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Volume 58, Issue 6
Displaying 1-22 of 22 articles from this issue
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Regular Articles
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Shigeki Kobayashi, Akihiko Takagi, Toshiyuki Chikuma, Osamu Tamura, Ei ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 775-781
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSOxidative thymine damage was investigated using a new non-heme oxygenation model, Fe(MeCN)62+–H2O2–Ac2O, based on high-spin Fe(MeCN)62+ in a non-aqueous solution, Ac2O–MeCN. Thymine and 1,3-dimethylthymine oxidized by the system gave the corresponding trans-thymine glycol derivatives in good yield. Thymineglycol is equivalent to an oxidative product as a measure of oxidative DNA damage in living cells. It is suggested that the activation of Fe(MeCN)62+–H2O2–Ac2O in Ac2O–MeCN forms the oxoiron O=FeIV(AcO)(MeCN)4+ as an active species via a hetelolytic two-electron mechanism, not a Haber–Weiss–Fenton-type reaction with a one-electron process by treatment with a radical scavenger. In addition, we also demonstrated the transition state (TS) for the interaction between thymine and O=FeIV(AcO)(MeCN)4+ in the triplet spin (spin multiplicity; M=3). This model of oxidative thymine damage may provide new insight into the oxidative mechanism of thymine glycol production in non-aqueous reactions of thymine.View full abstractDownload PDF (855K) -
Surendra Ganeshlal Gattani, Pankaj Jayantilal Savaliya, Veena Shailend ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 782-787
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSAn objective of the present study was to develop alginate/hydroxypropyl methylcellulose (HPMC) based floating-mucoadhesive beads of clarithromycin to provide prolonged contact time of antibiotic to treat stomach ulcer. Floating-mucoadhesive beads were prepared and characterized for in vitro performance followed by investigation of ex vivo study in albino-wistar rats. Beads were prepared by ionic gelation technique where calcium chloride used as gelating agent and incorporated liquid paraffin for floating of the beads. Prepared beads were evaluated extensively for particle size, drug entrapment; swelling and surface morphology by using scanning electron microscopy. X-ray radioimaging study in rabbits, in vitro mucoadhesion using rat stomach mucosal membrane and in vitro drug release studies were carried out. Ex vivo performance of alginate-HPMC beads were studied using albino rats in comparison to simple alginate-calcium beads. Alginate-HPMC beads may be suitable floating-muco-adhesive drug delivery system for delivering clarithromycin to treat stomach ulcers.View full abstractDownload PDF (2417K) -
Xiongwei Xu, Qihuang Lin, Ailin Liu, Wei Chen, Xiuhua Weng, Changlian ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 788-793
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA sensitive and selective electrochemical method for simultaneous determination of ascorbic acid (AA), dopamine (DA), and uric acid (UA) using an electropolymerized bromothymol blue (BTB)-modified glassy carbon electrode (GCE) was developed. The electrochemically synthesized film was investigated using electrochemical impedance spectroscopy and voltammetric methods. The electrochemical behavior of the polymer-modified electrode depends on film thickness, i.e., the electropolymyerization time. The poly-BTB-modified GCE shows excellent electrocatalytic activity toward the oxidation of AA, DA, and UA in phosphate buffer solution (pH 5.0). The voltametric peak separations of AA/DA, DA/UA, and AA/UA on this modified electrode are 118 mV, 298 mV, and 455 mV, respectively. Therefore the voltammetric responses of these three compounds can be resolved well on the polymer-modified electrode, and simultaneous determination of these three compounds can be achieved. In addition, this modified electrode can be successfully applied to determine AA and DA in injection and UA in urine samples without interference.View full abstractDownload PDF (581K) -
Yoshiko Kagoshima, Makoto Mori, Eiko Suzuki, Nobue Kobayashi, Takahiro ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 794-804
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSCS-758 was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, phosphoryl ester prodrugs were designed. In this study, the synthesis and evaluation of these injectable prodrugs are described. Phosphoryl ester 17h was soluble in water, and was stable in both water and in a solid state. 17h was converted to CS-758 in human liver microsome and was also converted to CS-758 in rats after intravenous (i.v.) administration with good conversion speed and efficiency. 17h (i.v.) reduced the viable cell counts in kidneys in a murine hematogenous Candida albicans infection model and in lungs in a murine pulmonary Aspergillus fumigatus infection model, wherein the effects were comparable to or slightly superior to that of CS-758 (per os).View full abstractDownload PDF (1016K) -
Cherkupally Sanjeeva Reddy, Dasari Chandrashekar Rao, Vookanti Yakub, ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 805-810
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA new series of 3-(5-3-methyl-5-[(3-methyl-7-5-[2-(aryl)-4-oxo-1,3-thiazolan-3-yl]-1,3,4-thiadiazol-2-ylbenzo[b]furan-5-yl)methyl]benzo[b]furan-7-yl-1,3,4-thiadiazol-2-yl)-2-(aryl)-1,3-thiazolan-4-one 5a—j has been synthesized by the reaction of N2-[(E)-1-(4-methylphenyl)methylidene]-5-(3-methyl-5-[3-methyl-7-(5-[(E)-1-(4-methylphenyl)methylidene]amino-1,3,4-thiadiazol-2-yl)benzo[b]furan-5-yl]methylbenzo[b]furan-7-yl)-1,3,4-thiadiazol-2-amine 4a—j with thioglycolic acid. Chemical structures of all the new compounds were established by their IR, 1H-NMR, 13C-NMR, MS and elemental data. The 5a—j have been assayed for their nematicidal activity against Ditylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. The screened data reveal that, the 5e is most effective against D. myceliophagus and C. elegans with 50% lethal dose (LD50) of 170 and 190 ppm, respectively and is almost equal to the activity of standard levamisole. The 5h and 5j are also most active against C. elegans with LD50 of 200 ppm and D. myceliophagus with LD50 of 190 ppm, respectively. Further, the 5a—j were screened for their antibacterial activity against three representative, Gram-positive bacteria viz. Bacillus subtilis ATCC 6633, Staphylococcus aureus ATCC 6538p and Micrococcus luteus IFC 12708, and three Gram-negative bacteria viz. Proteus vulgaris ATCC 3851, Salmonella typhimurium ATCC 14028 and Escherichia coli ATCC 25922, and also screened for their antifungal activity against four fungal organisms viz. Candida albicans ATCC 10231, Aspergillus fumigatus HIC 6094, Trichophyton rubrum IFO 9185 and Trichophyton mentagrophytes IFO 40996. Most of these new compounds showed appreciable activity against the test bacteria and fungi, and emerged as potential molecules for further development.View full abstractDownload PDF (284K) -
Takayuki Kanaya, Satomi Yagi, Frank Schweizer, Tadahiro Takeda, Fumiyu ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 811-817
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSSynthetic access to three neutral glycosphingolipids from the parasite Schistosoma mansoni adult worm has been achieved. These structures differ significantly from those of other parasites and exhibit a unique structural motif termed “schisto-core” consisting of GalNAcβ1→4Glcβ1→sequence. We have synthesized glycosphingolipids, β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (1), β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (2) and β-D-Galp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (3).View full abstractDownload PDF (475K) -
Masahiro Tada, Jun Kurabe, Takashi Yoshida, Tomoyuki Ohkanda, Yusuke M ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 818-824
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSNatural catechol, quinone and quinone methide diterpenes with abietane (15-deoxyfuerstione, taxodione) and totarane (dispermone, 12,13-dihydroxy-8,11,13-totaratriene-6-one), and podocarpane (nimbidiol, deoxynimbidiol) skeletons were synthesized using ortho-oxidation of phenol with meta-chlorobenzoyl peroxide. Minimum inhibitory activities of these diterpenes and previously synthesized natural diterpenes were measured against methicillin-resistant Staphylococcus aureus (MRSA) and Propionibacterium acnes, which cause serious skin infection associated with acne. Abietaquinone methide and 8,11,13-totaratriene-12,13-diol showed potent activities against S. aureus (MRSA) and P. acnes, and no serious toxicity by oral dose to mice.View full abstractDownload PDF (461K) -
Shigeru Ito, Shinji Takechi, Kazuhide Nakahara, Nobuhiro Kashige, Tada ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 825-828
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSMonophenyl-substituted dihydropyrazines (Ph-DHP-1 to 4) of 2,3-dihydro-5,6-dimethylpyrazine (Me-DHP-1), which have the inductive effects of apoptosis and mutagenesis, were synthesized and their biological effect was investigated in terms of DNA strand-breakage. Differences between the phenyl- and methyl-substituted dihydropyrazines were examined.View full abstractDownload PDF (466K) -
Hiroyuki Yamazaki, Satoshi Ōmura, Hiroshi TomodaArticle type: Regular Article
2010 Volume 58 Issue 6 Pages 829-832
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA new mitorubrin congener designated 6′-hydroxy-3′-methoxy-mitorubrin (1) was isolated along with structurally related 4′-hydroxy-3′-methoxy-(S)-mitorubrin (2) and monomethyl-(S)-mitorubrin (3) from the culture broth of Penicillium radicum FKI-3765-2 by solvent extraction, octadecyl silyl (ODS) column chromatography and HPLC. The structure of 1 was elucidated by various spectral analyses, including NMR experiments. They have a common isochromane-like ring with a similar hydrophobic side chain. These compounds moderately potentiated miconazole activity against Candida albicans.View full abstractDownload PDF (177K) -
Eligeti Rajanarendar, Samala Raju, Atthunuri Siva Rami Reddy, Kundur G ...Article type: Regular Article
2010 Volume 58 Issue 6 Pages 833-839
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSWe report a mild, fast, highly efficient and eco-friendly protocol for the green synthesis of pyrrolo[2,3-d]isoxazoles and a new series of novel benzyl bis-pyrrolo[2,3-d]isoxazoles from nitro styrylisoxazoles in SnCl2-ionic liquid by reductive cyclization. These reactions were performed at ambient temperature which resulted in good yields in short reaction time, without requiring any organic solvent and catalyst.View full abstractDownload PDF (278K)
Notes
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De-Wu Zhang, Gui-Hai Li, Qun-Ying Yu, Sheng-Jun DaiArticle type: Note
2010 Volume 58 Issue 6 Pages 840-842
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSThree new 4-hydroxyisoflavans, named lyratin A (1), lyratin B (2) and lyratin C (3), along with a known compound, 4,7,2′trihydroxy-4′-methoxyisoflavan (4), were isolated from the whole plant of Solanum lyratum. Their structures were established by means of detailed physical data analyses. In vitro, four compounds showed anti-inflammatory activities with inhibitory ratios of release of β-glucuronidase from polymorphonuclear leukocytes of rats in the range of 30.3—38.6% at 10 μM.View full abstractDownload PDF (214K) -
Chun-Nian He, Yong Peng, Li-Jia Xu, Zheng-An Liu, Jing Gu, Ai-Guo Zhon ...Article type: Note
2010 Volume 58 Issue 6 Pages 843-847
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSThree new oligostilbenes, trans-suffruticosol D (1), cis-suffruticosol D (2), and cis-gnetin H (7), were isolated along with the eight known stilbenes, trans-resveratrol (3), trans-ε-viniferin (4), cis-ε-viniferin (5), gnetin H (6), suffruticosol A (8), suffruticosol B (9), suffruticosol C (10), and cis-ampelopsin E (11) from the seeds of Paeonia suffruticosa. Compounds 3—6 were isolated for the first time from this plant species, and compound 11 was isolated for the first time from the genus Paeonia. The structures of the new compounds were elucidated based on spectral analyses, including 1D and 2D NMR experiments. The absolute configuration of compound 1 was determined by quantum chemical calculation of the electronic circular dichroism and comparison with the experimental circular dichroism spectrum.View full abstractDownload PDF (507K) -
Shi-Yie Cheng, En-Hung Lin, Zhi-Hong Wen, Michael Yen-Nan Chiang, Chan ...Article type: Note
2010 Volume 58 Issue 6 Pages 848-851
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSChemical investigations of the Formosan soft coral Cespitularia hypotentaculata ROXAS led to the isolation of two new verticillane diterpenoids, cespitularins R and S (1, 2), along with seven known compounds (3—9). The structures of these isolated compounds were elucidated on the basis of extensive spectroscopic analysis and by comparison with those of reported in literature. The anti-inflammatory activity using RAW 264.7 macrophages of compounds 1—9 were evaluated in vitro.View full abstractDownload PDF (517K) -
Wei-Lie Xiao, Liu-Meng Yang, Hai-Bo Zhang, Yong-Bo Xue, Guang-Yu Yang, ...Article type: Note
2010 Volume 58 Issue 6 Pages 852-855
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA new nortriterpenoid, 20-hydroxymicrandilactone D (1) and a novel lignan glycoside, lancilignanside A (2) were isolated from leaves and stems of Schisandra lancifolia, together with three known nortriterpenoids (3—5) and nine known phenolics (6—14). The structures of new compounds 1 and 2 were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences. In addition, compounds 1—2, 6—7, and 9—11 showed anti-human immunodeficiency virus (HIV)-1 activities with 50% effective concentration (EC50) in the range of 3.0—99.0 μg/ml. Compound 12 was not bioactive in this assay with EC50 more than 200 μg/ml.View full abstractDownload PDF (344K) -
Yan Peng, Jianxian Zheng, Riming Huang, Yifei Wang, Tunhai Xu, Xuefeng ...Article type: Note
2010 Volume 58 Issue 6 Pages 856-858
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA new polyhydroxy sterol ester, (25S)-5α-cholestane-3β,6α,7α,8,15α,16β-hexahydroxyl-26-O-14′Z-eicosenoate (1), together with seven known steroid derivatives (2—8), were isolated from the EtOH extract of the whole body of China Sea starfish Asterina pectinifera. The structure of 1 was determined by using extensive spectra analysis (IR, 1D and 2D NMR, and MS), chemical degradation, and comparison with the known compound (25S)-5α-cholestane-3β,6α,7α,8,15α,16β,26-heptol (2). All the isolates were evaluated for their antiviral activity against herpes simplex virus type 1 (HSV-1) and their cytotoxicity against human liver carcinoma HepG2 cell line in vitro. Compounds 3—6, and 8 exhibited antiviral activity against HSV-1 virus with the minimal inhibitory concentration (MIC) values of 0.2, 0.05, 0.2, 0.22, and 0.07 μM, respectively. While compounds 4 and 5 exhibited cytotoxicity against HepG2 cells with IC50 values of 0.2 and 1.6 μM, respectively.View full abstractDownload PDF (189K) -
Hari Prasad Devkota, Masato Watanabe, Takashi Watanabe, Shoji YaharaArticle type: Note
2010 Volume 58 Issue 6 Pages 859-861
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSTwo new C-methyl flavonoids, (2R,3S)-6,8-di-C-methyldihydrokaempferol (1) and (2R,3R)-6,8-di-C-methyldihydrokaempferol (2) were isolated from the aerial parts of Diplomorpha canescens (MEISN.) C. A. MEYER along with eleven known flavonoids such as genkwanin (3), rhamnocitrin 3-O-β-D-glucopyranoside (4), genkwanin 5-O-β-D-glucopyranoside (5), apigenin (6), kaempferol (7), kaempferol 3-O-β-D-glucopyranoside (8), rhamnetin 3-O-β-D-glucopyranoside (9), luteolin (10), quercetin (11), quercetin 3-O-β-D-glucopyranoside (12) and genkwanin 5-O-primeveroside (13). Structures of these compounds were elucidated on the basis of spectroscopic data.View full abstractDownload PDF (159K) -
Takashi Masuko, Shuhei Yoshida, Koichi Metori, Yasuo Kizawa, Tadashi K ...Article type: Note
2010 Volume 58 Issue 6 Pages 862-867
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSThe novel water-soluble N-methyl-D-aspartate (NMDA) receptor antagonists, N-{4-[4-(4-Guanidinobutylamino)butylamino]butyl}-p-toluenesulfonamide trihydrochloride (1a, TsHSPMG), N-{4-[4-(4-Guanidinobutylamino)butylamino]butyl}butane-1-sulfonamide trihydrochloride (1b, BsHSPMG), N-{3-[4-(3-Guanidinopropylamino)butylamino]propyl}-p-toluenesulfonamide trihydrochroride (2a, TsSPMG) and N-{3-[4-(3-Guanidinopropylamino)butylamino]propyl}butane-1-sulfonamide trihydrochroride (2b, BsSPMG), were synthesized, and the effects of these polyamine derivatives on NMDA receptors were studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. Although spermine potentiates 153% and 310% of NMDA (NR1A/NR2B) receptors in the presence of saturated and unsaturated glycine, respectively, all the novel polyamine derivatives, TsHSPMG (1a), BsHSPMG (1b), TsSPMG (2a) and BsSPMG (2b), significantly inhibited NR1A/NR2B receptors in both conditions. The degree of NMDA receptor inhibition by TsHSPMG (1a) and BsHSPMG (1b) was stronger than that by TsSPMG (2a) and BsSPMG (2b).View full abstractDownload PDF (403K) -
Kou Wang, Ming-Ming Li, Xuan-Qin Chen, Li-Yan Peng, Xiao Cheng, Yan Li ...Article type: Note
2010 Volume 58 Issue 6 Pages 868-871
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSPhytochemical investigation on the methanol extract of Brainea insignis led to the isolation of 16 phenolic compounds, including an unusual flavanol coupled with phenylpropyl and shikimic acid units, brainicin (1), and a new flavonol acylglycosides brainoside B (2). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis. Compounds 1—5 were evaluated for their cytotoxic effects. However, none of the compounds showed significant cytotoxic activity against the HL-60, A549, SMMC-7721, MCF-7, SW480 cell lines (IC50>40 μM).View full abstractDownload PDF (293K) -
Hiroaki Saito, Ryo Iwai, Taketo Uchiyama, Muneharu Miyake, Shinichi Mi ...Article type: Note
2010 Volume 58 Issue 6 Pages 872-874
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSCinchona alkaloids are effective additives for enantioselective O–H insertion of α-phenyldiazoacetate and water by rhodium(II) complexes. Addition of silica gel promotes O–H insertion in the reaction rate and the reaction proceeds smoothly at less than the freezing point of water, e.g., −10 °C, and provided mandelate in up to 50% ee. The results reported here are the highest asymmetric inductions obtained to date for O–H insertions via a Rh-carbenoid.View full abstractDownload PDF (199K) -
Hiroshi Yamada, Akina Shirai, Keisuke Kato, Junko Kimura, Hideaki Ichi ...Article type: Note
2010 Volume 58 Issue 6 Pages 875-878
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSA novel fluorescent chelating ligand, 2,4-[bis-(2-hydroxy-3-methoxybenzylidene)]-dihydrazinoquinazoline (HBQZ), was synthesized, and the fluorescence characteristics of its complex with metal ions were investigated. Among the 36 different metal ions tested in this study, it was found that HBQZ emits intense fluorescence at 506 nm with an excitation wavelength of 414 nm in the presence of Zn2+. The fluorescence intensity was almost constant in the pH range 3.5—10.5. Complexes of other metal ions with HBQZ did not show fluorescence, and the detection limit of Zn2+ was approximately 250 nM (16 ppb). The proposed method was applied to the validation test of a bioactive compound containing Zn2+ in its structure—an antibacterial and antifungal reagent, zinc pyrithione (ZnPT). In order to effectively release Zn2+ from ZnPT, a pretreatment procedure involving heating with H3PO4 at 100 °C for 60 min was adopted. Under these conditions, a linear calibration curve was obtained in the ZnPT concentration range of 0.79—15.7 μM (0.25—5.0 ppm); the correlation coefficient and the relative standard deviation were 0.996 and within 3.1% (n=5), respectively.View full abstractDownload PDF (172K)
Communicatin to the Editor
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Shenggu Xie, Su ZengArticle type: Communication to the Editor
2010 Volume 58 Issue 6 Pages 879-883
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSStereoselective glucuronidation of propafenone and its β-blocker analogues by human recombinant UGT1A3 and UGT1A9 from the recombinant baculovirus in insect sf9 cells was studied. The glucuronides produced in incubation mixtures were assayed by HPLC equipped with UV detector, and identified by β-glucuronidase. The stereoselective glucuronidation was measured by pre-column 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocynate (GITC) derivatization HPLC method for propafenone and esomolol. In all of ten β-blocker drugs studied, six showed the glucuronidation activity with UGT1A9, while four with UGT1A3. From roughly quantitative stereoselective glucuronidation study of racemic β-blocker analogues by UGT1A9, propranolol had a high ratio of the ratios of S- to R-isomer glucuronide (S-G/R-G), about 4.3, the ratios of terbutaline, atenolol and esomolol were 3.3, 3.1 and 2.8 respectively, sotalol and propafenone were 2.3 and 2.0. In a word, S-isomers of these drugs were glucuronidated by human UGT1A9 much faster than their antipodes.View full abstractDownload PDF (365K)
Retraction
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Shu-Hua Qi, Si Zhang, Cheng-Hai Gao, Qin-Xing LiArticle type: Retraction
2010 Volume 58 Issue 6 Pages 884
Published: June 01, 2010
Released on J-STAGE: June 02, 2010
JOURNAL FREE ACCESSDownload PDF (17K)
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