Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 50, Issue 5
Displaying 1-33 of 33 articles from this issue
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Regular Articles
  • Characterization of Physical State of Mannitol after Freeze-Drying: Effect of Acetylsalicylic Acid as a Second Crystalline Cosolute
    Susana Torrado, Santiago Torrado
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 567-570
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.567
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    Freeze-drying of mixed solutes is a preparative technique widely used in the pharmaceutical industry. The presence of an amorphous form or changes in the crystalline form can affect solid state stability. In this work, acetylsalicylic acid (AAS) was chosen as a model drug, and was mixed with mannitol, a commonly used bulking agent in formulation of tablets. Variations in the final freeze-dried crystalline forms were found after changing the ratios of the two co-solutes. Samples were analysed by powder X-ray diffractometry and differential scanning calorimetry. A major amorphous form and a minor crystalline δ-mannitol form were produced during the mannitol freeze-drying process. The crystal form of mannitol in the two-component system depended on the AAS:mannitol ratio. The AAS was mostly crystalline, regardless of the amount of mannitol present. A major δ-mannitol and a minor amorphous form were obtained when AAS was present in a high percentage (75% w/w). When AAS percentages of 50 and 25% (w/w) were present during the drying process, the mannitol was found in a highly crystalline form.
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  • Structural Studies on C-Amidated Amino Acids and Peptides: Function of Amide Group in Molecular Association in Crystal Structures of Val–Gly–NH2, Ser–Phe–NH2, Gly–Tyr–NH2 and Pro–Tyr–NH2 Hydrochloride Salts
    Yasuko In, Hiroto Ono, Toshimasa Ishida
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 571-577
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.571
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    As part of a series of elucidation of the structural features of peptides caused by C-terminal α-amidation, the crystal structures of H–Val–Gly–NH2, H–Ser–Phe–NH2, H–Gly–Tyr–NH2, and H–Pro–Tyr–NH2 hydrochloride salts were analyzed by the X-ray diffraction method. Although respective molecules take energetically allowable torsion angles concerning the backbone and side chains, their conformations are not necessarily the same as the corresponding unamidated ones. This results from the different molecular packing requirements, rather than from different conformational features inherent in the C-amidated and -unamidated peptides. As for the molecular packing feature, each peptide tended to form a repeated structure through those hydrogen bonds in which both amide NH and O=C groups participate. The chloride ions are located between the neighboring peptides and are hydrogen-bonded to the respective amide NHs, leading to the sheet structure. The hydrogen-bonding feature of the amide group and its function in molecular packing was discussed based on the results analyzed so far.
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  • Selective Inhibition of Fe- versus Cu/Zn-Superoxide Dismutases by 2,3-Dihydroxybenzoic Acid Derivatives
    Laurent Soulère, Cécile Viodé, Jacques Pér ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 578-582
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.578
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    A series of catechol derivatives were synthesised and tested for their ability to inactivate the iron-containing superoxide dismutase (Fe-SOD) from Escherichia coli and the bovine erythrocytes Cu/Zn-SOD. Incubation of catechols with Fe- or Cu/Zn SODs resulted in a time-dependent loss of enzyme activity with highly selective inhibition for the iron-dependent enzyme. Catechol-induced inactivation of SODs was correlated with the auto-oxidation of the catechol compounds to their corresponding ortho-quinone derivatives, which was found to be non-dependent on the presence of enzymes. Mass electrospray experiments on catechol-incubated Fe-SOD provided evidence for the irreversible nature of the inhibition process, yielding to a complex mixture of modified proteins.
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  • Studies on the Constituents from the Aerial Part of Baccharis dracunculifolia DC. II
    Yoshimi Nagatani, Tsutomu Warashina, Tadataka Noro
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 583-589
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.583
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    Ten new glycosides were obtained along with five known compounds from the aerial part of Baccharis dracunculifolia DC. (Compositae). The structures of these glycosides were determined based on spectral and chemical evidence. These new compounds consisted of β-D-glucopyranose or β-D-apiofuranosyl-(1→6)-β-D-glucopyranose, and most possessed an (E)-caffeoyl group the same as dracunculifosides A—J.
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  • Three New Naphthoquinone Derivatives from Diospyros maritima BLUME
    Matsutake Higa, Nobue Noha, Hiroto Yokaryo, Kazuhito Ogihara, Seiichi ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 590-593
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.590
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    Three new naphthoquinone derivatives, 6-(1-ethoxyethyl)plumbagin (16), ethylidene-3,3′-biplumbagin (17), and ethylidene-3,6′-biplumbagin (18), were isolated, in addition to six known naphthoquinones, isozeylanone (10), 3,3′-biplumbagin (11), chitranone (12), methylene-3,3′-biplumbagin (13), 2,3-epoxyplumbagin (14), and 3,8′-biplumbagin (15), from the fruits of Diospyros maritima BLUME (Ebenaceae). The structures of the new compounds were established by spectroscopic methods. The eight naphthoquinones 11—18 were examined for ichthyotoxic activity and germination inhibitory activity. The quinones 11, 12, and 14—16 showed strong ichthyotoxic activity and the quinone 14 mild germination inhibitory activity.
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  • A Cosolvency Model to Predict Solubility of Drugs at Several Temperatures from a Limited Number of Solubility Measurements
    Abolghasem Jouyban, Susana Romero, Hak-Kim Chan, Brian John Clark, Pil ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 594-599
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.594
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    A cosolvency model to predict the solubility of drugs at several temperatures was derived from the excess free energy model of Williams and Amidon. The solubility of oxolinic acid, an antibacterial drug, was measured in aqueous (water+ethanol) and non-aqueous (ethanol+ethyl acetate) mixtures at several temperatures (20, 30, 35, 40 °C). Oxolinic acid displays a solubility maximum in each solvent mixture at solubility parameter values of 32 and 22 MPa1/2. The temperature and heat of fusion were determined from differential scanning calorimetry. The solvent mixtures do not produce any solid phase change during the solubility experiments. The experimental results and those from the literature were employed to examine the accuracy and prediction capability of the proposed model. An equation was obtained to represent the drug solubility changes with cosolvent concentration and temperature. The model was also tested using a small number of experimental solubilities at 20 and 40 °C showing reasonably accurate predictions. This is important in pharmaceutics because it save experiments that are often expensive and time consuming.
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  • Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Amphoteric Glycolipid Analogues from the Porcine Nematode, Ascaris suum
    Isao Ohtsuka, Noriyasu Hada, Hiroko Ohtaka, Mutsumi Sugita, Tadahiro T ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 600-604
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.600
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    A novel amphoteric glycosphingolipid, cholinephosphoryl-(→6)-β-D-GlcpNAc-(1→3)-β-D-Manp-(1→4)-β-D-Glcp-(1→)-Cer, isolated from the porcine parasitic nematode, Ascaris suum, may be expected to be involved in host-parasite interactions. This glycosphingolipid analogue containing octyl residue in place of ceramide was synthesized as follows: The key reaction of this synthetic procedure is the formation of a intramolecular aglycon delivery (IAD) approach for β-selective mannosylation. Then, a coupling of phosphocholine group at the position C-6″ of 16 was attempted using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by reaction of the resulting cyclic phosphate intermediate with anhydrous trimethylamine to give 17. Subsequent debenzylation and debenzylidenation afforded target compound (2).
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  • Constituents from Polygonum cuspidatum
    Kai Xiao, Lijiang Xuan, Yaming Xu, Donglu Bai, Dexin Zhong
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 605-608
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.605
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    Two lignan sulfates, a stilbene derivative and a phenol sulfate, together with 10 known compounds, were isolated from an aqueous extract of the root of Polygonum cuspidatum. The new compounds were elucidated based on chemical evidence and spectroscopic techniques including two-dimensional NMR methods. They exhibited no inhibition of lipid peroxidation and no cytotoxic and DNA cleavage activities.
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  • Synthesis and Characterization of Radioiodinated MD-230254: A New Ligand for Potential Imaging of Monoamine Oxidase B Activity by Single Photon Emission Computed Tomography
    Masahiko Hirata, Shinya Kagawa, Mitsuyoshi Yoshimoto, Yoshiro Ohmomo
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 609-614
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.609
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    A series of iodinated analogues of MD-230254 was synthesized and evaluated for inhibitory potency and selectivity toward monoamine oxidase B (MAO-B). Among them, 5-[4-(2-iodobenzyloxy)phenyl]-3-(cyanoethyl)-1, 3, 4-oxadiazole-2(3H)one (2-IBPO) was found to have high inhibitory potency and selectivity toward MAO-B (IC50=2.0 nM, MAO-A/MAO-B >50000). Analysis of the inhibition kinetics indicated that 2-IBPO acts in a two-step mechanism as a competitive, slow, and tight-binding inhibitor of MAO-B with a Ki value of 2.4 nM and an overall Ki* value at an equilibrium of 3.8 nM. The new radioligand for MAO-B, [125I]2-IBPO was conveniently synthesized from a tributylstannyl precursor by an iododestannylation reaction using sodium [125I]iodide and hydrogen peroxide with high radiochemical yield. The in vivo tissue distribution studies of [125I]2-IBPO demonstrated its high initial uptake and prolonged retention in the brain. A selective interaction of [125I]2-IBPO with MAO-B was confirmed by the pretreatment experiment with well known MAO specific inhibitors, l-deprenyl, Ro-16-6491, clorgyline, and Ro-41-1049. These very desirable characteristics of [125I]2-IBPO suggested that a 123I-labeled counterpart, [123I]2-IBPO, would have great potential in in vivo studies of MAO-B in the human brain with single photon emission computed tomography (SPECT).
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  • Diastereoselective Imino–Aldol Condensation of Chiral 3-(p-Tolylsulfinyl)-2-furaldimine and Ester Enolates
    Yoshitsugu Arai, Shinya Yoneda, Tsutomu Masuda, Yukio Masaki
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 615-622
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.615
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    (Ss)-3-(p-Tolylsufinyl)-2-furaldimine was synthesized, and condensation of the chiral furaldimine with lithium ester enolates has been examined. The product distribution of the reaction is dependent upon reaction conditions and on the kind of the substituent placed on the esters. Disubstituted ester enolate resulted in the exclusive formation of (4R)-β-lactam, while unsubstituted, tert-butyl ester enolate preferentially gave (3R)-β-amino ester. With the monosubstituted ester enolates, the condensation afforded (4R)-β-lactams and/or (3R)-β-amino esters as major products. This method has been applied to an efficient route to chiral furyl β-lactams.
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  • Purification, Characterization, and Modification of T Lymphocyte-Stimulating Polysaccharide from Spores of Ganoderma lucidum
    Xing-Feng Bao, Yun Zhen, Li Ruan, Ji-Nian Fang
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 623-629
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.623
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    The hot-water extract of the spores of Ganoderma lucidum was shown to have a stimulating effect on concanavalin A-induced mitogenic activity of T lymphocytes. Bioassay-guided separation led to the isolation of a polysaccharide with potent T lymphocyte-stimulating activity by ethanol fractionation, anion-exchange, and size-exclusion chromatography. Based on the composition and methylation analyses, periodate oxidation, Smith degradation, and NMR spectroscopy, the native polysaccharide was shown to be a β-D-(1→3)-glucan with branches of terminal glucosyl residues substituted at C-6 of the glucose residues in the main chain. The branching ratio is approximately 20%. A series of sulfated or carboxymethylated derivatives were prepared and their structural features were elucidated by chemical and spectral analyses. The solution conformation and T lymphocyte proliferation effect of the glucans before and after derivatization were compared and discussed. The data obtained indicate that the introduction of ionic groups would significantly affect the original conformation of the native glucan in aqueous solution and further affect T lymphocyte-stimulating activity. The triple-helical structure of the glucans, the nature of the ionic groups, and the density of negative charge were considered to be closely related to this activity.
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  • Flavanone and Flavonol Glycosides from the Leaves of Thevetia peruviana and Their HIV-1 Reverse Transcriptase and HIV-1 Integrase Inhibitory Activities
    Supinya Tewtrakul, Norio Nakamura, Masao Hattori, Tamio Fujiwara, Tano ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 630-635
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.630
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    Two new flavanone glucosides, (2R)- and (2S)-5-O-β-D-glucopyranosyl-7,4′-dihydroxy-3′,5′-dimethoxyflavanone[pervianoside I (3), peruvianoside II (4)] and a new flavonol glycoside, quercetin 3-O-{β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside} (peruvianoside III, 13) were isolated from the leaves of Thevetia peruviana SCHUM., together with nine known flavonol glycosides and two known iridoid glucosides. The structures of all compounds were determined on the basis of chemical and spectroscopic methods. Their inhibitory effects against HIV-1 reverse transcriptase and HIV-1 integrase were also investigated.
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  • A Convenient 3-Step Synthesis of 3-Acetamido-6-arylpyridazines Directed to Novel Y5 Receptor Antagonist
    Sébastien Guéry, Yveline Rival, Camille-Georges Wermuth, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 636-639
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.636
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    A 3-step synthesis of 3-acetamido-6-arylpyridazines as potential NPY5 antagonists.
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  • Turpinionosides A—E: Megastigmane Glucosides from Leaves of Turpinia ternata NAKAI
    Qian Yu, Hideaki Otsuka, Eiji Hirata, Takakazu Shinzato, Yoshio Takeda
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 640-644
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.640
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    From leaves of Turpenia ternata (Staphylaceae), one megastigmane and seven of its glucosides (1—8) were isolated. Megastigmane and two of the glucosides were found to be known compounds, namely, 3S,5R,6R,9S-tetrahydroxymegastigmane (1), corchoionoside C (2), and icariside B4 (3). The structures of compounds 4—8 (turpinionosides A—E, respectively) were elucidated by means of spectroscopic analyses, and then their absolute structures were determined by the modified Mosher's method to be (3S,5R,6S,9S)-3,6,9-trihydroxymegastigman-7-ene 3-O- and 9-O-β-D-glucopyranosides (4, 5, respectively), (1S,3S,5R,6S,9R)-3,9,12-trihydroxymegastigmane 3-O-β-D-glucopyranoside (6), (3S,4R,9R)-3,4,6-trihydroxymegastigman-5-ene 3-O-β-D-glucopyranoside (7), and (2S,9R)-2,9-dihydroxymegastigman-5-en-4-one 2-O-β-D-glucopyranoside (8).
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Notes
  • A New Pentacyclic Cucurbitane Glucoside and a New Triterpene from the Fruits of Gymnopetalum integrifolium
    Toshikazu Sekine, Hiroshi Kurihara, Mayumi Waku, Fumio Ikegami, Nijsir ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 645-648
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.645
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    A new pentacyclic cucurbitane glucoside, named aoibaclyin (1) and a new triterpene (2) have been isolated from the EtOH extract of the fruits of Gymnopetalum integrifolium KURZ (Cucurbitaceae), together with three known compounds, bryoamaride (3), 25-O-acetylbryoamaride (4) and β-sitosterol 3-O-β-D-glucopyranoside (5). The structures of these compounds were elucidated by spectroscopic analyses.
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  • Synthesis and Fasciolicidal Activity of 5-Chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole
    Alicia Hernández-Campos, Froylán Ibarra-Velarde, Yolanda ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 649-652
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.649
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    The synthesis and fasciolicidal activity of 5-chloro-2-methylthio-6-(1-naphthyloxy)-1H-benzimidazole (6) is described. Compound 6 showed 100% activity in vitro at 146.70 and 29.34 μM concentrations. It also completely removed 3-d and 10-week-old Fasciola hepatica in sheep at a dose of 15 mg/kg.
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  • Two New Steroidal Saponins from “Gualou-xiebai-baijiu-tang” Consisting of Fructus trichosanthis and Bulbus allii macrostemi
    Xiangjiu He, Feng Qiu, Yukihiro Shoyama, Hiroyoki Tanaka, Xinsheng Yao
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 653-655
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.653
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    Two new steroidal saponins were isolated from the Chinese folk medicine called Gualou-xiebai-baijiu-tang. The structures were determined to be spirost 25(27)-ene-2β,3β-diol-3-O-β-D-glucopyranosyl(1→2)-β-D-galactopyranoside and 26-O-β-D-glucopyranosyl-22α-hydroxy-5β-furost-25(27)-ene-1β,3β,6β,26-tetraol-3-O-β-D-galactopyranoside, respectively, based on chemical evidences and spectral analysis.
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  • Synthesis, Photochemical Synthesis and Antitumor Evaluation of Novel Derivatives of Thieno[3′,2′:4,5]thieno[2,3-c]quinolones
    Jasna DoganKoruznjak, Neda Slade, Branimir Zamola, Kresimir Pavelic, G ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 656-660
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.656
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    The novel derivatives of thieno[3′,2′:4,5]thieno[2,3-c]quinolones 6a, 6b, 7, 10a and 10b were synthesized in multistep synthesis starting from thiophene-3-carboxaldehyde and malonic acid reacting in aldol condensation or from 3-bromothiophenes or methyl 4-bromothiophene-2-carboxylate reacting in Heck reaction. They resulted in corresponding substituted thienylacrylic acids 3a—c, which were cyclized into thieno[2,3-c]thiophene-2-carbonyl chlorides 4a—c and converted into thieno[2,3-c]thiophene-2-carboxamides 5a—d. Prepared carboxamides were photochemically dehydrohalogenated into corresponding substituted thieno[3′,2′:4,5]thieno[2,3-c]quinolones 6a—d. Compound 7 was prepared from 6d by alkylation with N-[3-(dimethylamino)propyl]chloride hydrochloride in the presence of NaH. Compounds 10a and 10b were prepared from 6c in the multistep synthesis over acid 8 and acid chloride 9. Compounds 6a, 6b, 7, 10a and 10b were found to exert cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (CaCo-2), melanoma (HBL), and human fibroblast cell lines (WI-38). The compound 6b, which bears the 3-dimethylaminopropyl substituent on quinolone nitrogen and methoxycarbonyl substituent on position 9, exhibiedt marked antitumor activity. On the contrary, compound 7, which also bears the 3-dimethylaminopropyl substituent on the quinolone nitrogen but anilido substituent on position 9, exhibited less antitumor activity than the others.
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  • Additional Cytotoxic Diacetylenes from the Stony Coral Montipora sp.
    Naseer Alam, Jongki Hong, Chong-Ok Lee, Jae Sue Choi, Kwang Sik Im, Je ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 661-662
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.661
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    Three new diacetylenes (1, 4, 6) have been isolated as cytotoxic constituents from the methanolic extract of the stony coral Montipora sp. The structures have been elucidated on the basis of spectroscopic evidence. The compounds were evaluated for cytotoxicity against a small panel of human tumor cell lines and showed moderate to significant activity.
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  • Androstane Alkaloids from Musk of Moschus moschiferus
    Sei-Ryang Oh, Jong Pill Lee, Seung-Yeup Chang, Dong-Hyuk Shin, Kyung-S ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 663-664
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.663
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    Two androstane alkaloids were isolated from the musk of Moschus moschiferus. The structures were elucidated to be 3α-ureido-androst-4-en-17-one (1) and 3α-ureido-androst-4-en-17β-ol (2) by two-dimensional NMR analysis (HMQC, 1H–1H COSY, HMBC, and NOESY).
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  • New Phenylethanoid Glycosides from Veronica pectinata var. glandulosa and Their Free Radical Scavenging Activities
    Iclal Saracoglu, Ummuhan Sebnem Harput, Makoto Inoue, Yukio Ogihara
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 665-668
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.665
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    A known phenylethanoid glycoside, ehrenoside (1), was isolated together with three new phenylethanoid glycosides, verpectoside A (2), B (3) and C (4) from the aerial parts of Veronica pectinata var. glandulosa. On the basis of spectral analysis (UV, FAB-MS, 1H-, 13C- and 2D-NMR), compounds 2—4 were determined to be 2-(3,4-dihydroxyphenyl)ethyl-O-α-L-arabinopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-(4-O-trans-feruloyl)-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-(4-O-trans-caffeoyl)-β-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)ethyl-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-(4-O-trans-feruloyl)-β-D-glucopyranoside, respectively. Isolated phenylethanoid glycosides exhibited potent radical scavenging activity against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.
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  • A New Lignan Glycoside from the Leaves of Sambucus sieboldiana (MIQ.) BLUME ex. GRAEBN
    Koichi Machida, Misako Takano, Rie Kakuda, Yasunori Yaoita, Masao Kiku ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 669-671
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.669
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    A new lignan glycoside, (−)-massoniresinol 4′-O-β-D-glucopyranoside (4), was isolated, together with six known ones (1—3, 5—7), from the leaves of Sambucus sieboldiana. Their structures were established on the basis of chemical and spectral data.
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  • Synthesis of 2-Alkoxy 1,4-Naphthoquinone Derivatives as Antiplatelet, Antiinflammatory, and Antiallergic Agents
    Jin-Cherng Lien, Li-Jiau Huang, Che-Ming Teng, Jih-Pyang Wang, Sheng-C ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 672-674
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.672
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    In our continuing search for novel antiplatelet, antiallergic, and antiinflammatory agents, 2-alkoxy derivatives of 1,4-naphthoquinone were prepared. Some of these compounds showed significant antiplatelet, antiallergic, and antiinflammatory activities. Among them, 2-propoxy-1,4-naphthoquinone and 2-butoxy-1,4-naphthoquinone exhibited potent inhibitory effect on neutrophil superoxide anion formation. These two compounds are worthy of further exploration.
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  • New Sesquiterpenes from Ferula ferulaeoides (STEUD.) KOROVIN. VI. Isolation and Identification of Three New Dihydrofuro[2,3-b]chromones
    Akito Nagatsu, Kimio Isaka, Keisuke Kojima, Purev Ondognii, Oyun Zevge ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 675-677
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.675
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    Three novel 2-prenyl-dihydrofurochromone-type sesquiterpenoid derivatives, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]-furo[2,3-b]chromone, 2,3-dihydro-7-hydroxy-2S*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E),7-pentenyl]-furo[2,3-b]chromone, and 2,3-dihydro-7-hydroxy-2R*,3R*-dimethyl-2-[4-methyl-5-(4-methyl-2-furyl)-3(E),7-pentenyl]-furo[2,3-b]chromone, were isolated from the roots of Ferula ferulaeoides. The structures were established by comprehensive spectral analysis. The biosynthetic pathway leading to these 2-prenyl-dihydrofurochromone-type sesquiterpenoids is proposed based on their structures.
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  • Iridoid Glycosides from Globularia davisiana
    Ihsan Çalis, Hasan Kirmizibekmez, Deniz Tasdemir, Chris M. Irel ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 678-680
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.678
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    From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), globularin (5), globularicisin (6), 10-O-benzoylcatalpol (7), lytanthosalin (8), melampyroside (9), agnuside (10), and three known phenylethanoid glycosides, verbascoside, isoacteoside and leucosceptoside A were also isolated and characterized. The structures of the isolates were established by spectroscopic methods (one-dimensional (1D)- and two-dimensional (2D)-NMR, MS).
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  • Ceramide Constituents from Five Mushrooms
    Yasunori Yaoita, Rie Kohata, Rie Kakuda, Koichi Machida, Masao Kikuchi
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 681-684
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.681
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    Five mushrooms, Panellus serotinus, Lyophyllum connatum, Amanita pantherina, Sarcodon aspratus and Lepista nuda, have been investigated chemically. Two new ceramides, (2S,3R,4E,8E)-N-hexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (1) and (2S,3R,4E,8E,9′Z,12′Z)-N-9′,12′-octadecadienoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lyophyllum connatum. Two new ceramides, (2S,2′R,3R,4E,8E)-N-2′-hydroxypentadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (4) and (2S,2′R,3R,4E,8E)-N-2′-hydroxytetradecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (5), have been isolated from Amanita pantherina with (2S,2′R,3R,4E,8E)-N-2′-hydroxyhexadecanoyl-2-amino-9-methyl-4,8-octadecadiene-1,3-diol (3), a known synthetic compound. Compounds 3 and 4 were also isolated from Sarcodon aspratus and compound 3 was isolated from Lepista nuda. The structures of the new compounds were elucidated on the basis of their spectral data.
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  • Polyacetylene Glycosides from Gymnaster koraiensis
    JinYoung Park, ByungSun Min, HyunJu Jung, YoungHo Kim, HyeongKyu Lee, ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 685-687
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.685
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    Two polyacetylene glycosides, gymnasterkoreasides A and B, were isolated from the roots of Gymnaster koraiensis. Their structures were elucidated to be (3R)-8-decene-4,6-diyne-1,3-diol 1-O-β-D-glucopyraside and (3R)-8-decene-4,6-diyne-1,3-diol 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyraside on the basis of spectroscopic analysis including COSY, HMQC, and HMBC experiments, as well as chemical methods, which confirmed the determination of a chiral center by the modified Mosher's method.
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  • N-to-C Solid-Phase Peptide and Peptide Trifluoromethylketone Synthesis Using Amino Acid tert-Butyl Esters
    William G. Gutheil, Qingchai Xu
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 688-691
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.688
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    Solid-phase peptide synthesis in the N-to-C direction, opposite to the classical C-to-N direction of peptide synthesis, provides the synthetically versatile C-terminal carboxyl group for further modification into C-terminally modified peptide mimetics. These are of general interest as potential bioactive agents, particularly as protease inhibitors. Elaboration of peptide mimetics on the solid-phase would facilitate synthesis of peptide mimetic combinatorial libraries. This report describes an effective strategy for solid-phase inverse peptide synthesis based on readily available amino acid tert-butyl esters. The potential of this approach for peptide mimetic synthesis is demonstrated by the solid-phase synthesis of two peptide trifluoromethylketones.
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  • Formal Total Synthesis of (+)-Macrosphelide A Based on Regioselective Hydrolysis Using Lipase
    Machiko Ono, Hiroshi Nakamura, Satoko Arakawa, Naoko Honda, Hiroyuki A ...
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 692-696
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.692
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    Three kinds of seco-macrosphelide A congeners, (4R,5S,10R,11S,15S)-6, (4R,5S,9S,14R,15S)-7 and (3S,8R,9S,14R,15S)-8 were chemically synthesized, and they were exposed to the lipase OF-360 from Candida rugosa to give three hydroxy carboxylic acids, respectively. Macrolactonization of the hydroxy acid (4R,5S,10R,11S)-18 derived from (4R,5S,10R,11S,15S)-6 gave 12-membered lactone (19) in 47% overall yield from 6, while that of the seco-acid (4) derived from (4R,5S,9S,14R,15S)-7 afforded (−)-dibenzyl macrosphelide A (25) in 27% overall yield from 7. Macrolactonization of the hydrolysis product, seco-acid (5) derived from (3S,8R,9S,14R,15S)-8, provided (−)-dibenzyl macrosphelide A (25) (5% overall yield from 8) and 12-membered lactone (19) (20% overall yield from 8) concurrently.
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  • Stereospecific Substitution of Enantiomerically Pure 1-(2-Pyridinyl)ethyl Methanesulfonate with β-Dicarbony Compounds
    Junichi Uenishi, Masahiro Hamada
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 697-700
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.697
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    The alkylation of the sodium salt of the malonic acid diester with (R)-1-(2-pyridinyl)ethyl methanesulfonate (2) gave the dimethyl (R)-[1-(2-pyridinyl)ethyl]malonate (3a), stereospecifically. The alkylation reaction of methyl acetoacetate gave the methyl (2′S,2R/2S)-3-oxo-2-[1-(2-pyridinyl)ethyl]butanoate (3d) along with the methyl (S)-3-[1-(2-pyridinyl)ethoxy]-2-butenoate (4d). The acid hydrolysis and decarboxylation of 3d under acidic conditions gave (R)-4-(2-pyridinyl)pentan-2-one (6), and the alkylation of methyl (R)-[1-(2-pyridinyl)ethyl]acetoacetate with benzyl bromide gave a mixture of C-benzylated and O-benzylated products 7 and 8.
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  • Lucidin Type Anthraquinone Glycosides from Putoria calabrica
    Ihsan Çalis, Deniz Tasdemir, Chris M. Ireland, Otto Sticher
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 701-702
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.701
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    Two new lucidin type anthraquinone glycosides, putorinoside A (1) and putorinoside B (2) were isolated from Putoria calabrica, in addition to two known anthraquinone glycosides, lucidin 3-O-β-glucopyranoside (3) and lucidin 3-O-primeveroside (4). Based on spectroscopic data, putorinosides A and B were identified as 2-hydroxymethyl-1-methoxy-3,5,6-trihydroxyanthraquinone 3-O-β-glucopyranoside and 2-hydroxymethyl-1-methoxy-3,6-dihydroxyanthraquinone 3-O-β-glucopyranoside, respectively.
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  • Improved Synthesis and Molecular Modeling of 4β,19-Dihydroxyandrost-5-en-17-one, an Excellent Inhibitor of Aromatase
    Mitsuteru Numazawa, Keiko Yamada, Yoko Watari, Momoko Ando
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 703-705
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.703
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    4β,19-Dihydroxyandrost-5-en-17-one (6) is an excellent competitive inhibitor of estrogen synthetase (aromatase). Alternate, improved synthesis of this inhibitor was established. Treatment of 19-(tert-butyldimethylsilyloxy)androst-4-en-17-one (8) with m-chloroperbenzoic acid gave a 1.4 : 1 mixture of 4α,5α-epoxide 9 and its 4β,5β-isomer 10. The mixture was reacted with dil. HClO4 in dioxane to produce principally 4β,5α-diol 11 (80%) of which acetylation followed by dehydration with SOCl2 yielded 4β,19-diacetoxy-5-ene compound 14 in good yield. Alkaline hydrolysis of diacetate 14 gave 4β,19-diol 6. The minimum energy conformation of the powerfull aromatase inhibitor 6 was obtained with the PM3 method and compared with that of the structurally related diol steroid, 4-ene-5β,19-diol 3, a weak competitive inhibitor.
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  • A Facile Method for the Stereoselective Horner–Wadsworth–Emmons Reaction of Aryl Alkyl Ketones
    Shigeki Sano, Kenji Yokoyama, Motoo Shiro, Yoshimitsu Nagao
    Article type: Note
    Subject area: [not specified]
    2002 Volume 50 Issue 5 Pages 706-709
    Published: 2002
    Released on J-STAGE: May 10, 2002
    DOIhttps://doi.org/10.1248/cpb.50.706
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    Excellent Z or E selectivity was observed in the Horner–Wadsworth–Emmons (HWE) reactions of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate or ethyl 2-fluoro-2-diethylphosphonoacetate with aryl alkyl ketones bearing substituents on an aromatic moiety employing Sn(OSO2CF3)2 in the presence of N-ethylpiperidine.
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