Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 52, Issue 1
Displaying 1-29 of 29 articles from this issue
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Reviews
  • Recent Developments in the Maytansinoid Antitumor Agents
    John M. Cassady, Kenneth K. Chan, Heinz G. Floss, Eckhard Leistner
    Article type: Review
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 1-26
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1
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    Maytansine and its congeners have been isolated from higher plants, mosses and from an Actinomycete, Actinosynnema pretiosum. Many of these compounds are antitumor agents of extraordinary potency, yet phase II clinical trials with maytansine proved disappointing. The chemistry and biology of maytansinoids has been reviewed repeatedly in the late 1970s and early 1980s; the present review covers new developments in this field during the last two decades. These include the use of maytansinoids as “warheads” in tumor-specific antibodies, preliminary metabolism studies, investigations of their biosynthesis at the biochemical and genetic level, and ecological issues related to the occurrence of such typical microbial metabolites in higher plants.
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Regular Articles
  • Cerebrosides and a Monoacylmonogalactosylglycerol from Clinacanthus nutans
    Pittaya Tuntiwachwuttikul, Yupa Pootaeng-on, Photchana Phansa, Walter ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 27-32
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.27
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    A mixture of nine cerebrosides and a monoacylmonogalactosylglycerol were seperated from the leaves of Clinacanthus nutans. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8Z)-2-amino-8(Z)-octadecene-1,3,4-triol with nine 2-hydroxy fatty acids of varying chain lengths (C16, C18, C20—26) linked to the amino group. The glycosylglyceride was characterized as (2S)-1-O-linolenoyl-3-O-β-D-galactopyranosylglycerol. The structures were established on the basis of the spectroscopic data and chemical reactions.
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  • Potentiometric and Spectroscopic Studies on Yttrium(III) Complexes of Dihydroxybenzoic Acids
    Rahmiye Aydın, Ulviye Özer
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 33-37
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.33
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    The equilibrium reactions of yttrium(III) ion with dihydroxybenzoic acids (2,3-dihydroxybenzoic acid (2,3-DHBA) and 3,4-dihydroxybenzoic acid (3,4-DHBA)) (H3L) were investigated in aqueous solution by means of potentiometric and spectroscopic methods, in 0.1 mol·l−1 ionic strength medium at 25 °C. The stability constants are reported for YL, YL(HL)2− and YL23−- type mononuclear complexes. 2,3-DHBA can bind Y(III) ion strongly and the salicylate mode is effective over the acidic pH range. But in higher pH range, 2,3-DHBA and 3,4-DHBA act more efficiently through catecholate groups. The complexes of 2,3-DHBA are more stable than the complexes of 3,4-DHBA.
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  • Indirect Potentiometric Titration of Ascorbic Acid in Pharmaceutical Preparations Using Copper Based Mercury Film Electrode
    Meeran Mohideen Abdul Kamal Nazer, Abdul Rahman Shahul Hameed, Patel R ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 38-40
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.38
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    A simple and rapid potentiometric method for the estimation of ascorbic acid in pharmaceutical dosage forms has been developed. The method is based on treating ascorbic acid with iodine and titration of the iodide produced equivalent to ascorbic acid with silver nitrate using Copper Based Mercury Film Electrode (CBMFE) as an indicator electrode. Interference study was carried to check possible interference of usual excipients and other vitamins. The precision and accuracy of the method was assessed by the application of lack-of-fit test and other statistical methods. The results of the proposed method and British Pharmacopoeia method were compared using F and t-statistical tests of significance.
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  • HPLC Retention Behavior of Poly-Aromatic-Hydrocarbons on Aminopropyl Silica Gels Modified with Cu(II)- and Ni(II)-Phthalocyanine Derivatives in Non-polar Eluent
    Hiromichi Akizawa, Yuji Kitamura, Minako Yamane, Akimasa Iwado, Junko ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 41-46
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.41
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    A comparative study was conducted to elucidate the mechanism underlying the separation of poly-aromatic-hydrocarbons (PAHs) and related compounds thereof on a column packed with silica gels modified with Ni(II)- or Cu(II)-phthalocyanine derivatives (PCS) (Ni- or Cu-PCSD column) and commercially available PYE® and NPE® columns with a non-polar eluent, such as n-hexane. It has been revealed that the dominant interaction responsible to the separation of PAHs on the Cu-PCSD and the PYE® columns with n-hexane is the π–π interaction; however, in the separation of PAHs having 4 rings such as pyrene on the Ni-PCSD column, participation of π–d interaction was indicated. The predominant role of π–π interaction in the separation of PAHs of less than three rings on the Ni-PCSD column was demonstrated using anthracene. All the columns possessed planar recognition ability and were estimated to be potentially useful in the separation and the analysis of PAHs.
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  • Structures of Platinum(II) Complexes of 2-Aminomethylaziridine and S-2-Aminomethylazetidine and Correlation of Anticancer Activities of (2-Aminomethylazacycloalkane)platinum(II) Complexes with the Geometry of the Chelate Rings Formed with Platinum(II)
    Masafumi Goto, Hisashi Tsutsui, Syuuichi Matsuda, Yoshitomo Tanaka, No ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 47-50
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.47
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    The spectroscopic properties of platinum(II) complexes with 2-aminomethyl-derivatives of small-membered 1-aza-cycloalkane, i.e., =2-aminomethylaziridine=azida and S-2-aminomethylazetidine=S-azeda, and the crystal structures of their dichloro complexes demonstrate that the conformation of the fused three- (azida) or four- (S-azeda) and five-membered chelate ring formed by the coordination of S-azida and S-azeda to platinum(II) has an S(N) absolute configuration at the secondary amine site and that the two alkyl groups extend axially from the five-membered chelate ring. The chelate ring of the azida is more planar than the S-azeda or other 2-aminomethyl-1-azacycloalkanes. The anticancer activity reported for azeda and 2-aminomethylpyrrolidine appears to be related to their coordination structure, namely the presence of cis-fused successive rings.
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  • Preparation and Characterization of Novel Branched β-Cyclodextrins Having β-D-Galactose Residues on the Non-reducing Terminal of the Side Chains and Their Specific Interactions with Peanut (Arachis hypogaea) Agglutinin
    Akiko Ikuta, Naomi Mizuta, Sumio Kitahata, Takeomi Murata, Taichi Usui ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 51-56
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.51
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    Six novel branched β-cyclodextrins (βCDs) having β-D-galactose residues on the non-reducing terminal of the sugar side chains, namely 61,64-di-O-(β-D-galactosyl)-βCD (10), 6-O-(β-D-galactosyl)-βCD (11), 61,64-di-O-(β-lactosyl)-βCD (14), 6-O-(β-lactosyl)-βCD (15), 61,64-di-O-(4′-O-β-D-galactosyl-β-lactosyl)-βCD (18), and 6-O-(4′-O-β-D-galactosyl-β-lactosyl)-βCD (19), were chemically synthesized using the trichloroacetimidate method. The reaction products were separated by HPLC on an amino column into dibranched and monobranched βCDs. Their structures were confirmed by mass spectrometry (MS) and two-dimensional (2D) NMR spectroscopic analysis. To study the length of the sugar side chains attached to the CD ring, which leads to differences in the functions of the branched CDs, interactions of these compounds with peanut (Arachis hypogaea) agglutinin (PNA) were investigated using an optical biosensor and an inhibition assay based on hemagglutination. The results showed that all branched βCDs interacted with PNA, and the binding affinity was 18>14>10 and 19>15>11 when the derivatives were compared on the basis of side chain length.
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  • Studies on Tellurium-Containing Heterocycles. Part 20.
    Reactions of 2-Benzoselenopyrylium Salts and 2-Benzotelluropyrylium Salts with Nucleophiles: Formation of 1-Functionalized 1H-Isoselenochromenes and 1H-Isotellurochromenes
    Haruki Sashida, Kazuo Ohyanagi
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 57-62
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.57
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    The reactions of the 2-benzoselenopyrylium (1A) and 2-benzotelluropyrylium cations (1B) with a variety of nucleophiles have been investigated. LiAlH4, sodium alkoxide (NaOMe, NaOi-Pr and NaOt-Bu), diethylamine, n-butylamine and acetone reacted with 1 to give the 1H-isochromenes (2) and the corresponding 1-substituted products (4—9) under mild conditions in almost good to high yields. The 1-alkyl(phenyl)isoselenochromenes (10—13) and 1-benzylisochromenes (18A, 18B), which were produced by the reaction of the salts 1 with Grignard reagents, were converted to the corresponding 1,3-disubstituted 2-benzopyrylium salts (14—17, 19) by treatment with triphenylcarbenium tetrafluoroborate (Ph3C+ BF4−), respectively. The 1-benzylselenopyrylium salts (19A) and 1-benzyltelluropyrylium salts (19B) exist in the solvent as an equilibrium mixture of the salts (19) and the corresponding (Z)-benzylidene compounds (20).
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  • CCR5 Antagonists as Anti-HIV-1 Agents. 1.
    Synthesis and Biological Evaluation of 5-Oxopyrrolidine-3-carboxamide Derivatives
    Shinichi Imamura, Yuji Ishihara, Taeko Hattori, Osamu Kurasawa, Yoshih ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 63-73
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.63
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    A novel lead compound, N-{3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl}-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [125I]RANTES and CCR5-expressing CHO cells. The IC50 value of 1 was 1.9 μM. In an effort to improve the binding affinity of 1, a series of 5-oxopyrrolidine-3-carboxamides was synthesized. Introduction of 3,4-dichloro substituents to the central phenyl ring (10i, IC50=0.057 μM; 11b, IC50=0.050 μM) or replacing the 1-methyl group of the 5-oxopyrrolidine moiety with a 1-benzyl group (12e, IC50=0.038 μM) was found to be effective for improving CCR5 affinity. Compound 10i, 11b, and 12e also inhibited CCR5-using HIV-1 envelope-mediated membrane fusion with IC50 values of 0.44, 0.19, and 0.49 μM, respectively.
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  • Stannyl Radical Addition-Cyclization of Oxime Ethers Connected with Olefins
    Hideto Miyabe, Hirotaka Tanaka, Takeaki Naito
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 74-78
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.74
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    Stannyl radical addition-cyclization of oxime ethers connected with olefin moieties was studied. The radical reactions proceeded effectively by the use of triethylborane as a radical initiator to provide the functionalized pyrrolidines via a carbon–carbon bond-forming process.
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  • A New Series of Estrogen Receptor Modulators: Effect of Alkyl Substituents on Receptor-Binding Affinity
    Atsushi Kamada, Atsushi Sasaki, Noritaka Kitazawa, Tadashi Okabe, Kazu ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 79-88
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.79
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    New types of selective estrogen receptor modulators (SERMs) were synthesized and evaluated for their binding affinity and biological effect on reproductive cells. A proposed lead structure (B) was derivatized to provide compounds 30 and 44, which showed good estrogen-receptor binding affinity (Ki values: 6.3 and 10 nM, respectively), as well as minimal impact on mammary and uterine carcinoma cells. Introduction of an alkyl group in the core structure considerably enhanced receptor-binding affinity of the compounds tested. Synthesis and structure–activity relationships of these compounds are described.
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  • Mechanistic Considerations for the Consecutive Cyclization of 2,3-Dibromopropylamine Hydrobromide Giving a Strained Molecule, 1-Azabicyclo[1.1.0]butane
    Kazuhiko Hayashi, Yoshifumi Ikee, Satoru Goto, Motoo Shiro, Yoshimitsu ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 89-94
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.89
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    The effective formation of 1-azabicyclo[1.1.0]butane (2) by treatment of 2,3-dibromopropylamine hydrobromide (1) with n-BuLi could be understood considering a rational reaction pathway via both transition states 10 and 19 based on the intramolecular Br···Li+ coordination. A similar cyclization pathway starting from N-benzyl-3-bromopropylamine hydrochloride (17) to afford N-benzylazetidine (18) could also be postulated on the basis of a transition state 20 involving the intramolecular Br···Li+ coordination.
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  • Stereochemistry of the Asymmetric Carbopalladation of Allenes Followed by Nucleophilic Substitution Reactions with Carbo- and Aminonucleophiles
    Fumiko Kato, Kunio Hiroi
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 95-103
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.95
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    The stereochemistry of the asymmetric palladium-catalyzed reaction of allenes with iodobenzene followed by nucleophilic substitution reaction with sodium malonate and N-methylbenzylamine is described. On the basis of the absolute configuration of the product and the stereochemical result of a similar reaction of a chiral allene, the mechanism of the above asymmetric reactions is discussed.
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  • Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum
    Jian-Mei Huang, Chun-Shu Yang, Ren Zhao, Hironobu Takahashi, Yoshiyasu ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 104-107
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.104
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    Seven new seco-prezizaane-type sesquiterpenes were isolated from the methanol extract of the pericarps of Illicium merrillianum. Their structures were elucidated as 3-deoxypseudoanisatin (1), 2β-hydroxy-3,6-dedioxypseudoanisatin (2), 8α-hydroxy-10-deoxycyclomerrillianolide (3), 10β-hydroxypseudoanisatin (4), 10β-hydroxycyclopseudoanisatin (5), 1,6-dihydroxy-3-deoxyminwanensin (6), and 8-deoxymerrilliortholactone (7) by analyses of their spectroscopic data and chemical transformation. Compounds 4 and 5 as well as 6 and 7 coexist as a keto/acetal equilibrated mixture in methanol solution.
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  • Two New Cytotoxic Clerodane Diterpenoids from Casearia membranacea
    Ya-Ching Shen, Li-Tung Wang, Chih-Hsin Wang, Ashraf Taha Khalil, Jih-H ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 108-110
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.108
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    In addition to casearlucin A (3), two new clerodane diterpenes, caseamembrols A (1) and B (2) have been isolated from the leaves and twigs of Casearia membranacea by bioassay-guided fractionation. The structures of the new compounds were established on the basis of extensive 1D- and 2D-NMR spectroscopic analysis. Compounds 1—3 exhibited significant cytotoxicity against human prostate (PC-3) cancer cells.
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  • Stereodivergent Synthesis of Chiral 2-Alkenylaziridines: Palladium(0)-Catalyzed 2,3-cis-Selective Aziridination and Base-Mediated 2,3-trans-Selective Aziridination
    Hiroaki Ohno, Yoshiji Takemoto, Nobutaka Fujii, Tetsuaki Tanaka, Toshi ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 111-119
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.111
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    Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding thermodynamically less stable 2,3-trans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols to a catalytic amount of Pd(PPh3)4 in THF or 1,4-dioxane affords predominantly the corresponding thermodynamically more stable 2,3-cis-2-alkenyl-3-alkylaziridines. The kinetically favored trans-selective aziridination would be attributed to the allylic 1,3-strain in aza-anionic intermediates. The conformational analysis of the sterically highly congested 2-alkenylaziridines thus obtained is also presented.
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  • Studies on Non-Thiazolidinedione Antidiabetic Agents. 3.
    Preparation and Biological Activity of the Metabolites of TAK-559
    Hiroshi Imoto, Mitsuharu Matsumoto, Hiroyuki Odaka, Junichi Sakamoto, ...
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 120-124
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.120
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    Preparation and biological activity of the metabolites of the potent antihyperglycemic and antihyperlipidemic agent, (E)-4-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyloxyimino}-4-phenylbutyric acid (TAK-559) (1), were investigated. Metabolites M-I (2), M-II (3), M-III (4) and M-IV (5) were synthesized and their biological activities were evaluated by in vitro and in vivo experiments. Compounds 2—4 activate human peroxisome proliferator-activated receptor gamma one (hPPARγ1) and hPPARα, but their activities are weaker than those of TAK-559 (1). Compound 5 only activates hPPARγ1 weakly. TAK-559 (1) showed potent in vivo plasma glucose and triglyceride lowering activities in Wistar fatty rats after intraperitoneal administration, while its metabolites (2—5) showed comparatively weak activities.
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  • Chiral Ligand-Controlled Asymmetric Conjugate Addition of α-Trimethylsilanylacetate to Acyclic and Cyclic Enones
    Mayu Iguchi, Hirohisa Doi, Seiji Hata, Kiyoshi Tomioka
    Article type: Regular Article
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 125-129
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.125
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    The reaction of lithium ester enolate with enones provides a challenge for chemoselectivity, that is, discrimination between a conjugate addition and a 1,2-addition. Asymmetric conjugate addition of a lithium enolate of α-trimethylsilanylacetate to acyclic and cyclic α,β-unsaturated ketones was mediated by an external chiral ligand to give the corresponding 1,4-adducts in good enantioselectivity of 74% and good chemoselectivity.
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Notes
  • Justicidone, a Novel p-Quinone-Lignan Derivative from Justicia hyssopifolia
    José Andrés Pérez, Carlos Boluda, Hermelo López, J ...
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 130-131
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.130
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    An uncommon, previously unreported p-quinone-lignan compound called justicidone (4-(1,3-benzodioxol-5-yl)-6-methoxynaphtho[2,3-c]furan-1,5,8(3H)-trione) (2), along with the known savinin (1) were isolated from Justicia hyssopifolia (Acanthaceae). Their structures were determined by spectroscopic methods.
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  • An Improved Synthesis of Benzocycloalkanone Derivatives
    Akimori Wada, Kyoko Sawada, Naomi Ono, Masayoshi Ito
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 132-135
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.132
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    A convenient and improved annulation method for the synthesis of bicyclic ketones was developed. A 2,2-dimethyl-6-(2-phenylsulfonyl)ethylcyclohexanone was converted into a sulfonylester by the addition of ethyl acetate and subsequent dehydration. A Dieckmann type condensation of the sulfonylester followed by desulfonylation afforded the 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-one in good yield. This annulation method was also applicable for the synthesis of the benzocyclooctanone derivative.
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  • Immunosuppressive Diterpenes from Veronicastrum sibiricum
    Wenyuan Gao, Rong Zhang, Wei Jia, Jun Zhang, Yoshihisa Takaishi, Hongq ...
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 136-137
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.136
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    Two new diterpenes, named sibiriquinone A (1) and B (2), along with four known diterpenes have been isolated from the aerial part of Veronicastrum sibiricum. Their structures were elucidated by spectroscopy. The isolated compounds showed significant immunosuppressive activities.
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  • Cytotoxic C-Benzylated Dihydrochalcones from Uvaria acuminata
    Momoyo Ichimaru, Noriyoshi Nakatani, Tomoko Takahashi, Yumi Nishiyama, ...
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 138-141
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.138
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    Two new C-benzylated dihydrochalcones, isochamuvaritin (1) and acumitin (2), have been isolated from the African medicinal plant Uvaria acuminata, together with the previously reported benzylbenzoate (3), uvaretin (4), isouvaretin (5), diuvaretin (6), and uvangoletin (7). The structural elucidation of compounds 1 and 2 in spectroscopic studies is described. C-Benzylated dihydrochalcones, especially 1, 2, 4, and 6, showed considerable cytotoxicity toward human promyelocytic leukemia HL-60 cells.
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  • Pregnane- and Furostane-Type Oligoglycosides from the Seeds of Allium tuberosum
    Tsuyoshi Ikeda, Hidetsugu Tsumagari, Masafumi Okawa, Toshihiro Nohara
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 142-145
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.142
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    Two furostane-type steroidal oligoglycosides (1, 2), together with a new pregnane-type oligoglycoside (3), were obtained from the seeds of Allium tuberosum ROTTLER. On the basis of spectroscopic analysis, the structures of three new oligoglycosides (1—3) were elucidated as 26-O-β-D-glucopyranosyl-(25R)-3β,22ξ,26-trihydroxyl-5α-furostane 3-O-β-chacotrioside, 26-O-β-D-glucopyranosyl-(25S)-3β,5β,6α,22ξ,26-pentahydroxyl-5β-furostane 3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside, and 3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl 3β,5β,6α,16β-tetrahydroxypregnane 16-(5-O-β-D-glucopyranoyl-4(S)-methyl-5-hydroxypentanoic acid) ester, respectively.
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  • Selective Scavenging Property of the Indole Moiety for the Nitrating Species of Peroxynitrite
    Hidehiko Nakagawa, Mitsuko Takusagawa, Hiromi Arima, Kumiko Furukawa, ...
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 146-149
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.146
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    The inhibitory effect on tyrosine nitration and oxidation of peroxynitrite was evaluated for more than 40 reagents including natural and synthetic compounds, and the inhibiting efficiency of each compound for nitration was compared with that for oxidation, to characterize its property as a peroxynitrite scavenger. In the presence of various concentrations of testing compounds, the nitrating and oxidizing activities were measured by monitoring the formation of 3-nitrotyrosine and dityrosine with an HPLC-UV-fluorescence detector. The IC50 values for nitration and oxidation were determined, and the ratio of these two IC50 values was calculated for each compound. Although the IC50 values varied from compound to compound, it was revealed that the ratio of two IC50 values (IC50 for oxidation/IC50 for nitration) was 1 in almost all the compounds tested, except five indole derivatives (L-tryptophan, melatonin, 5-methoxytryptamine, tryptamine, and tetrahydro-beta-carboline) and one synthetic selenium-containing compound ((2R,3R,4S)-2-amino-3,4-dihydroxy-5-phenylselenopentan-1-ol, ADPP). The indole derivatives showed a specific inhibitory effect on tyrosine nitration without affecting the oxidation. ADPP was confirmed to have a preferable inhibitory activity for tyrosine oxidation. It was suggested that compounds showing an IC50 value ratio of 1 scavenged the common species for nitration and oxidation, while the indole derivatives and ADPP preferably scavenged the nitrating and oxidizing species, respectively. From a stopped flow study, it was also revealed that the nitrotyrosine formation was relatively slow, unlike an OH radical reaction. These results imply that the peroxynirite reaction at least partly proceeds through specific species for nitration.
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  • Determination of α-Tocopherol in the Traditional Chinese Medicinal Preparation Sea Buckthorn Oil Capsule by Non-aqueous Reversed Phase-HPLC
    Zhao Luhua, Tu Ying, Zhao Zhengyu, Wang Guangji
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 150-152
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.150
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    A non-aqueous reversed phase HPLC was developed for determining α-tocopherol in Sea buckthorn oil capsule without the need for saponification. A reversed phase column (Alltima C18, 4.6×250 mm, 5 μm) was used with a mobile phase of methanol–acetonitrile (95 : 5, v/v) and flow rate of 1 ml/min. The contents in capsule were extracted with n-hexane. Detection wavelength was set at 292 nm. Each analysis requires no longer than 20 min. The linearity range for α-tocopherol was 9.4—47.0 μg/ml. The detection limit was 0.94 μg/ml. The mean recovery was 95.82 (RSD 2.3%). This method is suitable for quantitative analysis of α-tocopherol in Sea buckthorn oil or its Traditional Chinese Medicinal preparation.
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  • 3-Epicabraleahydroxylactone and Other Triterpenoids from Camellia Oil and Their Inhibitory Effects on Epstein–Barr Virus Activation
    Toshihiro Akihisa, Harukuni Tokuda, Motohiko Ukiya, Toshie Suzuki, Fum ...
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 153-156
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.153
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    The structure of a triterpenoid isolated from the nonsaponifiable lipid (NSL) of the seed oil of the camellia (Camellia japonica L.; Theaceae) was established to be (20S)-3β-hydroxy-25,26,27-trisnordammaran-24,20-olide (1; 3-epicabraleahydroxylactone) on the basis of spectroscopic and chemical methods. Six other triterpenoids isolated from the NSL were identified as 3-epicabraleadiol (2), ocotillol II (3), ocotillol I (4), dammarenediol II (5), (20R)-taraxastane-3β,20-diol (6), and lupane-3β,20-diol (7). Upon evaluation of the seven triterpenoids (1—7) with respect to their inhibitory effects on the induction of Epstein–Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, three compounds (5—7) showed potent inhibitory effects against EBV-EA induction (IC50 values of 277—420 mol ratio/32 pmol TPA).
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  • A New Pentacyclic Triterpenoid Glucoside from Prunus serrulata var. spontanea
    Hyun Ah Jung, Hae Young Chung, Jee H. Jung, Jae Sue Choi
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 157-159
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.157
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    A new triterpenoid, 2α,3α,24-trihydroxyurs-12-en-28-oic acid-28-O-β-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2α-hydroxyursolic acid (2), 2α,3α,24-trihydroxyurs-12-en-28-oic acid (3), and 2α,3α,19α,24-tetrahydroxyurs-12-en-28-oic acid-28-O-β-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3—5 showed ONOO− scavenging activity, whereas compounds 1 and 2 were virtually inactive.
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  • Synthesis of Hexahydropyridazine-3-phosphonic Acid
    Mamoru Kaname, Kazuo Yoshinaga, Yasushi Arakawa, Shigeyuki Yoshifuji
    Article type: Note
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 160-162
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.160
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    The synthesis of hexahydropyridazine-3-phosphonic acid (piperidazine-3-phosphonic acid) was performed via a hetero-Diels–Alder reaction followed by Lewis acid-catalyzed phosphonylation. This two-step procedure was improved to a one-pot reaction.
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Communicatins to the Editor
  • Synthesis and Antifungal Activity of Novel 14-Membered Benzomacrolides, as Galbonolide Analogues
    Hiroki Sakoh, Shunji Sakuraba, Yuichi Sugimoto, Hideaki Imamura, Hidek ...
    Article type: Communication to the Editor
    Subject area: [not specified]
    2004 Volume 52 Issue 1 Pages 163-165
    Published: 2004
    Released on J-STAGE: January 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.163
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    Asymmetric total synthesis of benzene analogues of galbonolide, a 14-membered antifungal macrolide, possessing a benzene ring instead of a conjugated diene structure, was achieved starting from chiral 1-aryl-1-propanol obtained by enzyme-catalyzed kinetic resolution with high enantioselectivity. Representatively, a method for the introduction of a methylthio and chloride function at the vinyl position was also established. The resulting analogues unfortunately exhibited very little antifungal potency in comparison with galbonolide A.
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