Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 59, Issue 7
Displaying 1-18 of 18 articles from this issue
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Review
  • Naturally Occurring Iridoids and Secoiridoids. An Updated Review, Part 4
    Biswanath Dinda, Sudhan Debnath, Rajarshi Banik
    Article type: Review
    2011 Volume 59 Issue 7 Pages 803-833
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.803
    JOURNAL FREE ACCESS
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    A compilation of new naturally occurring iridoids and secoiridoids including their glycosides, esters, aglycones, derivatives and dimers reported during mid 2008—2010 is provided with available physical and spectral data: mp, [α]D, UV, IR, circular dichroism (CD), 1H- and 13C-NMR as well as natural source with family and references. The important bioactivity of new and known iridoids and secoiridoids reported during this period is also highlighted.
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Regular Articles
  • Plastoquinones from Sargassum yezoense; Chemical Structures and Effects on the Activation of Peroxisome Proliferator-Activated Receptor Gamma
    Min Cheol Kim, Hak Cheol Kwon, Su Nam Kim, Hyung Seop Kim, Byung Hun U ...
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 834-838
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.834
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    Four new plastoquinones, together with two known compounds, sargahydroquinoic acid and sargaquinoic acid, were isolated from the brown alga, Sargassum yezoense collected from the eastern coast of Korea. The structures of these compounds were elucidated based on spectroscopic analyses including NMR and MS. Their structures designated as meroterphenol A (1), B (2), C (3) and D (4) were characterized by a 6-methyl-1,4-benzohydroquinone moiety with an oxygenated diterpenoic acid chain. Meroterphenols A—D showed potent activation effects on peroxisome proliferator-activated receptor gamma (PPARγ).
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  • Quantitation of L-Arginine and Asymmetric Dimethylarginine in Human Plasma by LC-Selective Ion Mode-MS for Type 2 Diabetes Mellitus Study
    Lunzhao Yi, Pengfei Zhang, Xiaoyan Ji, Yizeng Liang, Yamin Wang, Zhigu ...
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 839-843
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.839
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    The article reports a simple, sensitive and fast LC/MS method for the analysis of L-arginine (L-Arg), asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA) in human plasma. The homoarginine was used as the internal standard (IS). The chromatographic separation was achieved on C18 (150 mm×2.1 mm, 5 μm) column with a mobile phase consisting of ammonium acetate (0.25 mmol/l) and methanol (93 : 7, v/v), at a flow rate of 0.2 ml/min. L-Arg, ADMA and SDMA were well separated by LC/MS with selective ion mode (SIM). The method was successfully applied to type 2 diabetes mellitus (T2DM) study. Twenty-one healthy controls and twenty-two T2DM patients before and after treatment two years were investigated. The results indicated that the level of ADMA in T2DM was significantly higher than that in healthy controls. Furthermore, ADMA has important association with the development of cardiovascular diseases.
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  • Dissolution-Enhancing Mechanism of Alkalizers in Poloxamer-Based Solid Dispersions and Physical Mixtures Containing Poorly Water-Soluble Valsartan
    Nam Sung Ha, Thao Truong-Dinh Tran, Phuong Ha-Lien Tran, Jun-Bom Park, ...
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 844-850
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.844
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    The purpose of this study was to investigate the effects of alkalizers in dissolution rate and crystal structure of valsartan (VAL) in Poloxamer 407 (POX)-based solid dispersions (SD). VAL, a poorly-water soluble drug was selected as a model drug because of its low solubility at low pH. The POX-based SDs containing alkalizers (Na2CO3, MgO, meglumine and arginine) were prepared by melting method. The dissolution tests were performed using the United States Pharmacopeia (USP) paddle II method in enzyme-free simulated gastric fluid (pH 1.2) for 2 h. Microenvironmental pH (pHM) was examined potentiometrically by using a surface pH electrode. Dissolution rate of SD incorporating Na2CO3 was drastically increased. The differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD) data indicated that crystalline structure of VAL in SD was transformed to amorphous form by the addition of alkalizers but could not explain the differences in the dissolution rates. The molecular interaction between VAL and Na2CO3 was observed in the Fourier transform infrared spectroscopy (FT-IR) spectra by the shift of C=O band from 1732 to 1719 cm−1 and the disappearance of carbonyl group at 1598 cm−1. Furthermore, Na2CO3 efficiently modulated pHM by providing a favorable microenvironment for drug dissolution. A combination of SD method and use of alkalizer is a promising approach to modulate release rate of poorly water-soluble and ionizable drug with an aid of changes of drug crystallinity, molecular interaction and pHM.
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  • Synthesis, Characterization and Biological Evaluation of Platinum(II) Complexes with a Chiral N-Monosubstituted 1,2-Cyclohexyldiamine Derivative
    Chuanzhu Gao, Shaohua Gou, Gang Xu
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 851-854
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.851
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    Eight platinum(II) compounds with a new chiral ligand, 2-(((1R,2R)-2-aminocyclohexylamino)methyl)phenol (HL), were designed, prepared and spectrally characterized. All compounds showed better aqueous solubility than cisplatin and oxaliplatin. In vitro cytotoxicity of these compounds against human HepG-2, MCF-7, A549 and HCT-116 cell lines was evaluated. Results indicated that all compounds showed cytotoxicity against A549 and HepG-2 cell lines. Particularly, compounds B1 and B8, which have CF3SO3− and (CH3)3COCH2COO− as leaving groups, respectively, exhibited better cytotoxicitiy than that of carboplatin in these two cell lines.
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  • seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity
    Carlos Andres Coy Barrera, Ericsson David Coy Barrera, Diana Susana Gr ...
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 855-859
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.855
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    A novel seco-limonoid, rel-(1S,5R,9S,7R,8S,9R,10S,11R,13S,14R,15R,17R)-11,19-dihydroxy-7-acetoxy-7-deoxoichangin (raputiolide) (1), and two novel quinolone alkaloids N-methyl-2-phenoxyquinolin-4(1H)-one (heptaphyllone A) (2) and 6-methylbenzofuro[2,3-b]quinolin-4(1H)-one (heptaphyllone B) (3), along with the known seco-limonoid ichangin (4), were isolated from Raputia heptaphylla PITTIER (Rutaceae) stem bark. Five known alkaloids, N-methyl-8-methoxyflindersine (5), skimmianine (6), kokusaginine (7), dictamnine (8) and flindersiamine (9), were also isolated from R. heptaphylla leaves. Their structures were established on the basis of full spectroscopic data interpretation supported by data from the pertinent literature. seco-Limonoid 1 configuration was determined by enhanced nuclear Overhauser effect spectroscopy (NOESY) experiments and density functional theory (DFT) molecular modeling. The antileishmanial effect of the isolated compounds was evaluated on Leishmania Viannia panamensis (promastigotes and amastigotes). Whereas alkaloids 2—3, 6—8 and limonoid 4 exhibited no significant parasitocide activity against internalized L. (V.) panamensis amastigotes, limonoid 1 and alkaloid 5 had leishmanicidal activity on intracellular amastigotes (EC50: 8.7 μg/ml) and promastigotes (EC50: 14.3 μg/ml), respectively.
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  • Steric and Allosteric Effects of Fatty Acids on the Binding of Warfarin to Human Serum Albumin Revealed by Molecular Dynamics and Free Energy Calculations
    Shin-ichi Fujiwara, Takashi Amisaki
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 860-867
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.860
    JOURNAL FREE ACCESS
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    Human serum albumin (HSA) binds with drugs and fatty acids (FAs). This study was initiated to elucidate the relationship between the warfarin binding affinity of HSA and the positions of bound FA molecules. Molecular dynamics simulations of 11 HSA-warfarin-myristate complexes were performed. HSA-warfarin binding free energy was then calculated for each of the complexes by the molecular mechanics-Poisson–Boltzmann surface area (MM-PBSA) method. The results indicated that the magnitude of the binding free energy was smaller in HSA-warfarin complexes that had 4 or more myristate molecules than in complexes with no myristate molecules. The unfavorable effect on the HSA-warfarin binding affinity was caused sterically by the binding of a myristate molecule to the FA binding site closest to the warfarin binding site. On the other hand, the magnitude of HSA-warfarin binding free energy was largest when 3 myristate molecules were bound to the high-affinity sites. The strongest HSA-warfarin binding was attributable to favorable entropic contribution related to larger atomic fluctuations of the amino acid residues at the warfarin binding site. In the binding of 2 myristate molecules to the sites with the highest and second-highest affinities, allosteric modulation that enhanced electrostatic interactions between warfarin and some of the amino acid residues around the warfarin binding site was observed. This study clarified the structural and energetic properties of steric/allosteric effects of FAs on the HSA-warfarin binding affinity and illustrated the approach to analyze protein–ligand interactions in situations such that multiple ligands bind to the other sites of the protein.
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  • Development of a Rapid Process Monitoring Method for Dry-Coated Tableting Process by Using Near-Infrared Spectroscopy
    Masatomo Ito, Tatsuya Suzuki, Naoki Wakiyama, Hiroshi Teramoto, Etsuo ...
    Article type: Regular Article
    2011 Volume 59 Issue 7 Pages 868-873
    Published: July 01, 2011
    Released on J-STAGE: July 01, 2011
    DOIhttps://doi.org/10.1248/cpb.59.868
    JOURNAL FREE ACCESS
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    A nondestructive transmittance near-infrared (NIR) method for detecting off-centered cores in dry-coated (DC) tablets was developed as a monitoring system in the DC tableting process. Caffeine anhydrate was used as a core active pharmaceutical ingredient (API), and DC tablets were made by the direct compression method. NIR spectra were obtained from these intact DC tablets using the transmittance method. The reference assay was performed with HPLC. Calibration models were generated by partial least squares (PLS) regression and principal component regression (PCR) utilizing external validations. Hierarchical cluster analysis (HCA) of the results confirmed that NIR spectroscopy correctly detected off-centered cores in DC tablets. We formulated and used the Centering Index (CI) to evaluate the precision of core alignment and generated an NIR calibration model that could correctly predict this index. The principal component (PC) 1 loading vector of the final calibration model indicated that it could specifically detect the misalignment of tablet cores. The model also had good linearity and accuracy. The CIs of unknown sample tablets predicted by the final calibration model and those calculated through the HPLC analysis were closely parallel with each other. These results demonstrate the validity of the final calibration model and the utility of the transmittance NIR spectroscopic method developed in this study as a monitoring system in DC tableting process.
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