巻号一覧
62 巻, 8 号
選択された号の論文の17件中1～17を表示しています
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Review
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Takayuki Doi2014 年 62 巻 8 号 p. 735-743
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLThis paper describes the synthetic studies conducted on a marine natural product, cyclodepsipeptide apratoxin A. Total synthesis of the oxazoline analogue of apratoxin A was achieved. The conversion of oxazoline to thioamide, as well as thioamide formation from a serine-derived compound, were both unsuccessful. However, thiazoline formation from a cysteine-derived compound led to the total synthesis of apratoxin A. An in vivo study on synthetic apratoxin A revealed that it has potent antitumor activity, but with significant toxicity. Solid-phase synthesis of apratoxin A was accomplished using a preformed thiazoline derivative as a coupling unit. This method was used to synthesize several azido-containing analogues as precursors of molecular probes, and these analogues exhibited potent biological activity.抄録全体を表示PDF形式でダウンロード (1513K) HTML形式で全画面表示
Regular Articles
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Genki Terashi, Yuuki Nakamura, Hiromitsu Shimoyama, Mayuko Takeda-Shit ...2014 年 62 巻 8 号 p. 744-753
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLIn the absence of experimentally determined three dimensional (3D) structures of proteins, the prediction of protein structures using computational methods is a standard alternative approach in bioinformatics. When using the predicted protein models to compute the native structure of an unknown target protein, estimating the actual quality of the protein models is important for selecting the best or near-best model. Moreover, estimates of the differences between the protein models and the native protein structure are obviously useful to end users who can then decide on the utility of the models for their specific problems. This article describes two new single-model quality assessment (QA) programs, pure single-model QA method (psQA) and a template based QA method (tbQA), that we developed. psQA is a pure single-model QA program that uses a neural network method to predict residue–residue distance matrices of the native protein structures. tbQA is a quasi-single-model QA program that mainly uses target-template sequence alignments and template structures. The performance of these two model QA programs was analyzed in a data set of 24022 models for 94 targets from the 10th critical assessment of protein structure prediction (CASP10) experiment.抄録全体を表示PDF形式でダウンロード (1656K) HTML形式で全画面表示 -
Wipa Tupchiangmai, Saowanaporn Choksakulporn, Supinya Tewtrakul, Somsa ...2014 年 62 巻 8 号 p. 754-763
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTML
電子付録The highly directional hexasubstituted benzene moiety was used as the central scaffold to create new human immunodeficiency virus (HIV)-1 integrase inhibitors through the attachment of multiple active groups. A series of potential inhibitors having substituted polyhydroxylated mono, bis and tris-cinnamoyl derivatives connected on the scaffold were prepared through Claisen–Schmidt condensations with substituted benzaldehydes, followed by partial demethylation to uncover the active phenolic groups required for the interactions with the integrase enzyme active sites. Using a multiplate integration assay method, four compounds carrying at least two sets of interacting moieties were found to be relatively potent integrase inhibitors with IC50 values in the low micromolar range. The results confirmed that multiple polyhydroxylated groups were required on the platform in order to effectively interact with the enzyme. The results from molecular docking studies consistently complemented the experimental results and revealed the nature of the potential key binding interactions responsible for the apparent activity of the active compounds.抄録全体を表示PDF形式でダウンロード (1780K) HTML形式で全画面表示 -
Chun-hui Zhao, Jie Xu, Ying-qiu Zhang, Long-xuan Zhao, Bin Feng2014 年 62 巻 8 号 p. 764-771
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLA large number of bioactive pentacyclic triterpenoids have been shown to have multiple biological activities. This study was conducted to evaluate the inhibitory activities of 6 newly synthesized and novel pentacyclic triterpenoids against enterovirus 71 (EV71). The parent compound, ursolic acid (UA), showed the greatest inhibitory activity against EV71, while oleanolic acid (OA), asiatic acid (AA), and synthetic derivatives of 18-β-glycyrrhetinic acid (GA) and OA also exhibited inhibitory effects, although to lesser extents. The results suggest these compounds show potential for further optimization as antiviral candidates for treatment of EV71 infections.抄録全体を表示PDF形式でダウンロード (922K) HTML形式で全画面表示 -
Shizuyo Horiyama, Yuta Takahashi, Mayuko Hatai, Chie Honda, Kiyoko Suw ...2014 年 62 巻 8 号 p. 772-778
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLCigarette smoke contains many harmful chemicals, which contribute to the pathogenesis of smoking-related diseases such as chronic obstructive pulmonary disease, cancer and cardiovascular disease. The cytotoxicity of cigarette smoke is well documented, but the definitive mechanism behind its toxicity remains unknown. Ingredients in cigarette smoke are known to deplete intracellular glutathione (GSH), the most abundant cellular thiol antioxidant, and to cause oxidative stress. In the present study, we investigated the mechanism of cigarette smoke extract (CSE)-induced cytotoxicity in B16-BL6 mouse melanoma (B16-BL6) cells using liquid chromatography-tandem mass spectrometry. CSE and ingredients in cigarette smoke, methyl vinyl ketone (MVK) and crotonaldehyde (CA), reduced cell viability in a concentration-dependent manner. Also, CSE and the ingredients (m/z 70, each) irreversibly reacted with GSH (m/z 308) to form GSH adducts (m/z 378) in cells and considerably decreased cellular GSH levels at concentrations that do not cause cell death. Mass spectral data showed that the major product formed in cells exposed to CSE was the GSH-MVK adduct via Michael-addition and was not the GSH-CA adduct. These results indicate that MVK included in CSE reacts with GSH in cells to form the GSH-MVK adduct, and thus a possible reason for CSE-induced cytotoxicity is a decrease in intracellular GSH levels.抄録全体を表示PDF形式でダウンロード (689K) HTML形式で全画面表示 -
Shan Qian, Quan Long Chen, Jin Long Guan, Yong Wu, Zhou Yu Wang2014 年 62 巻 8 号 p. 779-785
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLFirst, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of 1H-NMR, 13C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs’ inhibitory activity of Raddeanin A may contribute to its cytotoxicity.抄録全体を表示PDF形式でダウンロード (636K) HTML形式で全画面表示 -
Yasuo Inoue, Noboru Sekiya, Kazunori Katayama, Shoji Narutaki, Masanob ...2014 年 62 巻 8 号 p. 786-792
発行日: 2014/08/01
公開日: 2014/08/01
[早期公開] 公開日: 2014/05/23ジャーナル フリー HTMLStabilization against humidity of Limaprost (a prostaglandin E1 derivative), which is currently marketed as Opalmon®, was undertaken using β-cyclodextrin (β-CD). Aqueous solutions of Limaprost alfadex/dextran 40 were lyophilized with and without β-CD. Limaprost alfadex lyophilized with β-CD was more chemically stable in humid conditions than that without β-CD. Moreover, the addition of β-CD as an excipient to tablets of these lyophilized composites remarkably improved the stability of Limaprost, and Limaprost in this moisture-resistant formulation was chemically stable for 19 weeks at 30°C, 75% relative humidity (R.H.). Chemical analysis of Limaprost and its degradation products indicated that degradation proceeded in the inclusion form (i.e., within the CD cavity). Solid 2H-NMR spectroscopic studies showed that β-CD constrained the molecular mobility of water in the solid state. These results suggested that the stabilization of Limaprost by β-CD was at least partly due to the restricted molecular mobility of water, which acted as a catalytic species for the degradation, and also to the protection of the five-membered ring of Limaprost from water catalytic dehydration through inclusion complex formation with β-CD.抄録全体を表示PDF形式でダウンロード (1421K) HTML形式で全画面表示 -
Seh Hyon Song, Kyung Min Lee, Jong Boo Kang, Sang Gon Lee, Myung Joo K ...2014 年 62 巻 8 号 p. 793-798
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLIn order to develop topical preparations of voriconazole (VRC) for the treatment of mycotic infections of the skin, a nanostructured lipid carrier-based hydrogel (NLC-gel) formulation was developed and its physical characteristics, in vitro skin permeation, and retention profiles were examined. A VRC-loaded NLC dispersion, consisting of Precirol ATO 5, Labrafil 1944 CS, and Tween 80, was prepared by high-pressure homogenization and embedded into Carbopol 940 hydrogel. The lipid nanoparticles in the hydrogel were approximately 210 nm in size, with a spherical shape and zeta potential of −30 mV. In a skin permeation study using a Franz diffusion cell mounted with depilated mouse skin, the NLC-gel was superior to conventional cream and microemulsion-based gel formulations, showing 2.8- and 1.7-fold greater flux values, respectively. In addition, the NLC-gel led to markedly greater accumulation of VRC in deeper skin layers as compared with the reference formulations. In conclusion, the novel topical formulation reported here represents an alternative treatment for skin infections such as candidiasis, with less potential for systemic adverse effects than oral therapy.抄録全体を表示PDF形式でダウンロード (1129K) HTML形式で全画面表示 -
Fumihiko Ogata, Ayaka Ueda, Naohito Kawasaki2014 年 62 巻 8 号 p. 799-805
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLIn this research, gibbsite (GB) samples calcined at 200–1000°C (GB200–GB1000) were produced. These GBs were used to adsorb orthophosphoric, pyrophosphoric, and tripolyphosphoric acids from aqueous solutions. The properties (amounts of hydroxyl groups, specific surface areas, mean pore diameters, and solution pHs) of the GBs were investigated, and their adsorption capacities for phosphoric acids evaluated. The amount of hydroxyl groups (0.46 mmol/g) and specific surface area (295.3 m2/g) of GB400 were greater than those of the other GBs. The mechanism of phosphoric acid adsorption on the GBs was related to the amount of hydroxyl groups and specific surface area. The optimal pH for phosphoric acid adsorption by GBs was 2.0–3.0. Equilibrium adsorption was reached within 24 h. The adsorption processes followed a pseudo-second-order kinetic model (correlation coefficient, 0.998–0.999). The adsorption capacity increased with increasing temperature. The adsorption isotherm data fitted the Langmuir (correlation coefficient: 0.921–0.992) and Freundlich (correlation coefficient: 0.948–0.997) equations well. Our results will be useful when developing methods for the adsorption of phosphoric acids from aqueous solutions.抄録全体を表示PDF形式でダウンロード (1533K) HTML形式で全画面表示 -
Hidemichi Mitome, Erika Sugiyama, Hitoshi Sato, Kazuki Akira2014 年 62 巻 8 号 p. 806-809
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTML13C-Labeled lidocaine, 2-di[1-13C]ethylamino-N-(2,6-dimethylphenyl)acetamide (1), was synthesized from [1-13C]acetic acid in six steps, as a probe for a breath test to evaluate in vivo cytochrome P450 activity. The measurement of 13CO2 in breath was successfully performed following oral administration of 13C-lidocaine 1 to mice.抄録全体を表示PDF形式でダウンロード (326K) HTML形式で全画面表示 -
Koichi Takao, Ryo Ishikawa, Yoshiaki Sugita2014 年 62 巻 8 号 p. 810-815
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLA series of 3-styrylchromone derivatives (4–20) were synthesized and the structure–activity relationships for α-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC50=17 µM; 20: EC50=23 µM) and α-glucosidase inhibitory activity (15: IC50=16 µM; 20: IC50=10 µM). Our data suggest that 3-styrylchromone derivatives are novel α-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.抄録全体を表示PDF形式でダウンロード (446K) HTML形式で全画面表示
Notes
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Jyunichi Koyanagi, Tomoyo Kamei, Miyuki Ishizaki, Hiroshi Nakamura, Ta ...2014 年 62 巻 8 号 p. 816-819
発行日: 2014/08/01
公開日: 2014/08/01
[早期公開] 公開日: 2014/06/10ジャーナル フリー HTMLAn improved synthetic route has been developed for the preparation of methyl 1-fluoroindan-1-carboxylate (FICA Me ester) from 1-indanone. Methyl 4-methyl-1-fluoroindan-1-carboxylate (4-Me-FICA Me ester) was also prepared following the same procedure.抄録全体を表示PDF形式でダウンロード (392K) HTML形式で全画面表示 -
Kazuaki Katakawa, Ayaka Sato, Mari Iwasaki, Tomofumi Horikawa, Takuya ...2014 年 62 巻 8 号 p. 820-823
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLWe describe the total synthesis of angular chromenoquinone 1 isolated from Conospermum plants. Iodophenol, a precursor of pyranobenzyne, was prepared by Claisen rearrangement of an iodoresorcinol derivative. Diels–Alder reaction of the pyranobenzyne and a substituted furan proceeded in low regioselectivity to afford desired 1 and its regioisomer.抄録全体を表示PDF形式でダウンロード (510K) HTML形式で全画面表示 -
Xin-Chuan Tian, Xing Huang, Dan Wang, Feng Gao2014 年 62 巻 8 号 p. 824-829
発行日: 2014/08/01
公開日: 2014/08/01
[早期公開] 公開日: 2014/06/10ジャーナル フリー HTML
電子付録An efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones was developed. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with NaOH afforded the monosodium salts of benzoylene urea. Finally, HCl treatment afforded the desired products in near-quantitative yields. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration. The aqueous filtrate was the only waste generated from the reaction. We scaled up the reaction to 1 kg starting material, thus establishing an alternative approach for the green synthesis of quinazoline-2,4(1H,3H)-diones in the chemical and pharmaceutical industries.抄録全体を表示PDF形式でダウンロード (710K) HTML形式で全画面表示 -
Masateru Ono, Kousuke Akiyama, Kazutaka Yamamoto, Tomoko Mineno, Masaf ...2014 年 62 巻 8 号 p. 830-835
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLFour new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction obtained from the seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.抄録全体を表示PDF形式でダウンロード (572K) HTML形式で全画面表示 -
Susumu Kayama, Norihiko Tani, Yuka Takahashi, Hidetsugu Tabata, Shinta ...2014 年 62 巻 8 号 p. 836-838
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLWe previously reported the atropisomeric properties of 2′-t-butyl-6′-iodo-substituted N-benzoyl-3-bromocarbazole, i.e., the steric or electronic effects of the substituents restricted the rotation about the N–C7′ and C7′–C1′ bonds to separate four stereoisomers (cis/trans for the N–C7′ axis, aR/aS for the C7′–C1′ axis). Furthermore, the 2′-t-butyl-6′-iodo-substituted N-benzoyl 3-bromocarbazole was confirmed to be a gear molecule, in which the rotation about the C7′–C1′ bond was in perfect concert with that about the N–C7′ bond. Herein, we report a unique crystallization-induced diastereomeric transformation found in this molecule. In the isolation process, where the product is recrystallized from the diastereoisomeric mixture, in situ isomerization and selective crystallization could lead to a diastereomeric transformation, and a mixture of diastereomers (trans/cis=54 : 46) was converted to trans-isomer-enriched crystals (trans/cis>96 : 4) in 95% yield. Conformational analysis clarified the preference for the trans versus cis isomer.抄録全体を表示PDF形式でダウンロード (559K) HTML形式で全画面表示 -
Masateru Ono, Gen Kawakami, Ayako Takigawa, Kiyotaka Kabata, Masafumi ...2014 年 62 巻 8 号 p. 839-844
発行日: 2014/08/01
公開日: 2014/08/01
ジャーナル フリー HTMLFour new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)–XIII (4), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The sugar moieties of 1–4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1–4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.抄録全体を表示PDF形式でダウンロード (434K) HTML形式で全画面表示
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