Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 51, Issue 12
Displaying 1-26 of 26 articles from this issue
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Regular Articles
  • Antiedematogenic Activity of Two Thiazolidine Derivatives: N-Tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene) Rhodanine (GS26) and N-Tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,4-thiazolidinedione (GS28)
    Antonio Alfredo Rodrigues e Silva, Alexandre José da Silva G&oa ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1351-1355
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1351
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    The search for new anti-inflammatory drugs has been constant in several research centers. The use of the Bioisostery concept allows the elaboration of new bioactive compounds with different properties through the introduction of substitute groups in one or more positions of a main molecule with known biological activity. Preliminary works accomplished at our laboratory with 2,4-thiazolidinedione isosters demonstrated inhibitory activity on edema formation for N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-2,4-thiazolidinedione (GS28) and N-tryptophyl-5-(3,5-di-tert-butyl-4-hydroxybenzylidene) rhodanine (GS26). We verified the antiedematogenic and ulcerogenic activity of these two compounds in Wistar rats. The carrageenan induced paw edema suffered significant (p<0.05) inhibition (28.36% on average) for GS28 (100 mg/kg; v.o.) during the entire time of the experiment. GS26 (50 and 100 mg/kg; v.o.) significantly inhibited (p<0.05) the paw edema dextran induced (22.1 and 27.8%, for the respective doses) after 180 min. The compounds GS26 and GS28 did not show ulcerogenic activity on gastric mucous. The results suggest antiedematogenic action for both compounds without the appearance of gastric lesions.
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  • In Situ Observation of the Four-step Dehydration Process of the 1β-Methylcarbapenem Antibiotic CS-834 Crystal by X-Rays
    Katsuhiro Kobayashi, Hiroshi Fukuhara, Tadashi Hata, Yuji Ohashi
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1356-1362
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1356
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    The 1β-methylcarbapenem antibiotic CS-834 takes six crystalline forms depending on ambient conditions. The X-ray powder diffraction revealed that the dihydrate crystal (B2-form) was changed to the monohydrate (B1-form) through the intermediate form (B2′-form). The monohydrate form was then changed to the dehydrate (B0-form) through the intermediate B1′-form. The progress of the dehydration along the needle axis (c-axis) was observed under a microscope. When a single crystal of the B2-form was mounted on a diffractometer and the humidity was reduced, the crystal was gradually changed to the various dehydration forms with retention of the single crystal. The crystals of B2- to B0-forms form isostructures to each other except the solvent water molecules. In the crystal structure of the B1-form, the pivaloyloxymethyl moiety is disordered. One is nearly similar to that of the B2-form, while another is similar to that of the B0-form. Each crystal structure consists of a columnar arrangement of CS-834 along the c-axis, and the water molecules are located between the columns and form a characteristic hydrogen bond network. When the water molecules leave the crystal, the columns slide slightly following the slight conformational change in the pivaloyloxymethyl groups and are connected by another type of hydrogen bond network. Such a rearrangement of the hydrogen bond network should be a motive force of the phase change to the next step due to the dehydration. Since the hydrogen bond network extends along the c-axis, the dehydration proceeds along the c-axis as observed microscopically.
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  • Preparation of Optically Active threo-2-Amino-3-hydroxy-3-phenylpropanoic Acid (threo-β-Phenylserine) via Optical Resolution
    Tadashi Shiraiwa, Reiichi Saijoh, Masahiro Suzuki, Kyosuke Yoshida, Sa ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1363-1367
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1363
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    To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1), (2RS,3SR)-2-benzoylamino-3-hydroxy-3-phenylpropanoic acid [(2RS,3SR)-2] was first optically resolved using (1S,2S)- and (1R,2R)-2-amino-1-(4-nitrophenyl)-1,3-propanediol as the resolving agents to afford (2R,3S)- and (2S,3R)-2 in yields of 73% and 66%, based on half of the starting amount of (2RS,3SR)-2. Next, the racemic structures of ammonium and some organic ammonium salts of (2RS,3SR)-2 were examined based on melting point, solubility, and infrared spectrum, with the aim of optical resolution by preferential crystallization. The benzylammonium salt of (2RS,3SR)-2 was suggested to exist as a conglomerate at room temperature, although it forms a racemic compound at the melting point. The optical resolution by preferential crystallization of the racemic salt afforded the (2R,3S)- and (2S,3R)-salts with optical purities of 90—97%. The (2R,3S)- and (2S,3R)-2 obtained from the purified salts were hydrolyzed by reflux in hydrochloric acid to give (2R,3S)- and (2S,3R)-1.
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  • A Synthesis of Chiral 1,1,3-Trisubstituted 1,2,3,4-Tetrahydro-β-carbolines by the Pictet–Spengler Reaction of Tryptophan and Ketones: Conversion of (1R,3S)-Diastereomers into Their (1S,3S)-Counterparts by Scission of the C(1)–N(2) Bond
    Yoshie Horiguchi, Masayoshi Nakamura, Toshiaki Saitoh, Takehiro Sano
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1368-1373
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1368
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    The Pictet–Spengler cyclization of the imines (3) prepared by the condensation of L-tryptophan methyl ester (1) and aryl methyl ketones (2), using titanium(IV) isopropoxide as an iminating reagent, quantitatively proceeded, when treated with trifluoroacetic acid (TFA) or formic acid, to provide two diastereomers, that is (1S,3S)-1-aryl-3-isopropoxycarbonyl-1-methyl-1,2,3,4-tetrahydro-β-carbolines (4) and their (1R,3S)-diastereomers (5), of which the diastereomer ratios varied from 1 to 5 depending on the reaction conditions. The (1R,3S)-diastereomers (5) are thermodynamically more stable than their (1S,3S)-congeners (4), as shown by equilibration experiments in TFA. The conversion of 4 to 5 (also 5 to 4) should occur under acidic conditions by cleavage of the C(1)–N(2) bond with complete retention of configuration at the C-3 chiral center. The low diastereo-selectivity observed in the Pictet–Spengler reaction of 1 and 2 is concluded to be a stereochemical outcome under conditions of kinetic control (lower temperature, shorter reaction time), while the high diastereo selectivity with preferential formation of the more stable isomer (5) is the result of thermodynamically controlled experiments (higher temperature, longer reaction time).
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  • Flavonoids from Andrographis viscosula
    Yerra Koteswara Rao, Amooru Gangaiah Damu, Alahari Janardhan Rao, Shan ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1374-1376
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1374
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    Phytochemical investigation of the whole plant of Andrographis viscosula has led to the isolation of three new 2′-oxygenated flavonoids, (2R)-5-hydroxy-7,2′,3′-trimethoxyflavanone (1), 7,2′,5′-trimethoxyflavone (2), 5,7,2′,3′-tetramethoxyflavone (3), and eight known flavones, 5,7,2′-trimethoxyflavone (4), 5,7,2′,4′,5′-pentamethoxyflavone (5), echioidinin (6), 5,2′,6′-trihydroxy-7-methoxyflavone (7), 5-hydroxy-7,2′-dimethoxyflavone (8), echioidin (9), echioidinin 5-O-glucoside (10), and 5,2′,6′-trihydroxy-7-methoxyflavone 2′-O-glucoside (11). The structures of 1—11 were elucidated by physical and spectral methods, including extensive 2D NMR studies. The presence of 2′-oxygenated flavonoids is apparently restricted to Andrographis species in Acanthaceae. Therefore, 2′-oxygenated flavonoids are regarded as chemotaxonomic markers of Andrographis genus in the Acanthaceae family.
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  • Structures of 1,4-Benzodioxane Derivatives from the Seeds of Phytolacca americana and Their Neuritogenic Activity in Primary Cultured Rat Cortical Neurons
    Hironobu Takahasi, Kazue Yanagi, Masumi Ueda, Kousuke Nakade, Yoshiyas ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1377-1381
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1377
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    The methanol extract of the seeds of Phytolacca americana was reinvestigated to yield three new 1,4-benzodioxane-type compounds, americanoic acid methyl ester (1), isoamericanoic acid A methyl ester (2), and 9′-O-methylamericanol A (3) along with the previously isolated neolignans 6—9. The structures of 1—3 were characterized by 2D NMR and long-range selective proton-decoupling (LSPD) techniques. The neuritogenic effects of compounds 1—3, and dicarboxilic acids 4 and 5, which had been previously synthesized with horseradish peroxidase-catalyzed oxidative coupling of caffeic acid, were examined in primary cultured rat cortical neurons. Americanoic acid A methyl ester (1) exhibited neurite outgrowth-promoting activity at concentration of 0.01—1.0 μM, whereas dicarboxilic acids 4 and 5 were found to induce neuritogenesis dose dependently at the concentrations from 0.1 μM to 10 μM.
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  • Quantitative Analysis of Ephedrine Analogues from Ephedra Species Using 1H-NMR
    Hye Kyong Kim, Young Hae Choi, Wen-Te Chang, Robert Verpoorte
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1382-1385
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1382
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    Four ephedrine analogues such as ephedrine, pseudoephedrine, methylephedrine, and methylpseudoephedrine were determined by 1H-NMR from Ephedra species. In the region of δ 5.0—4.0, the signals of H-1 attached to the same carbon with a hydroxyl, were well separated from each other in CDCl3. The amount of each alkaloid was calculated by the relative ratio of the intensity of H-1 signal to the known amount of internal standard, 200 μg of anthracene. This method allows rapid determination of the quantity of four ephedrine alkaloids from Ephedra species. The amount of these alkaloids was in the range of 1.0—2.0% of dry weight depending on the plant materials.
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  • Synthesis and Anti-influenza Evaluation of Polyvalent Sialidase Inhibitors Bearing 4-Guanidino-Neu5Ac2en Derivatives
    Takeshi Masuda, Shuku Yoshida, Masami Arai, Satoru Kaneko, Makoto Yama ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1386-1398
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1386
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    Polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives on a poly-L-glutamine backbone are described. Aiming for a longer retention time of 4-guanidino-Neu5Ac2en (zanamivir) in bronchi and lungs, we focused on supermolecules bearing 4-guanidino-Neu5Ac2en derivatives bound at their C-7 position through noncleavable alkyl ether linkages. We first found that alkylation of the 7-hydroxyl group of sialic acid derivative 8 proceeded smoothly, and produced 7-O-alkyl-4-guanidino-Neu5Ac2en derivatives 13, which exhibited equipotent inhibitory activity against not only influenza A virus sialidase but also influenza A virus in the cell culture. Next, we synthesized poly-L-glutamine bearing 7-O-alkyl-4-guanidino-Neu5Ac2en derivatives linked by amide bonds, 26, which showed enhanced antiviral activity against influenza A virus and more potent efficacy in vivo relative to a monomeric sialidase inhibitor.
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  • Preparation of Deuterated Methyl and Dimethyl Substituted Nicotinoylating Agents for Derivatization of the N-Terminal of Protein
    Hiroki Tsumoto, Chie Murata, Naoki Miyata, Ryo Taguchi, Kohfuku Kohda
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1399-1401
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1399
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    Methyl groups of 6-methylnicotinic acid and 2,6-dimethylnicotinic acid were deuterated by an H–D exchange reaction under conditions of 1% NaOD/D2O on heating. With a condensation reaction between the D-labeled nicotinic acid derivative and N-hydroxysuccinimide with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, the nicotinoylating agents, 1-(6-methyl[D3]nicotinoyloxy)succinimide (2c) and 1-(2,6-dimethyl[D6]nicotinoyloxy)succinimide (2f) were prepared. Both D-labeled nicotinoylating agents and their unlabeled counterparts quantitatively modified the N-terminal of protein.
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  • Stereostructure of Komodoquinone A, a Neuritogenic Anthracycline, from Marine Streptomyces sp. KS3
    Takuya Itoh, Masahiro Kinoshita, Hong Wei, Motomasa Kobayashi
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1402-1404
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1402
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    The absolute stereostructure of komodoquinone A (1), a neuritogenic anthracycline, which was isolated from a cultured marine Streptomyces sp. KS3, has been determined on the basis of chemical derivatization. Komodoquinone A (1) induces neuronal cell differentiation in the neuroblastoma cell line, Neuro 2A and arrests the cell cycle at the G1 phase. The effect of a solid-state medium on the production of 1 and its aglycone, komodoquinone B (2), was examined.
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  • A Novel 3,4-Bis(sulfenyl)- or 4-Selenenyl-3-sulfenylpenta-2,4-dienylation of Aldehydes Using 4-Ethoxy-1,2-bis(sulfenyl)- or 1-Selenenyl-2-sulfenyl-buta-1,3-dienyl Lithiums
    Mitsuhiro Yoshimatsu, Yasutaka Matsuura, Kohei Gotoh
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1405-1412
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1405
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    3,4-Dichalcogenopenta-2,4-dienylation of aldehydes proceeded in good to high yields using 4-ethoxy-1-(benzenesulfenyl)-2-(methanesulfenyl)- (5), 4-ethoxy-1,2-bis(benzenesulfenyl)but-1,3-diene (6), and 1-selenenyl derivatives 7 and 8. This novel four-carbon homologation could be applied to a synthesis of 3,4,7,8-tetrakis(benzenesulfenyl)-10,10-dimethylundeca-2,4,6,8-tetraenal (20).
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Notes
  • Synthesis and Biological Evaluation of Ebselen and Its Acyclic Derivatives
    Tsu-Chung Chang, Mei-Lan Huang, Wen-Lin Hsu, Jing-Min Hwang, Ling-Yih ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1413-1416
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1413
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    Five ebselen and three acyclic ebselen derivatives were synthesized. These compounds were screened for their glutathione peroxidase (GSH Px)-like activity and scavenging activity against 1,1-diphenyl-2-pycryl-hydrazyl (DPPH) and peroxynitrite radical. All tested compounds displayed similar significant GSH Px-like activity, which are slightly higher than that of ebselen. The peroxynitrite scavenging activity showed that the acyclic allylseleno 4c was five times more potent than ebselen.
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  • Studies on the Constituents of Gardenia Species. III.
    New Iridoid Glycosides from the Leaves of Gardenia jasminoides cv. fortuneana HARA
    Koichi Machida, Emiko Takehara, Hiroko Kobayashi, Masao Kikuchi
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1417-1419
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1417
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    Two new iridoid glycosides, 7β,8β-epoxy-8α-dihydrogeniposide (1) and 8-epiapodantheroside (2), were isolated, together with six known (3—8) and three artifact (9—11) iridoids, from the leaves of Gardenia jasminoides cv. fortuneana HARA. Their structures were established based on chemical and spectral data.
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  • Three Novel 5(6→7)Abeoabietane-Type Diterpenes from the Bark of Taiwania cryptomerioides
    Chi-I Chang, Shih-Chang Chien, Shue-Mei Lee, Yueh-Hsiung Kuo
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1420-1422
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1420
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    Three new 5(6→7)abeoabietane diterpenes with the uncommon skeleton of fused 6–5–6 rings were isolated from the bark of Taiwania cryptomerioides designated as taiwaniaquinone F (8), taiwaniaquinol C (9) and taiwaniaquinol D (10). Meanwhile, two known compounds, taiwaniaquinones A (1) and D (4), were also obtained. Their structures were determined principally from spectral evidence.
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  • Sulfur-Containing Compounds from Clinacanthus siamensis
    Pittaya Tuntiwachwuttikul, Yupa Pootaeng-on, Pootchana Pansa, Thongcha ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1423-1425
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1423
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    Two new sulfur-containing compounds, trans-3-methylsulfonyl-2-propenol (1) and trans-3-methylsulfinyl-2-propenol (2) were isolated together with trans-3-methylthioacrylamide (3), entadamide A (4) and entadamide C (5) from the leaves of Clinacanthus siamensis. The structures were established on the basis of the spectroscopic data. The compounds were tested for antimalarial and antimycobacterial activity.
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  • Urinary Metabolites of Nobiletin Orally Administered to Rats
    Takaaki Yasuda, Yukako Yoshimura, Hisako Yabuki, Takahiro Nakazawa, Ke ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1426-1428
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1426
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    During the course of our systematic investigation of the metabolism of flavonoids, the polymethoxyflavone nobiletin, occurring in the fruits of Citrus depressa, was orally administered to rats. The urinary metabolites were separated and identified by three-dimensional HPLC equipped with a photodiode array detector and the structure was determined by spectroscopic methods to be 4′-hydroxy-3′,5,6,7,8-pentamethoxyflavone (1).
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  • Briarane Derivatives from the Gorgonian Coral Junceella fragilis
    Ping-Jyun Sung, Tung-Yung Fan, Lee-Shing Fang, Shwu-Li Wu, Jan-Jung Li ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1429-1431
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1429
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    A new trihydroxyl briarane-type diterpenoid, junceellolide H (1), along with two known compounds, praelolide (2) and junceellin (3), have been isolated from the gorgonian coral Junceella fragilis. The structure, including the relative configuration of the new diterpenoid 1, was elucidated by extensive spectroscopic methods.
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  • Lupane-triterpene Carboxylic Acids from the Leaves of Acanthopanax trifoliatus
    Phan Van Kiem, Xing Fu Cai, Chau Van Minh, Jung Joon Lee, Young Ho Kim
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1432-1435
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1432
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    Two new lupane-triterpene carboxylic acids, called acantrifoic acid A (1) and acantrifoside C (2) have been isolated from the leaves of Acanthopanax trifoliatus. Based on extensive 1D and 2D NMR spectroscopic data, their chemical structures were determined as 3α-acetoxy-30-hydroxylup-20(29)-ene-23,28-dioic acid and 3α-acetoxy-30-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester.
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  • Further Studies on the Structure of Polysaccharides from the Lichen Flavoparmelia caperata (L.) HALE
    Tadahiro Takeda, Noriko Shimizu, Sachiko Watanabe, Yoshikuni Edagawa, ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1436-1438
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1436
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    A water-soluble polysaccharide called PC-2 was previously isolated from Flavoparmelia caperata (L.) HALE and assigned to α(1-3)(1-4)glucan. However, PC-2 separated into three components, PC-2A, PC-2B, and PC-2C (a single peak in HPLC, respectively) on further purification. Methylation analysis and 1H- and 13C-NMR spectroscopic studies suggested that PC-2A is composed of repeating units of [α-D-Glc1-3]3, : [α-D-Glc1-4]2, while PC-2B and PC-2C are partly branched galactoglucomannans consisting of (1-3)- and (1-4)-linked α-D-glucopyranosyl units as the main chain. In addition we confirmed that the polysaccharide fraction PB-2 from the lichen of the same genus, Flavoparmelia baltimorensis (GYELNIK & FORISS) HALE, is identical to PC-2 based on the chemical and spectroscopic data.
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  • Constituents of Hypericum laricifolium and Their Cyclooxygenase (COX) Enzyme Activities
    Hesham Rushdey El-Seedi, Therese Ringbom, Kurt Torssell, Lars Bohlin
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1439-1440
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1439
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    Investigation of the aerial parts of the medicinal plant Hypericum laricifolium led to the isolation of two new natural products, hentriacontanyl caffeate (1a), nonacosanyl caffeate (1b). In addition, stigmasterol, β-sitosterol, 3-epi-betulinic acid (2), caffeic acid (3), ferulic acid, docosanol, p-hydroxybenzoic acid, 3,4-dimethoxy benzoic acid, quercetin (4), quercetin-3-O-galactoside (5), quercetin-3-O-rutinoside (6), quercetin-3-O-rhamnoside (7), quercetin-3-O-glucuronide (8) and shikimic acid were also isolated. The structures were determined by 1D- and 2D-NMR, mass spectrometry, and chemical transformations. The anti-inflammatory effects of the isolated compounds were discussed briefly.
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  • Tyromycic Acids F and G: Two New Triterpenoids from the Mushroom Tyromyces fissilis
    Dang Ngoc Quang, Toshihiro Hashimoto, Masami Tanaka, Yoshinori Asakawa
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1441-1443
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1441
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    Phytochemical examination of the methanol extract of the fruit bodies of the Japanese fungus Tyromyces fissilis led to the isolation of two new lanostane derivatives called tyromycic acids F (1) and G (2), together with two known compounds, tyromycic acid (3) and trametenolic acid B (4). Their structures were identified by 2D NMR, IR, and UV spectroscopy.
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  • Spectrophotometric Determination of Some Drugs for Osteoporosis
    Elham Anwer Taha, Nadia Fayek Youssef
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1444-1447
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1444
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    Three simple, accurate and sensitive spectrophotometric methods are developed for the determination of some new drugs for the treatment of osteoporosis: risedronate sodium (I), alendronate sodium (II) and etidronate disodium (III). The first method is based on the measurement of difference in absorbance (ΔA) of risedronate sodium in 0.01 mol l−1 hydrochloric and 0.1 mol l−1 sodium hydroxide at 262 nm. Beer's law is obeyed over a concentration range of 15—150 μg ml−1 with mean recovery 99.75±1.22 and molar absorptivity (ε) 1.891×103. The second method is based on the reaction of the primary amino group of (II) with ninhydrin reagent in methanolic medium in the presence of 0.05 mol l−1 sodium bicarbonate. The colored product is measured at 568 nm, and the linearity range is found to be 3.75—45 μg ml−1 with mean recovery 99.77±0.73 and ε 9.425×103. The third method is based on oxidation of the three mentioned drugs with ceric (IV) sulphate in 0.5 mol l−1 sulphuric acid at room temperature and subsequent measurement of the excess unreacted cerium (IV) sulphate at 320 nm. The method obeyed Beer's law over a concentration range of 2—24 μg ml−1 for the three drugs with mean recovery 99.79±1.16, 99.73±1.38 and 99.86±1.13 and ε 14.427×103, 13.813×103 and 14.000×103 for drugs I, II, III respectively. The proposed methods were successfully applied for the determination of the studied drugs in bulk powder and in pharmaceutical formulations. The results were found to agree statistically with those obtained the reported methods. Furthermore, the methods were validated according to USP regulations and also assessed by applying the standard addition technique.
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  • Inhibitory Effects of 3-O-Acyl-(+)-catechins on Epstein-Barr Virus Activation
    Shinichi Uesato, Keisuke Taniuchi, Ayako Kumagai, Yasuo Nagaoka, Ryota ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1448-1450
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1448
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    In the course of an exploratory investigation of antitumor-promoting catechins, 3-O-acyl-(+)-catechins of varying carbon lengths from C4 to C18 were assessed for inhibitory effects on the activation of the Epstein-Barr virus early antigen. Like 3-O-acyl-(−)-epigallocatechins, the (+)-catechin derivatives showed promising effects with the C-3 acyl chain of C8–C11 carbon atoms.
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  • Synthesis of Pyrimidine Derivatives Possessing an Antioxidative Property and Their Inhibitory Effects on Picryl Chloride-Induced Contact Hypersensitivity Reaction
    Yoshiaki Isobe, Kosaku Hirota
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1451-1454
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1451
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    We conducted a preliminary structure–activity relationship (SAR) study of some barbituric acid and uracil derivatives against the picryl chloride-induced contact hypersensitivity reaction. The introduction of an antioxidative moiety to the side chain of the C(6)-position of uracil was effective against this model. The introduction of dimethoxyphenol (8b) or dimethylphenol (8c) instead of di-t-butylphenol (8a) as an antioxidative moiety gave diminished activities, so, the reactive oxygen would contribute to the inflammation of this model, and an antioxidative activity was required for exhibiting the inhibitory activity. The inhibitory activity was significantly affected by the substituent at the N(1)-phenyl moiety.
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  • Effect of Surface Covering of Lactose Carrier Particles on Dry Powder Inhalation Properties of Salbutamol Sulfate
    Kotaro Iida, Youhei Hayakawa, Hirokazu Okamoto, Kazumi Danjo, Hans Lue ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1455-1457
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1455
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    The effect of the surface covering of lactose carrier particles on the dry powder inhalation properties of salbutamol sulfate was investigated. Lactose carrier surfaces were covered with sucrose tristearate (J-1803F) by a high-speed elliptical-rotor-type powder mixer (Theta-Composer®). In the present study, drug/carrier powder mixtures were prepared consisting of micronized salbutamol sulfate and lactose carriers with various particle surface conditions prepared by surface covering. These powder mixtures were aerosolized by a Jethaler®, and the in vitro inhalation properties of salbutamol sulfate were evaluated by a twin impinger. Compared with the powder mixed with uncovered lactose carrier, the in vitro inhalation properties of the powder mixture prepared using the surface covering lactose carrier were significantly different, showing that the in vitro inhalation properties of salbutamol sulfate were improved. In vitro inhalation properties increased with the percentage of J-1803F added. Using this surface covering system would thus be valuable for increasing the inhalation properties of dry powder inhalation with lactose carrier particles.
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  • Microbial Transformation of Terreusinone, an Ultraviolet-A (UV-A) Protecting Dipyrroloquinone, by Streptomyces sp.
    XiFeng Li, Sang Mi Lee, Hong Dae Choi, Jung Sook Kang, Byeng Wha Son
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 12 Pages 1458-1459
    Published: 2003
    Released on J-STAGE: December 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.1458
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    Biotransformation study was conducted on the marine dipyrroloquinone, terreusinone (1) isolated from the marine-derived fungus Aspergillus terreus. Preparative-scale fermentation of terreusinone with Streptomyces sp. has resulted in the isolation of a new oxidized metabolite, terreusinol (2). The structure was elucidated as 2-[(1R)-1-hydroxyisobutyl]-6-[(1R)-1,2-dihydroxyisobutyl]-1H,5H-pyrrolo[2,3-b]indole-4,8-dione (2) on the basis of physicochemical evidence. Terreusinol (2) showed an ultraviolet-A (UV-A) (320—390 nm) protecting activity with ED50 values of 150 μM, which is more active than oxybenzone (ED50, 350 μM) currently being used as sunscreen.
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