Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 52, Issue 8
Displaying 1-32 of 32 articles from this issue
Review
  • Ken-ichi Harada
    2004 Volume 52 Issue 8 Pages 889-899
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Freshwater cyanobacteria produce lethal toxins such as microcystins and anatoxins. During the purification of microcystins in bloom samples we found that a toxic cyanobacterium produced not only microcystins but also other types-peptides in early 1990. Since then we have isolated approximately thirty peptides from freshwater cyanobacteria. In this manuscript we focused on the following topics concerning the isolated peptides: 1) how to isolate desired compounds and to determine their structures, 2) structural classification of isolated compounds, 3) isolation of similar peptides from laboratory strains and bloom materials, 4) structurally related peptides from freshwater and marine origins, 5) β-amino acid containing peptides from cyanobacteria, 6) comprehensive analysis system for the biosynthetic study of peptides produced by cyanobacteria, 7) biological activities of isolated compounds.
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  • Kaneto Uekama
    2004 Volume 52 Issue 8 Pages 900-915
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The pharmaceutically useful cyclodextrins (CyDs) are classified into hydrophilic, hydrophobic, and ionic derivatives. Because of the multi-functional characteristics and bioadaptability, these CyDs are capable of alleviating the undesirable properties of drug molecules through the formation of inclusion complexes or the form of CyD/drug conjugates. This review outlines the current application of CyDs in design and evaluation of CyD-based drug formulation, focusing on their ability to enhance the drug absorption across biological barriers, the ability to control the rate and time profiles of drug release, and the ability to deliver a drug to a targeted site.
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  • Hiromitsu Takayama
    2004 Volume 52 Issue 8 Pages 916-928
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.
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Regular Articles
  • Naciye Türkel, Melek Berker, Ulviye Özer
    2004 Volume 52 Issue 8 Pages 929-934
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The interactions of aluminium(III) ion with the triprotic catechol derivatives (H3L), 2,3-dihydroxybenzoic acid (2,3-DHBA), 3,4-dihydroxyphenylacetic acid (3,4-DHPA), 3,4-dihydroxybenzoic acid (3,4-DHBA), and 3,4-dihydroxyhydrocinnamic acid (3,4-DHHCA) were investigated in aqueous solution at 25.0 °C. The Calvin–Bjerrum titration method was adopted for the determination of formation constants of proton–ligand and aluminium(III)–ligand complexes. Potentiometric and spectroscopic results indicated that these catechol derivatives exhibit a true bidentate character. The chelation occurs via their catecholate sites, with the exception of 2,3-DHBA. In the case of 2,3-DHBA complexes, the dominant species are either the salicylate type (COO, O) or catecholate type (O, O) complex. The protonation constants of ligands and their formation constants of Al(III) complexes were also correlated. The order of decreasing stabilities of complexes is: 3,4-DHPA>3,4-DHBA>3,4-DHHCA>2,3-DHBA.
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  • Shunji Aoki, Dexin Kong, Kouhei Matsui, Rachmaniar Rachmat, Motomasa K ...
    2004 Volume 52 Issue 8 Pages 935-937
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    A new sesquiterpene aminoquinone, 5-epi-smenospongorine, together with nine known sesquiterpene quinone/phenols, was isolated as differentiation-inducing substances to K562 cells into erythroblast from the marine sponge Dactylospongia elegans. The structure–activity relationship study of these compounds clarified that the quinone skeleton is indispensable and the amino group plays an important role for their differentiation-inducing activity to K562 cells into erythroblast.
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  • Kotaro Iida, Yukari Inagaki, Hiroaki Todo, Hirokazu Okamoto, Kazumi Da ...
    2004 Volume 52 Issue 8 Pages 938-942
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The effects of the surface processing of lactose carrier particles on the dry powder inhalation properties of salbutamol sulfate were investigated. Lactose carrier particles were processed using 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 coarse lactose carriers with various particle surface conditions prepared by surface processing. These powder mixtures were aerosolized by a Jethaler®, and the in vitro inhalation properties of salbutamol sulfate were evaluated with a twin impinger. Compared with those of the powder mixed with unprocessed lactose carriers, the in vitro inhalation properties of the powder mixture prepared using the surface processed lactose carriers were significantly different, showing that the in vitro inhalation properties of salbutamol sulfate were improved. The in vitro inhalation properties increased with the rotor rotation rate. Using this surface processing system would thus be valuable for increasing the inhalation properties of dry powder inhalation with lactose carrier particles.
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  • Toshihiko Ishizaka, Yohko Miyanaga, Junji Mukai, Kiyokazu Asaka, Yuka ...
    2004 Volume 52 Issue 8 Pages 943-948
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The purpose of this study was to evaluate the bitterness of 18 different antibiotic and antiviral drug formulations, widely used to treat infectious diseases in children and infants, in human gustatory sensation tests and using an artificial taste sensor. Seven of the formulations were found to have a bitterness intensity exceeding 1.0 in gustatory sensation tests (evaluated against quinine as a standard) and were therefore assumed to have an unpleasant taste to children. The bitterness intensity scores of the medicines were examined using suspensions in water or an acidic sports drink. In the case of three macrolide antibiotic formulations containing erythromycin (ERYTHROCIN® dry syrup), clarithromycin (CLARITH® dry syrup for pediatric), and azithromycin (ZITHROMAC® fine granules for pediatric use), the bitterness intensities of suspensions in acidic sports drinks were dramatically enhanced compared with the corresponding scores of suspensions in water. This enhancement could be predicted using the taste sensor. On the other hand, a reduction of bitterness intensity was observed for an acidic sports drink suspension of an amantadine product (SYMMETREL® fine granules) compared with an aqueous suspension. This reduction in bitterness could also be predicted using the taste sensor output value. Thus, the taste sensor could predict whether or not suspension in an acidic sports drink would enhance or reduce the bitterness intensity of pediatric drug formulations, compared with suspensions in water.
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  • Fumihiro Nagashima, Moyoko Murakami, Shigeru Takaoka, Yoshinori Asakaw ...
    2004 Volume 52 Issue 8 Pages 949-952
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    A new aromadendrane-type sesquiterpenoid, 4(15)-aromadendren-12,5α-olide and an aromadendrane–guaianolide dimer have been isolated from the New Zealand liverwort Chiloscyphus subporosus. Their structures were established by extensive NMR techniques and X-ray crystallographic analysis.
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  • Hitoshi Kagawa, Tetsuya Takahashi, Mariko Uno, Shigeru Ohta, Yoshihiro ...
    2004 Volume 52 Issue 8 Pages 953-956
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Deuterium incorporation at the C-3 position of flavanones was achieved by treatment of flavanones and 2′-hydroxychalcones with D3PO4 and AcOD. We propose that the deuteration reaction mechanism for 2′-hydroxychalcones substrates is as follows. In the first step, 2′-hydroxychalcones cyclize to the corresponding flavanones by an intramolecular Michael-type reaction. Then deuteriums are incorporated into the flavanones via enolization.
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  • Beom Soo Shin, Ji Hoon Jung, Kang Choon Lee, Sun Dong Yoo
    2004 Volume 52 Issue 8 Pages 957-960
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    This study was performed to examine the absorption potential of polyethylene glycol (PEG)-modified salmon calcitonin (sCT) in rats administered via the nasal route. Previous studies have used relatively high molecular weight polyethylene glycols (e.g., ≥5000 daltons) for PEG-modification of sCT to provide increased metabolic stability and biological half-life. Unlike these studies, the present study utilized a low molecular weight succinimidyl-propionated monomethoxy-poly(ethylene glycol) (MW 2000). It was hypothesized that the potential for membrane transport would not be significantly altered due to a relatively small increase in the molecular size while the metabolic stability would be enhanced due to resistance to proteolytic degradation. After PEG-modification of sCT, the mono-PEG positional isomer (mono-PEG2k-sCT) was separated from di-PEG2k-sCT, tri-PEG2k-sCT, and unmodified sCT by size exclusion chromatography. The mono-PEG2k-sCT and unmodified sCT were radioiodinated, and the resulting 125I-sCT and 125I-mono-PEG2k-sCT were separated from free iodine by RP HPLC and confirmed by MALDI-TOF MS. The 125I-sCT and 125I-mono-PEG2k-sCT were administered to rats via the nasal route, and serial blood, tissue, and urine samples were taken for up to 36 h for the determination of radioactivity. Mono-PEG2k-sCT exhibited significantly increased AUC (20638 vs. 3650 ng·min/ml), tmax (520 vs. 77 min), and t1/2,λz (923 vs. 199 min) compared with unmodified sCT. This study demonstrates that mono-PEG2k-sCT is absorbed systemically when given by the intranasal route, exhibiting altered absorption kinetics compared with unmodified sCT.
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  • Toshiro Fukami, Atsushi Mugishima, Toyofumi Suzuki, Shinji Hidaka, Tom ...
    2004 Volume 52 Issue 8 Pages 961-964
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Improvement of solubility for fullerene (C60) was studied by cogrinding with cycloamyloses using a ball mill in the solid state. Cycloamylose is a novel cyclic α-1,4-glucan produced from synthetic amylose by enzymatic reaction. Although sample solutions showed a pale yellow for the initial period of cogrinding with cycloamyloses and C60, the color varied to brown after 48 h. Subsequently, the solubility of C60 was improved markedly to 560 (μg/ml) at 96 h. From powder X-ray diffraction analysis, the peak intensity of crystalline C60 decreased as the cogrinding time was extended. The UV–VIS absorption spectrum of C60 shows absorption bands at 262 and 340 nm in water with cycloamyloses, and 258 and 328 nm in n-hexane. These results suggested that C60 molecules were dispersed into cycloamyloses micellar system and the red-shift of the UV–VIS spectra was due to an intermolecular interaction between C60 and cycloamyloses.
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  • Martin Chwalek, Karen Plé, Laurence Voutquenne-Nazabadioko
    2004 Volume 52 Issue 8 Pages 965-971
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Glycosylation of hederagenin with the trichloroacetimidate derivatives of six commercial disaccharides (D-cellobiose, D-lactose, D-maltose, D-melibiose, D-gentiobiose, D-isomaltose) was performed giving the protected saponins in high yields. Deprotection then gave the saponins which were transformed into the corresponding methyl esters. The hemolytic activity of these synthetic hederagenin diglycosides was measured in order to establish structure–activity relationships based on the type and sequence of the attached sugar for the free carboxylic acid and methyl ester saponins.
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Notes
  • Feng-Qian Li, Jin-Hong Hu
    2004 Volume 52 Issue 8 Pages 972-973
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Solid dispersions of silymarin were prepared by the fusion method with the intention of improving the dissolution properties of silymarin. Polyethylene glycol 6000 (PEG 6000) was used as the inert hydrophilic matrix. The dissolution studies of the solid dispersions were performed in vitro. And the results obtained showed that the dissolution rate of silymarin was considerably improved when formulated in solid dispersions with PEG 6000 as compared to original drug, and the increased dissolution rate might be favorable for further oral absorption.
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  • Muchchintala Maheswara, Yerra Koteswara Rao, Vidavalur Siddaiah, Chund ...
    2004 Volume 52 Issue 8 Pages 974-975
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Two new 5-deoxyflavonoids, 7,2′,3′,4′-tetramethoxyflavone (1) and 7,2′,3′,4′-tetramethoxyflavanone (2) together with a known flavone 7,4′-dimethoxy-3′-hydroxyflavone (3) were isolated from the whole plant of Calliandra inermis. The structures of these new compounds were elucidated by high resolution electron impact mass spectrometry (HR-EI-MS) and 1D and 2D-NMR spectral studies including 1H–1H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser enhancement spectroscopy (NOESY).
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  • Magharla Dasaratha Dhanaraju, Rajadas Jayakumar, Chandrasekar Vamsadha ...
    2004 Volume 52 Issue 8 Pages 976-979
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The main objective of this work was to develop a system consisting of polymeric microspheres loaded with steroid drugs. The drugs were encapsulated using biodegradable poly(lactide-co-glycolide) (PLG) and poly(ε-caprolactone) (PCL) by double emulsion solvent evaporation method. The lipophilic drugs, levonorgestrel and ethinylestradiol were made soluble by adding ethanol/water mixture. The effects of parameters like polymer concentration and stabilizer concentration were studied on the size, size distribution, surface properties and loading efficiencies of microspheres. The formulated microspheres were smooth, spherical and uniform in shape and size. Fourier transformed infrared spectroscopy and differential scanning calorimetry studies seemed to confirm the absence of chemical interaction between the drugs and the polymers, while the drugs were dispersed in the polymer. The increase in polymer concentrations increased the size as well as the loading efficiency of microspheres. Data obtained in this study demonstrated that the PLG/PCL microspheres may be a suitable polymeric carrier for long acting injectable drug delivery.
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  • Tripetch Kanchanapoom, Somsak Ruchirawat, Ryoji Kasai, Hideaki Otsuka
    2004 Volume 52 Issue 8 Pages 980-982
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    An aliphatic alcohol glycoside (asystoside) and an iridoid diglucoside (3′-O-β-D-glucopyranosyl-catalpol) were isolated from the aerial part of Asystasia intrusa along with benzyl β-D-glucopyranoside, zizybeoside I, (6S,9R)-roseoside, verbascoside, ehrenoside, 6β-hydroxyantirrhide, angeloside, catalpol, ajugol, 6-deoxycatalpol, and scutellarioside II. The structural elucidations were based on analyses of physical and spectroscopic data.
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  • Masao Nagaoka, Mitsuteru Numazawa
    2004 Volume 52 Issue 8 Pages 983-985
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    C(10)–C(19) bond cleavage reaction of 19-hydroxy- and 19-oxoandrost-4-ene-3,6,17-triones (5, 6) was explored under various conditions. Treatment of steroids 5 and 6 with KOH in MeOH gave the A-ring aromatized product 6-oxoestrone (11) in a fair yield, respectively, in contrast, the treatment with a weak base yielded 4-methyl steroid 17 (20%) in the case of 19-alcohol 5 or 19-nor-Δ5(10)-steroid 9 (12—67%) along with compound 11 (6—27%) in the case of 19-aldehyde 6. Reaction of compound 6 with HCl in MeOH produced 3-methyl ethers of 6-oxoestrone and Δ6-estrone, compounds 12 and 14 (ca. 20% each). Thus, 6-oxosteroids 5 and 6 showed unique C(10)–C(19) bond cleavage reactions with a base or acid.
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  • Shu-Hua Qi, Si Zhang, Jian-She Huang, Zhi-Hui Xiao, Jun Wu, Li-Juan Lo ...
    2004 Volume 52 Issue 8 Pages 986-988
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Five glycerol derivatives (1—5) and three sterols (6—8) were isolated from the EtOH extraction of the brown alga of Sargassum parvivesiculosum. On the basis of spectroscopic methods, their structures were elucidated as 1,3-di-O-[2′,2′-di-(p-phenylene) isopropylidene] glycerol (1), (2S)-1-O-heptatriacontanoyl glycerol (2), (2S)-1,2-di-O-palmitoyl-3-O-(6-sulpho-α-D-quinovopyranosyl) glycerol (3), (2S)-1-O-palmitoyl glycerol (4), (2S)-1,3-di-(O-palmitoyl)-2-O-octadecanoyl glycerol (5), 24-ethylcholest-5,23Z-dien-3β,28ζ-diol (6), 24-vinylcholest-5-en-24ζ-hydroperoxy (7), 24-ethylcholest-4,24(28)-dien-3β-ol (8), respectively. Among them, 1 and 2 were new.
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  • Sandeep K. Ginotra, Bhupender S. Chhikara, Manish Singh, Ramesh Chandr ...
    2004 Volume 52 Issue 8 Pages 989-991
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Mild, efficient and eco-friendly oxidation of 17α-methylandrostan-3β-17β-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65 °C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17β-hydroxy-17α-methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17β-hydroxy-17α-methyl-Δ1-androsten-3-one (3) under the similar reaction conditions in good yield and single step reaction.
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  • Hiroki Sakoh, Hideki Jona, Yuichi Sugimoto, Hideaki Imamura, Shunji Sa ...
    2004 Volume 52 Issue 8 Pages 992-994
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The development of an efficient synthetic method enabled multi-gram synthesis of a key intermediate, which is useful for the modification at the C6-functional group of galbonolide analogues. The structure of a key intermediate including a conjugated diene was afforded by Horner–Emmons reaction, alkylation of Weinreb amide with alkyl lithium and a subsequent Wittig reaction.
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  • Shu Zhu, Kun Zou, Shaoqing Cai, Meselhy Ragab Meselhy, Katsuko Komatsu
    2004 Volume 52 Issue 8 Pages 995-998
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    A HPLC method for the simultaneous determination of 11 triterpene saponins with four-type aglycones (protopanaxadiol, protopanaxatriol, ocotillol and oleanolic acid types) in Ginseng drugs was developed and validated. Using a gradient of acetonitrile and 10 mM K-phosphate buffer (pH 5.80) as the mobile phase and UV detection at 196 nm, more than 18 ginsenosides with different aglycones were separated satisfactorily within 60 min. The detection limits (signal/noise≥3) were 0.1 μg for ginsenosides Rb1, Rc, Rd, Re and Rg1, chikusetsusaponin III, and notoginsenoside R2, 0.2 μg for gisenoside Ro and chikusetsusaponin IVa, 0.3 μg for chikusetsusaponin IV, and 3 μg for majonoside R2. The calibration curve of each saponin had a correlation coefficient close to 1. Intra- and interday precisions were less than 2.1% (n=5) and 3.3% (n=15), respectively. The recovery rates of extraction were in the range of 96.4—102.7% for all ginsenosides. By adopting this method, the determinations of 11 ginsenosides in three Ginseng drugs derived from Panax ginseng, Panax vietnamensis var. fuscidiscus and Panax japonicus (Japan) were achieved.
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  • Shuji Kitagawa, Hiromi Sakamoto, Hiromi Tano
    2004 Volume 52 Issue 8 Pages 999-1001
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    To investigate the effects of flavonoids on free radical-mediated biological membrane damage and the interaction of flavonoids with heme proteins, we studied the effects of quercetin, its glycosides (rutin and quercetin-3-O-glucoside), morin and (−)epicatechin on the hemolysis of the bovine erythrocytes induced by the hydrophilic free radical initiator, 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH), and their interaction with hemoglobin. These flavonoids retarded the onset of the hemolysis dose-dependently. The effects of quercetin and other flavonoids were much greater than those of dihydric-phenols studied previously. The inhibitory effects of quercetin and its glycosides were stronger than those of morin and (−)epicatechin. In the absence of AAPH, the relatively hydrophobic flavonoids quercetin and morin induced the oxidation of oxyhemoglobin to methemoglobin. Oxidation by quercetin was especially marked. However, this oxidation did not induce hemolysis. These findings indicate that relatively hydrophobic flavonoids penetrate the cytoplasm of erythrocytes, interact with hemoglobin, and oxidize the heme iron.
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  • Satoshi Kawatake, Masanori Inagaki, Ryuichi Isobe, Tomofumi Miyamoto, ...
    2004 Volume 52 Issue 8 Pages 1002-1004
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    A GD3-type ganglioside molecular species, LMG-4 (1), has been obtained from the polar lipid fraction of the chloroform/methanol extract of the starfish Luidia maculata. The structure of this ganglioside has been determined on the basis of chemical and spectroscopic evidence to be 1-O-[(N-acetyl-α-D-neuraminosyl)-(2→8)-(N-acetyl-α-D-neuraminosyl)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]-ceramide. The ceramide moiety was composed of heterogeneous 2-hydroxy fatty acid and phytosphingosine units. This is the first report on the isolation and structure elucidation of GD3-type ganglioside from echinoderms. Moreover, 1 exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.
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  • Haruhiro Fujimoto, Etsuko Nakamura, Emi Okuyama, Masami Ishibashi
    2004 Volume 52 Issue 8 Pages 1005-1008
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    In a screening study on immunomodulatory fungal metabolites, three known anthraquinones, carviolin (roseo-purpurin) (1), 1-O-methylemodin (2), ω-hydroxyemodin (citreorosein) (4), and a new anthraquinone, ω-acetylcarviolin (3), together with a known steroid, ergosta-4,6,8(14),22-tetraen-3-one (5) and a new steroid, 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one (6) were isolated from an Ascomycete, Zopfiella longicaudata, and found to have moderate immunosuppressive activities. The structure–activity relationships of these metabolites are discussed.
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  • Naotoshi Toki, Tsuyoshi Satoh
    2004 Volume 52 Issue 8 Pages 1009-1012
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    Benzeneseleninic anhydride in the presence of tert-butyl hydroperoxide in chlorobenzene at about 70 °C is an effective oxidizing agent for the selective oxidation of alcohols at the benzylic position.
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  • Junichi Kitajima, Toru Ishikawa, Atushi Urabe
    2004 Volume 52 Issue 8 Pages 1013-1014
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    From the polar portion of the methanol extract of thyme (leaf of Thymus vulgaris; Labiatae), which has been used as a stomachic, carminative, a component of prepared cough tea, and as a spice, a new hydroxyjasmone glucoside, (Z)-5′-hydroxyjasmone 5′-O-β-D-glucopyranoside was isolated together with five related compounds and four aromatic compounds. The structures of the new compound was clarified by spectral investigation.
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  • Kyoko Hayashi, S. M. Abdur Rahman, Hiroaki Ohno, Tetsuaki Tanaka, Naok ...
    2004 Volume 52 Issue 8 Pages 1015-1017
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    Herpes simplex virus type 1 thymidine kinase (HSV TK) is involved in both antiherpetic therapy and cancer gene therapy with acyclovir (ACV) and ganciclovir (GCV). Enhanced sensitivity to these drugs is advantageous in their clinical use. In the present study, scopadulciol (SDC) and its related compounds were evaluated for their stimulatory effect on the cytotoxicity of ACV and GCV by determination of selective toxicities against HSV TK-expressing HeLa cells. Although SDC remarkably potenciated the cytotoxicity of ACV and GCV, the other tested compounds showed only weak selectivity, except for compound 34.
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  • Nobuo Kawahara, Atsuyo Kurata, Takashi Hakamatsuka, Setsuko Sekita, Mo ...
    2004 Volume 52 Issue 8 Pages 1018-1020
    Published: 2004
    Released on J-STAGE: August 10, 2004
    JOURNAL FREE ACCESS
    The structures of two new cucurbitacin glucosides designated opercurins A (1) and B (2), isolated from the fruit of Luffa operculata, have been confirmed by extensive spectroscopic investigation.
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  • Hiroko Sano, Tomomi Noguchi, Aya Tanatani, Hiroyuki Miyachi, Yuichi Ha ...
    2004 Volume 52 Issue 8 Pages 1021-1022
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    Several N-substituted phenylphthalimide and phenylhomophthalimide derivatives with cyclooxygenase (COX)-inhibitory activity were prepared during structural development studies based on thalidomide as a lead compound. Substituent effects on the subtype selectivity were investigated.
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  • Sarot Cheenpracha, Chatchanok Karalai, Yanisa Rat-a-pa, Chanita Pongli ...
    2004 Volume 52 Issue 8 Pages 1023-1025
    Published: 2004
    Released on J-STAGE: August 10, 2004
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    A new cytotoxic cardenolide glycoside, 3β-O-(2′-O-acetyl-α-L-thevetosyl)-14β-hydroxy-7-en-5β-card-20(22)-enolide, (7,8-dehydrocerberin), together with five known cardenolides, 17β-neriifolin, deacetyltanghinin, tanghinin, cerberin and 2′-O-acetyl-cerleaside A were isolated from the seeds of Cerbera manghas L. Their structures were elucidated by 1D- and 2D-NMR techniques as well as UV, IR and mass spectral data. 7,8-Dehydrocerberin, deacetyltanghinin and tanghinin exhibited cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cells lung cancer (NCI-H187).
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