schisandra lancifolia. The structures of 1—3 were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1—3 were tested for their anti-human immunodeficiency virus-1 activities and showed weak bioactivities.View full abstractDownload PDF (230K) -
Takahiro Hosoya, Asami Nakata, Kazumasa Zaima, Jalifah Latip, Laily Bi ...Article type: Note
2010 Volume 58 Issue 5 Pages 738-741
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSTwo new dehydrohexahydroxydiphenoyl (DHHDP) esters of dihydrochalcone glycosides, papuabalanols A (1) and B (2) were isolated from the ethyl acetate extract of Balanophora papuana. Their structures were elucidated on the basis of spectroscopic data and chemical evidences. Papuabalanol A (1) showed moderate vasodilator effect on rat aorta and papuabalanol B (2) showed potent inhibition of mushroom tyrosinase and anti-melanogenesis in B16 mouse melanoma cells.View full abstractDownload PDF (192K) -
Naoki Iida, Yuka Inatomi, Hiroko Murata, Jin Murata, Frank A. Lang, To ...Article type: Note
2010 Volume 58 Issue 5 Pages 742-746
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSTwo new phenylpropanoid glycosides were isolated from the leaves and stems of Juniperus communis var. depressa (Cupressaceae) along with 14 known compounds. Their structures were determined by spectral analyses, in particular by 2D-NMR spectral evidence.View full abstractDownload PDF (334K) -
Hisashi Matsuda, Souichi Nakashima, Osama Bashir Abdel-Halim, Toshio M ...Article type: Note
2010 Volume 58 Issue 5 Pages 747-751
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSThe 90% aqueous ethanol extract of an Egyptian natural medicine, the roots of Bryonia cretica L., was found to exhibit a strong inhibitory effect on the proliferation of human leukemia U937 cells. By bioassay-guided fractionation, we isolated two new cucurbitane-type triterpene glycosides, bryoniaosides A and B, were isolated from the roots of Bryonia cretica L. together with 16 known cucurbitane-type triterpenes and glycosides. The chemical structures of bryoniaosides A and B were determined on the basis of chemical and spectroscopic evidence. Effects of principal cucurbitane-type triterpenes (cucurbitacins B, D, E, and J, 23,24-dihydrocucurbitacins B and E, and hexanorcucurbitacin D) on proliferation of the cells were examined. Cucurbitacins B and E showed the greater cytotoxic effects with IC50 values of 9.2 and 16 nM after 72 h, and their IC50 values were equivalent to that of camptothecin. An α,β-conjugated ketone moiety at the 22—24-positions and an acetoxy group at the 25-position are essential for the strong activity.View full abstractDownload PDF (284K) -
Wei Yi, Rihui Cao, Zhiyong Chen, Liang Yu, Huan Wen, Qin Yan, Lin Ma, ...Article type: Note
2010 Volume 58 Issue 5 Pages 752-754
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSIn continuing our program aimed to search for tyrosinase inhibitors, a series of novel 4-O-substituted phenylmethylenethiosemicarbazones were rational designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were also evaluated. A fair number of compounds were found to have significant tyrosinase inhibitiory activity. Particularly, the IC50 values of compounds 3a—g, 3j and 3s were of the same magnitude as tropolone, one of the best tyrosinase inhibitors known so far. Furthermore, the structure–activity relationships of these compounds were also investigated. All these data suggested that these molecules might be utilized for the development of new candidate for the treatment of dermatological disorders, and further development of such compounds may be of interest.View full abstractDownload PDF (173K) -
Kensuke Okuda, Hiroshi Deguchi, Takashi Hirota, Kenji SasakiArticle type: Note
2010 Volume 58 Issue 5 Pages 755-757
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSReaction of fused 2,3-dihydrofuro[2,3-b]pyridines with various nucleophiles (N and O) gave dihydrofuran ring cleaved products. The scope of this reaction was investigated in detail.View full abstractDownload PDF (300K) -
Tetsuya Kajimoto, Kenji Arimitsu, Minoru Ozeki, Manabu NodeArticle type: Note
2010 Volume 58 Issue 5 Pages 758-764
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSA glycosylation reaction was performed using a combination of thioglycoside and glycosyl sulfoxide, which were prepared with odorless p-octyloxybenzenethiol, as a glycosyl donor and an acceptor, respectively. Promising results were obtained when p-octyloxylphenyl N-phthaloyl-D-thio-glucosaminide was activated with N-iodosuccinimide (NIS) and triflic acid (TfOH) for glycosylation of the hydroxyl group of the C-6 position of derivatives of D-glucosyl sulfoxide. Successive reduction of the resulting disaccharyl sulfoxides provided the corresponding thioglycosides, which could be used as the glycosyl donors in another glycosylation reaction to afford trisaccharides in good yield. The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.View full abstractDownload PDF (402K) -
Hiroyuki Miyashita, Makiko Nishida, Masafumi Okawa, Toshihiro Nohara, ...Article type: Note
2010 Volume 58 Issue 5 Pages 765-768
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSFour new ent-kaurane diterpenoids (16R)-ent-kauran-17,19-diol (1), (16R)-17-hydroxy-ent-kauran-19-oic acid (2), (16S)-17-hydroxy-ent-kauran-19-oic acid (3), and (16R)-17-dimethoxy-ent-kauran-19-oic acid (4) have been isolated from the fresh fruits of Annona cherimola together with eight known compounds. Their structures are determined on the basis of spectroscopic data and optical rotation.View full abstractDownload PDF (151K)
Communicatins to the Editor
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Kenjirou Higashi, Saori Ideura, Haruka Waraya, Waree Limwikrant, Kunik ...Article type: Communication to the Editor
2010 Volume 58 Issue 5 Pages 769-772
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSA crystalline ternary complex was prepared by sealed-heating of naproxen (NPX) with a flurbiprofen (FBP)/γ-cyclodextrin (γ-CD) inclusion complex. The dissolution rates of NPX and FBP in the ternary complex were almost the same, indicating that FBP and NPX from the complex dissolved simultaneously. The ternary CD complex showing a fascinating dissolution property could be a new formulation for combination therapies.View full abstractDownload PDF (483K)
Errata
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Sanjay Singh, Rajeev Soni, Manoj Kumar Rawat, Achint Jain, Shripad Bhi ...Article type: Errata
2010 Volume 58 Issue 5 Pages 773
Published: May 01, 2010
Released on J-STAGE: May 01, 2010
JOURNAL FREE ACCESSDownload PDF (14K)
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