Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 58, Issue 12
Displaying 1-26 of 26 articles from this issue
Review
  • Tsutomu Ishikawa
    Article type: Review
    2010 Volume 58 Issue 12 Pages 1555-1564
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Guanidines are categorized as strong organobases; however, their catalytic utility in organic synthesis has not been discussed thoroughly. The author's group has extensively and systematically studied their potential ability focusing on: 1) modified guanidines as chiral auxiliaries; 2) guanidinium ylides for aziridine formation; 3) the affinity of bisguanidine for proton and metal salts; and 4) the potential chirality of bisguanidine. Under the first topic, a variety of chiral guanidines was designed by the introduction of chirality on the three guanidinyl nitrogens, and the modified guanidines prepared using our original methods were found to be effective not only in catalytic but also in stoichiometric asymmetric syntheses. Under the second topic, the reaction of guanidinium salts carrying a glycinate function with aromatic or unsaturated aldehydes under basic conditions unexpectedly afforded aziridine-2-carboxylates, which were available as useful building blocks in organic synthesis due to their convertibility to functionalized amino acid derivatives in the ring-opening reaction, together with urea compounds recyclable to the starting guanidinium salts. The introduction of a chiral template to the guanidinium salt allowed us to expand the cyclic aziridination reaction to an asymmetric version. Under the third topic, effective complexabilty of bisguanidines with either proton or metal ions in water was observed, suggesting their possible application to the removal of toxic substances from polluted water and recovery of rare elements as material sources. Under the final topic, monomethylation or monoethylation of bisguanidine afforded a chiral product via asymmetric crystallization, indicating that bisguanidines have a potential chiral character due to the plane asymmetry.
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Regular Articles
  • Kazuyuki Kakimi, Toshiyuki Niwa, Kazumi Danjo
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1565-1568
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    A rotary tablet machine fitted with 8-mm diameter flat-faced punches was used to measure scraper pressure (SCR), a type of shear stress, to evaluate sticking behavior. The shear stress between the surfaces of the tablet and lower punch was determined using an SCR detection system. Mean surface roughness (Ra) of tablets, measured by a scanning laser-microscope, was used to estimate the magnitude of sticking. Tablet tensile strength tended to increase with compression pressure at either of the tablet production velocities tested, which was consistent with previous reports. SCR decreased with increasing compression pressure for samples at all compression velocities, and showed a tendency to increase with binder concentration. SCR also tended to increase with compression velocity for samples at all compression pressures, suggesting that the frequency of tablet sticking increased as compression velocity increased. Ra associated with sticking increased with SCR, indicating that the adhesive force between the particles of the tablet surface and the lower punch surface plays an important role in sticking.
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  • Naveen Vasudev Kulkarni, Srinivasa Budagumpi, Gurunath Suresh Kurdekar ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1569-1575
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    A novel CuII and ZnII complexes of triazolo-quinoline derivatives were synthesized by in situ method and were characterized by the spectro-analytical methods and their pharmacological properties were evaluated. The compound C3 has exhibited promising anticonvulsant activity towards the electroshock induced seizures in Wistar rats and possesses low toxicity, providing a high safety profile.
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  • Junichi Odo, Ayumi Kimura, Atsushi Matsu-ura, Yuki Ohnishi, Yoshiro Sa ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1576-1581
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    The scavenging effects of metal complexes of thiacalix[4]arenetetrasulfonate (Me-TCAS[4], Me=H2, Fe3+, Mn3+, Mn2+, Cu2+, and Zn2+) on superoxide anion radicals (O2) generated from the xanthine–xanthine oxidase system were investigated by the nitroblue tetrazolium (NBT) method and electron spin resonance (ESR) spin-trapping method using 5,5-dimethyl-1-pyrroline-N-oxide as a trapping reagent. As a reference, calix[4]arenetetrasulfonate (H2-CAS[4]), calix[6]arenehexasulfonate (H2-CAS[6]) and calix[8]areneoctasulfonate (H2-CAS[8]) were also examined. The results by the NBT method indicated that Fe3+- and Mn3+-TCAS[4] exhibited the highest O2 scavenging activity among Me-TCAS[4] and H2-CAS[n] (n=4, 6, 8) in this study. The IC50 values of Fe3+- and Mn3+-TCAS[4] for O2 scavenging activity were estimated to be 5.3 and 7.8 μM, respectively, and were almost the same as those of tannin acid, catechin and their derivatives, which are known as very effective scavengers of O2. Scavenging activities were in the order of Fe3+- and Mn3+-TCAS[4]>>Mn2+-, Cu2+-, and Zn2+-TCAS[4]>>H2-TCAS[4] and H2-CAS[n] (n=4, 6, 8). Each activity of Me-TCAS[4] (Me=Fe3+, Mn3+, Mn2+, Cu2+, and Zn2+) was higher than that of the corresponding metal ion, indicating that H2-TCAS[4] has the ability to raise the activity of the metal ion itself by forming a complex. Also, the ESR spin-trapping method revealed that Fe3+- and Mn3+-TCAS[4] showed high O2 scavenging activities, similarly to the results by the NBT method.
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  • Yasuhiko Sato, Takuma Oba, Nobuyuki Natori, Kazumi Danjo
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1582-1586
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    To design a suitable periodontal disease formulation using basic fibroblast growth factor (bFGF), legally available thickeners were evaluated focusing on their viscosity, extrusive force from a syringe, flow property and inertness to bFGF. Thirteen candidate thickeners showed appropriate viscosity (about 1×104 mPa·s), and further evaluations were conducted on them. Flow property was evaluated by the tilting test tube method. As a result, most thickener solutions with the optimum viscosity showed appropriate flow time (about 100 s) and the flow time did not depend on thickener concentration, whereas the extrusive force from a syringe depended on thickener concentration despite the thickener type and grade. Thickener solutions of 2—3% showed ideal result (10—20 N) and thickener solutions prepared outside of the concentration range (2—3%) were found to show unsuitable extrusive force. Consequently, to obtain required properties for a dental drug formulation, thickener solutions needed to show adequate viscosity (about 1×104 mPa·s) at 2—3% thickener concentration. In addition, several types of cellulose derivatives showed inertness to the bFGF because of their structure, without strong ionic dissociable groups, and neutral pH. Overall, the present work demonstrates that some water-soluble cellulose derivatives, such as hydroxypropylcellulose (HPC) and hydroxyethylcellulose (HEC), were suggested to have required properties for a dental drug formulation including bFGF.
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  • Shuang Song, Xiuping Zheng, Weidong Liu, Ruifang Du, Lifu Bi, Peicheng ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1587-1590
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Three new flavonol 3-O-glycosides, rhamnetin 3-O-[(S)-3-hydroxy-3-methyl-glutaroyl(1→6)]-β-D-glucopyranoside (1), rhamnocitrin 3-O-[(S)-3-hydroxy-3-methylglutaroyl(1→6)]-β-D-glucopyranoside (2), and isorhamnetin 3-O-[(S)-3-hydroxy-3-methylglutaroyl(1→6)]-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside (3), along with 13 known compounds, were isolated from Oxytropis racemosa TURCZ. Their structures were deduced by means of spectroscopic methods and chemical evidence. 2 and 6 showed cytotoxic activities against HCT-8 (IC50 6.38 μM) and A549 (IC50 5.20 μM), respectively.
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  • Pengcheng Yan, Zhiwei Deng, Leen van Ofwegen, Peter Proksch, Wenhan Li ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1591-1595
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Chemical examination of a Chinese soft coral Lobophytum pauciflorum resulted in the isolation of seven new biscembranoids, named lobophytones H—N (17). Their structures were determined by interpretation of 1D- and 2D-NMR (correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), and nuclear Overhauser effect spectroscopy (NOESY)) spectroscopic data in association with MS and IR data. All compounds were tested for the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production, cytotoxicity of mouse peritoneal macrophage, and antibacterial activities.
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  • Amira Samir Wanas, Katsuyoshi Matsunami, Hideaki Otsuka, Samar Yahie D ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1596-1601
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    From the EtOAc and 1-BuOH fractions, three new ursane-type and four new lupane-type triterpenes, along with nine known glycosides and glycosyl esters of lupane-type were isolated from the leaves of Schefflera actinophylla. All the isolated compounds were obtained for the first time from this plant. The structures of the new triterpenes were determined through a combination of spectroscopic and chemical analyses.
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  • Rosaria Gitto, Laura De Luca, Stefania Ferro, Stefano Agnello, Emilio ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1602-1605
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    We have previously disclosed that some 6,7-dimethoxyisoquinoline derivatives are able to produce anticonvulsant effects in different animal models of epilepsy. Following these studies this paper describes the synthesis of a small series of new 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines strictly related to previously reported analogues. This novel series of isoquinolines was designed on the basis of well defined structure–active relationship (SAR) information already acquired for this class of anticonvulsant agents. The pharmacological effects of the new synthesized compounds were evaluated against audiogenic seizures in Dilute Brown non-Agouti (DBA/2) mice. The preliminary pharmacological screening led to the identification of a new active molecule the 2-acetyl-1-(4′-methylphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (6d) that displayed significant anticonvulsant activity. Computational studies helped to rationalize these obtained pharmacological results.
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  • Yong-Bo Xue, Yan-Long Zhang, Jian-Hong Yang, Xue Du, Jian-Xin Pu, Wei ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1606-1611
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Phytochemical investigation of the fruit of Schisandra chinensis led to the isolation of a schisanartane nortriterpenoid, schindilactone H (1); an 18-norschiartane bisnortriterpenoid, wuweizidilactone I (2); two tetrahydrofuran-type lignans, schinlignins A and B (18 and 19); and three dibenzyl butane-type lignans, schineolignins A—C (2022), together with 16 known compounds. The structures of these new compounds were elucidated on the basis of extensive analysis of spectroscopic data.
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  • Jianheng Zheng, Ge Zhang, Yang Lu, Fang Fang, Jiake He, Ning Li, Amer ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1612-1616
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    The purpose of the present study was to evaluate the enhancement effect of the natural pulmonary surfactant (PS) or its artificial substitute, phospholipid hexadecanol tyloxapol (PHT) on the bioavailability and hypoglycemic activity of recombinant human insulin (rh-insulin) in a pulmonary delivery system. PS- or PHT-loaded insulin formulation was administered to streptozotocin induced diabetic rats, at doses of 5 U/kg, 10 U/kg and 20 U/kg insulin, respectively. The hypoglycemic effect caused by PS or PHT containing rh-insulin was analyzed and the area above the curves (AAC) of serum glucose levels versus time, the minimum glucose concentration (Cmin), the time to Cmin (Tmin) and the pharmacological availability (PA%) were derived from the serum glucose profiles. Results showed that PS and PHT caused significantly decrease in serum glucose levels. The decrease in plasma glucose levels continued for about 5 h after the nadir. The highest AAC value was obtained when 20 U/kg rh-insulin with PS or PHT as absorption enhancer was administered to rats. AAC0—360 min of PS- or PHT-loaded rh-insulin was 2—3 times as much as that without PS or PHT and PA% increased by 1.3—2 fold. Thus, the extent of oral absorption of insulin from PS- or PHT-loaded particles was significantly greater when compared with that without them. In addition, PHT as well as PS did not change the lactate dehydrogenase (LDH) activity, alkaline phosphatase (AKP) activity and N-acetyl-β-D-glucoaminidase (NAG) activity in bronch fluid which are sensitive indicators of acute toxicity to lung cells in bronchoalveolar lavage (BAL). It is concluded that PS and PHT is a promising absorption enhancer for pulmonary delivery systems of large molecule drugs as rh-insulin.
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  • Hisashi Matsuda, Seikou Nakamura, Katsuyoshi Fujimoto, Ryo Moriuchi, Y ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1617-1621
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of β-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponins I—V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I—III, with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of β-hexosaminidase and some structure–activity relationships were reported.
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  • Cherkupally Sanjeeva Reddy, Macherla Vani Devi, Malladi Sunitha, Adki ...
    Article type: Regular Article
    2010 Volume 58 Issue 12 Pages 1622-1626
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    A new series of linked heterocyclics, 3-[4-(4-chlorophenyl)-6-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-2-pyrimidinyl]-2-(aryl/heteryl)-1,3-thiazolan-4-ones (6aj), has been synthesized by the one-pot cyclo-condensation of 4-(4-chlorophenyl)-6-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-2-pyrimidinamine (5), aryl/heteroaryl aldehyde and thioglycolic acid. The structures of the synthesized compounds have been confirmed via IR, 1H-NMR, 13C-NMR, MS and elemental analyses. Further, all the newly synthesized compounds 6aj have been assayed for their antimicrobial activity against Gram-positive and Gram-negative bacteria and fungi. The compounds containing moieties like 4-nitrophenyl (6c), 3-nitrophenyl (6d), 4-dimethylaminophenyl (6g), 2-furyl (6i) and 1,3-benzodioxole (6j), at 2-position of thiazolidin-4-one ring exhibited good inhibitory activity against all the tested organisms.
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Notes
  • Yibing Guo, Yahong Zhao, Cheng Zheng, Ying Meng, Yumin Yang
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1627-1629
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs–Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl)methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.
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  • Dao-Jing Zhang, Rong-Feng Liu, Yuan-Guang Li, Li-Ming Tao, Li Tian
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1630-1634
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Two new cyclic lipopeptides maribasins A (1) and B (2) were isolated from the fermentation broth of the marine microorganism Bacillus marinus B-9987 isolated from Suaeda salsa in Bohai coastline of P. R. China. Both structures were established to be cyclo (D-Pro-L-Gln-L-Asn-L-Ser-D-Asn1-D-Tyr-D-Asn2-D-β-aminoisopentadecanoic acid) (1) and cyclo (D-Pro-L-Gln-L-Asn-L-Ser-D-Asn1-D-Tyr-D-Asn2-D-β-aminoanteisopentadecanoic acid) (2) by spectroscopic analysis and exhibited broad-spectrum activity against phytopathogens by the antifungal bioassay.
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  • Sultan Samran Al-Lihaibi, Seif-Eldin Nasr Ayyad, Fekry Shaher, Walied ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1635-1638
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    From the black coral Antipathies dichotoma, a sphingolipid (2S*,3S*,4E,8E)-2N-[tetradecanoyl]-4(E),8(E)-icosadiene-1,3-diol (1) and a steroid (22E)-methylcholesta-5,22-diene-1α,3β,7α-triol (2) were isolated. Other known compounds, 3β,7α-dihydroxy-cholest-5-ene (3), (22E,24S),5α,8α-epidioxy-24-methylcholesta-6,22-dien-3β-ol (4) and (22E,24S),5α,8α-epidioxy-24-methylcholesta-6,9(11),22-trien-3β-ol (5). The structures were established on the basis of NMR spectroscopic analysis and comparison with literature. The antibacterial activity of five compounds was evaluated.
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  • Chiy-Rong Chen, Yun-Wen Liao, Lai Wang, Yueh-Hsiung Kuo, Hung-Jen Liu, ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1639-1642
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Two novel pentanorcucurbitane triterpenes, 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one (1) and 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid (2) together with a new trinorcucurbitane triterpene, 25,26,27-trinorcucurbit-5-ene-3,7,23-trione (3) were isolated from the methyl alcohol extract of the stems of Momordica charantia. The structures of the new compounds were elucidated by spectroscopic methods. Compounds 2 and 3 showed potent cytoprotective activity in tert-butyl hydroperoxide (t-BHP)-induced hepatotoxicity of HepG2 cells.
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  • Mohammad Sayed Alam, Dong-Ung Lee
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1643-1645
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    A convenient synthesis of 5-methoxyfuroflavone (6, pongaglabol methyl ether), a constituent of some Pongamia or Millettia genus, was achieved by starting from 2,4-dihydroxy-6-methoxyacetophenone via a chalcone precursor, followed by treatment with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). This five-step reaction (total yield: 21.6%) is more facile with that of previously utilized procedures using each different starting material. Antibacterial activities of the above compound and its precursor chalcones, which also belongs to the class of furoflavonoids, were tested by the disc diffusion method against Shigella dysenteriae, Salmonella typhi, Streptococcus-β-haemolyticus, and Staphylococcus aureus. 5-Methoxyfuroflavone showed moderate bactericidal activity against all tested bacterial strains, whereas its corresponding chalcone compound revealed a selective activity.
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  • Liang Wu, Yong-Li Li, Su-Mei Li, Xian-Wen Yang, Jia-Han Xia, Le Zhou, ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1646-1649
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Systematical phytochemical investigations on Abies spectabilis afforded 72 chemical constituents. On the basis of physical and spectroscopic data, including 1D and 2D homo- and heteronuclear NMR experiments (heteronuclear single quantum coherence (HSQC), 1H–1H correlation spectroscopy (COSY), heteronuclear multiple bond connectivity (HMBC), and nuclear Overhauser effect spectroscopy (NOESY)), and by comparison with the literature references, they were identified as 3 triterpenoids, 23 diterpenoids, 1 sesquiterpenoid, 13 flavonoids, 12 lignans, and 20 other components. Among these compounds, three were identified as new including abieta-7,13-diene-12α-methoxy-18-oic acid (1), 7α-methoxy-dehydroabietic acid (2), and 5-hydroxy-6-methyl-7,4′-dimethoxyflavone-8-O-β-D-glucopyranoside (3). These three new compounds (13) and all the known terpenoids (428) were tested for cytotoxic activities against four tumor cell lines: A549, COLO-25, QGY-25, and THP-1. However, none of them showed a positive effect (IC50>100 μM).
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  • Peng Shao, Xue Zhang, Bo Li, Wei-hua Jiao, Li-jun Wu, Xin-Sheng Yao
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1650-1654
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Five new compounds (15), were isolated from the rhizomes of Matteuccia orientalis (HOOK.) TREV. The structures of new compounds were elucidated on the basis of their 1D-, 2D-NMR, MS, IR and circular dichroism (CD) data.
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  • Masako Okamoto, Yoshiaki Masuda, Ayumu Muroya, Kazuhiro Yasuno, Osamu ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1655-1657
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    We are participating in the challenge of identifying active compounds for target proteins using structure-based virtual screening (SBVS). We use an in-house customized docking program, CONSENSUS-DOCK, which is a customized version of the DOCK4 program in which three scoring functions (DOCK4, FlexX and PMF) and consensus scoring have been implemented. This paper compares the docking calculation results obtained using CONSENSUS-DOCK and DOCK4, and demonstrates that CONSENSUS-DOCK produces better results than DOCK4 for major X-ray structures obtained from the Protein Data Bank (PDB).
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  • Takehisa Matsukawa, Hiroshi Hasegawa, Yoshihiko Shinohara, Jun Kobayas ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1658-1660
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    The synthesis of D- and L-selenomethionine labeled with 82Se and three deuteriums at Se-methyl group (D- and L-[2H3, 82Se]selenomethionine) was described. D- And L-[2H3, 82Se]selenomethionine were prepared by condensation of (R)- and (S)-2-amino-4-bromobutylic acid with lithium [2H3, 82Se]methaneselenolate, which was prepared from metal 82Se and [2H3]methyl iodide. The optical purities of D- and L-[2H3, 82Se]selenomethionine were determined by HPLC with a chiral stationary phase column and were found more than 99% ee. The chemical ionization mass spectra showed that the molecular related ion for N-isobutyloxycarbonyl ethyl ester derivatives of [2H3, 82Se]selenomethionine did not overlap with the m/z values known from that of non-labeled selenomethionine.
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  • Jean Jules Kezetas Bankeu, Sufyan Awad Alkarim Mustafa, Anar Sahib Goj ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1661-1665
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    Two new sphingolipids mucusamide (1) and mucusoside (2) have been isolated from methanol soluble part of the stem bark of Ficus mucuso WELW., together with fifteen known secondary metabolites including cellobiosylsterol (3), β-sitosterol (4), stigmasterol (5), β-sitosterol 3-O-β-D-glucopyranoside (6), lupeol acetate (7), ursolic acid (8), procatechuic acid (9), 2-methyl-5,7-dihydroxychromone 8-C-β-D-glucoside (10), apigenin (11), (−)-epicatechin (12), (+)-catechin (13), N-benzoyl-L-phenylalanilol (14), α-acetylamino-phenylpropyl α-benzoylamino-phenylpropionate (15), asperphenamate (16) and bejaminamide (17). Structures of compounds 1 and 2 were elucidated by spectroscopic analysis and chemical methods.
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  • Yu-Chia Chang, I-Chu Huang, Michael Yen-Nan Chiang, Tsong-Long Hwang, ...
    Article type: Note
    2010 Volume 58 Issue 12 Pages 1666-1668
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    A new cembrane diterpenoid, briaviodiol A (1), has been isolated from a soft coral Briareum violacea. The structure of 1 was determined by spectroscopic methods and further confirmed by a single-crystal X-ray diffraction analysis.
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Communication to the Editor
  • Naganori Numao, Tetsuya Fukui, Yoshiyuki Fukazawa
    Article type: Communication to the Editor
    2010 Volume 58 Issue 12 Pages 1669-1671
    Published: December 01, 2010
    Released on J-STAGE: December 01, 2010
    JOURNAL FREE ACCESS
    We found a new method that a specific interaction between prion, i.e., high-molecular compound, and Cp-60, i.e., low-molecular one, could be successfully elucidated with intermolecular frequency symmetry (IFS). To accomplish this, the former sequence is analyzed with a sequence Fourier analysis used average nuclear (N) resonant frequency scale as a fourth one, and the latter structure with a 13C-NMR software. Further, such the symmetry could be observed in a specific interaction between a segment of human immunodeficiency virus (HIV)gag and PA-457 or between 1918 neuraminidase and peramivir. Therefore, the IFS rule seems to be evolutionarily conserved as a necessary condition even in a specific protein-organic compound interaction.
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