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Volume 55, Issue 8
Displaying 1-34 of 34 articles from this issue
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Review
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Mitsuhiro Arisawa2007 Volume 55 Issue 8 Pages 1099-1118
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSWe have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki–Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). We also describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis, selective isomerization of terminal olefin, enamide metathesis and cycloisomerization and its application to the syntheis of 4 natural products, (−)-coniceine, (S)-pyrrolam A, angustureine, and fistulosin.View full abstractDownload PDF (1323K)
Regular Articles
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Liang Wang, Fu-De Cui, Hisakazu Sunada2007 Volume 55 Issue 8 Pages 1119-1125
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSSolid dispersions (SDs) of nitrendipine (NTD), a poorly water-soluble drug, were prepared with the Hypulcon pulse combustion dryer system, and the physicochemical properties of particles were investigated and compared with those of particles prepared with a spray dryer. The SD particles prepared with Hypulcon using Aerosil and Tween 80 as carriers showed improved properties over those prepared with a conventional spray dryer, such as smaller particle size, tighter particle size distribution, and no agglomeration. Powder X-ray diffraction and differential scanning calorimetry evaluation showed that the drug in the NTD–Aerosil SD prepared with 5% (v/v) Tween 80 solution was dispersed in an amorphous state. Fourier transformation IR spectroscopy indicated the presence of hydrogen bonds between NTD and Aerosil. Aerosil had greater ability to improve the dissolution of NTD than Sylysia and other polymers. The highest drug supersaturation concentration was maintained continuously during the dissolution test of the NTD–Aerosil SD prepared with 5% (v/v) Tween 80 solution using Hypulcon. The good hydrophilicity and dispersibility of Aerosil, solubilization of Tween 80, and actions of shock waves and ultrasonic waves might account for the amorphization of NTD and improved dissolution rate of SDs. Pulse combustion drying with low drying costs and high thermal efficiency is a promising method for the preparation of SD particles with improved properties without using organic solvent.View full abstractDownload PDF (762K) -
Mei-Hsiu Shih, Yu-Sheng Su, Cheng-Ling Wu2007 Volume 55 Issue 8 Pages 1126-1135
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThis work clarifies the structural characterization and antioxidant activity between aromatic and 3-arylsydnonyl substituted hydrazino-thiazoles by further synthesizing a series of aromatic ring-substituted hydrazino-thiazole derivatives 8a—h and 9a—h. Hydrazino-thiazole derivatives 8a—h and 9a—h were obtained by reacting aromatic or heterocyclic aromatic aldehyde thiosemicarbazones 7a—h with cyclization reagents ethyl 2-chloroacetoacetate (2a) and 2-bromoacetophenone (2b), respectively. The ORTEP drawings of compounds 8g, 8h and 9f provide strong evidence of the structure of aromatic thiazole derivatives 8a—h and 9a—h. Undoubtedly, the structure of compounds 3e—h and 4e—h synthesized by the reaction of 3-aryl-4-formylsydnone thiosemicarbazones 1e—h with cyclization reagents 2a and 2b in the previous work should have the thiazole moiety, and not the thiazoline moiety. Both the new thiazole derivatives 8a—h and 9a—h and the 3-arylsydnonyl-substituted derivatives 3e—h and 4e—h were investigated to determine their antioxidant activity by two tests that have been highly documented—the direct scavenging effect on a stable free 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and the inhibition of the 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical. Results of this study demonstrate that not only the thiazole ring and the aryl ring has the contribution to the antioxidant activities, the sydnone ring of 3-arylsydnonyl moiety also has its considerable contribution.View full abstractDownload PDF (943K) -
Ahmad Bani-Jaber, Imad Hamdan, Bashar Al-Khalidi2007 Volume 55 Issue 8 Pages 1136-1140
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSSodium salt formation of mefenamic acid (MA) was studied as a way to solve the formulation and dissolution problems of MA. For this purpose, sodium salt of mefenamic acid (Na-MA) was prepared by reacting MA powder with equimolar sodium hydroxide in an aqueous phase, and consequently, Na-MA solution was obtained. The resultant solution was lyophilized and Na-MA powder was collected. The salt formation was confirmed by the results of fourier transformation–infrared (FTIR) spectroscopy and differential scanning calorimetry (DSC) studies on Na-MA powder in comparison to MA powder. Na-MA powder was assessed for direct compressibility, in comparison to MA powder, when formulated as a mixture with minimum amount of Avicel® pH 101 and then compressed into tablets using a hydraulic tablet press. Na-MA tablets exhibited satisfactory hardness and friability, and did not show capping or lamination. On the other hand, some MA tablets showed capping or lamination upon compression and all the tested MA tablets for friability capped. Na-MA tablets were also studied for drug dissolution, in comparison to MA tablets, in water, a pH 7.4 phosphate buffer, and a pH 7.4 phosphate buffer after soaking in 0.1 m HCl. Under these different dissolution conditions, Na-MA tablets showed much higher dissolution rate and extent than MA tablets. The results of the study suggested that Na-MA can be considered as a solution form for the formulation and dissolution problems of MA.View full abstractDownload PDF (119K) -
Witold Musial2007 Volume 55 Issue 8 Pages 1141-1147
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSTopical treatment of acne rosacea, a chronic condition characterized by recurrent course for many years, is primarily based on metronidazole preparations. The aim of this study was to evaluate the effect of various acrylic acid polymers, in composition with methylcellulose on metronidazole release rate from hydrogels proposed for the treatment of acne rosacea. Viscosity and release studies using “Paddle over Disk” system with semipermeable membrane of MWCO 3500 were performed. Compositions of Carbopol 971P and methylcellulose revealed an increase in viscosity with increasing concentration of methylcellulose in the range of 17200—26166 mPa·s. In all the examined formulations, the release process was characterized by a two-stage course. Among bipolymeric formulations, the highest first-stage release rate of 9.18×10−3 min−1 was determined for the gel consisting of 2.00% Carbopol 980NF with 1.00% methylcellulose. The second-stage release rates ranged between 2.88×10−3 and 8.00×10−3 min−1. Two-stage release course can thus be attributed to metronidazole distribution into two compartments of hydrogel matrix. Proposed gels, with similar rheological properties, may be used for ex vivo and in vivo studies to obtain a suitable drug activity of metronidazole in the treatment of acne rosacea.View full abstractDownload PDF (575K) -
Wei-Wei Zhou, Wen-Han Lin, Shun-Xing Guo2007 Volume 55 Issue 8 Pages 1148-1150
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSIn the course of searching for marker components, two new polyporusterones were isolated from the sclerotia of Polyporus umbellatus, together with another three known analogs. The structures of the new ones were elucidated as (20S,22R,24R)-16,22-epoxy-3β,14α,23β,25-tetrahydroxyergost-7-en-6-one (1) and (23R,24R,25R)-23,26-epoxy-3β,14α,21α,22α-tetrahydroxyergost-7-en-6-one (2) by chemical and spectroscopic means, including HR-FAB-MS, 1D- and 2D-NMR.View full abstractDownload PDF (125K) -
Jong-Hyun Lee, Naoko Kiyota, Tsuyoshi Ikeda, Toshihiro Nohara2007 Volume 55 Issue 8 Pages 1151-1156
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSAcyclic diterpene glycosides, named capsianosides I′, II, III (1), C (2), D (3), E (4) and F (5), have been isolated from the dried hot red pepper fruits of Capsicum annuum L. used in Kimchi. The structures of these compounds have been revised in the sugar connectivities by 1D- and 2D-NMR spectroscopic and chemical methods.View full abstractDownload PDF (171K) -
María Magdalena Jiménez, María José Fresno ...2007 Volume 55 Issue 8 Pages 1157-1163
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe objective of this study is to provide a rheological characterization of binary hydroalcoholic gels made with Carbopol® UltrezTM 10 (U10) and Hyaluronic Acid (HA) as a function of polymer concentration: U10 (0.0—2.0% w/w) and HA (0.00—0.20% w/w), and to determine the influence of this combination on the thixotropic properties of the resulting binary systems. Interaction of the two polymers was measured using the Viscose Synergy Index (IS) and thixotropic analysis, which indicate the structural changes that take place in binary gels attributable to molecular interactions between the gelling agents. The maximum values for viscose synergy (IS=1.22—1.44) are obtained for the U10 : HA mixtures with a polymer proportion of 10 : 1. The behavior of the binary gels studied is the result of the formation of a more structured three-dimensional network between the U10 and HA molecules. Shearing of this polymer network requires application of a greater force than is needed to shear the structure of the separate gels. Inclusion of HA in a proportion of 1 : 10 has a fixing effect on the polymer network, resulting in greater resistance to shearing in the compound gel. The relative thixotropic area —AR— shows maximum values (AR=17.215%) for the same polymer composition. The evolution of the two parameters indicates that restructuring of the molecular interactions for this polymer proportion (10 : 1) takes place; the result is a reinforced three-dimensional structure in the gelled system, which increases the thixotropic properties. The same composition leads to a maximum of thixotropic properties as well as viscose synergy because both characteristics are closely related to structural changes observed in the binary systems of this composition. Thixotropic systems have a very wide area of application in the pharmaceutical industry. For this reason, the results obtained here considerably increase the use of the gels studied. In fact, incorporation of HA significantly improves a property of acrylic gels which has direct repercussions on the ease and efficiency of their application to the skin.View full abstractDownload PDF (135K) -
Chikako Takeda, Yuri Takahashi, Isamu Seto, Genji Kawano, Kozo Takayam ...2007 Volume 55 Issue 8 Pages 1164-1168
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSFor the treatment of chronic inflammation in the oral cavity, we attempted to develop bioadhesive tablets of bovine lactoferrin (B-LF). Pectin was used as a bioadhesive polymer, and the influence of the degree of esterification and the molecular weight of pectins on the characteristics of B-LF tablets were investigated. Concerning bioadhesive force, a tendency increasing the value according to increase of the esterification of the pectin was confirmed. Sustained release of B-LF from the tablets was observed as the esterification increased, and a possibility for prediction of the time required to release 50% of B-LF by using the equation given by the degree of esterification and the logarithm of the molecular weight was suggested. Pectin cross-linked with Ca2+ (Ca-PC) was also used for the preparation of the B-LF tablets. Prolonged release of B-LF from the tablets was observed as the Ca2+ in Ca-PC increased. Our findings suggest that pectin with a high degree of esterification is suitable as a bioadhesive polymer since high bioadhesive force and sustained release are shown. Furthermore, a possibility that the B-LF release could be controlled by adjusting the Ca2+ concentration in Ca-PC was suggested.View full abstractDownload PDF (292K) -
Tomohiro Hamashita, Yasuo Nakagawa, Takao Aketo, Satoru Watano2007 Volume 55 Issue 8 Pages 1169-1174
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSTo prepare powdered medicines without bitter taste, film coating is required to cover the surface of core particles. In this study, effect of formulation and operating conditions of agitation fluidized bed on the core particle properties was investigated. In order to prevent breakage of the core particles during coating process, which sometimes causes variation of drug dissolution rate, addition of maltose syrup powder during the formulation process of the core particles was investigated. Also, a method for friability test in which the core particles were subjected to strong impact was proposed to evaluate strength of the core particles. The friability of the core particles determined by this test method correlated well with the actual friability of the particles during the coating process. Based on this result, we confirmed this novel friability test method could predict the core particle endurance during the coating process.View full abstractDownload PDF (442K) -
Shuyun Bao, Yi Ding, Zhiwei Deng, Peter Proksch, Wenhan Lin2007 Volume 55 Issue 8 Pages 1175-1180
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSChemical investigation on the stem of a Chinese mangrove plant Bruguiera sexangula var. rhynchopetala (Rhizophoraceae) resulted in the isolation and characterization of four new phenolic glycosides rhyncosides A—D (1—4), and two new lignan derivatives namely rhyncosides E—F (5—6), along with twelve known phenolic constituents. Their structures were determined by extensive spectroscopic data analyses.View full abstractDownload PDF (132K) -
Sheng-Gao Chen, Jian-Jun Chen, Kun Gao2007 Volume 55 Issue 8 Pages 1181-1184
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSFour new prenylisoflavone derivatives, namely, 5-hydroxy-4′-methoxy-8-prenyl-2″-hydroxyisopropyldihydrofurano[4,5:6,7]-isoflavone (1), 5-hydroxy-4′-methoxy-6-prenyl-2′′′-hydroxyisopropyldihydrofurano[4,5:8,7]-isoflavone (2), 5-hydroxy-4′-methoxy-8-prenyl-1″,2″-peroxyl-3″,3″-dimethyldihydropyrano[5,6:6,7]-isoflavone (3), and 5-hydroxy-4′-methoxy-6-prenyl-1′′′,2′′′-peroxyl-3′′′,3′′′-dimethyldihydropyrano[5,6:8,7]-isoflavone (4), together with three known ones 5—7, were isolated from the roots of Hedysarum scoparium. Their structures were established by means of detailed spectroscopic analysis (IR, EI- or HR-ESI-MS as well as 1D- and 2D-NMR), and by comparison of their spectroscopic data with those reported for structurally related compounds.View full abstractDownload PDF (117K) -
Kiyofumi Ninomiya, Toshio Morikawa, Yi Zhang, Seikou Nakamura, Hisashi ...2007 Volume 55 Issue 8 Pages 1185-1191
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A4, A5, A6, H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F1 (IC50=47 μM), (3S,5R,6S,9R)-megastigmane-3,9-diol (61 μM), and myrsinionosides A (52 μM) and D (62 μM) were found to show the strong hepatoprotective activity.View full abstractDownload PDF (219K) -
Jing Qin, DaWei Chen, HaiYang Hu, Qiao Cui, MingXi Qiao, BaoYu Chen2007 Volume 55 Issue 8 Pages 1192-1197
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSIn the present study, RGD peptide was coupled with ferulic acid (FA) liposomes for binding to monocytes and neutrophils in peripheral blood for brain targeting in response to leukocyte recruitment. Cholesterol (Ch) was esterified with succinic anhydride to introduce a carboxylic end group (Ch-COOH). Soybean phosphatidylcholine, cholesterol and Ch-COOH were in a molar ratio of 1 : 0.23 : 0.05. FA was loaded into liposomes with 80.2±5.2% entrapment efficiency (EE) using a calcium acetate gradient method since it was difficult to load FA by other methods. RGD peptide was a novel compound coupled with Ch-COOH via carbodiimide and N-hydroxysulfosuccinimide. The results of the in vitro flow cytometric study showed that RGD conjugation liposomes (RGD-liposomes) could bind to monocytes/neutrophils efficiently. The rats were subjected to intrastriatal microinjections of 100 μl of human recombinant IL-1β to produce brain inflammation and subsequently sacrificed after 15, 30, 60 and 120 min of administration of three formulations (FA solution, FA liposome, RGD-coated FA liposome). The body distribution results showed that RGD-liposomes could be directed to the target site, i.e. the brain, by cell selectivity in case of an inflammatory response. For RGD coated liposomes, the concentration of FA in brain was 6-fold higher than that of FA solution and 3-fold higher than that of uncoated liposomes. MTT assay and flow cytometry were used in the pharmacodynamic studies where it was found that FA liposomes exhibited greater antioxidant activity to FA solution on U937 cell.View full abstractDownload PDF (644K) -
Saied Saeed Hosseiny Davarani, Mojtaba Shamsipur, Davood Nematollahi, ...2007 Volume 55 Issue 8 Pages 1198-1202
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSElectrochemical oxidation of catechols (1a—c) has been studied in the presence of 2-hydroxy-1,4-naphtoquinone (3b) in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicated that the electrochemically generated o-benzoquinones (2a—c) participate in Michael addition reaction with 3b to the corresponding benzofuranoquinones (8a—c, 10a—c). The electrochemical synthesis of these compounds has been successfully preformed at a carbon rod electrode with good yields using an environmentally friendly method.View full abstractDownload PDF (307K) -
Ryuichi Narazaki, Ritesh Sanghvi, Samuel H. Yalkowsky2007 Volume 55 Issue 8 Pages 1203-1206
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThis manuscript is a study of precipitation of insoluble drug upon dilution from the pH–cosolvent solubilized formulation with simulated blood fluid. An equation is developed to estimate drug precipitation upon dilution of combined pH–cosolvent solubilized formulations. This is an extension of a previous equation used for the estimation of drug precipitation from simple pH controlled formulations. The proposed equation considers the effect of the cosolvent and its concentration on the pKa of the drug as well as all buffering species. According to the proposed equation and our experimental data, the addition of cosolvent on the pH solubilized formulation could increase total drug solubility in the formulation. However, the solubility after dilution became lower than the 0% ethanol formulation because of the change in both drug and buffer pKa values. Since this equation is based on the equilibrium condition, it is the worst case scenario for precipitation. This equation provides useful information regarding the feasibility of the successful use of pH–cosolvent combinations in drug formulation.View full abstractDownload PDF (136K) -
Kayoko Tahara, Yuka Yano, Kiyotada Kanagawa, Yoshihiro Abe, Junko Yama ...2007 Volume 55 Issue 8 Pages 1207-1212
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSA simple, rapid and efficient system utilizing a coulometric electrode was developed for the preparation of drug metabolites. Trace amounts of reactants are usually generated in electrochemical reactions, which are not suitable for the sufficient preparation of products to obtain NMR and other spectral data for chemical structure confirmation or to obtain data from pharmacological activity screening tests of products. In the developed system, called the “in-flow electrochemical reaction system,” a drug, troglitazone, was dissolved in a volatile flow solvent, and pumped into a coulometric electrode under optimized conditions, and the effluent was evaporated. Without any further purification, milligram amounts of a pure oxidation product of troglitazone could be obtained within several hours. The amount obtained was enough for 1H- and 13C-NMR analysis by which the structure could be confirmed and was found to be identical to one of the metabolites of troglitazone detected in human plasma. This system will be useful to prepare standard compounds of the required amount for pharmacokinetic study and for toxicokinetic study.View full abstractDownload PDF (443K) -
Shintaro Tobiishi, Toru Sasada, Yumiko Nojiri, Fumihiko Yamamoto, Taka ...2007 Volume 55 Issue 8 Pages 1213-1217
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSMethoxy and fluorine analogs substituted on the terminal carbon of the pentyl chain of N-(piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-pentylphenyl)-1H-pyrazole-3-carboxamide (O-1302) were synthesized in a multi-step process from 5-phenyl-1-pentanol, which was based on the 1,5-diarylpyrazole core template of N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) through condensation of the respective amine with pyrazole carboxylic acid, in order to develop tracers for medical imaging. Their potency for inhibiting the binding of the CB1 antagonist [3H]SR141716 was evaluated with the aim of developing positron emission tomography (PET) ligands for the cerebral cannabinoid CB1 receptor. These analogs bearing a piperidinyl carboxamide at the C3 of the pyrazole ring exhibited affinities comparable to those of the CB1 reference antagonist SR141716, which warrants further investigation using the radiolabeled form for biological imaging studies. A morpholine ring substituted at the C3 of the pyrazole ring resulted in a reduction of the CB1 affinity.View full abstractDownload PDF (120K) -
Sheng-Jun Dai, Gong-Fu Wang, Meng Chen, Ke Liu, Li Shen2007 Volume 55 Issue 8 Pages 1218-1221
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSFive new neo-clerodane diterpenoid alkaloids, named scutebarbatine G (1), 6,7-di-O-nicotinoylscutebarbatine G (2), 6-O-nicotinoyl-7-O-acetylscutebarbatine G (3), scutebarbatine H (4) and 7-O-nicotinoylscutebarbatine H (5) were isolated from the whole plant of Scutellaria barbata D. DON. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR analyses. In vitro, compounds 1—5 showed significant cytotoxic activities against three human cancer lines, namely, HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells, and gave IC50 values in the range 3.4—8.5 μM.View full abstractDownload PDF (129K) -
Yuki Nakajima, Yuzo Sato, Tetsuya Konishi2007 Volume 55 Issue 8 Pages 1222-1226
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSInonotus obliquus (persoon) Pilat (Chaga, in Russia, kabanoanatake in Japan) is a fungus having been used as a folk medicine in Russia and said to have many health beneficial functions such as immune modulating and anti-cancer activities. In the present study, the antioxidant activity of hot water extract (decoction) of Chaga was precisely compared with those of other medicinal fungi (Agaricus blazei Mycelia, Ganoderma lucidum and Phellinus linteus) showing Chaga had the strongest antioxidant activity among fungi examined in terms of both superoxide and hydroxyl radicals scavenging activities. Further determination of the antioxidant potential of isolated fruiting body (brown part) and Sclerotium (black part) revealed the 80% MeOH extract of fruiting body had the highest potential as high as that of Chaga decoction. Finally, seven antioxidant components were isolated and purified from the 80% MeOH extract of Chaga fruiting body, and their chemical structures were determined as small phenolics as follows: 4-hydroxy-3,5-dimethoxy benzoic acid 2-hydroxy-1-hydroxymethyl ethyl ester (BAEE), protocatechic acid (PCA), caffeic acid (CA), 3,4-dihybenzaladehyde (DB), 2,5-dihydroxyterephtalic acid (DTA), syringic acid (SA) and 3,4-dihydroxybenzalacetone (DBL). Notably, BAEE was assigned as the new compound firstly identified from the natural source in the present study.View full abstractDownload PDF (334K) -
Yukio Aso, Sumie Yoshioka, Tamaki Miyazaki, Tohru Kawanishi, Kazuyuki ...2007 Volume 55 Issue 8 Pages 1227-1231
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe miscibility of a drug with excipients in solid dispersions is considered to be one of the most important factors for preparation of stable amorphous solid dispersions. The purpose of the present study was to elucidate the feasibility of 1H-NMR spin–lattice relaxation measurements to assess the miscibility of a drug with excipients. Solid dispersions of nifedipine with the hydrophilic polymers poly(vinylpyrrolidone) (PVP), hydroxypropylmethylcellulose (HPMC) and α,β-poly(N-5-hydroxypentyl)-L-aspartamide (PHPA) with various weight ratios were prepared by spray drying, and the spin–lattice relaxation decay of the solid dispersions in a laboratory frame (T1 decay) and in a rotating frame (T1ρ decay) were measured. T1ρ decay of nifedipine–PVP solid dispersions (3 : 7, 5 : 5 and 7 : 3) was describable with a mono-exponential equation, whereas T1ρ decay of nifedipine–PHPA solid dispersions (3 : 7, 4 : 6 and 5 : 5) was describable with a bi-exponential equation. Because a mono-exponential T1ρ decay indicates that the domain sizes of nifedipine and polymer in solid dispersion are less than several nm, it is speculated that nifedipine is miscible with PVP but not miscible with PHPA. All the nifedipine–PVP solid dispersions studied showed a single glass transition temperature (Tg), whereas two glass transitions were observed for the nifedipine–PHPA solid dispersion (3 : 7), thus supporting the above speculation. For nifedipine–HPMC solid dispersions (3 : 7 and 5 : 5), the miscibility of nifedipine and HPMC could not be determined by DSC measurements due to the lack of obviously evident Tg. In contrast, 1H-NMR spin–lattice relaxation measurements showed that nifedipine and HPMC are miscible, since T1ρ decay of the solid dispersions (3 : 7, 5 : 5 and 7 : 3) was describable with a mono-exponential equation. These results indicate that 1H-NMR spin–lattice relaxation measurements are useful for assessing the miscibility of a drug and an excipient in solid dispersions.View full abstractDownload PDF (484K) -
Dai Nozawa, Taketoshi Okubo, Shigeyuki Chaki, Shigeru Okuyama, Atsuro ...2007 Volume 55 Issue 8 Pages 1232-1239
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSIn the present study, conducted to explore potent and small molecular melanocortin-4 (MC4) receptor ligands, we found that tripeptide 3a, containing a D-Phe-Arg-2-Nal (Nal; naphthylalanine) sequence, exhibited a moderate affinity for the MC4 receptor. Structural optimization led to the identification of a compound with a high affinity for the MC4 receptor, namely, tripeptide 3e, which showed a 70-fold higher affinity for the MC4 receptor than the lead compound 3a. Moreover, in an effort to further reduce the peptidic characters of tripeptide 3e, we found that dipeptide 3g exhibited a relatively high affinity for the MC4 receptor. Furthermore, in these analogues, the substituted position (1′ vs. 2′) of the naphthyl ring of Nal residue at position 7 was found to be important for the differentiation of agonist and antagonist activity. The synthesis and structure–activity relationships of the arginine analogues as MC4 receptor ligands were described in this paper.View full abstractDownload PDF (185K) -
Minpei Kuroda, Akihito Yokosuka, Ryosuke Kobayashi, Maki Jitsuno, Hiro ...2007 Volume 55 Issue 8 Pages 1240-1244
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSCytotoxicity-guided fractionation of the 80% EtOH extract of Tithonia diversifolia has resulted in the isolation of twelve sesquiterpenoids (1—12), including three new ones (4, 10, 12), and three known flavonoids (13—15). The structures of the new compounds were determined by analysis of their spectroscopic data. The isolated compounds showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 0.13 to 13.0 μM, when etoposide used as a positive control gave an IC50 value of 0.43 μM. The cancer growth inhibitory property of 9, the main cytotoxic compound in T. diversifolia, was examined using a disease-oriented panel composed of 39 human cancer cell lines in the Japanese Foundation for Cancer Research.View full abstractDownload PDF (181K) -
Shinya Harusawa, Makoto Kawamura, Lisa Araki, Ryusuke Taniguchi, Hirok ...2007 Volume 55 Issue 8 Pages 1245-1253
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe (2R,5S)-trans- and (2S,5S)-cis-stereoisomers 1a and 1b of 4(5)-(5-aminotetrahydropyran-2-yl)imidazole, which have two chiral centers and adopt a stable chair conformation, were synthesized via cyclization of diol intermediates 7 using L-glutamine as the starting material. Their enantiomers, (2S,5R)-trans-1c and (2R,5R)-cis-1d, were synthesized by the same methodology from D-glutamine. Stereo isomers 1a—d were converted into cyanoguanidines 11a—d, and into N-isopropyl and N-3,3-dimethylbutyl derivatives 12a—d and 13a—d, respectively. The results of in vivo brain microdialysis of the derivatives apparently indicated that only (2S,5R)-isomers increased the release of neuronal histamine. Among the many (2S,5R)-N-alkyl derivatives, 13c (OUP-133) and 18 (OUP-153) increased histamine release to 180—190% and 180—200% of basal levels, respectively, and were found to be novel histamine H3 antagonists.View full abstractDownload PDF (689K)
Notes
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Varala Ravi, Enugala Ramu, Kotra Vijay, Adapa Srinivas Rao2007 Volume 55 Issue 8 Pages 1254-1257
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSZn-proline (5 mol%) performs as a novel water-soluble and recyclable Lewis acid catalyst for the selective synthesis of 1,2-disubstituted benzimidazoles from wide range of substituted o-phenylenediamines and aldehydes in moderate to excellent isolated yields (42—92%) using water as solvent at ambient temperature.View full abstractDownload PDF (125K) -
Hong-Gang Xie, Hong Chen, Bo Cao, Hong-Wu Zhang, Zhong-Mei Zou2007 Volume 55 Issue 8 Pages 1258-1260
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSA new germacranolide, inulacappolide (1), was isolated from the EtOH extract of the whole plant of Inula cappa along with 16 known compounds. The structure of inulacappolide was a rare 1(10)-saturated type of germacran-6,12-olide, identified as 2α-acetoxy-3β-hydroxy-9β-angeloyloxygermacra-4-en-6α,12-olide by spectral analysis (IR, HR-ESI/MS, 1H-NMR, 13C-NMR, HMQC, HMBC, NOESY). In vitro, it showed antiproliferative effects against human cervical cancer HeLa, human leukemia K562 and human nasopharyngeal carcinoma KB cell lines with IC50 values of 1.2 μM, 3.8 μM and 5.3 μM, respectively.View full abstractDownload PDF (122K) -
Xiangrong Zhang, Yanjiao Wang, Jing Wang, Yan Wang, Sanming Li2007 Volume 55 Issue 8 Pages 1261-1263
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe casted films of aqueous dispersions of Eudragit® NE30 D and Eudragit® L30 D-55 containing pore former were prepared. The study investigated the influence of pore former on basic model drug clarithromycin release, water uptake and water vapor permeability from casted film prepared from the blends of neutral polymer dispersion of Eudragit® NE30 D and enteric polymer dispersion of Eudragit® L30 D-55. This study was concluded that pore former hydroxypropyl methyl cellulose, lactose, polyethylene glycol (PEG) and polyvinyl pyrrolidon (PVP) was released at the beginning of the release process, the rate and extent of water uptake of the polymeric films were much higher in phosphate buffer pH 6.8 than in pH 5.0 and the concentration of pore former have a significant influence on the permeability to water vapour.View full abstractDownload PDF (85K) -
Fathi Abdelmohsen Abdelhalim Behery, Zain Elabdin Metwally Naeem, Gala ...2007 Volume 55 Issue 8 Pages 1264-1266
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSThe novel natural product juncutol (1), 1,4,7-trimethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene-2,6-diol, along with the three related metabolites juncusol (2), dehydrojuncusol (3), and 6-hydroxymethyl-1-methyl-5-vinyl-9,10-dihydrophenanthrene-2-ol (4), were isolated from the rhizomes of Juncus acutus L. (Juncaceae) growing in Egypt. The structural identity of 1 was determined on the basis of spectroscopic analyses, including 2D NMR spectroscopy. The inhibitory effect of these natural products on the expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide-stimulated RAW264.7 macrophage cells was determined for the first time. The unprecedented symmetrical compound juncutol (1) was found to be the most potent inhibitor against the induction of the proinflammatory iNOS protein.View full abstractDownload PDF (149K) -
Lin Zhang, Zhuang Yang, Jing-Kui Tian2007 Volume 55 Issue 8 Pages 1267-1269
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSTwo new indolopyridoquinazoline alkaloidal glycosides, 11-O-β-D-glucopyranosyl rutaecarpine (ternatoside C) and 11-O-α-L-rhamnosyl-(1→6)-β-D-glucopyranosyl rutaecarpine (ternatoside D) were isolated from the roots of Ranunculus ternatus. Their structures were determined on the basis of spectroscopic and chemical methods.View full abstractDownload PDF (77K) -
Ah-Reum Han, Jong-Bin Kim, Jun Lee, Joo-Won Nam, Ik-Soo Lee, Chang-Koo ...2007 Volume 55 Issue 8 Pages 1270-1273
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSA new flavanone glycoside, (2R)-5-hydroxy-4′-methoxyflavanone-7-O-{β-glucopyranosyl-(1→2)-β-glucopyranoside} (1), was isolated from the EtOAc extract of dried immature fruit of Poncirus trifoliata, together with three known compounds, (2S)-poncirin (2), (2S)-naringin (3), and (2S)-poncirenin (4). The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. Among the isolates, compound 2 exhibited considerable inhibitory activity against lipopolysaccharide (LPS)-induced prostaglandin E2 (PGE2) and interleukin-6 (IL-6) production, and mRNA expression in RAW 264.7 murine macrophage cells.View full abstractDownload PDF (198K) -
Biswanath Das, Nikhil Chowdhury, Kongara Damodar, Joydeep Banerjee2007 Volume 55 Issue 8 Pages 1274-1276
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSA facile stereoselective synthesis of (Z)- and (E)-allyl sulfides has been accomplished from Morita–Baylis–Hillman acetates in one-pot by treatment with benzene thiol in the presence of catalytic amounts of 15% aqueous NaOH and TBAI in DMSO at room temperature. The method has been applied for the synthesis of (Z)-3-(4-methoxybenzylidene)thiochroman-4-one, a potent antifungal compound.View full abstractDownload PDF (120K) -
Tripetch Kanchanapoom, Hideaki Otsuka, Somsak Ruchirawat2007 Volume 55 Issue 8 Pages 1277-1280
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSA new megastigmane diglucoside, (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3,9-O-β-D-diglucopyranoside (3), was isolated from the aerial portion of Equisetum debile along with macarangioside D (debiloside A), sammangaoside A, (6R,9S)-3-oxo-α-ionol 9-O-β-D-glucopyranoside, debiloside B, kaempferol 3-O-sophoroside, kaempferol 3,7-O-β-D-diglucopyranoside, kaempferol 3-O-sophoroside-7-O-β-D-glucopyranoside, phenylethyl O-β-D-glucopyranoside, (Z)-3-hexenyl O-β-D-glucopyranoside, (7S,8R)-dehydrodiconiferyl 4-O-β-D-glucopyranoside, and L-tryptophan. The absolute configuration at C-6 of the original structure of debilo-side A was revised to 6R-configuration, and was identical with macarangioside D (1). From the aerial portion of E. diffusum, four compounds, sammangaoside A, kaempferol 3-O-sophoroside and L-tryptophan and (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-β-D-glucopyranoside were identified. The spectroscopic data of (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-β-D-glucopyranoside (13) were found to be identical with corchoionoside A (9R-isomeric compound). The structure of corchoionoside A was also discussed. Structure determinations were based on physical data and spectroscopic evidence.View full abstractDownload PDF (79K) -
Chun Lei, Sheng-Xiong Huang, Ji-Jun Chen, Jian-Xin Pu, Li-Bin Yang, Yo ...2007 Volume 55 Issue 8 Pages 1281-1283
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSTwo new dibenzocyclooctadiene lignans angeloyl-(+)-gomisin K3 (1) and methylisogomisin O (2), together with six known ones, isogomisin O, angeloylisogomisin O, gomisin O, angeloygomisin O, benzoylgomisin O, epigomisin O, and four 1,4-bis(phenyl)-2,3-dimethylbutane type lignans, pregomisin, meso-dihydroguaiaretic acid, isoanwulignan, and sphenanlignan were isolated from the aerial parts of Schisandra propinqua var. propinqua. The structures of 1 and 2 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques.View full abstractDownload PDF (109K)
Communicatins to the Editor
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Takayuki Yakura, Seiichi Sato, Yuya Yoshimoto2007 Volume 55 Issue 8 Pages 1284-1286
Published: August 01, 2007
Released on J-STAGE: August 01, 2007
JOURNAL FREE ACCESSEnantioselective total synthesis of anhydrophytosphingosine pachastrissamine (jaspin B) was achieved using Sharpless asymmetric dihydroxylation and dirhodium(II)-catalyzed C–H amination as key steps.View full abstractDownload PDF (117K)
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