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Volume 58, Issue 3
Displaying 1-33 of 33 articles from this issue
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Review
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Narihiro Toda, Tsugio Kaneko, Hiroshi KogenArticle type: Review
2010 Volume 58 Issue 3 Pages 273-287
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTo date, acetylcholinesterase (AChE) inhibitors have been clinically effective drugs for the palliative treatment of Alzheimer's disease, but their clinical efficacy is limited, mainly due to their adverse effects on peripheral organs. Since patients of Alzheimer's disease often exhibit depression as well as memory impairment, dual inhibitors of AChE and serotonin transporter (SERT) would be a better therapeutic method. Anti-depressive effects based on SERT inhibition would reduce the dose-related side effects of AChE inhibitors. Such dual inhibitors were designed by the hybridization of rivastigmine and fluoxetine based on a hypothetical model of the AChE active site. Various derivatives were synthesized and evaluated for their in vitro inhibition, and then (S)-5j (RS-1259), which possessed balanced inhibitory activities of AChE (IC50=101 nM) and SERT (IC50=42 nM), was successfully obtained. An ex vivo experiment in mice indicated that (S)-5j (RS-1259) simultaneously inhibited AChE and SERT in the brain following an oral administration. The simultaneous elevation of extracellular levels of acetylcholine and serotonin in the rat hippocampus was actually confirmed by microdialysis.View full abstractDownload PDF (3672K)
Regular Articles
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Myung Joo Kang, Jung Min Park, Woo Sik Choi, Jonghwi Lee, Byung Kook K ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 288-292
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe aim of this study was to fabricate deformable chitosan (CS) microspheres for arterial embolization. CS microspheres containing poly(ethylene glycol) (PEG) were prepared by ionotropic gelation; PEG was then removed from the CS microspheres to produce the highly porous structure to allow deformability. The porosity was controlled by blending ratios of CS/PEG polymers (CS/PEG=from 100/0 to 15/85) and the effect of porosity on microcatheter delivery was examined. The size range of porous microspheres was 500—600 μm with sphericity between 1.012—1.041. Scanning electron microscope observation confirmed that microporous networks were effectively obtained by PEG extraction proportional to the initial amount of PEG. Water retention capacities, indicative of internal porosities of microspheres, increased with increasing initial amounts of blended PEG. CS microspheres with water retention values of greater than 28% exhibited noticeable deformation and smooth passage through the microcatheter tip. Novel deformable microspheres are, therefore, expected to be clinically applicable for arterial embolization.View full abstractDownload PDF (2228K) -
Balasubramaniam Jagadish, Rajesh Yelchuri, Bindu K, Hemalatha Tangi, S ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 293-300
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe present study investigated the effect of co-grinding raloxifene HCL (RHCL) with different superdisintegrants, namely crospovidone (CP), croscarmellose sodium (CCS) and sodium starch glycolate (SSG), using a ball mill, in order to determine the potential effect on dissolution rate and bioavailability of raloxifene hydrochloride (RHCL). The dissolution studies of the co-ground compositions and the corresponding physical mixtures were carried out in U.S. Pharmacopeia (USP) Type II apparatus. The solid state interactions of the co-ground and the physical mixtures were evaluated by differential scanning calorimetry (DSC) and X-ray diffraction (XRD). The pharmacokinetics of co-ground mixture (1 : 5 RHCL : CP) and milled RHCL was evaluated following oral administration (25 mg/kg) in healthy female Sprague-Dawley rats. DSC studies showed that the crystalline nature of RHCL was reduced after co-grinding with superdisintegrants, while co-grinding with CP resulted in significant particle-size reduction of the mixture. Significant enhancement in dissolution rate was observed with co-ground mixture of RHCL with CP (1 : 5). The extent of the mean plasma exposures of RHCL was 7-fold higher in animals treated with co-ground mixture of RHCL, CP (1 : 5) compared to animals treated with milled RHCL. Co-grinding of RHCL with CP, reduced drug crystallinity, increased the rate and extent of dissolution, and improved bioavailability.View full abstractDownload PDF (1122K) -
Syed Umar Farooq Rizvi, Hamid Latif Siddiqui, Masood Parvez, Matloob A ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 301-306
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThirty eight heterocyclic chalcones were synthesized by condensing formylquinolines with diverse methyl arylketones. The target compounds were characterized by spectroscopic techniques (NMR, IR, MS) and elemental analysis. The X-ray crystallographic study of (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one (1p) was also performed for the structure confirmation. The title compounds were screened for anti-microbial and antileishmanial activities. The compounds 1c—e, 1g, 1j—m, 1p, 1r—s, 2g, 2j—p, and 2r—s were found potentially active antileishmanial agents, while 1f—i, 1l, 1o—p, 2f—i, 2l, and 2o—p showed remarkable antibacterial activity. Only compounds 1g and 2g—h exhibited significant antifungal activity.View full abstractDownload PDF (288K) -
Sanjay Singh, Rajeev Soni, Manoj Kumar Rawat, Achint Jain, Shripad Bhe ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 307-311
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe aim of present study was to prepare and evaluate buccal bioadhesive films of salbutamol sulphate (SS) for the treatment of asthma. The films were designed to release the drug for a prolonged period of time so as to reduce the frequency of administration of the available conventional dosage forms of SS. The different proportions of sodium carboxymethylcellulose (SCMC) and Carbopol 940P (CP 940P) were used for the preparation of films. Carbopol was used to incorporate the desired bioadhesiveness in the films. The films were prepared by solvent casting method and evaluated for bioadhesion, in vitro drug release and anti asthmatic effect (bronchoprotection) in histamine induced bronchospasm of guinea pigs. In vitro drug release from the film was determined using a modified Franz diffusion cell while bioadhesiveness was evaluated with a modified two-arm balance using guinea pig buccal mucosa as a model tissue. Films containing SCMC : CP 940P ratio of 76 : 24 was found to be the best with moderate swelling along with favorable bioadhesion force and in vitro drug release. The drug release mechanism was found to follow non-Fickian diffusion as release mechanism. The prolonged in vivo effect (bronchoprotection) obtained from the buccal bioadhesive film of SS administered via buccal route may improve the treatment of asthmatic disorders by reducing the frequency of administration which is associated with the tolerance effect of SS. Additionally for the clinical benefit, it is also expected to reduce the major adverse effects of SS such as tachycardia and arrhythmias via buccal absorption.View full abstractDownload PDF (118K) -
Hiroshi Watanabe, Yasuko Obata, Yoshinori Onuki, Kenya Ishida, Kozo Ta ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 312-317
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe microstructure formed by intercellular lipids in the stratum corneum is important for the barrier function of the skin. However, the correlation between lipid composition and microstructure has not yet been clarified. To elucidate the microstructure of intercellular lipids in the stratum corneum, an intercellular lipid model was prepared from ceramide 5 (CER5), cholesterol (CHOL), and palmitic acid (PA), considering the nonuniformity of the lipid components of the stratum corneum. A response surface method incorporating thin-plate spline interpolation (RSM-S) was employed to prepare the CER5/CHOL/PA lipid bilayers. Fluorescence anisotropy of the CER5/CHOL/PA bilayers showed four distinct clusters based on Kohonen's self-organizing maps (SOM). At the centroid formulation of those clusters, the microstructures of CER5/CHOL/PA bilayers were determined using synchrotron X-ray scattering. Three kinds of lamellar structures and two kinds of lateral packing—namely, hexagonal and orthorhombic—were formed. The microstructure of the CER5/CHOL/PA bilayers was likely to be intrinsic to the intercellular lipids in the stratum corneum. In conclusion, the CER5/CHOL/PA bilayers prepared based on RSM-S and SOM were useful as models of the intercellular lipids in the stratum corneum.View full abstractDownload PDF (1049K) -
Sartaj Tabassum, Irshad-ul-Haq BhatArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 318-325
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe D-glucose-bis pyrazolyl complexes of Cu(II) 1 and Ni(II) 2 were synthesized and characterized by elemental analysis, molar conductance measurements and spectroscopic methods. The solution structures of the complex have been assessed to square pyramidal using electronic absorption and electronic paramagnetic resonance (EPR) spectroscopy. The interaction of 1 and 2 with calf thymus DNA (CT DNA) has been carried out by absorption, emission, viscometric and electrochemical methods. The intrinsic binding constant Kb was determined as 13.4×105 M−1, 4.5×105 M−1 for 1 and 2, respectively suggestive of strong binding of complexes with DNA. Furthermore, higher value of Kb for 1 implies that this complex interacts more strongly with CT DNA in comparison to 2. The quenching constant “K” of 1 and 2 obtained from emission spectral methods was 1.33, 0.55, respectively. Complex 1 hydrolytically cleaved pBR322 supercoiled DNA in absence of an activating agent. The enhanced cleavage of pBR322 DNA was observed in presence of ascorbic acid as a reducing agent, 1 also displays efficient photonuclease activity through double strand DNA breaks when irradiated at 365 nm through mechanistic pathway involving hydroxyl radicals. In addition to the above binding studies, an in vitro binding study of complex 1 with protein human serum albumin (HSA), tyrptophan and mixtures of HSA, L-tryptophan with CT DNA was carried out. The in vitro “binding study” also supports that 1 shows higher binding affinity towards CT DNA.View full abstractDownload PDF (992K) -
Li-Qiu Zhang, Li-Ping Guan, Cheng-Xi Wei, Xian-Qing Deng, Zhe-Shan Qua ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 326-331
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSA series of 7-alkoxy-2H-1,4-benzothiazin-3(4H)-ones and a new series of 7-alkoxy-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazine derivatives were synthesized using 5-methoxybenzo[d]thiazol-2-amine as starting material. The structures of the compounds were elucidated by IR, 1H-NMR spectroscopic data and microanalyses. The anticonvulsant activity of these compounds was evaluated by maximal electroshock (MES) test and rotarod test following intraperitoneal injection in KunMing mice. Among the synthesized compounds 3a—v, 7-(hexyloxy)-2H-benzo[b][1,4]thiazin-3(4H)-one (3f) could be considered potentially the most useful and safe therapeutic compound. Among the synthesized compounds 4a—u, compound 7-(2-fluorobenzyloxy)-4H-[1,2,4]triazolo[4,3-d]benzo[b][1,4]thiazine (4k) was the most active compound with an ED50 of 17.0 mg/kg, TD50 of 243.9 mg/kg and protective index (PI) of 14.3. Its neurotoxicity was lower than all the other synthesized compounds and also markedly lower than that of the reference drug carbamazepine.View full abstractDownload PDF (228K) -
Hongli Zhao, Xianjiang Meng, Huihui Yuan, Minbo LanArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 332-335
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSA series of spin-labeled melphalan and chlorambucil derivatives, coupling the alkylating agents with 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) radicals, were synthesized, characterized, and their biological properties in vitro were evaluated. These compounds showed much higher cytotoxic activity against human leukemia cell line K562 in vitro than their parent compounds.View full abstractDownload PDF (187K) -
Yohei Ishida, Osamu Shirota, Setsuko Sekita, Keita Someya, Fumihiko To ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 336-343
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSHyperici erecti herba (Hypericum erectum THUNB.) showed a suppressive effect on generation of isovaleric acid by Corynebacterium xerosis. An ethyl acetate (AcOEt) soluble fraction of methanol extract of H. erectum showed the activity. The AcOEt fraction was separated by various successive choromatographical methods to give seven new compounds 1—7 along with some known compounds. The structures of the new compounds were elucidated to be polyprenylated benzoylphloroglucinol derivatives by means of HR-MS and NMR spectra including 2D-NMR. Some of these compounds had novel cage structures having benzoyltricyclo[3,3,1,13,7]decane and benzoyltricyclo[4,3,1,13,8]undecane skeletons arising from a polyprenylated phloroglucinol precursor by a transannular cyclization reaction. The isolated compounds were tested for suppressive activity, but they showed only weak activity.View full abstractDownload PDF (612K) -
Rika Okihara, Kuniko Mitamura, Maki Hasegawa, Megumi Mori, Akina Muto, ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 344-353
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSHere, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5α- and 5β-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of Δ4-3-ketosteroids with 10% Pd(OH)2/C to yield 3-oxo-5β-steroids and reductive allomerization with 10% Pd/C to yield 3-oxo-5α-isomers; (3) reduction of the resulting 3-oxo-5β- and 3-oxo-5α-steroids to the corresponding 3α-hydroxy-compounds with Zn(BH4)2 and K-Selectride®, respectively; and (4) sulfation of hydroxy groups at C-3 and/or C-21 in the tetrahydrocorticosteroid derivatives with sulfur trioxide-triethylamine complex.View full abstractDownload PDF (894K) -
Yousuke Kashima, Takashi Kitade, Yuuko Kashima, Yoshito OkabayashiArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 354-358
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSAn automated synthesis system using a solid-phase extraction (SPE) system and column packed with octadecylsilica (ODS), which was coated with phospholipid and loaded with dog liver microsomes, was developed for synthesis of glucuronides. Preparation of the microsome-immobilized SPE column, glucuronidation of drugs to synthesize the glucuronides and elution of the products were performed by an automated synthesis system. The phospholipid-coated SPE column and then the microsome-immobilized SPE column were readily prepared by allowing a solution containing L-α-dipalmitoylphosphatidylcholine to flow through the SPE column, and then by recycling a buffer solution containing dog liver microsomes through the resulting phospholipid-coated SPE column. The microsome-immobilized SPE column exhibiting the uridine diphosphate (UDP)-glucuronosyltransferase activity catalyzed the glucuronidation of mefenamic acid and estradiol to the corresponding glucuronides in the presence of UDP-glucuronic acid, and three glucuronides of mefenamic acid and estradiol were synthesized using the automated synthesis system, by simply recycling a buffer solution containing UDP-glucuronic acid through the microsome-immobilized SPE column loaded with the substrate. We used β-cyclodextrin as a solubilizing agent for the synthesis of the glucuronides of estradiol that is practically insoluble in aqueous solutions. The productivity of these glucuronides using the microsome-immobilized SPE column was higher than that using the free microsomes (batch method). Furthermore, we developed a fully automated synthesis-isolation system by coupling the automated synthesis system to an automated preparative HPLC system. The automated synthesis system as well as the fully automated synthesis-isolation system should be very useful for synthesizing glucuronides for drug development.View full abstractDownload PDF (286K) -
Megumi Fujita, Satoshi Himi, Motokazu IwataArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 359-362
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSSX-3228, 6-benzyl-3-(5-methoxy-1,3,4-oxadiazol-2-yl)-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one, is a newly-synthesized benzodiazepine receptor agonist intended to be developed as a tablet preparation. This compound, however, becomes chemically unstable due to decreased crystallinity when it undergoes mechanical treatments such as grinding and compression. A wet-granule tableting method, where wet granules are compressed before being dried, was therefore investigated as it has the advantage of producing tablets of sufficient hardness at quite low compression pressures. The results of the stability testing showed that the drug substance was chemically considerably more stable in wet-granule compression tablets compared to conventional tablets. Furthermore, the drug substance was found to be relatively chemically stable in wet-granule compression tablets even when high compression pressure was used and the effect of this pressure was small. After investigating the reason for this excellent stability, it became evident that near-isotropic pressure was exerted on the crystals of the drug substance because almost all the empty spaces in the tablets were occupied with water during the wet-granule compression process. Decreases in crystallinity of the drug substance were thus small, making the drug substance chemically stable in the wet-granule compression tablets. We believe that this novel approach could be useful for many other compounds that are destabilized by mechanical treatments.View full abstractDownload PDF (196K) -
Kensuke Okuda, Masahiko Yoshida, Takashi Hirota, Kenji SasakiArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 363-368
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSAn improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinoline has been achieved using a slight modification of reaction conditions for the Truce–Smiles rearrangement. Acid treatment of the obtained 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines gave unexpected ring-opened spiro ring compounds. The previously unreported parent compound, furo[2,3-c]isoquinoline, was also synthesized.View full abstractDownload PDF (399K) -
Kensuke Okuda, Ying-Xue Zhang, Hiromi Ohtomo, Takashi Hirota, Kenji Sa ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 369-374
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe reactions of N-(5,6,7,8-tetrahydroquinazolin-4-yl)amidines and their amide oximes with hydroxylamine hydrochloride gave abnormal cyclization products via a ring cleavage of pyrimidine component accompanied with a ring closure of 1,2,4-oxadiazole to give N-[2-([1,2,4]oxadiazol-5-yl)cyclohexen-1-yl]formamide oximes. Similarly, N-(quinazolin-4-yl)amidines reacted with hydroxylamine hydrochloride gave the same results. The evaluation of inhibitory activities against platelet aggregation in vitro is also described to show one derivative has potent activity.View full abstractDownload PDF (249K) -
Gyanendra Kumar Sharma, Devender PathakArticle type: Regular Article
2010 Volume 58 Issue 3 Pages 375-380
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSSolvent free microwave assisted synthesis of some novel substituted imidazoles of biological interest is reported. First, primary aromatic or heteryl amine was condensed with aryl or heteryl aldehydes to afford corresponding Schiff's base. The Schiff's base further on treatment with ammonium acetate (NH4OAC) and isatin using silica gel as the solid support, yielded the corresponding aryl imidazoles. In this paper a comparative study between the developed microwave method and conventional method is described. The synthesized compounds were analyzed by physical and analytical data. The synthesized compounds were evaluated for their antibacterial, anthelmintic, short-term anticancer and antitubercular activity. All the synthesized substituted imidazoles have shown good antibacterial activity against gram negative bacterial strains Klebsiella pneumoniae and Escherichia coli and moderate to good anthelmintic activity. The synthesized imidazole derivative possessed significant cytotoxic activity against Ehrlich's ascites carcinoma (EAC) cell lines. None of the compounds exhibited prominent antitubercular activity.View full abstractDownload PDF (249K) -
Shi-Yie Cheng, En-Hung Lin, Jing-Shi Huang, Zhi-Hong Wen, Chang-Yih Du ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 381-385
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSChemical investigations of the Formosan soft coral Lemnalia flava have obtained a new ylangene-type sesquiterpenoid, (1S,2S,4R,6S,7R,8S)-4α-formyloxy-β-ylangene (1), along with two known sesquiterpenoids, lemnalol (2) and isolemnalol (3). Three new nardosinane-type sesquiterpenoids, designated as paralemnolins J—L (4—6), and five known sesquiterpenoids (7—11), were isolated from the other soft coral Paralemnalia thyrsoides. The structures of metabolites 1 and 4—6 were elucidated through extensive spectroscopic analysis and chemical methods. Moreover, the anti-inflammatory activity of metabolites 1—7 and 11 was evaluated in vitro.View full abstractDownload PDF (336K) -
Nawong Boonnak, Chatchanok Karalai, Suchada Chantrapromma, Chanita Pon ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 386-389
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTwo new xanthones, namely pruniflorone K (1) and L (2), have been isolated from the roots of Cratoxylum formosum ssp. pruniflorum, along with thirteen known xanthones (3—15). Their structures were mainly established using the spectroscopic methods. Only isolated compounds with sufficient amount were evaluated for antibacterial and antifungal activities.View full abstractDownload PDF (207K) -
Guo-cai Wang, Ying Wang, Xiao-qi Zhang, Yao-lan Li, Xin-sheng Yao, Wen ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 390-393
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSSix new Securinega alkaloids (1, 3, 5, 7, 9, 10) together with four known ones were isolated from the twigs and leaves of Flueggea leucopyra. The structures of new compounds were established on the basis of the spectroscopic methods including UV, IR, HR-electrospray ionization (ESI)-MS, 1D and 2D NMR, and the absolute configurations of these new alkaloids were assigned by the modified Mosher's method and the circular dichroism (CD) spectra.View full abstractDownload PDF (339K) -
Toshihiro Murata, Mai Watahiki, Yu Tanaka, Toshio Miyase, Fumihiko Yos ...Article type: Regular Article
2010 Volume 58 Issue 3 Pages 394-397
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTakuran is a traditional herbal medicine that is produced from the herbal plant Lycopus lucidas TURCZ. (Lamiaceae). Takuran is used as a treatment for diseases in women. From Takuran, four new phenylpropanoids along with 18 known compounds were isolated, and their structures were elucidated by spectroscopic analyses. Five phenylpropanoids isolated from the plant showed hyaluronidase inhibitory activity comparable to that of rosmarinic acid.View full abstractDownload PDF (294K)
Notes
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Shuji Kitagawa, Kana Inoue, Reiko Teraoka, Shin-ya MoritaArticle type: Notes
2010 Volume 58 Issue 3 Pages 398-401
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTo improve the efficiency of the intradermal delivery of genistein and other two isoflavones (daidzein and biochanin A), we tried to clarify the usefulness of microemulsion by in vitro study on excised guinea pig dorsal skin and Yucatan micropig skin. Using microemulsion consisting of isopropyl myristate (IPM), 150 mM NaCl solution, Tween 80 and ethanol as a vehicle, the solubility of all the isoflavones markedly increased and significant amounts of isoflavones were delivered to the skin. The effect of water-in-oil (w/o)-type microemulsion D was larger than that of oil-in-water (o/w)-type microemulsion A. Among three isoflavones tested, the increase of genistein was most marked on both solubility and skin accumulation. Genistein retained in the skin significantly inhibited lipid peroxidation in vitro dose-dependently. Furthermore, pretreatment of guinea pig dorsal skin with genistein containing gel-like microemulsion D prevented UV irradiation-induced erythema formation. These findings indicate the potential use of w/o-type microemulsion for the delivery of genistein to protect skin against UV-induced oxidative damage.View full abstractDownload PDF (2176K) -
Fan Yang, Hong-Jun Zhang, Yuan-Yuan Zhang, Wan-Sheng Chen, Hai-Long Yu ...Article type: Notes
2010 Volume 58 Issue 3 Pages 402-404
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSA new dihydrobenzofuran neolignan, herpepropenal, was isolated from the seeds of Herpetospermum caudigerum. Its chemical structure was established based on spectroscopic analysis. In this work, the inhibitory effects of herpepropenal on hepatitis B virus DNA and on the replication and expression of hepatitis B surface antigen and hepatitis B e antigen were also evaluated. The new compound exhibited inhibitory effects against hepatitis B virus.View full abstractDownload PDF (198K) -
Makoto Hashimoto, Keitaro Furukawa, Takenori Tomohiro, Yasumaru Hatana ...Article type: Notes
2010 Volume 58 Issue 3 Pages 405-407
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSSynthesis of diazirinyl organo-platinum complexes, which specifically interact with purine base, characterization of photoreactivity and interaction between guanosine 5′-monophosphate (GMP) were examined. The results indicated that the diazirinyl organo-platinum complex was useful for manipulations of photoaffinity labeled components.View full abstractDownload PDF (298K) -
Chiy-Rong Chen, Yun-Wen Liao, Hui-Ting Wu, Wen-Ling Shih, Chih-Ying Tz ...Article type: Notes
2010 Volume 58 Issue 3 Pages 408-411
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTwo new fernane triterpenoids, 7α-hydroxyfern-8-en-11-one (1) and 11β-hydroxyfern-8-en-7-one (2), and two new filicane triterpenoids, 3β-hydroxyfilic-4(23)-ene (3) and filicenol (5), together with one known filicane-type triterpenoid, 3α-hydroxyfilic-4(23)-ene (4), were isolated from the methyl alcohol extract of the leaves of Angiopteris palmiformis. Their structures were elucidated on the basis of extensive analyses of their spectroscopic data (NMR, MS, IR) and comparison with spectroscopic data in the literature.View full abstractDownload PDF (267K) -
Qing Chen, Jian-Guang Luo, Ling-Yi KongArticle type: Notes
2010 Volume 58 Issue 3 Pages 412-414
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSTwo new triterpenoid saponins (1, 2) were isolated from the roots of Gypsophila altissima L. (Caryophyllaceae), together with a known compound (3). The structures of new saponins were established as quillaic acid 3-O-β-D-xylopyranosyl-(1→3)-β-D-glucuronopyranoside (1), and 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-(6-O-acetyl)-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside (2), on the basis of various spectroscopic analyses (including heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), nuclear Overhauser effect spectroscopy (NOESY), total correlation spectroscopy (TOCSY), and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS)) and chemical degradations.View full abstractDownload PDF (187K) -
Tadahiro Yahagi, Yumiko Yamashita, Akihiro Daikonnya, Jin-bin Wu, Susu ...Article type: Notes
2010 Volume 58 Issue 3 Pages 415-417
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThree new feruloyl tyramine glycosides, N-cis-feruloyl tyramine-4‴-O-β-D-glucopyranoside (1), N-trans-ferloyl tyramine-4‴-O-β-D-glucopyranoside (2), and N-trans-feruloyl tyramine-4′-O-β-D-glucopyranoside (3), along with six known compounds, N-trans-feruloyl-3‴-methoxydopamine-4′-O-β-D-glucopyranoside (4), haitinosporine (5), tubocurine (6), fuzitine (7), (+)-lyoniresinol-3α-O-β-D-glucopyranoside (8), and (−)-lyoniresinol-2α-O-β-D-glucopyranoside (9), were isolated from the stem of Stephania hispidula YAMAMOTO. The structures were elucidated by spectroscopic and chemical analysis.View full abstractDownload PDF (172K) -
Takashi Okitsu, Daisuke Nakazawa, Kimie Nakagawa, Toshio Okano, Akimor ...Article type: Notes
2010 Volume 58 Issue 3 Pages 418-422
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSPalladium-catalyzed cross-coupling reactions of a 2-substituted 3-iodobenzo[b]furans and stannanyl ester afforded the stereoselective production of 9Z-retinoic acid ester analogs in good yields. These esters were then converted to the corresponding acids via basic hydrolysis in excellent yields, and their biological activities were evaluated. The analog changed the connected position of polyene side chain from 2-position to 3-position of benzo[b]furan decreased the biological activities dramatically, and the introduction of various substituents at 2-position afforded almost no effect on the activities.View full abstractDownload PDF (280K) -
Yousuke Kashima, Yoshito OkabayashiArticle type: Notes
2010 Volume 58 Issue 3 Pages 423-425
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSImmobilized enzyme reactors (IMERs) integrated into an LC-NMR system were developed for rapid and detailed structural identification of enzymatic reaction products. An on-column enzymatic reaction was achieved for immobilized cytochrome-c and dog microsomes. After the reaction, these products were analyzed by LC-NMR without any work-up processes. The immobilized cytochrome-c column integrated into LC-NMR was used to characterize the reaction product formed on N-demethylation by measurement of 1H-NMR. In the case of reaction taking place on the microsome column, a glucuronidation product was identified by 1H-NMR and 1H–1H correlated spectroscopy. The chemical structures of the enzymatic reaction products could be elucidated by IMER-LC-NMR without the need for authentic samples or isolation processes.View full abstractDownload PDF (208K) -
Hiromichi Fujioka, Kento Senami, Ozora Kubo, Kenzo Yahata, Yutaka Mina ...Article type: Notes
2010 Volume 58 Issue 3 Pages 426-428
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe facile deprotection of methylene acetal protection of diols under mild conditions is established. The combination of trimethylsilyl triflate (TMSOTf) and 2,2′-bipyridyl followed by a weakly acidic hydrolysis was effective and the substrates having acid sensitive functional groups can be tolerated under the stated conditions. The selective deprotection between methylene acetal and benzophenone ketal was achieved.View full abstractDownload PDF (482K) -
Yuka Shimoyama, Makiko Fujii, Yoshimi Kanda, Asako Mizoguchi, Hiroshi ...Article type: Notes
2010 Volume 58 Issue 3 Pages 429-431
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSWe investigated the skin penetration of liposomes under two different application conditions; occluded and large application amount (1 ml/cm2), and open and small application amount (10 μl/cm2). Liposomes containing fluorescence-labeled phospholipids or carboxyfluorescein (CF) were used. In application under occluded conditions, phospholipids showed no penetration, even in the stratum corneum (SC). CF penetration in the skin after application of liposome was no different that after application of CF solution. In contrast, phospholipids penetrated the skin, particularly the SC and hair follicles, under open conditions. CF in liposome showed enhanced penetration in the SC and epidermis, but not in the dermis. On observation of the drying process, CF recrystallized from solution, but this did not occur with CF incorporated into liposome. It is possible that crystallization of CF is prevented by encapsulation in liposome, or that penetration occurs more readily with liposome.View full abstractDownload PDF (4074K) -
Martin Werle, Abdallah Makhlof, Hirofumi TakeuchiArticle type: Notes
2010 Volume 58 Issue 3 Pages 432-434
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSWithin the current study, a delivery system based on a novel polymer-lectin conjugate (carbopol-lectin) was evaluated for the oral delivery of therapeutic peptides and proteins. It was demonstrated that covalent attachment of lectin to carbopol does neither decrease nor abolish the specific binding properties of lectin. Bioadhesion studies revealed that liposomes coated with carbopol lectin are more bioadhesive than liposomes coated with unmodified carbopol. Finally, the in vivo data suggest that carbopol-lectin conjugate coated liposomes are effective oral peptide delivery systems which are capable of increasing the pharmacological effect of orally administered calcitonin.View full abstractDownload PDF (3971K)
Communicatins to the Editor
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Kazuma Shioe, Yasuo Takeuchi, Takashi Harayama, Hitoshi AbeArticle type: Communications to the Editor
2010 Volume 58 Issue 3 Pages 435-437
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSAll-methylated isorugosin B was synthesized via two-step esterification between optically active valoneic acid and glucose derivatives.View full abstractDownload PDF (400K) -
Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio TakedaArticle type: Communications to the Editor
2010 Volume 58 Issue 3 Pages 438-441
Published: March 01, 2010
Released on J-STAGE: March 01, 2010
JOURNAL FREE ACCESSThe absolute stereochemistry of blumenol C glucoside and byzantionoside B was revised here as (6R,9S)- and (6R,9R)-9-hydroxymegastigman-4-en-3-one 9-O-β-D-glucopyranosides, respectively, by modified Mosher's method. The empirical rules of 13C-NMR chemical shift to determine the absolute stereochemistry of C-9 of 9-hydroxymegastigmane 9-O-β-D-glucopyranoside were also discussed.View full abstractDownload PDF (247K)
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