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Volume 57, Issue 10
Displaying 1-33 of 33 articles from this issue
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Review
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Masahiro OnoArticle type: Review
2009 Volume 57 Issue 10 Pages 1029-1039
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSCurrently, the development of radiotracers for in vivo imaging of β-amyloid plaques in Alzheimer's disease (AD) brains is an important, active area of molecular imaging. Postmortem brains of AD patients reveal neuropathologic features: the presence of β-amyloid plaques and neurofibrillary tangles, which contain β-amyloid peptides and highly phosphorylated tau proteins. Increases in the concentration of β-amyloid in the course of the disease lead to changes in AD brains. Thus, when used in combination with positron-emission tomography/single-photon emission computed tomography (PET/SPECT), β-amyloid imaging agents could serve as surrogate markers for the early diagnosis and neuropathogenetic studies of AD. Furthermore, quantitative evaluation of β-amyloid plaques in the brain could facilitate the evaluation of the efficacy of antiamyloid therapies that are currently being investigated. This paper reviews our research on the development of PET/SPECT imaging agents for in vivo detection of β-amyloid plaques in Alzheimer's brains.View full abstractDownload PDF (3290K)
Regular Articles
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Improvement of Dissolution Property of Poorly Water-Soluble Drug by Supercritical Freeze GranulationRyoichi Sonoda, Yuko Hara, Tomohiro Iwasaki, Satoru WatanoArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1040-1044
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThe dissolution property of the poorly water-soluble drug, flurbiprofen (FP) was improved by a novel supercritical freeze granulation using supercritical carbon dioxide. Supercritical freeze granulation was defined as a production method of the granulated substances by using the dry ice to generate intentionally for the rapid atomization of the supercritical carbon dioxide to the atmospheric pressure. This process utilized a rapid expansion of supercritical solutions (RESS) process with the mixture of the drug and lactose. In the supercritical freeze granulation, needle-like FP fine particles were obtained which adhered to the surface of lactose particles, which did not dissolve in supercritical carbon dioxide. The number of FP particles that adhered to the surface of particles decreased with an increase in the ratio of lactose added, leading to markedly improve the dissolution rate. This improvement was caused not only by the increase in the specific surface area but also the improvement of the dispersibility of FP in water. It is thus concluded that the supercritical freeze granulation is a useful technique to improve the dissolution property of the poorly water-soluble flurbiprofen.View full abstractDownload PDF (1079K) -
Feng-Qian Li, Yi-Bo Fei, Xu Chen, Xian-Ju Qin, Ji-Yong Liu, Quan-Gang ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1045-1049
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFocused on the natural biodegradable material of chitosan (CS), this investigation concerned its spray-dried nanoparticles-in-microparticles (NiMPs) modified with ulex europaeus agglutinin (UEA). Chitosan nanoparticles were obtained by ionotropic gelation process with pentasodium tripolyphosphate as gelatinizer. Then UEA lectin was bound onto the CS nanoparticles activated by glutaraldehyde. The conjugated spherical UEA-CS-NiMPs, prepared by spray drying method, exhibited 12—85% coupling efficiency of UEA depending upon the amount of activator glutaraldehyde. And the UEA-grafted particles showed additional higher binding tendency with bovine submaxillary gland mucin as compared to the plain chitosan microparticles. Furthermore, the activity and intrinsic fucose-specificity of UEA were still maintained after the covalent modification. It is thus evident that the UEA anchored CS-NiMPs might be used as a potential drug delivery system targeted to the specific regions of gastrointestinal tract.View full abstractDownload PDF (574K) -
Yusuke Tanaka, Mitsugi Inkyo, Ryoko Yumoto, Junya Nagai, Mikihisa Taka ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1050-1057
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSIn order to improve the dissolution and oral absorption properties of poorly water soluble drugs such as omeprazole, albendazole and danazol, various dispersing agents were added to prepare nanopowder formulations using an ULTRA APEX MILL, which is a wet-mill instrument, and their physicochemical properties were evaluated. Using Pluronic F-108 or F-68 as dispersing agents, slurries containing drug particles having nanometer size were obtained for all model drugs tested. Omeprazole, a heat labile drug, was not degraded by wet-milling and the omeprazole nanoparticles in a milled slurry did not aggregate for 24 h after wet-milling. After lyophilization of these milled slurries containing drug nanoparticles, fine solid white nanopowders were obtained. Scanning electron microscopy (SEM) suggested that the model drugs were milled into nanometer size. X-ray powder diffraction (XRPD) patterns and Differential Scanning Calorimetry (DSC) curves confirmed that all milled drug nanopowders were crystalline, although milling of albendazole nanopowder transformed it to another crystal form. Wet-milling using an ULTRA APEX MILL offers a highly effective approach to produce stable drug nanopowders and is a very useful tool for bioavailability enhancement of poorly water soluble and heat labile drugs.View full abstractDownload PDF (1933K) -
Kenta Yamamoto, Akihiko Ito, Yoshiharu MachidaArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1058-1060
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSMedicinal carbon (MC) tablets were prepared with several saccharides to improve the formability and absorption ability of MC tablets made with maltitol (MT). The MC tablets were made by the wet granule compression method, in which maltitol, xylitol (XYL), mannitol (MAN), and sorbitol (SOR) were used as binders. Granule and tablet formability, tablet strength, disintegration, and MC adsorption potential were evaluated for each formulation. Acetaminophen (AA) was used in checking effect of binders on adsorption. Due to low water solubility, MAN was added only up to 30% (w/w) of MC; in greater concentrations, the tablet could not be formed. However, tablets formed easily when using XYL or SOR at 120% (w/w) of the MC amount. This result was similar for MT. The XYL, SOR, and MT tablets displayed sufficient hardness and rapid disintegration. The tensile strength of the SOR tablets exceeded that of the MT tablets, which in turn had greater tensile strength than the XYL tablets. In addition, the XYL tablets disintegrated more quickly than the MT tablets, which disintegrated more quickly than the SOR tablets. The MC adsorption capacity was slightly decreased by XYL and SOR, but to a lesser extent than the decrease caused by MT. Overall, XYL and SOR were superior to MT as binding agents for preparation of MC tablets. Therefore, we recommend preparing the tablets with XYL or SOR as a binder using the wet granule compression method to produce a compact dosage form of MC.View full abstractDownload PDF (103K) -
Takayuki Takatsuka, Tomoko Endo, Yao Jianguo, Kayo Yuminoki, Naofumi H ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1061-1067
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSIn this study, nanoparticles of various poorly water soluble compounds were prepared by wet milling that was carried out using a rotation/revolution mixer and zirconia balls. To be compared with Beads mill, rotation/revolution mixer has superior in very quick process (5 min) and needs very few amounts of zirconia balls (2.4 g) for pulverizing drugs to nanometer range. Phenytoin, indomethacin, nifedipine, danazol, and naproxen were selected as the standard poorly water soluble compounds. Various parameters of the rotation/revolution mixer were studied to decide the optimal pulverization conditions for the production of nanoparticles of the abovementioned compounds. The rotation/revolution speed, shape of the mixing vessel, amount of zirconia balls, and volume of the vehicle (methylcellulose solution) mainly affected the pulverization of the compounds. Using the mixer, phenytoin could be pulverized to nanoparticles within a few minutes. The particle size was confirmed by using a scanning electron microscope and a particle size analyzer. The crystallinity of the pulverized phenytoin particles was confirmed by X-ray diffractometry (XRD) and differential scanning calorimetry (DSC). It was observed that the pulverized phenytoin particles retained their crystallinity, and amorphous phenytoin was not detected. Particles of other poorly water soluble compounds were also reduced to the nanometer range by using this method.View full abstractDownload PDF (906K) -
Paruvathanahalli Siddalingam Rajinikanth, Brahmeshwar MishraArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1068-1075
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSGellan gum based floating beads containing clarithromycin (FBC) were prepared by iontotropic gelation method for stomach-specific drug delivery against Helicobacter pylori. The scanning electron microscope photograph indicated that prepared beads were spherical in shape with rough outer surface. Formulation variables such as concentrations of gellan, calcium carbonate and drug loading influenced the in vitro drug release characteristics of prepared beads. In vitro release rate of clarithromycin was corrected using first order degradation rate constant which is degraded significantly during the release study in simulated gastric fluid pH 2.0. Further, the absence of interactions between drug and polymer was confirmed by differential scanning calorimetry analysis. Kinetic treatment of the in vitro drug release data with different kinetic equations revealed matrix diffusion mechanism. Prepared beads showed good anti-microbial activity against isolated H. pylori strain. The prepared beads have shown good in vivo floating efficiency in rabbit stomach. The stability studies of beads did not show any significant changes after storage of beads at 40 °C/75% relative humidity for 6 months. The preliminary results from this study suggest that floating beads of gellan can be used to incorporate antibiotics like clarithromycin and may be effective when administered locally in the stomach against H. pylori.View full abstractDownload PDF (1050K) -
Naoto Sato, Qun Zhang, Chao-Mei Ma, Masao HattoriArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1076-1080
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFive new highly oxygenated lanostane-type triterpenoids [ganoderic acid GS-1 (1), ganoderic acid GS-2 (2), ganoderic acid GS-3 (3), 20(21)-dehydrolucidenic acid N (4) and 20-hydroxylucidenic acid A (5)] were isolated from the fruiting body of Ganoderma sinense, together with known compounds including 6 triterpenoids and 3 sterols. The structures of the new triterpenoids determined by spectroscopic means including 2D NMR were 7β-hydroxy-3,11,15-trioxo-lanosta-8,24(E)-dien-26-oic acid (1), 7β,15α-dihydroxy-3,11-dioxo-lanosta-8,24(E)-dien-26-oic acid (2), 12β-acetoxy-3β,7β-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid (3), 3β,7β-dihydroxy-11,15-dioxo-25,26,27-trinorlanosta-8,20-dien-24-oic acid (4), and 7β,20ξ-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid (5), respectively. Among these, ganoderic acid GS-2, 20-hydroxylucidenic acid N, 20(21)-dehydrolucidenic acid N and ganoderiol F inhibited human immunodeficiency virus-1 protease with IC50 values of 20—40 μM.View full abstractDownload PDF (181K) -
Noriyasu Hada, Yukihiko Shida, Natsuko Negishi, Frank Schweizer, Tadah ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1081-1088
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThree types of glycoclusters related to an amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi were synthesized. The glycoclusters were prepared from a common precursor and a simple approach for the rational design of a glycocluster was developed.View full abstractDownload PDF (311K) -
Fengming Xu, Hisashi Matsuda, Hiroki Hata, Kaoru Sugawara, Seikou Naka ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1089-1095
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThree new flavonoid glycosides (cissosides I, II, and III) and a new benzofuran-type stilbene (cissusin) were isolated from the methanolic extract of the aerial parts of Cissus sicyoides cultivated in Brazil. Their structures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on the release of β-hexosaminidase as a marker of degranulation in rat basophilic leukemia (RBL-2H3) cells were examined. Cissusin, flavonols (kaempferol, quercetin), flavones (7,3′,4′-trihydroxyflavone, lanceolatin B), pterocarpanes (homopterocarpin), chalcones (isoliquiritigenin, E-7-O-methylpongamol), and tryptanthrin markedly inhibited the release of β-hexosaminidase.View full abstractDownload PDF (225K) -
Megumi Fujita, Tomohiko Ueda, Tetsurou HandaArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1096-1099
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFormaldehyde is a well-known air impurity. The possibility was investigated in this study that pharmaceutical excipients commonly used in oral solid dosage forms might also be sources of formaldehyde. The results showed that formaldehyde is generated by the excipients lactose, D-mannitol, microcrystalline cellulose, low-substituted hydroxypropylcellulose, magnesium stearate and light anhydrous silicic acid. Since the quality and safety of pharmaceutical products can be significantly affected by the presence of formaldehyde, various amines were then investigated for their ability to decrease levels of formaldehyde using an aqueous solution system. Of the four amines investigated, only meglumine proved capable of reducing formaldehyde levels. The reaction product between formaldehyde and meglumine was obtained by fractionation using the preparative HPLC system and the structure was clarified by 1H-, 13C-NMR, various types of two-dimensional NMR and mass spectroscopy. The reaction product was determined to be a compound with a 1,3-oxazinane skeleton and containing one more carbon than meglumine. It was presumed that formaldehyde reacted with the secondary amino group in meglumine to form the reaction product via an iminium salt intermediate by cyclization. As meglumine is permitted to be used as a pharmaceutical excipient in both oral and parenteral dosage forms by regulations worldwide, the addition of meglumine to pharmaceutical products can be expected to contribute to the stabilization of many drug substances.View full abstractDownload PDF (199K) -
Kongkiat Trisuwan, Vatcharin Rukachaisirikul, Yaowapa Sukpondma, Souwa ...Article type: Regular Article
2009 Volume 57 Issue 10 Pages 1100-1102
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSTwo new fungal metabolites, penicipyrone (1), and penicilactone (2), were isolated from the marine-derived fungus Penicillium sp. PSU-F44 along with three known macrolides, (+)-brefeldin A (3), (+)-brefeldin C (4), and 7-oxobrefeldin A (5). Their antimicrobial activities against methicillin-resistant Staphylococcus aureus SK1 and Microsporum gypseum SH-MU-4 were examined.View full abstractDownload PDF (71K) -
Sadayuki Ishii, Mikio Fujii, Hiroyuki AkitaArticle type: Regular Article
2009 Volume 57 Issue 10 Pages 1103-1106
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFirst syntheses of sesquiterpene quinones (−)-tauranin and (−)-BE-40644 which exhibited strong cytotoxicity against several cancer cell lines, were achieved from (8aS)-albicanol obtained by enzymatic optical resolution. By comparison of the sign of specific rotation between synthetic (12bS)-BE-40644 and natural (−)-BE-40644, the absolute configurations of natural (−)-BE-40644 were determined to be 4aS, 6aS, 12aR, 12bS.View full abstractDownload PDF (182K)
Notes
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Makoto Obata, Masafumi Harada, Hiromi Ohi, Shiho Hirohara, Michael Got ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1107-1109
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSReactions of cis-diamminedichloroplatinum(II) (cisplatin) and 1,1-cyclobutanedicarboxylatodiammineplatinum(II) (carboplatin) with reduced glutathione, a tripeptide that is abundant in cells, were studied by means of X-ray absorption spectroscopy. Back-scattering amplitudes Fi(k) and phase shifts Φi(k) were theoretically derived, and validated by applying them to calculate extended X-ray absorption fine structure (EXAFS) oscillations of cisplatin and K2[Pt(SCN)4] in the solid state. EXAFS oscillations of reaction mixtures of cisplatin or carboplatin with reduced glutathione were fitted to the standard EXAFS equation using the Fi(k) and Φi(k) functions to give the coordination numbers of N or O atoms (NN/O) and of Cl or S atoms (NCl/S). For both cisplatin and carboplatin, the NN/O value decreased and the NCl/S values increased monotonically as the reaction proceeded. However, the reaction rate for carboplatin was significantly slower than that for cisplatin.View full abstractDownload PDF (140K) -
Yuko Ogawa, Tenji KonishiArticle type: Notes
2009 Volume 57 Issue 10 Pages 1110-1112
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSAs part of our search for sedative substances from natural sources, we isolated two novel amino acid amides connected with the fructopyranose, kwansonine A (1) and kwansonine B (2), together with three known amino acid amides, longitubanine A (3), longitubanine B (4), and pinnatanine (5), from Hemerocallis fulva L. var. sempervirens (ARAKI) M. HOTTA. The structures of 1 and 2 have been determined on the spectroscopic evidences as N2-(1-β-D-fructopyranosyl)-N5-(2′,5′-dihydro-2′-furyl-3′-hydroxymethyl)-γ-hydroxyglutamine and N2-(1-β-D-fructopyranosyl)-N5-(2-hydroxymethylbutadienyl)-γ-hydroxyglutamine. This is the first report on the isolation of amino acid amide N-furctoside from Hemerocallis genus plant.View full abstractDownload PDF (105K) -
Maurice Tsaffack, Jean Robert Nguemeving, Victor Kuete, Basile Le Sage ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1113-1118
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFebrifuquinone (1), a new vismione-anthraquinone coupled pigment and a new bianthrone named adamabianthrone (2), were isolated respectively, from the roots of Psorospermum febrifugum and from the bark of Psorospermum adamauense along with eight known compounds including: two bianthrones [(bianthrone A1 (3) and bianthrone A2b], one vismione [(vismione D (4)], one anthrone (3-geranyloxyemodin anthrone) and four anthraquinones [(1,8-dihydroxy-3-isoprenyloxy-6-methylanthraquinone, emodin (5), 3-geranyloxy-1,8-dihydroxy-6-methylanthraquinone and 2-geranyl-1,8-dihydroxy-6-methylanthraquinone]. Their structures were determined using modern spectroscopic methods including one and two dimensional-NMR techniques as well as MS. Compounds 1 and 2 showed significant antimicrobial activities against a wide range of bacteria and fungi.View full abstractDownload PDF (168K) -
David Dako Chiozem, Hanh Trinh-Van-Dufat, Jean Duplex Wansi, Cé ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1119-1122
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSTwo new friedelane-type triterpenes named 12α-hydroxyfriedelane-3,15-dione and 3β-hydroxyfriedelan-25-al, together with six known compounds were isolated from the stems of Drypetes paxii HUTCH. (Euphorbiaceae). Their structures were established on the basis of conventional 1 dimensional (1D) NMR methods, 2D shift-correlated NMR experiments and mass spectra. The five friedelane-type triterpene derivatives and one olean-12-ene triterpene saponin were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria, and they appeared to be modestly active.View full abstractDownload PDF (104K) -
Ming-Ming Li, Kou Wang, Zheng-Hong Pan, Xuan-Qin Chen, Li-Yan Peng, Ya ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1123-1125
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSTwo new sesquiterpene glucosides onitioside A (1) and dennstoside B (2), were isolated from the 95% EtOH extract of Dennstaedtia scabra (WALL.) MOORE, together with seven known compounds, onitisin (3), pterosin A (4), pinocembrin (5), pinocembrin 7-rutinoside (6), kaempferol (7), nicotiflorin (8), and galangin (9). Their structures were determined by extensive spectroscopic analysis.View full abstractDownload PDF (96K) -
Lin Zhang, Jiang-Yun Liu, Li-Zhen Xu, Shi-Lin YangArticle type: Notes
2009 Volume 57 Issue 10 Pages 1126-1128
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSA new withanolide, chantriolide C (1) and a new spirostanol saponin, chantrieroside A (2) were isolated from the rhizomes of Tacca chantrieri, together with another five known steroidal compounds. Their structures were established as (22R)-1α,12α-diacetoxy-2α,3α;6α,7α-diepoxy-27-[(β-D-glucopyranosyl)oxy]-5α-hydroxywith-24-enolide (1) and (25R)-spirost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1→2)-O-[O-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (2). The structures of the new saponins were determined by detailed analysis of their 1 dimensional (1D) and 2D NMR spectra, and chemical evidences.View full abstractDownload PDF (139K) -
Xuan-Qin Chen, Yan Li, Juan He, Kou Wang, Ming-Ming Li, Zheng-Hong Pan ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1129-1131
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThe 70% aqueous acetone extract of the aerial part of Viburnum foetidum var. foedidum afforded four new lignans (1—4) together with six known ones. The structures of the four new compounds were elucidated on the basis of 1D (dimensional), 2D-NMR, and mass spectral analysis. The structure of compound 1, with a novel spirocyclic moiety, was also confirmed by X-ray diffraction analysis. Compounds 1—10 were evaluated for their cytotoxic activity. However, none of the compounds showed significant cytotoxic activity.View full abstractDownload PDF (99K) -
Masateru Ono, Yumiko Nagasawa, Tsuyoshi Ikeda, Ryota Tsuchihashi, Masa ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1132-1135
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThree new labdane-type diterpenoids, viteagnusins F, G, and H, were isolated from the hexane extract of fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with seven known compounds including four labdane-type diterpenoids, one norlabdane-type diterpenoid, one aromadendrane-type sesquiterpenoid, and one flavonoid. The chemical structures of the three new labdane-type diterpenoids were determined on the basis of spectroscopic data as well as chemical evidence.View full abstractDownload PDF (231K) -
Masayoshi Arai, Shunsuke Ishida, Andi Setiawan, Motomasa KobayashiArticle type: Notes
2009 Volume 57 Issue 10 Pages 1136-1138
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSA new tetracyclic alkylpiperidine alkaloid, 22-hydroxyhaliclonacyclamine B (1), together with two known alkaloids, haliclonacyclamine A (2) and B (3), were isolated from a marine sponge of Haliclona sp. as anti-dormant mycobacterial substances. The chemical structure of 22-hydroxyhaliclonacyclamine B (1) was determined on the basis of spectroscopic study. The compounds 2 and 3 showed strong anti-mycobacterial activity against Mycobacterium smegmatis and M. bovis Bacille de Calmette et Guérin (BCG) under both aerobic condition and hypoxic condition inducing dormant state with minimum inhibitory concentrations (MICs) in the ranges of 1.0—2.5 μg/ml. In addition, the anti-microbial activity of compound 3 was bactericidal against M. bovis BCG under both aerobic and hypoxic conditions. The 22-hydroxy group in 1 was found to reduce anti-mycobacterial activity, because 22-hydroxyhaliclonacyclamine B (1) exhibited weaker anti-microbial activities against Mycobacterium bacilli with MICs in the ranges of 12.5—50 μg/ml.View full abstractDownload PDF (134K) -
Biswanath Das, Ponnaboina Thirupathi, Bommena Ravikanth, Rathod Aravin ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1139-1141
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSOne new homoisoflavonoid, (3E)-2,3-dihydro-6,7-dimethoxy-3[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and four naturally new analogues, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-dihydro-7-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one, along with four known homoisoflavonoids, bonducellin, sappanone A, 2′-methoxybonducellin and 7-O-methylbonducellin were isolated from aerial parts of Caesalpinia pulcherrima. The structures of the new compounds were elucidated by interpretation of their 1D and 2D NMR spectra. Syntheses of the naturally new compounds and the known compounds have also been accomplished. The antibacterial and antifungal activities of the isolated homoisoflavonoids were studied.View full abstractDownload PDF (128K) -
Kazuhiko Hayashi, Eiko Kujime, Hajime Katayama, Shigeki Sano, Motoo Sh ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1142-1146
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThe effective formation of 1-azabicyclo[3.1.0]hexane (5) by treatment of 2-(bromomethyl)pyrrolidine hydrobromide (4) with n-BuLi was established, with the reaction occurring by a rational reaction pathway via the open chain transition state 8 based on intermolecular Br···Li+ coordination (SN2 process). The reaction of 5 with electrophiles 13a—n gave the corresponding pyrrolidines 14a—n and piperidine 6, 15a—g, i—n. The selectivity of the products in this reaction appeared to be controlled by equilibrium.View full abstractDownload PDF (360K) -
Makoto Yoshida, Kentaro YamaguchiArticle type: Notes
2009 Volume 57 Issue 10 Pages 1147-1149
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThe first total synthesis of moloka'iakitamide (1), a recently reported bromotyrosine alkaloid from Pseudoceratina arabica with oxalamide moiety, was achieved in 7 steps from commercially available tyramine (26% overall).View full abstractDownload PDF (119K) -
Kazuto Washida, Tohru Yamagaki, Takashi Iwashita, Kyosuke NomotoArticle type: Notes
2009 Volume 57 Issue 10 Pages 1150-1152
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSTwo new galloylated monoterpene glycosides, 4-O-galloylalbiflorin and 4′-O-galloylpaeoniflorin, were isolated from the roots of Paeonia lactiflora that had been grown and processed in Nara prefecture, Japan. Their structures were elucidated based on spectroscopic analysis. These compounds showed androgen receptor (AR) binding activity.View full abstractDownload PDF (133K) -
Maki Jitsuno, Akihito Yokosuka, Hiroshi Sakagami, Yoshihiro MimakiArticle type: Notes
2009 Volume 57 Issue 10 Pages 1153-1157
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSThe bulbs of Habranthus brachyandrus (Amaryllidaceae) have been extensively analyzed for their chemical constituents, resulting in the isolation of eight flavan derivatives (1—8), four of which are new naturally occurring compounds; a new hydroxybutyric acid glucoside (9); three known phenolic compounds (10—12); and six known alkaloids (13—18). The structures of the new compounds were determined on the basis of spectroscopic analysis, including two-dimensional (2D) NMR data, and chemical evidence. The isolated compounds and a few derivatives were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.View full abstractDownload PDF (157K) -
Yasuhiro Inui, Masakazu Tanaka, Masanori Imai, Keitaro Tanaka, Hiroshi ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1158-1160
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSAsymmetric intermolecular hydroacylation between salicylaldehyde (1) and 1,5-hexadiene (2) using a combination of [RhCl(C8H14)2]2 (0.10 eq), (S)-BINAP (0.10 eq), and ZnBr2 (0.20 eq) afforded an enantiomerically enriched hydroacylated product iso-3 of 84% ee, along with an achiral product normal-3.View full abstractDownload PDF (129K) -
Akihito Yokosuka, Tomoe Sano, Ken Hashimoto, Hiroshi Sakagami, Yoshihi ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1161-1166
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSTwo new spirostanol glycosides (1, 2) and a new furostanol glycoside (3), together with nine known steroidal glycosides (4—12) were isolated from the leaves of Furcraea foetida (Agavaceae). The structures of the new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, HSC-2 human oral squamous carcinoma cells, and HSC-4 human oral squamous carcinoma cells.View full abstractDownload PDF (157K) -
Tomoko Mineno, Nana Nikaido, Hisao KansuiArticle type: Notes
2009 Volume 57 Issue 10 Pages 1167-1170
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSA convergent one-step transformation of tetrahydropyranyl (THP) ethers is described. According to our earlier experiments, indium(III) triflate has proven to be an efficient catalyst for the transformation of THP ethers into their corresponding acetates. In further intensive work, we have developed a useful transforming reaction of THP ethers using various anhydride moieties. Indium(III) triflate was confirmed as a suitable catalyst, furnishing good to excellent yields. The details of this one-step transformation are described.View full abstractDownload PDF (212K) -
Naonobu Tanaka, Takaaki Kubota, Yoshiki Kashiwada, Yoshihisa Takaishi, ...Article type: Notes
2009 Volume 57 Issue 10 Pages 1171-1173
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSFour new benzophenone-O-rhamnosides, petiolins F—I (1—4), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum, and the structures were elucidated by spectroscopic data and chemical means.View full abstractDownload PDF (85K)
Communicatins to the Editor
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Sanjeeva Yarkala, Sivakumar Amaravadi, Vinay U. Rao, Vijaykumar V, Sam ...Article type: Communications to the Editor
2009 Volume 57 Issue 10 Pages 1174-1177
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSRaloxifene HCl (RHCl) is known to be susceptible to oxidation and forms the corresponding N-oxide derivative as the primary degradation product. The purpose of this study was to evaluate the role of excipients on the generation of the N-oxide derivative from the corresponding RHCl–excipient binary mixtures. Binary mixtures of RHCl with crospovidone, povidone, magnesium stearate, Tween 80 and anhydrous lactose in drug: excipients ratio of 1 : 1 (crospovidone and povidone); 10 : 1 (Tween 80 and magnesium stearate) and 1 : 5 (anhydrous lactose) were prepared by both dry blending (trituration) and wet blending (to improve contact between drug and excipients). The prepared binary mixtures were then stored at 25, 40, 75 and 125 °C and generation of the N-oxide derivative was monitored over six months using a validated HPLC method. Pure drug and excipients stored similarly acted as controls. Further, all the individual excipients (used as control) were monitored for peroxide impurity generation using an in-house colorimetric method. The results showed that N-oxide generation was observed from all binary mixtures and the amount of N-oxide derivative formed were always higher from the mixtures prepared by wet blending and the amount of N-oxide derivative formed was dependent on storage temperature. This study thus shows that the presence of peroxide in the excipient and its role in oxidative degradation of drug substance calls for monitoring of the peroxide impurity present in the excipients used for formulating of drug sensitive to oxidation as used herein.View full abstractDownload PDF (148K)
Errata
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Kazutaka Tachibana, Ikuhiro Imaoka, Takuya Shiraishi, Hitoshi Yoshino, ...Article type: Errata
2009 Volume 57 Issue 10 Pages 1178
Published: October 01, 2009
Released on J-STAGE: October 03, 2009
JOURNAL FREE ACCESSDownload PDF (1506K)
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