Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 61, Issue 5
Displaying 1-16 of 16 articles from this issue
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Regular Articles
  • Two New Labdane Diterpenes from Fresh Leaves of Leonurus japonicus and Their Degradation during Drying
    Hiroyuki Fuchino, Akihiro Daikonya, Takeo Kumagai, Yukihiro Goda, Yuta ...
    2013 Volume 61 Issue 5 Pages 497-503
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-00670
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    Degradation of the components of Leonurus Herb was examined during drying. Compounds 1 and 2 were detected on TLC at lower temperature, but not at higher temperature. Their chemical structures were determined by spectral methods. They immediately decomposed even at 40°C in chloroform solution. They are believed to be transformed through a retro-aldol reaction. Compounds 1 and 2 have not been previously reported.
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  • Azoles and bis-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents
    Nabila Abdelshafy Kheder, Sayed Mohamed Riyadh, Ahlam Maade Asiry
    2013 Volume 61 Issue 5 Pages 504-510
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248//cpb.c12-00939
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    Novel hydrazonoyl halides 3, 5 and bis-hydrazonoyl halides 7, 9 were synthesized. The synthetic utility of bis-hydrazonoyl halide 7 was explored to prepare novel bis-azole 13 with antipyrine moiety. On the other hand, [1,3,4]thiadiazol-2(3H)-ylidene 17 and thiazol-2(3H)-ylidene 21 derivatives, with antipyrine moiety, were prepared from the reaction of 3-mercapto-3-(phenylamino)acrylamide derivative 10 with N-phenyl benzenecarbohydrazonoyl chloride (14) and 3-(2-bromoacetyl)-2H-chromen-2-one (18), respectively. The structures of the isolated products were confirmed by spectral data (IR, 1H-NMR, 13C-NMR, MS) and elemental analyses. The anti-cancer activitiy of the synthesized products against the colon carcinoma (HCT) cell line was determined and the results revealed promising activity of compound 3. In addition, the antimicrobial activity of some selected products was evaluated. The results proclaimed that compounds 9, 17, and 21 have high antibacterial activity against Gram-positive bacteria (SA, BS) and Gram-negative bacteria (PA, EC).
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  • Nocapyrones H–J, 3,6-Disubstituted α-Pyrones from the Marine Actinomycete Nocardiopsis sp. KMF-001
    Min Cheol Kim, Oh-Wook Kwon, Jin-Soo Park, Sun Yeou Kim, Hak Cheol Kwo ...
    2013 Volume 61 Issue 5 Pages 511-515
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    Advance online publication: February 05, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-00956
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    Three new 3,6-disubstituted α-pyrones, nocapyrones H–J (1–3), were isolated from the marine actinomycete Nocardiopsis sp. KMF-001. Their structures were assigned to be 3-alkylated 6-(1-methyl-1-propenyl)-2H-pyran-2-ones on the basis of UV, MS, NMR, and high resolution (HR)-FAB-MS analyses. Nocapyrone H (1) reduced the pro-inflammatory factor such as nitric oxide (NO), prostaglandin E2 (PGE2) and interleukin-1β (IL-1β). Moreover, nocapyrone H showed 5.82% stronger inhibitory effect on NO production than chrysin at a concentration of 10 µm in lipopolysaccharide (LPS)-stimulated BV-2 microglial cells.
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  • Synthesis and Antimicrobial Activity of Azole Derivatives
    Talapuru Bhanu Prakash, Lingaladinne Mallikarjuna Reddy, Adivireddy Pa ...
    2013 Volume 61 Issue 5 Pages 516-523
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-00975
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    A new class of mono and bis heterocycles, sulfonylmethaneamido linked oxazoles, thiazoles, imidazoles, pyrrolyl oxazoles, pyrrolyl thiazoles and pyrrolyl imidazoles were prepared adopting simple and versatile synthetic methodologies. The compound chloro substituted imidazolyl styrylsulfonylacetamide is the most potent antimicrobial agent particularly against Pseudomonas aeruginosa and Penicillium chrysogenum.
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  • Synthesis, Docking Studies, Pharmacological Activity and Toxicity of a Novel Pyrazole Derivative (LQFM 021)—Possible Effects on Phosphodiesterase
    Daniella Ramos Martins, Francine Pazini, Vinícius de Medeiros Alves, S ...
    2013 Volume 61 Issue 5 Pages 524-531
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01016
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    This study describes the synthetic route and molecular computational docking of LQFM 021, as well as examines its biological effects and toxicity. The docking studies revealed strong interaction of LQFM 021 to phosphodiesterase-3 (PDE-3). In isolated arteries, the presence of endothelium potentiates the relaxation for LQFM 021 and the inhibition cyclic nucleotides reduced the relaxation. Pre-contraction with KCl (45 mm), the treatment with tetraethylammonium (TEA) (5 mm) and inhibition of reticular Ca2+-ATPase showed an inhibitory effect on relaxation. Moreover, the compound reduced the contraction evoked by the Ca2+ influx. Acute toxicity tests revealed that the compound was practically nontoxic. In conclusion, this study showed that a new synthetic derivative of pyrazole is a possible PDE-3 inhibitor and has vasorelaxant activity and low toxicity.
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  • Synthesis of Diosgenin-Ibuprofen Derivatives and Their Activities against Insulin-Dependent Diabetes Mellitus
    Guang Xin, Yanyan Wang, Xiurong Guo, Baozhan Huang, Dan Du, Shiliang H ...
    2013 Volume 61 Issue 5 Pages 532-538
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01024
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    The synthesis and anti-diabetes activities of diosgenin-ibuprofen derivatives were investigated. Ibuprofen (IBU) was chemically coupled with diosgenin either directly or through amino acid esters linkers. The effects of these compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) generation were assessed. The results showed spirost-5-en-3β-yl (2-(4-isobutyl-phenyl)-propionate) (4) was of better activity to suppress the production of NO in the supernatant of LPS-stimulated RAW264.7 cells. In vivo investigation on nonobese diabetic (NOD) mice indicated that compound 4 decreased the incidence of insulin-dependent diabetes mellitus (IDDM; type 1 diabetes) of NOD mice which suggested a potential activity of compound 4 against type 1 diabetes.
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  • Effects of Phosphate Buffer in Parenteral Drugs on Particle Formation from Glass Vials
    Toru Ogawa, Makoto Miyajima, Naoki Wakiyama, Katsuhide Terada
    2013 Volume 61 Issue 5 Pages 539-545
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    Advance online publication: February 18, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01025
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    The characteristics of inorganic particles generated in glass vials filled with phosphate buffer solutions were investigated. During storage, particles were visually detected in the phosphate buffer solution in particular glass vials which pass compendial tests of containers for injectable drugs. These particles were considered to be different from ordinal glass delamination, which has been reported in a number of papers because the particles were mainly composed of Al, P and O, but not Si. The formation of the particles accelerated at higher storage temperatures. Among the surface treatments tested for the glass vials, sulfur treatment showed a protective effect on the particle formation in the vials, whereas the SiO2 coating did not have any protective effects. It was found that the elution ratio of Al and Si in the solution stored in the glass vials after the heating was similar to the ratio of Al and Si in borosilicate glass. However, the Al concentration decreased during storage (5°C, 6 months), and consequently, particle formation was observed in the solution. Adding citrate, which is a chelating agent for Al, effectively suppressed the particle formation in the heated solution. When 50 ppb and higher concentrations of Al ion were added to the phosphate buffer solution, the formation of white particles containing Al, P and O was detected. It is suggested that a phosphate buffer solution in a borosilicate glass vial has the ability to form particles due to interactions with the Al that is eluted from the glass during storage.
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  • A Study of the Various Factors That Affect the Properties of Molecularly Imprinted Polymers
    Takuro Yasuyama, Hirofumi Matsunaga, Shin Ando, Tadao Ishizuka
    2013 Volume 61 Issue 5 Pages 546-550
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01044
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    We evaluated the adsorbability and selectivity of (S)-valine anilide imprinted molecularly imprinted polymer (MIP) using a batch procedure that is both independent and precise. This study revealed important information about the relationship between the performance of MIPs and experimental factors such as the components of MIP synthesis and a reaction solvent. Herein, we also describe the problems associated with the preparation of a “non-imprinted polymer,” which is often used to evaluate the effect of a template molecule, and we propose a new type of reference polymer, “blank polymer.”
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  • Isolation of Six Isoprenylated Biflavonoids from the Leaves of Garcinia subelliptica
    Tetsuro Ito, Renpei Yokota, Tatsuya Watarai, Koki Mori, Masayoshi Oyam ...
    2013 Volume 61 Issue 5 Pages 551-558
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c12-01057
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    The acetone-soluble parts of Garcinia subelliptica leaves were analyzed and six new biflavonoids were isolated, i.e., garciniaflavones A–F (1–6), as well as the five known biflavonoids amentoflavone (7), podocarpusflavone A (8), (+)-morelloflavone (9), (+)-morelloflavone-7″-O-β-glucopyranoside (10), and (+)-4‴-O-methylmorelloflavone (11) and the three triterpenoids oleanan-3-one, β-amyrin, and cycloartenol. The structures of the isolates were established based on spectroscopic analyses, including a detailed NMR spectroscopic investigation. The new biflavonoids are rare mono-isoprenylated derivatives that have a flavone-(3′–8″)-flavone core (1–4: amentoflavone type) and a flavanone-(3–8″)-flavone core (5, 6: morelloflavone type). The absolute configurations of the morelloflavone-type biflavonoids (5, 6) were confirmed by circular dichroism to be 2R,3S. The biflavonoids with an isoprenyloxy group (1) and a 2-hydroxy-3-methyl-3-butenyl group (2), and the morelloflavone-type biflavonoids with a C5 unit are the first examples in nature. We found that 7, one of the major biflavonoids, strongly inhibited hypoxia-inducible factor-1 in human embryonic kidney 293 cells under hypoxic conditions.
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  • Measurement of Transport Activities of 3β-Hydroxy-Δ5-bile Acids in Bile Salt Export Pump and Multidrug Resistance-Associated Proteins Using LC-MS/MS
    Tsuyoshi Murai, Kana Oda, Terutake Toyo, Hiroshi Nittono, Hajime Takei ...
    2013 Volume 61 Issue 5 Pages 559-566
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    Advance online publication: March 07, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00001
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    A method has been developed for the measurement of transport activities in membrane vesicles obtained from Sf9 cells for 3β-hydroxy-Δ5-bile acids by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Calibration curves for the bile acids were linear over the range of 10 to 2000 pmol/mL, and the detection limit was less than 1 pmol/mL for 3β-hydroxy-Δ5-bile acids using selected reaction monitoring analysis. The analytical method was applied to measurements of transport activities in membrane vesicles obtained from human multidrug resistance-associated protein 2-, 3-, and human bile salt export pump-expressing Sf9 cells for conjugated 3β-hydroxy-Δ5-bile acids. The present study demonstrated that human multidrug resistance-associated protein 3 vesicles accepted conjugated 3β-hydroxy-Δ5-bile acids along with common bile acids such as glycocholic acid and taurolithocholic acid 3-sulfate.
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  • Prediction of Compatibility between Ozagrel Sodium Preparation for Injection and Calcium on the Basis of the Solubility Product
    Mio Tange, Miyako Yoshida, Mai Hazekawa, Tamami Haraguchi, Yuka Nakai, ...
    2013 Volume 61 Issue 5 Pages 567-571
    Published: May 01, 2013
    Released on J-STAGE: May 01, 2013
    Advance online publication: March 01, 2013
    DOIhttps://doi.org/10.1248/cpb.c13-00042
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    The purpose of the study was to evaluate the compatibility of ozagrel sodium solution and calcium-containing transfusions using solubility product constants. We calculated the solubility product constant of mixtures of ozagrel sodium and calcium chloride and evaluated the compatibility of ozagrel sodium solution (both the original and generic products) with calcium chloride solution using a light obscuration particle counter. Various volumes of ozagrel solution were added to the calcium solutions to make final ozagrel concentrations of 0, 0.8, 1.6, 2.0, 2.4, 3.2 and 4.0 mmol/L. The solutions were gently agitated and stored at 25 and 40°C. The ozagrel concentration, calcium ion concentration and number of microparticles were measured. The solubility product constants obtained were 11.89×10−9 mol3/L3 (at 25°C) and 7.82×10−9 mol3/L3 (40°C). The number of insoluble microparticles was significantly increased when the ionic product was larger than the solubility product constant. In all ozagrel sodium products, the number of insoluble microparticles was within the allowable range according to the Japanese Pharmacopoeia. These results suggest that mixing ozagrel sodium with calcium-containing products is safe and without appreciable risk of incompatibility under clinical conditions.
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