Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 57, Issue 11
Displaying 1-26 of 26 articles from this issue
Review
  • Shinobu Takizawa
    Article type: Review
    2009 Volume 57 Issue 11 Pages 1179-1188
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    This review describes our recent efforts in the development of chiral dinuclear vanadium complexes which work as dual activation catalysts for oxidative coupling of 2-naphthols. A chiral dinuclear vanadium(IV) complex (Ra,S,S)-1a possessing (S)-tert-leucine moieties at the 3,3′-positions of the (R)-binaphthyl skeleton was developed, and found to promote oxidative coupling of 2-naphthol to afford (S)-1,1′-bi-2-naphthol (BINOL) with 91% ee. To verify the dual activation mechanism, mononuclear vanadium(IV) complex (S)-10 was also prepared. Kinetic analysis revealed that the reaction rate of oxidative coupling of 2-naphthol promoted by (Ra,S,S)-1a is 48.3 times faster than that of (S)-10. In the coupling reaction, the two vanadium metals in the chiral complex activate two molecules of 2-naphthol simultaneously achieving a high reaction rate with high enantiocontrol. Since the dinuclear vanadium(IV) complex was found to be readily oxidized to afford a corresponding vanadium(V) species during preparation in air, a new synthetic procedure using VOCl3 and a convenient one-pot procedure using VOSO4 under O2 have been applied towards dinuclear vanadium(V) complexes (Ra,S,S)-2. The coupling of 2-naphthol was catalyzed by (Ra,S,S)-2 with reaction rates enhanced 2.3 times faster than that of (Ra,S,S)-1a, which is likely a precatalyst. To the best of our knowledge, (Ra,S,S)-1a, 2, and 3 show considerably higher catalytic activity than previously reported vanadium complexes for oxidative coupling of 2-naphthols.
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Regular Articles
  • Jui-Hsin Su, Yu-Fang Lin, Yi Lu, Hsiao-Chien Yeh, Wei-Hsien Wang, Tung ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1189-1192
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Two new cembranoids, flexibilisolide A (1) and flexibilisin A (2), along with one known combranoid 5 have been isolated from the cultured soft coral Sinularia flexibilis. Furthermore, two new cembranoids, flexibilisolide B (3) and flexibilisin B (4), along with two known combranoids (5, 6), have been isolated from the wild-type soft coral S. flexibilis. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis and by comparison of NMR data with those of known compounds. The metabolites 5 and 6 have been shown to exhibit weak cytotoxic activity against MCF-7 cancer cell line.
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  • Hiroyuki Nojima, Kazuhiko Kanou, Kenshu Kamiya, Koichiro Atsuda, Hidea ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1193-1199
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Major histocompatibility complexes (MHCs) mainly fall into class I and class II. The two classes have similar structures, with two membrane-proximal immunoglobulin-like domains and a peptide-binding platform domain, though their organizations are different. We simulated the dynamics of a whole and partial model deficient in either of the two membrane-proximal domains for class I and class II using normal mode analysis. Our study showed that the influence of the two membrane-proximal domains upon the dynamics of the platform domain were decisively different between class II and class I. Both membrane-proximal domains (the α2 and β2 domains) of class II MHC, especially the α2 domain, influenced the most important pocket that accommodates a large hydrophobic anchor side chain of the N-terminal side of the bound peptide, though the pocket was not in the α2 domain neighborhood. By contrast, the two membrane-proximal domains (the α3 and β2m domains) of class I MHC had little influence upon the most important pocket that accommodates the N-terminal residue of the bound peptide. These results suggest that the two membrane-proximal domains of class II MHC have a greater influence upon peptide-binding than those of class I MHC.
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  • Venkatapuram Padmavathi, Thunga Radha Lakshmi, Konda Mahesh, Adiviredd ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1200-1205
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A new class of sulfone-linked bis heterocycles, methyl-3-(4′-aryl-1′H-pyrazol-3′-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (8), methyl-3-(1′-phenyl-3′,5′-diaryl-1′H-pyrazol-4′-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (9) and methyl-3-(3′,5′-diarylisoxazol-4′-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (10) were prepared by the regioselective reaction of methyl-3-aryl-2-(E-arylethenesulfonyl)acrylate (2) with tosylmethyl isocyanide followed by fuctionalization of olefin moiety with 1,3-dipolar reagents. The lead compounds were tested for their antimicrobial activity.
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  • Keiichi Motoyama, Kiyoshi Nagatomo, Soliman Osama Abd Elazim, Fumitosh ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1206-1212
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    To expand the application of a drug in orally disintegrating tablets, the potential use of β-cyclodextrin (β-CyD) and 2-hydroxypropyl-β-cyclodextrin (HP-β-CyD) as excipients for the tablets containing dl-α-tocopheryl acetate (VE), an oily drug, was evaluated. HP-β-CyD, not β-CyD, solubilized VE in water through the formation of higher order of complexes at the molar ratio of 1 : 2 (VE : HP-β-CyD). When prepared under the optimal preparation conditions, the VE tablets containing lactose and 5% (w/w) of HP-β-CyD, not β-CyD, had high hardness more than 4 kg and rapid disintegration within 100 s both in vitro and in vivo. In addition, VE tablets containing lactose and 5% (w/w) of HP-β-CyD, not β-CyD, maintained the high hardness and rapid disintegration under the accelerated stability test using different conditions for 4 weeks. Therefore, these results suggest the potential use of HP-β-CyD, not β-CyD, as an excipient for orally disintegrating tablets containing VE, an oily drug, in the molding method.
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  • Ashish Babulal Rane, Surendra Ganeshlal Gattani, Vinayak Dinkar Kadam, ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1213-1217
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The aim of present investigation was to develop press coated tablet for pulsatile drug delivery of ketoprofen using hydrophilic and hydrophobic polymers. The drug delivery system was designed to deliver the drug at such a time when it could be most needful to patient of rheumatoid arthritis. The press coated tablets containing ketoprofen in the inner core was formulated with an outer shell by different weight ratio of hydrophobic polymer (micronized ethyl cellulose powder) and hydrophilic polymers (glycinemax husk or sodium alginate). The release profile of press coated tablet exhibited a lag time followed by burst release, in which outer shell ruptured into two halves. Authors also investigated factors influencing on lag time such as particle size and viscosity of ethyl cellulose, outer coating weight and paddle rpm. The surface morphology of the tablet was examined by a scanning electron microscopy. Differential scanning calorimeter and Fourier transformed infrared spectroscopy study showed compatibility between ketoprofen and coating material.
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  • Zhangyu Yao, Shubo Gong, Teng Guan, Yunman Li, Xiaoming Wu, Hongbin Su ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1218-1222
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The anti-anginal drug Ranolazine, a partial fatty acid oxidation (pFOX) inhibitor, is thought to modulate the metabolism during myocardial ischemia by activating pyruvate dehydrogenase activity to promote glucose oxidation. Ranolazine and its five principal metabolites: CVT-2512, CVT-2513, CVT-2514, CVT-2738 and CVT-4786, were synthesized. The effect of Ranolazine and its metabolites on the ECG (electrocardiogram) of mice with myocardial ischemia induced by isoprenaline and their effect on alleviating the symptom of myocardial ischemia were tested and compared. The results showed that CVT-2738 and CVT-2513 could be protective against mice myocardial ischemia induced by isoprenaline. Within all the metabolites tested in this study, CVT-2738 exhibited the best potency, however, it was still less potent than Ranolazine.
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  • Aya Shibata, Hiroshi Abe, Kazuhiro Furukawa, Satoshi Tsuneda, Yoshihir ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1223-1226
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    We developed a new nucleic acid-based fluorescence probe for protein detection. The method is based on the scission of an aptamer into two probes, which are then attached with a chemically reactive fluorogenic compound. The protein-dependent association of the two probes accelerates a reduction-triggered fluorogenic reaction and indicates the presence of the target protein, which is detected using a fluorescence readout. The fluorescence signal is generated via the deprotection of the azidomethyl group of fluorescein. The arginine-rich motif peptide of the human immunodeficiency virus-1 Rev protein was targeted by this type of probe. Emission was detected at 522 nm and was enhanced by about 19.4-fold in the presence of the target peptide. An oligonucleotide-based reduction-triggered fluorescence probe was successfully applied to the detection of the Rev peptide in solution.
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  • Shu-Chen Chou, Chung-Ren Su, Yuh-Chi Ku, Tian-Shung Wu
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1227-1230
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Chemical investigation on the whole plant of Houttuynia cordata has resulted in the isolation of two new compounds, named as houttuynoside A (1) and houttuynamide A (2), together with thirty-eight known compounds. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis. In the inhibitory effects on herpes simplex virus type 1 (HSV-1) assay, norcepharadione B (10) showed good inhibitory activity against the replication of HSV-1. In addition, the antioxidant and antityrosinase activities of some isolated compounds were also evaluated. Among these compounds, quercitrin (25) and quercetin-3-O-β-D-galactopyranoside (26) showed excellent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging property with IC50 values of 31 and 63 μM, respectively. Cepharadione B (9) exhibited strong tyrosinase inhibitory activity with an IC50 value of 170 μM.
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  • Ken-ichi Izutsu, Saori Kadoya, Chikako Yomota, Toru Kawanishi, Etsuo Y ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1231-1236
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The purpose of this study was to elucidate the physical properties and protein-stabilizing effects of some pH-adjusting excipients (carboxylic acids and their sodium salts) in frozen solutions and in freeze-dried solids. Thermal and powder X-ray diffraction (XRD) analysis indicated a high propensity of sodium citrates to form glass-state amorphous solids upon freeze-drying. Some salts (e.g., sodium succinate) crystallized in the single-solute frozen solutions. FT-IR analysis of bovine serum albumin (BSA) and bovine immunoglobulin G (IgG) in the aqueous solutions and the freeze-dried solids showed that some glass-forming salts (e.g., monosodium citrate) protected the secondary structure from lyophilization-induced perturbation. Freeze-drying of BSA at different concentrations indicated retention of the secondary structure at similar monosodium citrate/protein concentration ratios, suggesting stabilization through direct interaction that substitute water molecules inevitable for the conformation integrity. The carboxylic acid salts should provide rigid hydrogen bonds and electrostatic interactions that raise the glass transition temperature of the amorphous solids and stabilize protein structure. The relevance of the structural stabilization to the protein formulation design was discussed.
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  • Hong-yan Liu, Zhi-hong Xu, Xiao-hui Liu, Pin-xian Xi, Zheng-zhi Zeng
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1237-1242
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The interaction between bovine serum albumin (BSA) and the cobalt(II) complex with salicylaldehyde-2-phenylquinoline-4-carboylhydrazone (Co-SPC) was investigated using fluorescence spectroscopy, UV absorption, and circular dichroism (CD) under simulated physiologic conditions for the first time. Fluorescence data and UV absorption spectra revealed that the intrinsic fluorescence of BSA was strongly quenched by Co-SPC in terms of a static quenching process at a lower concentration of the complex and a combined quenching process at a higher concentration of the complex. Binding constants and binding sites were evaluated. The average binding distance between Co-SPC and BSA was obtained (2.28 nm) on the basis of Förster's theory. The thermodynamic parameters indicated that hydrophobic force played a major role in the binding. The binding of Co-SPC to BSA leads to changes in the conformation of BSA according to synchronous fluorescence spectra and CD data.
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  • Ravindra Abhykumar Fursule, Pravin Onkar Patil, Bharti Devaji Shewale, ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1243-1245
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.
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  • Chaisak Chansriniyom, Nijsiri Ruangrungsi, Vimolmas Lipipun, Takuya Ku ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1246-1250
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Six acridone alkaloids including a new glycosparvarine (1), three limonoids, and four N-[(4-monoterpenyloxy)phenylethyl]-substituted sulfur-containing propanamide derivatives including two new species, (+)-S-deoxydihydroglyparvin (10) and (+)-S-deoxytetrahydroglyparvin (11), were isolated from the branches and the leaves of Glycosmis parva CRAIB collected in the east of Thailand. Antiviral activity evaluation of isolates against herpes simplex virus (HSV) type 1 and 2 disclosed that two acridone alkaloids, glycosparvarine (1) and glycofolinine (4), showed moderate inhibitory activities with 50% effective concentration (EC50) of 348 μM and 151 μM, respectively; as well, (+)-S-deoxydihydroglyparvin (10) exhibited anti-HSV activity at the lower concentration.
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  • Zhengxing Su, Fengying Sun, Yanan Shi, Chaojun Jiang, Qingfan Meng, Li ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1251-1256
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A 4-week sustained release risperidone biodegradable poly(D,L-lactide-co-glycolide) (PLGA) microsphere for the therapy of schizophrenia, the effects of formulation parameters on encapsulation efficiency and release behavior were studied. The risperidone PLGA microspheres were prepared by O/W solvent evaporation method and characterized by HPLC, SEM, laser particle size analysis, GC and HPLC-MS. The results indicated that the morphology of the risperidone PLGA microspheres presented a spherical shape with smooth surface, the particle size was distributed from 32 to 92 μm and the drug encapsulation efficiency was influenced by homogeneous rotation speed, intrinsic viscosity, carboxylic terminal group, the polymer concentration in the oil phase and the molecular weight of the polymer. These changes were also reflected in drug release. When the Mw of the polymers increased from ca. 28000 to ca. 90000, the initial burst release of risperidone PLGA microspheres decreased from 13 to 0.8% and the sustained-release could be extended to 4 weeks. Pharmacokinetic study on beagle dogs showed that the 4-week sustained release profile of the risperidone loaded microspheres prepared with 75253A was verified. The PLGA 75253A and 75255A show the potential as excipients for the monthly sustained release risperidone PLGA microspheres due to higher encapsulation efficiency and almost zero-order release kinetics of release profile.
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  • Yoshiyuki Kageyama, Ryosuke Ohshima, Kazusa Sakurama, Yoshihisa Fujiwa ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1257-1266
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300—330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl moiety and the benzene ring on the photolysis reactions were examined. Based on steady-state mechanistic studies using a triplet sensitizer, a triplet quencher, and electron donors, it was suggested that the photolysis proceeds mainly via the homolytic cleavage of S–O bonds in the excited triplet state.
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  • Seikou Nakamura, Junko Iwami, Hisashi Matsuda, Hiroko Wakayama, Yutana ...
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1267-1272
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The methanolic (MeOH) extract from the rhizomes of Zingiber cassumunar showed nitric oxide (NO) production inhibitory effects induced by lipopolysaccharide (LPS) in mouse peritoneal macrophages. From the MeOH extract, six new phenylbutanoids, phlains I—VI, were isolated together with 16 known constituents. The structures of new phenylbutanoids were determined on the basis of physicochemical and chemical evidence. In addition, the inhibitory effects of the principal constituents on the NO production were examined. Among them, phlain III (IC50=24 μM), (E)-1-(3,4-dimethoxyphenyl)buta-1,3-diene (69 μM), (E)-1-(2,4,5-trimethoxyphenyl)buta-1,3-diene (83 μM), and cassumunaquinone 1 (47 μM) were found to show the inhibitory effects.
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  • Wei Yi, Ri-Hui Cao, Zhi-Yong Chen, Liang Yu, Lin Ma, Hua-Can Song
    Article type: Regular Article
    2009 Volume 57 Issue 11 Pages 1273-1277
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A series of hydroxy- or methoxy-substituted phenylmethylenethiosemicarbazones were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. The results demonstrated that most of target compounds had remarkable inhibitory activities on mushroom tyrosinase. Interestingly, compound 2h was found to be the most potent tyrosinase inhibitor with IC50 value of 0.18 μM. The possible interaction mode between compound 2h and tyrosinase was proposed. In addition, the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities of select compounds (IC50<10.0 μM) were also investigated. Compounds 2d, 2e, 2h, 2i and 2l exhibited more potent DPPH radical scavenging activity than well-known antioxidants ascorbic acid (Vc) and tertiary butyl hydroquinone (TBHQ). These results suggested that such compounds might be utilized for the development of new candidate for treatment of dermatological disorders.
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Notes
  • Satoko Nagano, Hiroyuki Hosono, Fumiko Negishi, Mashiho Yanagi, Masato ...
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1278-1281
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    We developed a sensitive high performance liquid chromatography (HPLC) method for determining CYP2D6 mRNA in peripheral blood leukocytes (PBL) by using competitive reverse transcriptase polymerase chain reaction (RT-PCR). The method is specific, reproducible, and sensitive enough to quantify the absolute amount of low and high abundant CYP2D6 mRNA. The native CYP2D6 transcript and the internal standard, a CYP2D6 deletion RNA, were amplified with similar efficiency in RT-PCR. The PCR products were separated as the corresponding peaks in optimized HPLC. The coefficients of variation for competitive RT-PCR and HPLC determination were 1.5—6.5% and 0.6—2.4%, respectively, showing high reproducibility and reliability. This approach could also be applicable to the quantification of mRNA expressing on various tissues, including PBL, of which the expression levels were so low that they were hard to determine by existing agarose gel electrophoresis methods.
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  • Seyed Mahdi Ziaratnia, Kiyoshi Ohyama, Ahmed Abdel-Fattah Hussein, Tos ...
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1282-1283
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A novel chlorophenol, 4-chloro-2-(hepta-1,3,5-triyn-1-yl)-phenol (1), was isolated as the major phenolic compound from the cells of Helichrysum aureonitens suspension cultures. Compound 1 has been proposed to be an intermediate in the acetylene biosynthetic pathway of other acetylenic compounds in Helichrysum spp. The ethanol extract of cell suspension cultures and compound 1 were evaluated for their cytotoxicity against monkey kidney Vero (Vero cells) and human prostate epithelial carcinoma (DU145) cell lines, also, the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against Mycobacterium tuberculosis H37Rv were determined as well.
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  • Kensuke Yagi, Keiichi Goto, Fumio Nanjo
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1284-1288
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The polyphenolic composition of Camellia irrawadiensis, which is a closely related species of Camellia sinensis (cultivated tea), was investigated. The most predominant polyphenol, a kind of ellagitannin, was isolated from leaves of C. irrawadiensis. Its structure was established as 1,2-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-D-glucose (2) on the basis of spectral and chemical evidence. Moreover, the polyphenols [catechins, strictinin (1), compound 2, theogallin, and gallic acid] and two methylxanthines (theobromine and caffeine) in leaves of C. irrawadiensis were determined by HPLC-Photodiode array detector analysis, and were compared to those in C. sinensis and Camellia taliensis. Total catechin content in C. irrawadiensis was lower than that in C. sinensis and C. taliensis. Theobromine content in C. irrawadiensis was higher than that in C. sinensis and C. taliensis. The content of 2 in C. irrawadiensis was 8.4% of dry leaf weight and comprised approximately 60% of the total polyphenols detected, while the compound was not detected in C. sinensis and was reported to be 2.4% in C. taliensis.
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  • Hari Prasad Devkota, Purusotam Basnet, Shoji Yahara
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1289-1291
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    From the leaves of Sapium insigne (ROYLE) BENTH. ex HOOK. fil., two new phorbol derivatives, such as 16-hydroxyphorbol-16-acetate (4) and 4β-deoxy-16-hydroxyphorbol-16-acetate (5) along with twelve known phenolic compounds such as 3-O-caffeoyl quinic acid (1), 1-O-galloyl-β-D-glucose (2), 1,3-di-O-galloyl-β-D-glucose (3), rutin (6), 1,3,4,6-tetra-O-galloyl-β-D-glucose (7), quercetin (8), guaijaverin (9), nicotiflorin (10), scopolin (11), methyl gallate (12), corilagin (13) and 1,3,6-tri-O-galloyl-β-D-glucose (14) were isolated. All of these compounds have been isolated for the first time from this plant.
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  • Toshio Morikawa, Itadaki Yamaguchi, Hisashi Matsuda, Masayuki Yoshikaw ...
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1292-1295
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A new amide, piperchabamide F (1), and two new phenylpropanoid glycosides, piperchabaosides A (2) and B (3), were isolated from 80% aqueous acetone extract from fruit of Piper chaba. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence.
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  • Kensuke Okuda, Tsuyoshi Tagata, Setsuo Kashino, Takashi Hirota, Kenji ...
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1296-1299
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    The reaction of 3-(2-cyanophenyl)quinazolin-4(3H)-one with various primary alkylamines gave 3-alkylquinazolin-4(3H)-ones via an addition of the nucleophile, ring opening, and ring closure (ANRORC) mechanism. This type of reaction required hydroxy group functionality in either the solvent or reagent. When hydroxylamine was used as nitrogen nucleophile, the intermediate of this reaction was isolated and found to be an amide oxime. When ethylenediamine was used as the nucleophile, the amidine moiety of the intermediate decomposed to give a benzanilide.
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  • Vanessa Gonnot, Marc Nicolas, Charles Mioskowski, Rachid Baati
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1300-1302
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    A short and straightforward synthesis of the antihistaminic drug mequitazine is reported, based on an efficient palladium catalyzed allylic alkylation of 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate using sodium phenothiazinate in mild conditions.
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  • Akira Inada, Chiharu Morimoto, Tomomi Yoshikawa, Yuka Inatomi, Hiroko ...
    Article type: Notes
    2009 Volume 57 Issue 11 Pages 1303-1304
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Two new 24-ethyl,24-methyl-29-nor-lanostanes (1, 2) were isolated from the MeOH extract of leaves of Freycinetia formosana (Pandanaceae). Their structures were elucidated based on spectroscopic evidence.
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Communicatins to the Editor
  • Naganori Numao, Yoshihito Kamimoto
    Article type: Communications to the Editor
    2009 Volume 57 Issue 11 Pages 1305-1307
    Published: November 01, 2009
    Released on J-STAGE: November 01, 2009
    JOURNAL FREE ACCESS
    Here, we first report that a specific protein–DNA (RNA) interaction between p53 protein and divergent I kappa B kinase interacting protein (IKIP)-Apaf1 DNA promoter region, and between poliovirus 3CD protein and the 5′ terminal region of the RNA sequence can be successfully elucidated with a sequence Fourier analysis, alike various specific protein–protein interactions described previously. Based on these, the intermolecular frequency symmetry would be evolutionarily conserved in a specific interaction of the bioactive structure of various long-chain sequences. In addition, the symmetry is fairly sensitive to a substitution (or a point mutation) on the sequence.
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