Chemical and Pharmaceutical Bulletin
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ISSN-L : 0009-2363
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Volume 49, Issue 7
Displaying 1-27 of 27 articles from this issue
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Regular Articles
  • Purification and Characterization of Ginsenoside-β-Glucosidase from Ginseng
    Chunzhi ZHANG, Hongshan YU, Yongming BAO, Lijia AN, Fengxie JIN
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 795-798
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.795
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    The ginsenoside-β-glucosidase that hydrolyzes the β-(1→2)-glucoside of the ginsenoside Rg3 sugar moiety to ginsenoside Rh2 was isolated from the ginseng root, and the enzyme was purified and characterized. The enzyme was purified to one spot in SDS polyacrylamide gel electrophoresis, and its molecular weight was about 59 kDa. The optimum temperature of the ginsenoside-β-glucosidase was 60 °C, and the optimum pH was 5.0. Ca2+ ion had positive effect on ginsenoside-β-glucosidase, while Cu2+ had negative effect on it. The ginsenoside-β-glucosidase may be a special β-glucosidase that is different from the original exocellulase such as β-glucosidase (EC 3.2.1.21).
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  • 4-(Benzoylindolizinyl)butyric Acids; Novel Nonsteroidal Inhibitors of Steroid 5α-Reductase. III.
    Kozo SAWADA, Satoshi OKADA, Akio KURODA, Shinya WATANABE, Yuki SAWADA, ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 799-813
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.799
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    A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yl]butyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.
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  • New Hemisynthetic Manoyl Oxide Derivatives with Antimicrobial Activity
    Eleftherios KALPOUTZAKIS, Nektarios ALIGIANNIS, Sofia MITAKU, Ioanna C ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 814-817
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.814
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    The synthesis and antimicrobial activity of ten labdane-type diterpenes derived from ent-3-β-hydroxy-13-epi-manoyl oxide (ribenol) is reported. The chloroethyl carbamidic ester 9 showed the strongest antimicrobial activity against all the tested gram (+), gram (−) bacteria and pathogenic fungi. Moreover, the glycoside 11 exhibited an interesting activity against the three tested fungi.
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  • The Inclusion Compound of a New Ionizable Derivative of β-Cyclodextrin with Ferrocenium Drug
    Chang-Sheng LU, Xiao-Ming REN, Chuan-Jiang HU, Hui-Zhen ZHU, Qing-Jin ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 818-821
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.818
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    A new β-cyclodextrin (β-CD) derivative, mono[6-deoxy-6-(2-butenedinitrile-2, 3-dimercapto sodium salt)]-β-CD (6-mnt-β-CD), and its inclusion compound with a ferrocenium drug, have been prepared and characterized by IR, UV, 13C-NMR spectroscopy, and mass spectrometry, elemental analysis, thermogravimetry, and cyclic voltammetry (CV). The interplay between the side-arm anion of β-CD and the ferrocenium (guest) in the inclusion compound 6-mnt-β-CD-/Fc+ has been investigated by 13C-NMR, UV, IR, and thermogravimetric methods. Charge transfer from the anion to the cation in 6-mnt-β-CD-/Fc+ was then experimentally identified. The interaction between the guest and the host with side-arm in 6-mnt-β-CD-/Fc+ resulted in smaller positive potential shifts compared to that in the inclusion compound [β-CD/Fc+]BF4-.
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  • Studies on New Platelet Aggregation Inhibitors 1. Synthesis of 7-Nitro-3, 4-dihydroquinoline-2(1H)-one Derivatives
    Akira IYOBE, Masahiko UCHIDA, Kouji KAMATA, Yukihiko HOTEI, Hiroshi KU ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 822-829
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.822
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    A series of 6-cyclic aliphatic amino-7-nitro-3, 4-dihydroquinoline-2(1H)-ones were prepared and tested for platelet aggregation inhibitory effect, cardiotonic activity and chronotropic activity. These compounds appeared to show selective inhibitory activity against platelet aggregation. Among them, 6-(4-ethoxycarbonylpiperidino)-7-nitro-3, 4-dihydroquinoline-2(1H)-one (22f) showed the most potent inhibitory activity and high selectivity. A divergent synthetic route to 6-cyclic aliphatic amino-7-nitro-3, 4-dihydroquinoline-2(1H)-one derivatives has also been investigated.
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  • Structure-Activity Relationships of N-(3,5-Dimethoxy-4-n-octyloxycinnamoyl)-N'-(3,4-dimethylphenyl)piperazine and Analogues as Inhibitors of Acyl-CoA: Cholesterol O-Acyltransferase
    Kenji OHISHI, Ritsuo AIYAMA, Hiroshi HATANO, Yasuto YOSHIDA, Yasue WAD ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 830-839
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.830
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    A novel series of acyl-CoA: cholesterol O-acyltransferase (ACAT) inhibitors were synthesized from a lead compound, 1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one (1, Yakuchinone B) through a modification of three regions (A, B, C) in the molecule. In this study, the compounds prepared were tested for in vitro inhibitory activity on microsomal ACAT from the liver of rats and for in vivo hypocholesterolemic activity in rats given a high cholesterol diet. N-(3,5-Dimethoxy-4-n-octyloxycinnamoyl)-N'-(3,4-dimethylphenyl)piperazine (45), which belongs to the amide compounds, has finally been discovered. Compound 45 inhibited rat hepatic ACAT in a more striking manner than CI-976, an amide compound ACAT inhibitor, and it exhibited a high level of hypocholesterolemic activity in vivo. Since 45 strongly inhibited both microsomal ACAT prepared from HepG2 (a cell line derived from human hepatocarcinoma) and Caco2 (a cell line derived from human colon adenocarcinoma), there is speculation that 45 might have the ability to inhibit ACAT in both the human intestine and liver independent of the difference in the distribution of ACAT isozymes. On the other hand, 45 did not induce adrenotoxicity in subacute toxicity studies in rats. These results suggest that it has promise for development as a new therapeutic agent for hypercholesterolemia and atherosclerosis.
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  • Water-Soluble Constituents of Ajowan
    Toru ISHIKAWA, Yukiko SEGA, Junichi KITAJIMA
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 840-844
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.840
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    From the water-soluble portion of the methanol extract of the fruit of Carum ajowan (ajowan), which has been used as a spice and medicine, 25 compounds, including five new monoterpenoid glucosides, a new monoterpenoid, two new aromatic compound glucosides, and two new glucides, were obtained. Their structures were clarified by spectral investigation.
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  • Medicinal Foodstuffs. XXIV. Chemical Constituents of the Processed Leaves of Apocynum venetum L.: Absolute Stereostructures of Apocynosides I and II
    Toshiyuki MURAKAMI, Akinobu KISHI, Hisashi MATSUDA, Masao HATTORI, Mas ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 845-848
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.845
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    Two new ionone glucosides, named apocynosides I and II, were isolated from the roasted leaves of Apocynum venetum L. together with nine known compounds. The absolute stereostructures of apocynosides I and II were determined by chemical and physicochemical evidence, which included the application of a modified Mosher’s method and the circular dichroism helicity rule.
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  • The Reaction of (4R, 5R)- and (4S, 5S)-4, 5-Epoxy-2(E)-Hexenoates and Secondary Amines
    Chikako SAOTOME, Machiko ONO, Hiroyuki AKITA
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 849-853
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.849
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    A reaction of methyl (4R, 5R)-4, 5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R, 5R)-4, 5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S, 5R)-4-N-benzylmethylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (−)-osmundalactone 11, which is an aglycone of osmundalin. On the other hand, the directly conjugated addition of dimethylamine to methyl (4S, 5S)-4, 5-epoxy-2(E)-hexenoate 1 followed by treatment with MeOH at 40 °C exclusively provided methyl (4R, 5S)-4-dimethylamino-5-hydroxy-2(E)-hexenoate 16, which was converted into L-(−)-forosamine 18.
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  • New Rearranged Clerodane Diterpenes from Tinospora baenzigeri
    Pittaya TUNTIWACHWUTTIKUL, Walter Charles TAYLOR
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 854-857
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.854
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    Baenzigeroside B, a new rearranged clerodane diterpene glucoside, was isolated from the stems of Tinospora baenzigeri. The aglycone of baenzigeroside B, baenzigeride B (isolated as its acetate), was found together with baenzigeride A, baenzigerosides A and B in the leaves of the same plant. Baenzigeride B and baenzigeroside B are the first examples of a new class of rearranged clerodane diterpenes. The possible biogenesis of the compounds is discussed.
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  • Stilbenoids in Lianas of Gnetum parvifolium
    Toshiyuki TANAKA, Ibrahim ILIYA, Tetsuro ITO, Miyuki FURUSAWA, Ken-ich ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 858-862
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.858
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    Five new stilbene dimers were isolated from the lianas of Gnetum parvifolium in addition to known stilbenoids. The structures of the compounds were established on the basis of spectroscopic evidence, including long-range coupling and nuclear Overhauser effect experiments, in NMR spectrum. Among the isolates, 2b-hydroxyampelopsin F showed potent inhibitory activity in the Maillard reaction.
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  • Medicinal Flowers. III. Marigold.(1): Hypoglycemic, Gastric Emptying Inhibitory, and Gastroprotective Principles and New Oleanane-Type Triterpene Oligoglycosides, Calendasaponins A, B, C, and D, from Egyptian Calendula officinalis
    Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Akinobu KISHI, Tadashi KAGEURA ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 863-870
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.863
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    The methanolic extract and its 1-butanol-soluble fraction from the flowers of Calendula officinalis were found to show a hypoglycemic effect, inhibitory activity of gastric emptying, and gastroprotective effect. From the 1-butanol-soluble fraction, four new triterpene oligoglycosides, calendasaponins A, B, C, and D, were isolated, together with eight known saponins, seven known flavonol glycosides, and a known sesquiterpene glucoside. Their structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, glycosides A, B, C, D, and F, exhibited potent inhibitory effects on an increase in serum glucose levels in glucose-loaded rats, gastric emptying in mice, and ethanol- and indomethacin-induced gastric lesions in rats. Some structure-activity relationships are discussed.
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  • Halofantrine-Phospholipid Interactions: Monolayer Studies
    Mei-Lin GO, Si-Shen FENG
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 871-876
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.871
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    The antimalarial agent halofantrine penetrates dipalmitolylphosphatidylcholine (DPPC) monolayers resulting in an increase in surface pressure and an expansion in area occupied by the lipid components of the monolayer. This phenomenon is observed at concentrations (0.05-0.2 μM) of halofantrine that have no surface activity. Penetration increases with drug concentration and is greatest at low initial surface pressures of the monolayer. A critical surface pressure of the DPPC monolayer has been determined from constant area and constant pressure conditions. The magnitude of these values support the hypothesis that halofantrine readily penetrates the DPPC monolayers. The presence of cholesterol in the DPPC monolayer hampers penetration and a lower critical surface pressure is obtained under such conditions. Even then, a slower rate of penetration is observed only in monolayers maintained at high initial surface pressures (10, 15 mN/m), corresponding to the liquid condensed phase of the monolayer, and not at low surface pressures (2.5, 5.0 mN/m). These results help to give a better understanding of the dynamics of the halofantrine-phospholipid interaction as well as the pharmacodynamic character of the drug.
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  • Chemical Constituents of Prangos tschimganica; Structure Elucidation and Absolute Configuration of Coumarin and Furanocoumarin Derivatives with Anti-HIV Activity
    Yasuhiro SHIKISHIMA, Yoshihisa TAKAISHI, Gisho HONDA, Michiho ITO, Yos ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 877-880
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.877
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    The methanol extract of the dried aerial parts of Prangos tschimganica gave three new coumarin derivatives and 30 known coumarin derivatives. Their structures were established on the basis of chemical and spectroscopic evidence. Absolute configuration of the isolated compounds were determined by using a modified Mosher’s method. Some of the isolated compounds showed anti-HIV activity.
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  • Novel Syntheses of Murrayaquinone A and Furostifoline through 4-Oxygenated Carbazoles by Allene-Mediated Electrocyclic Reactions Starting from 2-Chloroindole-3-carbaldehyde
    Hitomi HAGIWARA, Tominari CHOSHI, Junko NOBUHIRO, Hiroyuki FUJIMOTO, S ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 881-886
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.881
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    The formal total synthesis of murrayaquinone A (1) and the total synthesis of furostifoline (5) were completed by the construction of 4-oxygenated 3-methylcarbazoles 7 based on a new type of electrocyclic reaction through 2-alkenyl-3-allenylindole intermediates 8 derived from the 2-alkenyl-3-propargylindoles 9, starting from 2-chloroindole-3-carbaldehyde (11). The N, O-bisbenzyloxymethyl group of 16c and 22 underwent a Birch reduction followed by treatment with Triton B to produce the known 4-hydroxy-3-methylcarbazole (7a) and 4-hydroxy-3-methylfuro[3, 2-a]carbazole (7b) as precursors of murrayaquinone A (1) and furostifoline (5), respectively. The trifluoromethanesulfonyloxy-3-methylfuro[3, 2-a]carbazole (24), prepared from 7b, was subjected to reductive cleavage to provide furostifoline (5).
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  • Caffeoyl, Coumaroyl, Galloyl, and Hexahydroxydiphenoyl Glucoses from Balanophora japonica
    Zhi-Hong JIANG, Yoko HIROSE, Hiromi IWATA, Saori SAKAMOTO, Takashi TAN ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 887-892
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.887
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    Eighteen new and sixteen known acyl glucoses having caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl groups were isolated from a medicinal parasitic plant, Balanophora japonica. Their structures were determined by spectroscopic and chemical methods. Caffeoyl ellagitannins, which have been rarely found in nature, were major phenolic constituents of this plant, and this is the first report of the isolation of ellagitannins from Balanophoraceae.
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  • Diels-Alder Cycloadditions of 2(1H)-Quinolones Having an Electron-Withdrowing Group at the 3-Position Acting as Dienophiles with Dienes
    Reiko FUJITA, Kazuhiro WATANABE, Toshiteru YOSHISUJI, Chizuko KABUTO, ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 893-899
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.893
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    Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1, 3-butadienes (2a, b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examined using MO calculation.
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  • Diels-Alder Reaction of 1, 3-Butadiene Derivatives with 1-Methyl-2(1H)-quinolones Having an Electron-Withdrawing Group at the 4-Position
    Reiko FUJITA, Kazuhiro WATANABE, Toshiteru YOSHISUJI, Hiroshi HONGO, H ...
    Article type: scientific monograph
    2001 Volume 49 Issue 7 Pages 900-904
    Published: 2001
    Released on J-STAGE: May 31, 2002
    DOIhttps://doi.org/10.1248/cpb.49.900
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    Diels-Alder reactions of 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position with isoprene, butadiene sulfone, and cyclohexadiene were performed to yield functionalized phenanthridones stereoselectively at atmospheric and at high pressure. Regioselectivity and stereochemistry of a methoxycarbonyl group were studied using the semi-empirical and ab initio MO methods, respectively.
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