All issues
Volume 53, Issue 8
Displaying 1-41 of 41 articles from this issue
- |<
- <
- 1
- >
- >|
Review
-
Mitsuru Hashida, Shigeru Kawakami, Fumiyoshi Yamashita2005 Volume 53 Issue 8 Pages 871-880
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFor effective chemotherapy, it is necessary to deliver therapeutic agents selectively to their target sites, since most drugs are associated with both beneficial effects and side effects. The use of lipid dispersion carrier systems, such as lipid emulsions and liposomes, as carriers of lipophilic drugs has attracted particular interest. A drug delivery system can be defined as a methodology for manipulating drug distribution in the body. Since drug distribution depends on the carrier, administration route, particle size of the carrier, lipid composition of the carrier, electric charge of the carrier and ligand density of the targeting carrier, these factors must be optimized. Recently, the lipid carrier system has also been applied to gene delivery systems for gene therapy. However, in both drug and gene medicine cases, a lack of cell-selectivity limits the wide application of this kind of drug and/or gene therapy. Therefore, lipid carrier systems for targeted drug and gene delivery must be developed for the rational therapy. In this review, we shall focus on the progress of research into lipid carrier systems for drug and gene delivery following systemic or local injection.View full abstractDownload PDF (510K)
Regular Articles
-
Marcelo Aparecido da Silva, Bruna Paola Murino Rafacho, Clelia Akiko H ...2005 Volume 53 Issue 8 Pages 881-885
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSStrychnos pseudoquina ST. HIL. (Loganiaceae) was investigated for its ability to protect the gastric mucosa against injuries caused by non-steroidal anti-inflammatory drugs (piroxicam) and a necrotizing agent (HCl/EtOH) in mice. The MeOH extract and enriched alkaloidic fraction (EAF) provided significant protection in experimental models wheer used at doses of 250 and 1000 mg/kg. In vivo tests were carried out to evaluate for possible toxic effects and no mortality was observed up to the 5 g/kg dose level. Phytochemical investigation led to the isolation of a new indole alkaloid, which elucidated the observed pharmacological effects.View full abstractDownload PDF (182K) -
Guang-Fu Sun, Xu-Xiang Chen, Fen-Er Chen, Yue-Ping Wang, Erik De Clerc ...2005 Volume 53 Issue 8 Pages 886-892
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSAs part of a series of studies to discover new HIV reverse-transcriptase inhibitors, various novel 6α- and 6β-naphthylthio 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) derivatives were synthesized, and in vitro anti-HIV-1 activity was evaluated. The results revealed that most of 6α-naphthylthio HEPT derivatives (7a—w) showed good activity [for 7e, IC50 value of 0.048 μM and selectivity index (SI) value of 735; for 7h, IC50 value of 0.057 μM and SI value of 579; for 7k, IC50 value of 0.063 μM and SI value of 565], 6β-naphthylthio HEPT derivatives (8a—f) showed low activity, but the introduction of α nitro group to the C-1 position of the 6β-naphthyl ring in the 6β-naphthylthio series (11a—c) resulted in a dramatic increase in anti-HIV-1 activity.View full abstractDownload PDF (214K) -
Jiahui Yin, Yasuhiro Noda, Norio Hazemoto, Toshihisa Yotsuyanagi2005 Volume 53 Issue 8 Pages 893-898
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSGabexate mesilate (GM) and camostat mesilate (CM) are protease inhibitors used for the treatment of pancreatitis, and have been reported to show anticancer effects in vivo. Lipid emulsions (20% fractionated soybean oil) were investigated in terms of physicochemical interaction between the drugs and lipid emulsions as a possible drug carrier. The result showed that the drugs did not distribute in the oil phase but were adsorbed at the phospholipid interface of oil droplets. With increasing concentration of the drugs, the adsorption amount at the interface rose steeply to around 2.2×10−11 mol/cm2 for GM and 1.2×10−11 mol/cm2 for CM, respectively, followed by further adsorption deviated from the Langmuir adsorption manner after the inflection. To interpret this two-stage adsorption of the drugs, surface potential and fluorescence changes were examined in addition to thermodynamics for their interaction with the interfacial lipid layer. The primary adsorption was exothermic and was due to electrostatic interaction and van der Waals interaction between drug molecules and phospholipid molecules. Both acidic and neutral phospholipids in the lipid were involved in the adsorption of GM, while acidic phospholipids were mainly involved in the adsorption of CM. On the other hand, the secondary adsorption was endothermic and was entropy-driven most probably due to hydrophobic interaction for GM and CM in common, including peripheral penetration of drug molecules into the interfacial lipid layer.View full abstractDownload PDF (219K) -
Erdal Dinç, Abdil Özdemir2005 Volume 53 Issue 8 Pages 899-906
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSIn the presence of closely overlapping spectra, the quantitative multiresolution of ternary mixtures of three active compounds paracetamol (PAR), caffeine (CAF) and acetylsalycilic acid (ASP) in tablets, without using pretreatment such as separation step and graphical procedure of spectra was accomplished by the multivariate spectral calibration models, tri-linear regression calibration (TLRC), multi-linear regression calibration (MLRC) and Cramer's rule solution (CRS) of three linear equation functions in the matrix form. In the first two models, TLRC and MLRC are based on the use of the linear regression functions at selected wavelength sets in the spectral region of 210—300 nm. In the case of CRS model, A11 (1%, 1 cm) were used to obtain three linear equation functions and this linear equation system was resolved by the Cramer's rule for the prediction of PAR, CAF and ASP in samples. In the TLRC and CRS models, the selection of the appropriate wavelength set was performed by the Kaiser's technique. The algorithms of these mathematical calibration models were briefly described. The validation of TLRC, MLRC and CRS models was carried out by analyzing various synthetic ternary mixtures and by using the standard addition technique. These three calibration approaches were applied to the analysis of the real pharmaceutical tablets containing PAR, CAF and ASP. The obtained results were statistically compared with each other by using experimental and statistical tests. In the comparison of TLRC and MLRC models to the classical approach, CRS technique, the successful assay results were observed for the quantitative multiresolution of ternary mixture of the subject active compounds.View full abstractDownload PDF (489K) -
Ijaz Ahmad, Sarfraz Ahmad Nawaz, Nighat Afza, Abdul Malik, Itrat Fatim ...2005 Volume 53 Issue 8 Pages 907-910
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSOnosmins A (1) and B (2), lipoxygenase inhibitors, have been isolated from Onosma hispida. Their structures were established as 2-[(4-methylbenzyl)amino]benzoic acid (1) and methyl 2-[(4-methylbenzyl)amino]benzoate (2) through spectroscopic studies, including 2D-NMR. The known compounds apigenin (3), 6,4′-dimethoxy-3,5,7-trihydroxyflavone (4), 6,7-dimethoxy-3,5,4′-trihydroxyflavone (5) and apigenin 7-O-β-D-glucoside (6) are also reported for the first time from this species. Compounds (1) and (2) inhibited lipoxygenase (LOX, EC 1.13.11.12) enzyme in a concentration-dependent fashion with IC50 values of 24.0 and 36.2 μM, respectively. Lineweaver–Burk as well as Dixon plots and their secondary replots indicated that the nature of inhibition was purely a non-competitive type, with Ki values 22.0 μM and 31.1, respectively.View full abstractDownload PDF (145K) -
Srguleng Qian, Hongshan Yu, Chunzhi Zhang, Mingchun Lu, Hongying Wang, ...2005 Volume 53 Issue 8 Pages 911-914
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSDioscin-α-L-rhamnosidase was isolated, purified and partially characterized from pig liver. The maximum activity was reached at pH 7, 42 °C, 24 h, and 2% of substrate concentration. Fe3+ and Cu2+ inhibited the enzyme; the ion Ca2+ activated it. Mg2+ was an inhibitor at 100 mM, but it was an activator at 200 mM. Zn2+ could be a weak activator of the enzyme. The molecular weight of dioscin-α-L-rhamnosidase was about 47 kDa as determined by the method of SDS–polyacrylamide gel electrophoresis.View full abstractDownload PDF (186K) -
Yorinobu Yonezawa, Sumio Ishida, Hisakazu Sunada2005 Volume 53 Issue 8 Pages 915-918
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSAnalysis of the entire release process of the wax matrix tablet was examined. Wax matrix tablet was prepared from a physical mixture of drug and wax powder to obtain basic or clear release properties. The release process began to deviate from Higuchi equation when the released amount reached at around the half of the initial drug amount. Simulated release amount increase infinitely when the Higuchi equation was applied. Then, the Higuchi equation was modified to estimate the release process of the wax matrix tablet. The modified Higuchi equation was named as the H-my equation. Release process was well treated by the H-my equation. Release process simulated by the H-my equation fitted well with the measured entire release process. Also, release properties from and through wax matrix well coincident each other. Furthermore, it is possible to predict an optional release process when the amount of matrix and composition of matrix system were defined.View full abstractDownload PDF (217K) -
Huong Doan Thi Mai, Thomas Gaslonde, Sylvie Michel, Michel Koch, Fran& ...2005 Volume 53 Issue 8 Pages 919-922
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA series of 2-acyl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (4—6) was prepared by treatment of 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (3) with an excess of an appropriate acyl chloride in the presence of aluminum chloride. Treatment of (±)-cis-1-hydroxy-2-acyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (9, 10) or (±)-cis-1,2-diacyloxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones (2, 11) with hydrochloric acid gave the corresponding 2-acyloxy-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-ones, exemplified by acetate 7 and butyrate 8. None of the Michael acceptors 4—6 showed significant antiproliferative activity. Enol esters 7 and 8 were markedly cytotoxic toward L1210 leukemia cells, with IC50 values within the same range of magnitude as (±)-cis-1,2-diacetoxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (S23906-1), currently under phase I clinical trials. In contrast with S23906-1, enol esters 7 and 8 were not reactive toward purified DNA.View full abstractDownload PDF (106K) -
Haruhiro Fujimoto, Yoshie Okamoto, Eriko Sone, Satomi Maeda, Kohki Aki ...2005 Volume 53 Issue 8 Pages 923-929
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSIn a screening study on immunomodulatory fungal constituents, eleven new 2-pyrones tentatively named TT-1 (1), and TT-2—11 (2—11) have been isolated from a Fungi Imperfecti, Trichurus terrophilus, and designated rasfonin (1), and trichurusin B—K (2—11), respectively. Compounds 1—4 exhibited considerably high immunosuppressive activities, and compounds 8—11 have shown moderate ones. The structure–activity relationships of these constituents have also been discussed.View full abstractDownload PDF (213K) -
Carlos J. Boluda, Hermelo López, José A. Pérez, J ...2005 Volume 53 Issue 8 Pages 930-933
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe first synthesis of justicidone (4-(1′,3′-Benzodioxol-5′-yl)-6-methoxynaphtho[2,3-c]furan-1,5,8(3H)-trione) was carried out from piperonal, as a starting compound, through a lineal process using well known reactions.View full abstractDownload PDF (146K) -
Koichi Machida, Erika Matsuoka, Takayuki Kasahara, Masao Kikuchi2005 Volume 53 Issue 8 Pages 934-937
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFour enantiomerically pure new α-tetralones, (4S)- and (4R)-5-hydroxy-4-methoxy-α-tetralones and (4S)- and (4R)-5,8-dihydroxy-4-methoxy-α-tetralones were isolated, together with five known ones, (4S)- and (4R)-4,8-dihydroxy-α-tetralones, (4S)-4,8-dihydroxy-5-methoxy-α-tetralone and (4S)- and (4R)-4-hydroxy-α-tetralones, from the fruit of Juglans mandshurica MAXIM. var. sieboldiana MAKINO. Their structures were established on the basis of spectral analysis. To the best of our knowledge, this is the first isolation of the (4R)-4-hydroxy-α-tetralone derivative from Juglans species.View full abstractDownload PDF (186K) -
Phan Minh Giang, Phan Tong Son, Katsuyoshi Matsunami, Hideaki Otsuka2005 Volume 53 Issue 8 Pages 938-941
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFive new natural labdane-type diterpenoids (5—9), designated leoheteronins A—E, together with four known diterpenoids (1—4), two phytosterols as a mixture of β-sitosterol and stigmasterol, and the flavone genkwanin (10) were isolated from the aerial parts of Leonurus heterophyllus SW. (Lamiaceae) collected in northern Vietnam. Compound 1 was isolated for the first time from a Leonurus species, and 10 is considered to be a chemotaxonomic marker of the Leonurus genus. Their structures were determined using spectroscopic analyses.View full abstractDownload PDF (103K) -
Nafisur Rahman, Habibur Rahman, Syed Najmul Hejaz Azmi2005 Volume 53 Issue 8 Pages 942-948
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA kinetic spectrophotometric method has been described for the determination of metoprolol tartrate in pharmaceutical formulations. The method is based on reaction of the drug with alkaline potassium permanganate at 25±1 °C. The reaction is followed spectrophotometrically by measuring the change in absorbance at 610 nm as a function of time. The initial rate and fixed time (at 15.0 min) methods are utilized for constructing the calibration graphs to determine the concentration of the drug. Both the calibration graphs are linear in the concentration range of 1.46×10−6—8.76×10−6 M (10.0—60.0 μg per 10 ml). The calibration data resulted in the linear regression equations of log (rate)=3.634+0.999 log C and A=6.300×10−4+6.491×10−2 C for initial-rate and fixed time methods, respectively. The limits of quantitation for initial rate and fixed time methods are 0.04 and 0.10 μg ml−1, respectively. The activation parameters such as Ea, ΔH‡, ΔS‡ and ΔG‡ are also evaluated for the reaction and found to be 90.73 kJ mol−1, 88.20 kJ mol−1, 84.54 J K−1 mol−1 and 63.01 kJ mol−1, respectively. The results are validated statistically and through recovery studies. The method has been successfully applied to the determination of metoprolol tartrate in pharmaceutical formulations. Statistical comparison of the results with the reference method shows excellent agreement and indicates no significant difference in accuracy and precision.View full abstractDownload PDF (168K) -
Effat Souri, Hassan Jalalizadeh, Hassan Farsam, Roksana Ghadiri, Masso ...2005 Volume 53 Issue 8 Pages 949-951
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSDerivative spectrophotometry offers a useful approach for the analysis of drugs in multi-component mixtures. In this study a third-derivative spectrophotometric method was used for simultaneous determination of cyproterone acetate and ethinylestradiol using the zero-crossing technique. The measurements were carried out at wavelengths of 316 and 226 nm for cyproterone acetate and ethinylestradiol respectively. The method was found to be linear (r2>0.999) in the range of 0.5—6 mg/100 ml for cyproterone acetate in the presence of 35 μg/100 ml ethinylestsradiol at 316 nm. The same linear correlation (r2>0.999) was obtained in the range of 10—80 μg/100 ml of ethinylestradiol in the presence of 2 mg/100 ml of cyproterone acetate at 226 nm. The limit of determination was 0.5 mg/100 ml and 10 μg/100 ml for cyproterone acetate and ethinylestradiol respectively. The method was successfully applied for simultaneous determination of cyproterone acetate and ethinylestradiol in pharmaceutical preparations without any interferences from excipients.View full abstractDownload PDF (134K) -
Hiromichi Fujioka, Naoyuki Kotoku, Yoshinari Sawama, Hidetoshi Kitagaw ...2005 Volume 53 Issue 8 Pages 952-957
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA novel asymmetric synthesis of the cyclohexane derivative functionalized by some substituents has been developed from the diene acetals (1), prepared from the corresponding diene aldehyde and (+)-hydrobenzoin. The treatment of 1 with NBS in the presence of MeOCH2CH2OH predominantly afforded 2 in a stereoselective manner. Subsequent alkylation of the methoxyethoxy group produced the optically active cyclohexene compounds (3) in good yields. The stereoselective chemical modification of the remaining olefin in 3 was made by OsO4-oxidation.View full abstractDownload PDF (230K) -
Már Másson, Birna Vigdís Sigurdardóttir, K ...2005 Volume 53 Issue 8 Pages 958-964
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe purpose of the study was to evaluate an octanol–water phase distribution method for investigation of drug/cyclodextrin (D/CD) complexes and to compare stability constant values obtained by this method to values obtained by the phase solubility method. A general equation for determination of 1 : 1 D/CD complex stability constant (K1 : 1) from the slope of a phase-distribution diagram (a diagram of the reciprocal of the apparent partition coefficient vs. the total CD concentration) was derived. The equation accounted for the possible inclusion of the organic solvent in the CD cavity and the gradual saturation of the CD binding with increasing concentration of the guest compound. This method was used to determine K1 : 1 for 2-hydroxypropyl-β-cyclodextrin (HPβCD) complexes of hydrocortisone, prednisolone, diazepam, β-estradiol and diethylstilbestrol. These values were comparable to K1 : 1 values determined by the phase-solubility method. The phase-distribution method could also be applied to determine stability constants for the neutral and ionic forms of the weakly acidic drugs, naproxen and triclosan and the weakly basic drug lidocaine. The phase-distribution method is a very versatile and fast method and has the advantage, compared to the phase-solubility method, that it only requires very small drug samples. Thus, this method would be suitable for screening of new drug candidates.View full abstractDownload PDF (346K) -
Takashi Mano, Rodney W. Stevens, Kazuo Ando, Makoto Kawai, Kiyoshi Kaw ...2005 Volume 53 Issue 8 Pages 965-973
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSStructural modification of imidazole 5-lipoxygenase (5-LO) inhibitors for optimizing inhibitory potency, pharmacokinetic behavior and toxicity (ocular) profile led to 4-{3-[4-(2-methyl-1H-imidazol-1-yl)phenylthio]}phenyl-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide (6) with no observable ocular toxicity. The orally active and safe imidazole 5-LO inhibitor 6 was selected as a clinical candidate and advanced to clinical studies. An improved synthesis of 6 is also discussed.View full abstractDownload PDF (261K) -
Yuichi Tozuka, Arpansiree Wongmekiat, Kyoko Kimura, Kunikazu Moribe, S ...2005 Volume 53 Issue 8 Pages 974-977
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe interaction between FSM-16 and flurbiprofen (FBP) in the mesopores of FSM-16 was investigated by using three types of FSM-16 with different pore diameters, i.e., FSM-16(Oc), FSM-16(Do) and FSM-16(Doc) (pore diameters 16.0, 21.6, 45.0 Å, respectively). Solid dispersions of 30% FBP–70% FSM-16 were prepared by solvent evaporation and sealed-heating of the physical mixture at 100 °C for 6 h. Changes in the molecular state of FBP were investigated using powder X-ray diffractometry, thermal analysis and FT-IR spectroscopy. The changes in pore diameter and specific surface area of FSM-16 systems were investigated by small angle X-ray scattering and nitrogen gas adsorption. Powder X-ray diffractometry and thermal analysis revealed that FBP was adsorbed onto the mesopores of FSM-16(Do) and FSM-16(Doc), leading to an amorphous state, while no change was observed for FSM-16(Oc). Fourier-transformed IR spectroscopy showed a hydrogen bond interaction between the carbonyl groups of FBP and the silanol groups of FSM-16. The pore diameter and specific surface area of FSM-16 in solid dispersions decreased due to the adsorption of FBP. Improved dissolution of FBP from solid dispersions prepared by the evaporation and the sealed-heating methods was observed in comparison with FBP crystals.View full abstractDownload PDF (233K) -
Nian-Ping Feng, Bin Di, Wen-Ying Liu2005 Volume 53 Issue 8 Pages 978-983
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSShuang-Huang-Lian (SHL) is a traditional Chinese formula containing Flos lonicerae, Radix scutellariae (RS) and Fructus forsythiae, and is commonly used for treating acute upper respiratory tract infection, acute bronchitis and light pneumonia. The aim of the present study is to compare the metabolites of baicalin in rats when orally administered with SHL and Radix scutellariae, and try to explore the principle of SHL compatibility. By using LC-MSn and HPLC-DAD, the metabolites of baicalin were analyzed from bile, urine and feces of rats dosed with SHL and RS. Our results showed significant difference of baicalin metabolism between RS and SHL. However, baicalein was found to be the main metabolites of baicalin in intestinal tract after oral administration of RS and SHL, glucuronide, glucoside and methylated products were also found in rat urine after administration of either RS or SHL. Meanwhile, several sulphates were found in rat urine after RS administration, but not found after SHL. Among the metabolites of the SHL, potentially there existed a isomerized baicalin and methylated product: 5,7-dihydroxy-6-methoxyisoflavone-7-O-β-glucopyranuronoside, but without unidentified metabolite M3. Baicalein-6-O-β-glucopyranuronoside-7-O-β-glucopyranuronoside and baicalein-6-O-β-glucose-7-O-β-glucopyranuronoside were first reported by this study. The major metabolites of baicalin of RS and SHL in rat bile were the same, including baicalin-6-O-β-glucopyranuronoside-7-O-β-glucopyranuronoside, baicalin-6-β-glucopyranuronoside and 6-O-methyl-baicalin-7-O-β-glucopyranuronoside. Moreover, baicalein-6-O-β-glucose-7-O-β-glucopyranuronoside was also first found in rat bile by this study. Although baicalin-6-O-sulfate-7-O-β-glucopyranuronoside was found in rat bile after RS administration, no sulphated products were found after oral administration of SHL. These differences of baicalin metabolism between RS and SHL indicated that compatibility of medicines could result in the differences of metabolites.View full abstractDownload PDF (585K) -
Mai Thanh Thi Nguyen, Suresh Awale, Yasuhiro Tezuka, Quan Le Tran, Shi ...2005 Volume 53 Issue 8 Pages 984-988
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFrom the MeOH extract of Vietnamese Caesalpinia sappan, a novel biogenetically exclusive benzindenopyran, with a new carbon framework, neoprotosappanin (1), and a new compound, protosappanin A dimethyl acetal (3), were isolated together with protosappanin E-2 (2), neosappanone A (4), and 13 previously reported phenolic compounds (5—17). Their structures were elucidated on the basis of spectroscopic data. Compounds 1—4, 7, 13, and 15—17 showed significant xanthine oxidase inhibitory activity in a concentration-dependent manner, and sappanchalcone (17) showed the most potent activity with an IC50 value of 3.9 μM, comparable to that of positive control allopurinol (IC50, 2.5 μM). The kinetic study of these inhibitors indicated that they are competitive inhibitors, the same as allopurinol, except for 1 and 16 which are noncompetitive inhibitors.View full abstractDownload PDF (195K) -
Takayuki Yakura, Wataru Muramatsu, Jun'ichi Uenishi2005 Volume 53 Issue 8 Pages 989-994
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSCopper-catalyzed oxonium ylide formation–[2,3] shift of (5S,7R)-5-allyloxy-1-diazo-8-(p-methoxybenzyloxy)-7-methyl-2-octanone (3) proceeded in tetrahydrofuran-dichloromethane (4 : 1) under reflux with an excellent stereoselectivity (97 : 3) to give (2R,6S)-2-allyl-6-[(2R)-3-(p-methoxybenzyloxy)-2-methylpropyl]-3-dihydropyranone (2) as a major isomer in 82% yield. The resultant pyranone (2) was converted to the key intermediate (1) of the Mulzer's laulimalide synthesis and its derivatives (14, 15).View full abstractDownload PDF (192K) -
Okiko Miyata, Seiko Kajisa, Masafumi Ueda, Masashige Yamauchi, Takeaki ...2005 Volume 53 Issue 8 Pages 995-1002
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSRelationship between a radical species and radical acceptors of three different types of double bond in radical addition–cyclization was systematically investigated. Substrates carrying α,β-unsaturated amide, isolated olefin, and oxime ether moieties underwent radical addition–cyclization to give differently substituted lactams depending upon the radicals used. The sulfanyl radical addition–cyclization of the substrate proceeded smoothly to give the 5-membered lactam having an alkoxyamino group as a result of preferable addition of an intermediary α-carbonyl radical to the oxime ether. On the other hand, the triethylborane-mediated radical addition-cyclization gave the lactam bearing an iodomethyl group as a result of addition to an intermediary α-carbonyl radical to isolated olefin. The different regioselectivity was explained by the stability of the intermediary radical and the interaction between SOMO and HOMO.View full abstractDownload PDF (238K) -
Noriko Motohashi, Ayumi Takahashi, Chisako Yamagami, Yutaka Saito2005 Volume 53 Issue 8 Pages 1003-1005
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSAntioxidant activity of a series of hydroxybenzalacetones was determined against peroxynitrite-induced lipid peroxidation in red blood cell membrane and SOS response through DNA damage in bacterial cells. Hydroxybenzalacetone derivatives with hydroxy, methoxy, ethoxy or methyl substitution were analyzed and found to be more effective than the water-soluble vitamin E analogue Trolox. The inhibitory effect against lipid peroxidation correlated well to that against the SOS response, which is dependent on decomposition of peroxynitrite by hydroxybenzalacetones outside of the cell membrane. The antioxidant activity was shown to correlate well with the electric parameter σ+. Electron-donating substituents with more negative σ+ values increased the potencies. The result suggests that hydroxybenzalacetones with more electron-donating substituents will protect tissue more effectively against oxidative stress.View full abstractDownload PDF (118K) -
Masaki Mifune, Daiki Hino, Hikaru Sugita, Akimasa Iwado, Youji Kitamur ...2005 Volume 53 Issue 8 Pages 1006-1010
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSTo elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metal-tetrakis(sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of M-TSPPrs. Among six M-TSPPrs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.View full abstractDownload PDF (276K)
Notes
-
Muhammad Iqbal Choudhary, Syed Ghulam Musharraf, Zafar Ali Siddiqui, N ...2005 Volume 53 Issue 8 Pages 1011-1013
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe microbial transformation of an oral contraceptive, mestranol (1) by Cunninghamella elegans yielded two hydroxylated metabolites, 6β-hydroxymestranol (2) and 6β,12β-dihydroxymestranol (3). Metabolite 3 was found to be a new compound. These metabolites were structurally characterized on the basis of spectroscopic techniques.View full abstractDownload PDF (80K) -
Tomoko Fujimoto, Kohei Shirakami, Kakuji Tojo2005 Volume 53 Issue 8 Pages 1014-1016
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA new microdermabrasion system is used for peeling the stratum corneum in a controlled manner. The system uses inert corundum powders under various degrees of vacuum. The fine corundum powders ejected by suction power, being quickly in contact with the skin surface, abrade and remove a tiny fragment of stratum corneum. The fraction of the stratum corneum removed by microdermabrasion can be controlled by the operating conditions; the duration of application (L) and the degree of vacuum setting (V). The stratum corneum barrier function with respect to the rate of skin penetration is well correlated by the product of the square of the degree of the vacuum and the duration of the probe setting.View full abstractDownload PDF (173K) -
Yasuko Kamochi, Tadahiro Kudo, Toshinobu Masuda, Akira Takadate2005 Volume 53 Issue 8 Pages 1017-1020
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe reduction of α- and β-dicarbonyl compounds was investigated with samarium diiodide in the presence of additive. Diketones and ketocarboxylic acids were easily reduced at room temperature to give the mono-alcohols in good to excellent yield, and ketoester afforded the saturated ester as the major product in moderate yield. These reductions containing the reductive deoxygenation can be rapidly performed under the facile and mild conditions by this method.View full abstractDownload PDF (181K) -
Anand Swaroop, Arun Kumar Sinha, Raman Chawla, Rajesh Arora, Rakesh Ku ...2005 Volume 53 Issue 8 Pages 1021-1024
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESS1,3-Dicapryloyl-2-linoleoylglycerol (1), a novel triglyceride, was isolated from berries of Hippophae rhamnoides. The structure was elucidated on the basis of MS, 1D and 2D NMR experiments including HMQC and HMBC. The metal chelating, free radical scavenging, and lipid peroxidation inhibiting properties of the compound were also estimated with particular reference to radiation protection. In case of metal chelation and superoxide ion scavenging, 1 showed maximum inhibition at 50 μg/ml (11%) and 100 μg/ml (55%), respectively, whereas in lipid peroxidation, 1 showed maximum inhibition (57%) at 2 mg/ml as compared to quercetin as a control.View full abstractDownload PDF (362K) -
Kunikazu Moribe, Shun-ichiro Tsutsumi, Shoko Morishita, Hiroshi Shinoz ...2005 Volume 53 Issue 8 Pages 1025-1028
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSRapid expansion of supercritical solutions (RESS) technique was applied for the preparation of phenylbutazone fine particles. The operating temperature and pressure affected the yield of the drug fine particles, which was evaluated by dissolving the sprayed product of drug into ethanol. Effect of pre- and post-expansion conditions on the particle size distribution of phenylbutazone was investigated and the smallest sample (mean particle size: 1.59 μm) was obtained when the RESS method was operated at a pressure of 26 MPa combined with a temperature of 32 °C. Physicochemical properties of the fine particles were investigated by powder X-ray diffraction and differential scanning calorimetry. It was found that the phenylbutazone fine particles obtained were meta-stable β form under the experimental conditions tested, suggesting polymorphic transformation during the RESS process.View full abstractDownload PDF (235K) -
Koichi Metori, Yoshihisa Sei, Yumiko Kimura, Tomoyuki Ozawa, Kentaro Y ...2005 Volume 53 Issue 8 Pages 1029-1033
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSThe investigation of the host–guest complex formations between cyclophane (TGDMAP) (1) as a host and L-acidic amino acids such as L-glutamic acid (Glu) and L-aspartic acid (Asp) as guests was carried out using fast atom bombardment (FAB), electrospray ionization (ESI) and cold-spray ionization (CSI) mass spectrometry (MS). The stability constant (Ks) values obtained by the three different MS methods almost agreed. However, the complex ion peaks of a novel cyclophane (CPCn) (2) with Glu and Asp were not observed in FAB-MS. Then, these host–guest complex formations by use of CSI-MS and ESI-MS was examined, as the results, these complex ion peaks were observed clearly and the measurement values by the two MS methods are mostly in agreement. It was concluded that ESI-MS and CSI-MS are available for the determination of Ks value as well as FAB-MS.View full abstractDownload PDF (196K) -
Quan-Bin Han, Song-Fong Lee, Chun-Feng Qiao, Zhen-Dan He, Jing-Zheng S ...2005 Volume 53 Issue 8 Pages 1034-1036
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFrom the antibacterial fraction of the roots of Garcinia kola, 3″,4′,4′′′,5,5″,7,7″-heptahydroxy-3,8″-biflavanone (GB1) was isolated as the major constituent, whose interesting conformations were studied on the basis of its 1D and 2D NMR spectra obtained at different temperatures and in different solvents. GB1 showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) with MIC of 32 and 128 μg/ml, respectively.View full abstractDownload PDF (181K) -
Wataru Sakane, Noriyuki Hara, Yoshinori Fujimoto, Yoshihisa Takaishi, ...2005 Volume 53 Issue 8 Pages 1037-1039
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA new branched polyprenol, designated cupaniol, has been isolated from the methanol extract of the leaves of Cupania latifolia (Sapindaceae). The structure was determined to be (2E,6E,12E,16E)-3,7,13,17,21-pentamethyl-10-(1-methylethenyl)-2,6,12,16,20-docosapentaen-1-ol on the basis of spectral analysis and conversion to a known compound.View full abstractDownload PDF (132K) -
Takeshi Kinoshita, Nao Itaki, Maho Hikita, Yutaka Aoyagi, Yukio Hitots ...2005 Volume 53 Issue 8 Pages 1040-1042
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA new sesquiterpene lactone named coriarin was isolated from achenes (seeds) of Coriaria japonica (Coriariaceae) along with known constituents tutin, dihydrotutin and corianin, and its structure was deduced on a spectroscopic basis. The structure of coriarin was finally confirmed by the base-catalized chemical conversion of tutin into coriarin, in which the lactone ring linkage was transposed from C-3 to C-2. Chemical investigation of sarcocarps was also undertaken in parallel, but neither sesquiterpene lactones nor related constituents were obtained. The results indicate that sesquiterpene lactones occur only in achenes of C. japonica berry, as is the case in other Coriaria species.View full abstractDownload PDF (163K) -
Takahiro Kuramochi, Akio Kakefuda, Hiroyoshi Yamada, Takashi Ogiyama, ...2005 Volume 53 Issue 8 Pages 1043-1047
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSIn the setting of heart failure and myocardial ischemia-reperfusion, the sodium–calcium exchanger (NCX) can lead to calcium overload, which is responsible for contractile dysfunction and arrhythmia. NCX is an attractive target for treatment in heart failure and myocardial ischemia-reperfusion. We have designed and synthesized a series of benzyloxyphenyl derivatives based on compound 3. These derivatives have been evaluated for their inhibitory activity against both the reverse and forward modes of NCX. We have discovered a novel potent and selective reverse NCX inhibitor (12) with an IC50 value of 0.085 μM against reverse NCX.View full abstractDownload PDF (187K) -
Jin Hee Ahn, Sun Ho Jung, Jin Ah Kim, Seog Beom Song, Soon Ji Kwon, Kw ...2005 Volume 53 Issue 8 Pages 1048-1050
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSIn the continuation of efforts to modify the structure of our novel DP-IV inhibitors, a series of pyrazolidine derivatives with heteroaryl urea was synthesized and evaluated for their ability to inhibit dipeptidyl peptidase IV (DP-IV).View full abstractDownload PDF (135K) -
Jun Chang, Taichi Inui2005 Volume 53 Issue 8 Pages 1051-1053
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSFrom the water-soluble constituents of the whole herb of Pyrola rotundifolia (Pyrolaceae), one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4), were isolated. The structures were elucidated by spectroscopic analysis and confirmed with chemical degradation. In vitro tests for antimicrobial activity showed pyrolaside B (2) to possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Micrococcus luteus.View full abstractDownload PDF (84K) -
Lu-hua Zhao, Meng-hua Wu, Bing-ren Xiang2005 Volume 53 Issue 8 Pages 1054-1057
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSApplication of multivariate data analysis has become a popular method in the last decades, mainly because it can provide information not otherwise accessible. The information includes classification, searching similarities, finding relationships, finding physical significance to principal components, etc. Twenty-two Chinese medicinal herbs containing twelve constituents were collected and determined by HPLC. The results were studied by hierarchical cluster analysis (HCA) and principal components analysis (PCA). It was shown that the samples could be clustered reasonably into three groups, hence corresponding with the typical habitats of Psoralea corylifolia L.View full abstractDownload PDF (129K) -
Eiji Kawahara, Mikio Fujii, Keisuke Kato, Yoshiteru Ida, Hiroyuki Akit ...2005 Volume 53 Issue 8 Pages 1058-1061
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSDirect β-glucosidation between benzyl alcohol and D-glucose (5) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave a benzyl β-D-glucoside (1) in 53% yield. The coupling of the benzyl β-D-glucopyranoside congener (8) derived from 1 with phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (9), ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (13), and 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (15) afforded 10, 14, and 16, respectively, as coupled products. Deprotection of 10, 14, and 16 provided the synthetic benzyl β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (2), benzyl α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (3), and benzyl α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (4), respectively.View full abstractDownload PDF (153K) -
Yoshio Takeuchi, Hidehito Fujisawa, Tomoya Fujiwara, Mamoru Matsuura, ...2005 Volume 53 Issue 8 Pages 1062-1064
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSWe investigated the cyclooxygenase (COX) inhibitory and anticancer activities of 2-aryl-2-fluoropropionic acids 1a—e. These fluorinated compounds showed lower inhibitory activity toward COX-1 than the corresponding non-fluorinated compounds 2a—e with retained inhibitory activity against COX-2 resulting in modification of the balance of COX-1/COX-2 inhibitions, and they showed little anticancer activity. Interesting differences of the activities between (S)- and (R)-enantiomers were observed in some cases.View full abstractDownload PDF (85K) -
Qiong Wu, Da-Xu Fu, Ai-Jun Hou, Guang-Qing Lei, Zhi-Jun Liu, Jia-Kuan ...2005 Volume 53 Issue 8 Pages 1065-1067
Published: 2005
Released on J-STAGE: August 01, 2005
JOURNAL FREE ACCESSA new orcinol glucoside, orcinol-1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (3), was isolated from the rhizomes of Curculigo orchioides GAERTN., together with seven known compounds: orcinol glucoside (1), orcinol-1-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (2), curculigoside (4), curculigoside B (5), curculigoside C (6), 2,6-dimethoxyl benzoic acid (7), and syringic acid (8). The structures of these compounds were elucidated using spectroscopic methods. The antioxidant activities of these isolated compounds were evaluated by colorimetric methods based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. All the compounds showed potent antioxidative activities and the structure–activity relationship is discussed.View full abstractDownload PDF (91K)
- |<
- <
- 1
- >
- >|