Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 51, Issue 4
Displaying 1-29 of 29 articles from this issue
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Regular Articles
  • The Influence of Chitosan on in Vitro Properties of Eudragit RS Microspheres
    Bozena Kriznar, Tatjana Mateovic, Marija Bogataj, Aleš Mrhar
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 359-364
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.359
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    Eudragit RS microspheres containing chitosan hydrochloride were prepared by the solvent evaporation method using acetone/liquid paraffin solvent system and their properties were compared with Eudragit RS microspheres without chitosan, prepared in our previous study. Different stirring rates were applied (400—1200 rpm) and drug content, Higuchi dissolution rate constant, surface and structure characteristics of the microspheres were determined for each size fraction. An increase in average particle size with a reduction of stirring rate appeared in limited interval in both series. The average particle size of microspheres without chitosan, prepared at the same stirring rate, was smaller. Pipemidic acid content increased with increasing fraction particle size, but not with increasing stirring rate as it was observed for microspheres without chitosan. We presume that high pipemidic acid content in larger microspheres is a consequence of cumulation of undissolved pipemidic acid particles in larger droplets during microspheres preparation procedure. Pipemidic acid release was faster from microspheres with chitosan and no correlation between Higuchi dissolution rate constant and stirring rate or fraction particle size was found, though it existed in the system without chitosan. Structure and surface characteristics of microspheres observed by scanning electron microscope (SEM) were not changed significantly by incorporation of chitosan. But in contrast with microspheres without chitosan, the surface of chitosan microspheres was more porous after three hours of dissolution. It is supposed that the influence of particle size fraction and stirring rate on release characteristics is expressed to a great extent through porosity and indirectly through total effective surface area, but the incorporation of highly soluble component i.e. chitosan salt hides these effects on drug release. In conclusion, changes in biopharmaceutical properties due to varying stirring rate and fraction particle size exhibited the same direction as those reported for the microspheres without chitosan, although they are less expressed because of increased experimental variability, likely caused by chitosan.
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  • Antiproliferative Constituents from Umbelliferae Plants VI. New Ursane-Type Saikosaponin Analogs from the Fruits of Bupleurum rotundifolium
    Toshihiro Fujioka, Keisuke Yoshida, Hiroko Fujii, Tsuneatsu Nagao, Hik ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 365-372
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.365
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    The MeOH extract of the fruits of Bupleurum rotundifolium showed inhibitory activity against human gastric adenocarcinoma (MK-1) cell growth (GI50: 6.25 μg/ml). From this extract, 10 new ursane-type triterpene glycosides viz. three 3-O-triosides (called rotundifoliosides A, I, and J) of 13β,28-epoxy-3β,16α-dihydroxyurs-11-ene, two (G and H) of 13β,28-epoxy-3β,16α,23-trihydroxyurs-11-ene, two (E and F) of 13β,28-epoxy-3β,16α,21β-trihydroxyurs-11-ene, two (B and C) of 3β,11α,16α,28-tetrahydroxyurs-12-ene, and one (D) of 3β,11α,28-trihydroxy-15α,16α-epoxyurs-12-ene were isolated in addition to 16 new oleanane-type triterpene glycosides (rotundiosides J—Y), echinocystic acid 3-O-sulfate and 3 known oleanane-type triterpene glycosides (rotundiosides A, F and G). The isolation, structures and antiproliferative activity of the new ursane-type triterpene glycosides against MK-1, human uterus carcinoma (HeLa), and murine melanoma (B16F10) cell lines are described with some comments on the structural requirements for their activity.
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  • Determination of ppb Levels of Tryptophan Derivatives by Capillary Electrophoresis with Homogeneous Liquid–Liquid Extraction and Sweeping Method
    Yoshitaka Takagai, Shukuro Igarashi
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 373-377
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.373
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    Tryptophan (Trp) derivatives were selectively separated from 24 kinds of amino acid mixture solutions. Capillary electrophoresis (CE) with UV detection using the described pretreatment system was able to separate and determine 4 kinds of Trp derivatives: 5-hydroxy L-tryptophan, 5-methyl L-tryptophan, 1-methyl L-tryptophan and L-tryptophan. The pretreatment system used a combination of a homogeneous liquid–liquid extraction and a sweeping method, the two are different kinds of powerful preconcentration/separation methods. Trp derivatives were thus separated by two different separation systems. First, these derivatives were selectively extracted at 57—100% by a homogeneous liquid–liquid extraction; secondly, they were respectively separated by micellar electrokinetic chromatography (MEKC) with a sweeping effect. The detection limits following complete separation of the Trp derivatives were 10−8 mol l−1 levels, respectively. The proposed method provided a more than 10-fold the improvement in sensitivity compared with fluorescence labeling/fluorophotometric analysis; the proposed method was also applied to the component analysis of nutritious medicine.
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  • Transformation of Arctiin to Estrogenic and Antiestrogenic Substances by Human Intestinal Bacteria
    Li-Hua Xie, Eun-Mi Ahn, Teruaki Akao, Atef Abdel-Monem Abdel-Hafez, No ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 378-384
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.378
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    After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (−)-arctigenin (2), (2R,3R)-2-(3′,4′-dihydroxybenzyl)-3-(3″,4″-dimethoxybenzyl)butyrolactone (3), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″,4″-dimethoxybenzyl)butyrolactone (4), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″-hydroxy-4″-methoxybenzyl)butyrolactone (5), (2R,3R)-2-(3′-hydroxybenzyl)-3-(3″,4″-dihydroxybenzyl)butyrolactone (6), and (−)-enterolactone (7) by various spectroscopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. Enterolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (−)-(2R,3R) and (+)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferative effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 μM. These results indicate that the transformation of 1 by intestinal flora might be essential for the manifestation of the estrogenic and antiestrogenic activity of 1.
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  • Three New Quassinoids, Ailantinol E, F, and G, from Ailanthus altissima
    Sadaaki Tamura, Narihiko Fukamiya, Masayoshi Okano, Junko Koyama, Kazu ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 385-389
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.385
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    Three new quassinoids, ailantinol E (1), ailantinol F (2), and ailantinol G (3), and related compounds were isolated from Ailanthus altissima grown in Taiwan. Their structures were elucidated from spectral evidence. Each new quassinoid was evaluated for its antitumor promoting effects against Epstein-Barr virus early antigen activation introduced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The new quassinoids were found to show potent activity without showing any cytotoxicity. The screening for inhibitors against nitric oxide donor action was also conducted using the new quassinoids and some standard samples.
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  • Synthesis and Pharmacological Evaluation of 2-(3-Piperidyl)-1,2,3,4-tetrahydroisoquinoline Derivatives as Specific Bradycardic Agents
    Akio Kakefuda, Toshihiro Watanabe, Yasuko Taguchi, Noriyuki Masuda, Ak ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 390-398
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.390
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    Novel 1,2,3,4-tetrahydroisoquinoline derivatives bearing directly a cyclic amine at the 2-position were prepared and examined for their bradycardic activities in isolated right atria and in anesthetized rats. The structure–activity relationships (SAR) study revealed that the 2-(3-piperidyl)-1,2,3,4-tetrahydroisoquinoline skeleton is essential for the appearance of potent in vitro activity, and that the presence of at least one methoxy group at the 6- or 7-position of the 1,2,3,4-tetrahydroisoquinoline ring is important to exert potent in vitro activity. In vivo tests of selected compounds demonstrated that 2-(1-benzyl-3-piperidyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (6c) exhibited potent bradycardic activity with negligible influence on mean blood pressure in rats, although its potency is a half of that of Zatebradine.
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  • Synthesis of 1-β-D-(5-Deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (β-IAZA): A Novel Marker of Tissue Hypoxia
    Piyush Kumar, Kazue Ohkura, Davood Beiki, Leonard Irving Wiebe, Koh-ic ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 399-403
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.399
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    The present work describes the synthesis of the β-isomer of 1-α-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (IAZA). Radioiodinated IAZA (123I-IAZA) has been extensively studied as a radiopharmaceutical for the diagnosis of regional and/or focal tissue hypoxia in a variety of clinical pathologies. The β-anomer of IAZA, 1-β-D-(5-deoxy-5-iodoarabinofuranosyl)-2-nitroimidazole (β-IAZA, 1), was synthesized via an unconventional route starting from 1-β-D-(ribofuranosyl)-2-nitroimidazole (AZR), with a change of configuration at the C-2′-position to afford 1-β-D-(arabinofuranosyl)-2-nitroimidazole (β-AZA, 7). Nucleophilic iodination of the 5′-O-toluenesulfonyl-2′,3′-di-O-acetyl precursor of β-AZA, 9, followed by deprotection, afforded 1 in satisfactory yield. β-IAZA (1) was also synthesized from 7 using molecular iodine and triphenylphosphine.
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Notes
  • Enzymatic Preparation of Ginsenosides Rg2, Rh1, and F1
    Sung-Ryong Ko, Kang-Ju Choi, Kei Suzuki, Yukio Suzuki
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 404-408
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.404
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    During investigation of the hydrolysis of a protopanaxatriol-type saponin mixture by various glycoside hydrolases, crude preparations of β-galactosidase from Aspergillus oryzae and lactase from Penicillium sp. were found to produce two minor saponins, ginsenoside Rg2 [6-O-(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl)-20(S)-protopanaxatriol] and ginsenoside Rh1 (6-O-β-D-glucopyranosyl-20(S)-protopanaxatriol), respectively, in high yields. Moreover, a naringinase preparation from Penicillium decumbens readily gave an intestinal bacterial metabolite, ginsenoside F1 (20-O-β-D-glucopyranosyl-20(S)-protopanaxatriol), as the main product, with a small amount of 20(S)-protopanaxatriol from a protopanaxatriol-type saponin mixture. Also, a hesperidinase from Penicillium sp. selectively hydrolyzed ginsenoside Re into ginsenoside Rg1. This is the first report on the enzymatic preparation of minor saponins, ginsenosides Rg2 and Rh1, and of an intestinal bacterial metabolite, ginsenoside F1, with high efficiency from a protopanaxatriol-type saponin mixture.
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  • 1-Methyl-2-undecyl-4(1H)-quinolone as an Irreversible and Selective Inhibitor of Type B Monoamine Oxidase
    Myung Koo Lee, Bang Yeon Hwang, Seon A Lee, Gab Jin Oh, Woo Hoi Choi, ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 409-411
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.409
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    The inhibitory compound of monoamine oxidase (MAO) activity was isolated from the CH2Cl2 fraction of the fructus of Evodia rutaecarpa and identified as 1-methyl-2-undecyl-4(1H)-quinolone (1). Compound 1 showed a selective inhibition of type B MAO (MAO-B) activity with the IC50 value of 15.3 μM using a substrate kynuramine, but did not inhibit type A MAO (MAO-A) activity. The kinetic analysis using Lineweaver-Burk plots indicated that compound 1 competitively inhibited MAO-B activity with the Ki value of 9.91 μM. The inhibition of MAO-B by compound 1 was found to be irreversible by dialysis of the incubation mixture. These results suggest that compound 1 is a potent irreversible inhibitor of MAO-B, and may regulate catecholamine content in the neurons.
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  • Cholinesterase Inhibitory Constituents from Onosma hispida
    Ijaz Ahmad, Itrat Anis, Abdul Malik, Sarfraz Ahmad Nawaz, Muhammad Iqb ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 412-414
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.412
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    Hispidone, a new flavanone, has been isolated from Onosma hispida and assigned the structure (2S)-5,2′-dihydroxy-7,4′,5′-trimethoxyflavanone (1) by spectroscopic methods. In addition, (2S)-5,2′-dihydroxy-7,5′-dimethoxyflavanone (2), benzoic acid (3), and 4-hydroxy benzoic acid (4) are also reported for the first time from this species.
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  • Tetracyclic Triterpenoids from the Leaves of Azadirachta indica and Their Insecticidal Activities
    Bina Shaheen Siddiqui, Farhana Afshan, Tahsin Gulzar, Razia Sultana, S ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 415-417
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.415
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    A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6α-O-methyl, 7α-senecioyl(7-deacetyl)-11α,12α,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC50 values of 16 and 154 ppm, respectively.
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  • Capillary Electrophoresis for Simultaneous Determination of Emodin, Chrysophanol, and Their 8-β-D-Glucosides
    Junko Koyama, Izumi Morita, Kazuko Kawanishi, Kiyoshi Tagahara, Norihi ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 418-420
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.418
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    The simultaneous separation and determination of the major anthraquinones, emodin, chrysophanol, and their glucosides, of Rumex japonicus HOUTT., and emodin and emodin glucoside, of Cassia tora L., Rhamnus purshiana DC., Polygonum multiflorum THUNB., and P. cuspidatum SIEB. et ZUCC., were achieved by cyclodextrin modified capillary zone electrophoresis. The running electrolyte used in this method was 0.005 M α-cyclodextrin in 0.03 M borate buffer (pH 10.5) containing 10% acetonitrile, with an applied voltage of 20 kV.
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  • Simultaneous Determination of Chlorogenic Acid, Forsythin and Arctiin in Chinese Traditional Medicines Preparation by Reversed Phase-HPLC
    Bing-Sheng Yu, Xiao-Pin Yan, Jingyu Xiong, Qi Xin
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 421-424
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.421
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    A reversed phase (RP)-HPLC method was established for simultaneous determination of chlorogenic acid, arctiin and forsythin in Yinqiao Jiedu Granules, which was a commonly used Chinese herbal medical preparation for treatment of rheum ailments. The determination was based on a gradient elution (A: 1% acetic acid, pH=3.0, B: methanol) on a C18 column and an automatic wavelength switching program, where 325 nm was used for chlorogenic acid and 280 nm for arctiin and forsythin, respectively. Good linearities were obtained over the range of 2—200 mg·l−1 for the 3 objective compounds. The spike recoveries were within 96.0—97.9%.
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  • Two Novel Sesquiterpene Lactones, Cytotoxic Vernolide-A and -B, from Vernonia cinerea
    Yao-Haur Kuo, Yu-Jen Kuo, Ang-Su Yu, Ming-Der Wu, Chi-Wi Ong, Li-Ming ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 425-426
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.425
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    Bioassay-directed fractionation of an ethanolic extract of stems of Vernonia cinerea has resulted in the isolation of two novel sesquiterpene lactones, vernolide-A and -B. Their structures were elucidated on the basis of spectroscopic analysis. Biological evaluation showed that vernolide-A demonstrated potent cytotoxicity against human KB, DLD-1, NCI-661, and Hela tumor cell lines (ED50=0.02, 0.05, 0.53, 0.04 μg/ml for KB, DLD-1, NCI-661, and Hela, respectively); vernolide-B had marginal cytoxicity (ED50=3.78, 5.88, 6.42 μg/ml for KB, NCI-661, and Hela, respectively).
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  • Pyridazine Derivatives 32: Stille-Based Approaches in the Synthesis of 5-Substituted-6-phenyl-3(2H)-pyridazinones
    Eddy Sotelo, Alberto Coelho, Enrique Raviña
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 427-430
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.427
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    A series of 6-phenyl-3(2H)-pyridazinones bearing different substituents in the 5-position of the pyridazinone ring were prepared using Stille-based approaches in the search for new platelet-aggregation inhibitors.
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  • Three New Ingol Diterpenes from Euphorbia nivulia: Evaluation of Cytotoxic Activity
    Veluri Ravikanth, Vanimireddy Lakshmi Niranjan Reddy, Adelli Vijender ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 431-434
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.431
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    The latex of Euphorbia nivulia afforded three new ingol diterpenes, 3-acetyl-8-methoxyl-7-angolyl-12-hydroxylingol (7), 3,12-diacetyl-7-hydroxy-8-methoxylingol (8), and 3,12-diacetyl-7-angolyl-8-hydroxylingol (9) along with five known ingol diterpenes 2—6 and a known triterpene cyclonivulinol (1). Their structures were established by means of spectroscopic analysis. Diterpenes 2—9 were evaluated for their cytotoxic activity.
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  • Four New Saponins from the Starfish Certonardoa semiregularis
    Weihong Wang, Famei Li, Jongki Hong, Chong-Ok Lee, Hee Young Cho, Kwan ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 435-439
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.435
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    Four new saponins, designated as certonardosides K—N (1—3, 5), were isolated, along with culcitoside C6 (4), from the brine shrimp active fraction of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical derivatization. These compounds were evaluated for cytotoxicity and antibacterial activity.
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  • Medicinal Flowers. VIII. Radical Scavenging Constituents from the Flowers of Prunus mume: Structure of Prunose III
    Hisashi Matsuda, Toshio Morikawa, Tomoko Ishiwada, Hiromi Managi, Masa ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 440-443
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.440
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    The methanolic extract and its fractions from the fresh flowers of Prunus mume SIEB. et ZUCC. were found to show scavenging effects on 1,1-diphenylpicryl-2-hydrazyl (DPPH) radical and superoxide. The fragrance constituents of P. mume were analyzed by GC-MS and a new polyacylated sucrose, prunose III, was isolated from the ethyl acetate-soluble fraction. The structure of prunose III was determined on the basis of chemical and physicochemical evidence as 4,3′,4′,6′-tetra-O-acetyl-6-O-p-coumaroylsucrose. In addition, the scavenging effects of the principal constituents on DPPH radical and superoxide were examined.
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  • Trichloroacetylation of Some Cyclic Enamines
    Hülya Senöz, Nazan Tunoglu
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 444-447
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.444
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    The pyrrolidine and morpholine enamines of cyclic ketones such as cyclohexanone and cyclopentanone were successfully diacetylated at α- and α′-positions with trichloroacetyl chloride using zinc catalyst. Morpholine enamines of the cyclic ketones gave acetylated morpholine in good yields besides the corresponding diacetylated cyclic enamines. When the same reactions were performed by using triethylamine without using zinc, monoacetylation products of the same enamines were synthesized.
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  • Application of Modified Mosher's Method for Primary Alcohols with a Methyl Group at C2 Position
    Masashi Tsuda, Yuki Toriyabe, Tetsuya Endo, Jun'ichi Kobayashi
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 448-451
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.448
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    The absolute configurations of a series of primary alcohols possessing a branched methyl group at C2 position were examined on the basis of a modified Mosher's method proposed by Minale et al. It was revealed that in many cases the absolute configurations at C2 were assignable from the chemical shift differences of geminal protons of the methylene attached to the ester linkage in the α-methoxy-α-trifluoromethylphenylacetyl (MTPA) derivatives. The scope and limitation of this method are described.
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  • A New Triterpenoid Isolated from Lagerstronemia speciosa (L.) PERS.
    Yoshihito Okada, Ayako Omae, Toru Okuyama
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 452-454
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.452
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    A new triterpenoid along with four known compounds were isolated from the leaves of Lagerstronemia speciosa (L.) PERS. (Lythraceae). On the basis of chemical and spectroscopic evidence, the new compound was established as 3β,23-dihydroxy-1-oxo-olean-12-en-28-oic acid.
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  • Solid-Supported Robinson Annulation under Microwave Irradiation
    Kazuhiko Takatori, Masayasu Nakayama, Naoko Futaishi, Saori Yamada, Sh ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 455-457
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.455
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    Robinson annulation on alumina occurred efficiently on heating with microwave irradiation.
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  • A New Sesquiterpene Lactone from Bombax malabaricum
    Mopuru Vijaya Bhaskar Reddy, Muntha Kesava Reddy, Duvvuru Gunasekar, M ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 458-459
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.458
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    A new sesquiterpene lactone, 5-isopropyl-3-methyl-2,4,7-trimethoxy-8,1-naphthalene carbolactone (1) together with a known naphthoquinone, 8-formyl-7-hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone (2) were isolated from the root bark of Bombax malabaricum. The structures of these two compounds were established by extensive one- and two-dimensional (1D- and 2D)-NMR spectral studies.
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  • A Simple Determination Method of the Absolute Configuration of 1-Arylethanthiols by an Intramolecular CH/π Shielding Effect in 1H-NMR of Diastereomeric Thiol Esters
    Masato Matsugi, Yuri Hagimoto, Kinuyo Itoh, Masatomo Nojima, Yasuyuki ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 460-462
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.460
    JOURNAL FREE ACCESS
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    A simple method for the determination of the absolute configuration of 1-arylethanthiols was achieved by the observation of an intramolecular CH/π shielding effect in 1H-NMR of the corresponding thiol esters. (S)-Isomer of the diastereomers always shows remarkable shielding effect.
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  • Preparation and Cancer Cell Invasion Inhibitory Effects of C16-Alkynic Fatty Acids
    Kazuyoshi Ohashi, Hendig Winarno, Mutsuko Mukai, Hirotaka Shibuya
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 463-466
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.463
    JOURNAL FREE ACCESS
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    Five C16-alkynic fatty acids (2—6) were prepared and examined their inhibitory effects on cancer cell invasion. It has been found that hexadeca-6,8,10-triynoic acid (5) and hexadeca-8,10,12-triynoic acid (6) exhibit similar potent inhibitory activities with that of octadeca-8,10,12-triynoic acid (1) which was isolated from Scurrula atropurpurea (Loranthaceae).
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  • Phenylpropanoid Glycosides from Rhodiola rosea
    Ari Tolonen, Minna Pakonen, Anja Hohtola, Jorma Jalonen
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 467-470
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.467
    JOURNAL FREE ACCESS
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    Rhodiola rosea L. (Golden Root) has been used for a long time as an adaptogen in Chinese traditional medicine and is reported to have many pharmacological properties. Along its known secondary metabolites tyrosol (1), salidroside (rhodioloside) (2), rosin (3), rosarin (4), rosavin (5), sachaliside 1 (6) and 4-methoxy-cinnamyl-O-β-D-glucopyranoside (7), four compounds were isolated from aqueous methanol extract of the plant and identified as cinnamyl-(6′-O-β-xylopyranosyl)-O-β-glucopyranoside (8), 4-methoxy-cinnamyl-(6′-O-α-arabinopyranosyl)-O-β-glucopyranoside (9), picein (10) and benzyl-O-β-glucopyranoside (11) by UV, MS and NMR methods. Compounds 8 and 9 are new natural compounds whereas compounds 10 and 11 were isolated first time from R. rosea. Also the compounds 6 and 7 are isolated earlier only from the callus cultures of the plant but not from the differentiated plant.
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  • Asymmetric Synthesis of β-Hydroxy Acid via Stereoselective Dirhodium(II)-Catalyzed C–H Insertion of α-Alkoxydiazoketone
    Takayuki Yakura, Takeshi Tanaka, Masazumi Ikeda, Jun'ichi Uenishi
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 471-473
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.471
    JOURNAL FREE ACCESS
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    A new methodology for the asymmetric synthesis of β-hydroxy acid was developed. Dirhodium(II)-catalyzed C–H insertion of α-alkoxydiazoketone (3), which was prepared from primary alkyl halide (1) and readily available chiral α-hydroxy acid (2), gave stereoselectively 2,5-cis-disubstituted 3(2H)-furanone (4). The Baeyer-Villiger reaction of 4 followed by treatment with an acid afforded chiral β-hydroxy acid (6) with high optical purity.
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  • Preparation of (Cyanomethylene)trimethylphosphorane as a New Mitsunobu-Type Reagent
    Izumi Sakamoto, Hiroto Kaku, Tetsuto Tsunoda
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 474-476
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.474
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    (Cyanomethylene)trimethylphosphorane (CMMP) mediates Mitsunobu-type reactions, which are a versatile method for the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA. CMMP is quite effective for the reaction of carbon nucleophiles whose pKa value are higher than 13. CMMP, which is very sensitive to air and moisture, was synthesized in two steps starting from chloroacetonitrile.
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  • Synthesis of α,α-Dibromo Esters as Precursors of Ynolates
    Mitsuru Shindo, Yusuke Sato, Ryoko Koretsune, Takashi Yoshikawa, Kenji ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 4 Pages 477-478
    Published: 2003
    Released on J-STAGE: April 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.477
    JOURNAL FREE ACCESS
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    Aliphatic α,α-dibromo esters, precursors of ynolates, were synthesized via bromination of lithium α-bromo ester enolates with 1,2-dibromotetrafluoroethane in good yields. α-Trimethylsilyl-α,α-dibromo esters were synthesized via radical bromination.
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