Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 57, Issue 1
Displaying 1-22 of 22 articles from this issue
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Regular Articles
  • Three New Saponins from the Fresh Rhizomes of Polygonatum kingianum
    He-Shui Yu, Jie Zhang, Li-Ping Kang, Li-Feng Han, Peng Zou, Yang Zhao, ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 1-4
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.1
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    Further studies on the fresh rhizomes of Polygonatum kingianum led to the isolation of one new spirostanol saponin (25R)-kingianoside G (1), and two pairs mixture of 25R and 25S stereoisomeric spirostanol saponins (25R, S)-pratioside D1 (2a, 2b) and (25R, S)-kingianoside A (3a, 3b), among them 2b and 3b were new spirostanol saponins, together with another two known compounds, disporopsin (4) and daucosterol (5). The structures of the new saponins were determined by detailed analysis of their 1D and 2D NMR spectra, and chemical evidences.
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  • Heptacoordinate Tin(IV) Compounds Derived from Pyridine Schiff Bases: Synthesis, Characterization, in Vitro Cytotoxicity, Anti-inflammatory and Antioxidant Activity
    Arturo González, Elizabeth Gómez, Armando Cortés- ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 5-15
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.5
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    Tin(IV) complexes 2a—q derived from pyridine Schiff bases were prepared and characterized. Four complexes of this series were evaluated in vitro against different carcinogenic cell lines; besides their anti-inflammatory and antioxidant properties were also tested. Combination of mass spectrometry, multinuclear NMR and X-ray diffraction techniques evidenced the formation of heptacoordinated monomeric species. The X-ray diffraction analysis of 2a, 2b, 2i, 2j and 2n led to establish the heptacoordination around the tin atom in solid state and also revealed that the ligand occupies the equatorial positions of the distorted pentagonal bipyramidal geometry and the two alkyl or aryl groups the axial positions. The in-vitro study for complexes 2a—d against six tumor cell lines showed varied antiproliferative activity, the IC50 for all tested complexes was lower than that of the cis-platin. Compounds 2a—d also exhibited anti-inflammatory activity where complex 2c resulted to be more active (IC50=0.11 μM) than the indomethacin IC50=0.27 μM which was used as reference. The antioxidant activity in rat brain homogenate on inhibition of thiobarbituric acid reactive substances (TBARS) indicated that 2c (IC50=1.77 μM) is more active than the quercetine (4.11 μM) and α-tocopherol (IC50=569.09 μM).
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  • Synthesis and Evaluation of Benzophenone Oximes Derivatized with Sydnone as Inhibitors of Secretory Phospholipase A2 with Anti-inflammatory Activity
    Ravindra Ramappa Kamble, Sudha Sathyanarayanrao Belgur, Ravindranath A ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 16-21
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.16
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    A series of benzophenone oximes appended with sydnone (3a—h) bearing different substituents on aroyl moiety were synthesized to evaluate in vivo and in vitro for their inhibitory activity against purified phospholipase A2 (PLA2) enzymes from snake venom and human inflammatory pleural and ascites fluid. In vivo and in vitro inhibition studies were carried out against PLA2 with respect to the modification of the pharmacophore (substituent) to analyze the specificity for PLA2. The substituent at the aroyl ring was responsible for enhancing the inhibition towards PLA2 enzymes. Most of the newly synthesized compounds inhibit the purified PLA2 enzyme, and the inhibition was more in hydrophobic and aromatic substituents and less when no such substituents were present. The inhibitory effect of the compounds appeared to be due to the direct interaction of compounds with the enzyme. Inhibition is substrate dependent, and the inhibition competes with the substrate for the same binding site of the enzyme. The most active interacting compound 3h from in vitro inhibition of PLA2 activity showed similar potency in the in vivo neutralization of PLA2 induced mouse paw edema and hemolytic activity. Thus, the in vitro inhibition correlated well with the in vivo inhibition and hence the reported derivatives are therapeutically important anti-inflammatory drugs.
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  • Discovery of R-142086 as a Factor Xa (FXa) Inhibitor: Syntheses and Structure–Activity Relationships of Cinnamyl Derivatives
    Tetsuji Noguchi, Naoki Tanaka, Toyoki Nishimata, Riki Goto, Miho Hayak ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 22-33
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.22
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    To develop a novel and effective anticoagulant with potent and selective factor Xa (FXa) inhibitory activity, a new series of cinnamyl derivatives with enhanced lipophilicity and prodrug forms were synthesized and their biological activities were evaluated. As a result, we found that cinnamyl derivative (N-{4-[1-(acetimidoyl)piperidin-4-yloxy]-3-carbamoylphenyl}-N-[(Z)-3-(3-amidinophenyl)-2-fluoro-2-propenyl]sulfamoyl)acetic acid dihydrochloride (26d, R-142086) with a fluorine atom on the double bond exhibited potent anticoagulant activity and no mutagenic potential. Moreover, orally administered R-142086 exhibited potent anti-FXa activity and anticoagulant activity in dogs.
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  • Design and Synthesis of Piperazinylpyridine Derivatives as Novel 5-HT1A Agonists/5-HT3 Antagonists for the Treatment of Irritable Bowel Syndrome (IBS)
    Akira Asagarasu, Teruaki Matsui, Hiroyuki Hayashi, Satoru Tamaoki, Yuk ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 34-42
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.34
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    We have prepared a series of piperazinylpyridine derivatives for the treatment of irritable bowel syndrome (IBS). These compounds, which were designed by pharmacophore analysis, bind to both serotonin subtype 1A (5-HT1A) and subtype 3 (5-HT3) receptors. The nitrogen atom of the isoquinoline, a methoxy group and piperazine were essential to the pharmacophore for binding to these receptors. We also synthesized furo- and thienopyridine derivatives according to structure–activity relationship analyses. Compound 17c (TZB-20810) had high affinities to these receptors and exhibited 5-HT1A agonistic activity and 5-HT3 antagonistic activity concurrently, and is a promising drug for further development in the treatment of IBS.
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  • Freeze-Drying of Proteins in Glass Solids Formed by Basic Amino Acids and Dicarboxylic Acids
    Ken-ichi Izutsu, Saori Kadoya, Chikako Yomota, Toru Kawanishi, Etsuo Y ...
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 43-48
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.43
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    The purpose of this study was to produce and characterize glass-state amorphous solids containing amino acids and organic acids that protect co-lyophilized proteins. Thermal analysis of frozen solutions containing a basic amino acid (e.g., L-arginine, L-lysine, L-histidine) and a hydroxy di- or tricarboxylic acid (e.g., citric acid, L-tartaric acid, DL-malic acid) showed glass transition of maximally freeze-concentrated solute at temperatures (T′g) significantly higher than those of the individual solute solutions. Mixing of the amino acid with some dicarboxylic acids (e.g., oxalic acid) also suggested an upward shift of the transition temperature. Contrarily, combinations of the amino acid with monocarboxylic acids (e.g., acetic acid) had T′gs between those of the individual solute solutions. Co-lyophilization of the basic amino acids and citric acid or L-tartaric acid resulted in amorphous solids that have glass transition temperatures (Tg) higher than the individual components. Mid- and near-infrared analysis indicated altered environment around the functional groups of the consisting molecules. Some of the glass-state excipient combinations protected an enzyme (lactate dehydrogenase, LDH) from inactivation during freeze-drying. The glass-state excipient combinations formed by hydrogen-bonding and electrostatic interaction network would be potent alternative to stabilize therapeutic proteins in freeze-dried formulations.
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  • An Alternative Convenient Synthesis of Piperidazine-3-carboxylic Acid Derivatives
    Mamoru Kaname, Masae Yamada, Shigeyuki Yoshifuji, Haruki Sashida
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 49-54
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.49
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    The short-step synthesis of the unsubstituted, 5-hydroxy- and 5-chloropiperidazine-3-carboxylic acids using an aza Diels–Alder reaction between the 1,3-diene and azodicarboxylate was described. This synthetic methodology could be used for the preparation of the optically active piperazic acid in a 35% overall yield.
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  • Design and Evaluation of pH-Independent Pulsatile Release Pellets Containing Isosorbide-5-mononitrate
    Yao Liu, Songqing Liu, Qing Dai
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 55-60
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.55
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    A three-layered, pH-independent pulsatile release pellets system containing isosorbide-5-mononitrate (ISMN) was studied. The process of the heart disease such as angina has a close relationship to the chronobiology, which gives rise to the need of a pulsatile drug deliver system for the anti-anginal drug. In this study, pellets containing ISMN were firstly prepared as the core, and then layered with a swelling layer followed by an water-insoluble control layer. The core pellets were formulated with microcrystalline cellulose (MCC) and lactose, and were prepared by extrusion-spheronization. The preparation was optimized by Box–Behnken experimental design, when taking the MCC/lactose ratio as swell as the operating conditions of extrusion-spheronization as variables. The experimental results demonstrated the relationships between formulation, operation and properties of the product, and meanwhile provided optimized values for the parameters. The core pellets were coated by a fluidized bed coater, and pellets with various coating types and coating levels were studied by in vitro dissolution tests. The effects of both swelling layer and control layer on the lag time and the drug release time were studied, in order to predetermine the lag time and release time. The pellets were also evaluated in vivo by studying the pharmacokinetics after oral administration in beagle dogs. The pellets achieved a lag time of 4.1 h in vivo, which had a good consistency with the in vitro results, and the relative bioavailability was nearly 100% comparing to the normal tablets.
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  • Feasibility of 19F-NMR for Assessing the Molecular Mobility of Flufenamic Acid in Solid Dispersions
    Yukio Aso, Sumie Yoshioka, Tamaki Miyazaki, Toru Kawanishi
    Article type: Regular Article
    2009 Volume 57 Issue 1 Pages 61-64
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.61
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    The purpose of the present study was to clarify the feasibility of 19F-NMR for assessing the molecular mobility of flufenamic acid (FLF) in solid dispersions. Amorphous solid dispersions of FLF containing poly(vinylpyrrolidone) (PVP) or hydroxypropylmethylcellulose (HPMC) were prepared by melting and rapid cooling. Spin–lattice relaxation times (T1 and T1ρ) of FLF fluorine atoms in the solid dispersions were determined at various temperatures (−20 to 150 °C). Correlation time (τc), which is a measure of rotational molecular mobility, was calculated from the observed T1 or T1ρ value and that of the T1 or T1ρ minimum, assuming that the relaxation mechanism of spin–lattice relaxation of FLF fluorine atoms does not change with temperature. The τc value for solid dispersions containing 20% PVP was 2—3 times longer than that for solid dispersions containing 20% HPMC at 50 °C, indicating that the molecular mobility of FLF in solid dispersions containing 20% PVP was lower than that in solid dispersions containing 20% HPMC. The amount of amorphous FLF remaining in the solid dispersions stored at 60 °C was successfully estimated by analyzing the solid echo signals of FLF fluorine atoms, and it was possible to follow the overall crystallization of amorphous FLF in the solid dispersions. The solid dispersion containing 20% PVP was more stable than that containing 20% HPMC. The difference in stability between solid dispersions containing PVP and HPMC is considered due to the difference in molecular mobility as determined by τc. The molecular mobility determined by 19F-NMR seems to be a useful measure for assessing the stability of drugs containing fluorine atoms in amorphous solid dispersions.
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Notes
  • New Neolignan Component from Camellia amplexicaulis and Effects on Osteoblast Differentiation
    Nguyen Huu Tung, Yan Ding, Eun Mi Choi, Chau Van Minh, Young Ho Kim
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 65-68
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.65
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    A new neolignan named “camellioside A” (1) has been isolated from the leaves and branches of Camellia amplexicaulis, along with seven known glycosides (2—8). Their structures were determined by a variety of spectroscopic analyses. Among them, compounds 2, 3, 4, and 6 significantly (p<0.05) increased the alkaline phosphatase activity and the mineralization of the nodules of the MC3T3-E1 osteoblastic cells compared to those of the control.
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  • Synthesis, Characterization and DNA-Binding Properties of the Cu(II) Complex with 7-Methoxychromone-3-carbaldehyde-benzoylhydrazone
    Gao-Fei Qi, Zheng-Yin Yang, Dong-Dong Qin
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 69-73
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.69
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    A new chromone derivative (7-methoxychromone-3-carbaldehyde-benzoylhydrazone) ligand (HL) and its novel Cu(II) complex have been synthesized and characterized on the basis of elemental analyses, molar conductivities, proton nuclear magnetic resonance, infrared spectra and mass spectra analyses. The general formula of the Cu(II) complex is [CuL(HB2BO)]Cl·2H2O. In addition, the interaction of the Cu(II) complex and its free ligand with calf-thymus DNA was investigated by electronic absorption spectroscopy, fluorescence spectroscopy and viscosity measurement. Results suggest that both the two compounds can bind with calf-thymus DNA via an intercalation mechanism. Furthermore, the Cu(II) complex can bind to DNA more strongly than the free ligand due to the chelating effect of copper(II) ion to the free ligand.
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  • Syntheses and Doxorubicin-Inclusion Abilities of β-Cyclodextrin Derivatives with a Hydroquinone α-Glycoside Residue Attached at the Primary Side
    Yoshiki Oda, Masumi Miura, Kenjiro Hattori, Takashi Yamanoi
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 74-78
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.74
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    This paper describes syntheses and doxorubicin-inclusion abilities of β-cyclodextrin (CyD) derivatives with a hydroquinone α-glycoside residue attached at the primary side. The hydroquinone glycoside having an α-D-glucosidic or 2-acetamido-2-deoxy-α-D-glucosidic linkage became a useful component for providing an α-D-glucose- or 2-acetamido-2-deoxy-α-D-glucose–β-CyD conjugate. The surface plasmon resonance analyses of these β-CyD derivatives for the anticancer agent, doxorubicin, indicated that they had excellent inclusion associations on the order of 105 m−1 for the immobilized doxorubicin.
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  • Determination of Sweroside in Rat Plasma and Bile for Oral Bioavailability and Hepatobiliary Excretion
    Yong-Dong Luo, Jun Chen, Jun Cao, Xiao-Dong Wen, Ping Li
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 79-83
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.79
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    Sweroside is an active ingredient of iridoid glycoside isolated from the flower buds of Lonicera japonica THUNB. A quantitative HPLC-UV method was developed for monitoring sweroside in rat plasma, urine, feces and bile. The method was successfully applied for a basic pharmacokinetic study. The obtained data of pharmacokinetics were applied to evaluate the oral bioavailabilities of sweroside and the active ingredients of purified herbal extracts (IGEs-1). The absolute bioavailability was estimated to Fsweroside 0.31% and FIGEs-1 0.67%. The majority of sweroside excreted to feces revealed one reason of the low oral bioavailability. The values of FIGEs-1 much higher than that of Fsweroside reveals that ingredients in IGEs-1 such as loganin, secoxyloganin and some phenolic acids may promote the absorption of sweroside. The study of hepatobiliary excretion was achieved by an in vivo microdialysis sampling method after intravenous administration of sweroside. The percentage of accumulation of free form sweroside in bile duct was 31.2±7.2% of the total dosage. It may be one reason why sweroside possesses strong hepatoprotective effect.
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  • Anti Human Immunodeficiency Virus-1 (HIV-1) Agents 1. Discovery of Benzyl Phenyl Ethers as New HIV-1 Inhibitors in Vitro
    Hui-Ling Dai, Wu-Qing Liu, Hui Xu, Liu-Meng Yang, Min Lv, Yong-Tang Zh ...
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 84-86
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.84
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    Ten single benzyl phenyl ethers were synthesized and evaluated as human immunodeficiency virus-1 (HIV-1) inhibitors in vitro for the first time. Among these compounds, especially 4-nitrobenzyl phenyl ether (3h) exhibited the highest anti-HIV-1 activity with EC50 (concentration of drug that reduces syncytia formation by 50%) value of 5.96 μg/ml and therapeutic index value of 18.32. The preliminary structure–activity relationships of these benzyl phenyl ethers were also described.
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  • Alkaloids from the South China Sea Black Coral Antipathes dichotoma
    Shu-Hua Qi, Guo-Chen Su, Yi-Fei Wang, Qiu-Ying Liu, Cheng-Hai Gao
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 87-88
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.87
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    A new carbazole alkaloid, antipathine A (1), together with three known zoanthoxanthin alkaloids (2—4) was isolated from the EtOH/CH2Cl2 extracts of the South China Sea black coral Antipathes dichotoma. The structure of 1 was determined on the bases of extensive spectroscopic analysis, including 1D and 2D NMR data. Compounds 1 and 2 showed moderate cytotoxicity against human stomach carcinoma SGC-7901 cell line with IC50 of 67.38 and 86.40 μg/ml, respectively, and 1 and 2 also showed weak cytotoxicity toward human liver carcinoma Hep_G2 cell line.
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  • Acetylation of the Amino Group on Guanosine Induced by Nitric Oxide in Acetonitrile under Aerobic Conditions
    Toshinori Suzuki, Toshimitsu Fukai, Yusuke Seki, Michiyo Inukai
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 89-91
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.89
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    When nitric oxide was bubbled into acetonitrile under aerobic conditions, the solution showed a cobalt-blue color. Addition of guanosine into the solution generated N2-acetylguanosine as a major product. The result of the reaction using 15N labeled acetonitrile indicated that the nitrogen atom of the acetylated exocyclic amino group on N2-acetylguanosine originated from acetonitrile. We discuss the reaction mechanism for the acylation.
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  • Ginsenosides from Heat Processed Ginseng
    Sang Myung Lee, Hyun Ju Shon, Chung-Sig Choi, Tran Manh Hung, Byung Su ...
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 92-94
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.92
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    A new dammarane-glycoside, ginsenoside Rz1 (1), was isolated from heat-treated Panax ginseng C. A. MEYER (Araliaceae) with ginsenosides Rk1 and Rg5. The structure of 1 was established to be (Z)-12β-hydroxydammara-20(22),24-dien-3β-yl O-β-D-glucopyranosyl-(1→2)-β-D-glucospyranoside by spectroscopic means. HPLC analyses revealed that the ginsenosides Rz1, Rk1, and Rg5 were present in the ratios of 1 : 2 : 6, respectively.
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  • Synthesis of a Novel Water-Soluble Cleft-Type Cyclophane as an N-Methyl-D-aspartate Receptor Antagonist
    Takashi Masuko, Tadashi Kusama, Rie Namiki, Koichi Metori, Yasuo Kizaw ...
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 95-98
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.95
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    Novel water-soluble N-methyl-D-aspartate (NMDA) receptor antagonists, 4,4′-bis({2-[N-(1,4,8,11-tetraazacyclotetradecan-1-yl)acetyl]-N-phenethyl}aminoethoxy)diphenylmethane octahydrochloride (1, ACPCm) and 4,4′-bis({2-[N-(1,4,7,10-tetraazacyclododecan-1-yl)acetyl]-N-phenethyl}aminoethoxy)diphenylmethane octahydrochloride (2, ACPCn), were synthesized and the effect of these cleft-type cyclophanes on NMDA receptors was then studied using voltage-clamp recordings of recombinant NMDA receptors expressed in Xenopus oocytes. ACPCm (1) and ACPCn (2) inhibited macroscopic currents in the NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D receptor subtypes in oocytes voltage-clamped at −70 mV. The IC50 values of ACPCm (1) and ACPCn (2) for NR1/NR2A and NR1/NR2B receptors were 1.06 μM and, 0.92 μM and 1.47 μM and, 1.49 μM, respectively. The inhibition by these compounds was voltage-dependent, that is, the degree of inhibition was in the order of negative holding potentials, −100 mV>−70 mV>−20 mV. These findings indicate that the cleft-type cyclophanes, ACPCm (1) and ACPCn (2) directly act on the channel pore of the NMDA receptors.
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  • Cordyceamides A and B from the Culture Liquid of Cordyceps sinensis (BERK.) SACC.
    Jing-Ming Jia, Hai-Hua Tao, Bao-Min Feng
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 99-101
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.99
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    Two new aurantiamides named as cordyceamides A and B were isolated from the culture liquid of Cordyceps sinensis (BERK.) SACC., along with one known compound, aurantiamide acetate. Their structures were elucidated as N-benzoyl-L-tyrosinyl-L-phenylalaninol acetate and N-benzoyl-L-tyrosinyl-L-p-hydroxyphenylalaninol acetate by 1D, 2D-NMR techniques and comparison with literatures.
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  • New Triterpenoid Saponins from Glochidion eriocarpum and Their Cytotoxic Activity
    Phan Van Kiem, Vu Kim Thu, Pham Hai Yen, Nguyen Xuan Nhiem, Nguyen Huu ...
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 102-105
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.102
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    Combined chromatographic methods led to the isolation of two new triterpenoid saponins, glochieriosides A and B (1, 2), from the aerial parts of Glochidion eriocarpum, along with three known triterpenes, glochidone (3), lup-20(29)-en-3β,23-diol (4), and lup-20(29)-en-1β,3β-diol (5). The structures of the new saponins were determined to be 22β-benzoyloxy-3β,16β,28-trihydroxyolean-12-ene 3-O-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranoside] (1) and 22β-benzoyloxy-3β,16β,28-trihydroxyolean-12-ene 3-O-[β-D-glucopyranosyl-(1→3)-β-D-xylopyranoside] (2). The structural elucidation was accomplished by using a combination of the 1D-NMR (1H-, 13C-NMR, distortionless enhancement by polarization transfer (DEPT) 90°, and DEPT 135°), 2D-NMR (1H–1H correlation spectroscopy, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, and rotating frame Overhouser effect spectroscopy), ESI-MS, and HR-FAB-MS experiments. Glochieriosides A and B exhibited significant cytotoxic activity against HL-60, HT-29, MCF-7 and SK-OV-3 human cancer cell lines with the IC50 values of 5.5, 6.8, 29.1, and 22.7 μM for glochierioside A, respectively, and 6.6, 18.6, 36.1, and 16.0 μM for glochierioside B. Glochidone was less active with IC50 values greater than 100 μM while lup-20(29)-en-1β,3β-diol was moderately active with IC50 values of 43.3, 67.0, 66.1, and 48.0 μM, respectively.
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  • New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.
    Taeseong Park, Tayyab Ahmad Mansoor, Pramod Bapurao Shinde, Baoquan Ba ...
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 106-111
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.106
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    A chemical investigation of the MeOH extract of a marine sponge Haliclona (Reniera) sp., collected off the coast of Ulleung Island, Korea, led to the isolation of thirteen new cerebrosides (1—3, 5—14), along with a known analogue (4). Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy, MS spectrometry, and chemical method. The major new features of these glucocerebrosides are C15 and C19 acyl chains, long (C24–C28) acyl chains, or the S-configuration of the acyl chains. It is noteworthy that both R- and S-configurations of the acyl chains were observed in the same specimen.
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  • Iodine-Catalyzed Etherification of Morroniside
    Fortunatus Sunghwa, Hiroaki Sakurai, Ikuo Saiki, Mamoru Koketsu
    Article type: Notes
    2009 Volume 57 Issue 1 Pages 112-115
    Published: January 01, 2009
    Released on J-STAGE: January 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.112
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    In this study, we describe a highly selective etherification procedure of unprotected morroniside catalyzed by molecular iodine in acetone. The etherification reaction furnished 7-O-alkyl ether derivatives in reasonable yields within few hours under neutral conditions. Studies of the obtained products on cytotoxicity activity in colon 26-L5 cell line were examined. Among the tested compounds, 7-O-dodecylmorroniside showed moderate cytotoxic activity, having IC50 values equal to 20.9 μM.
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