Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
51 巻, 8 号
選択された号の論文の26件中1~26を表示しています
Regular Articles
  • Katsumasa Aoki, Yoshinobu Ishikawa, Miyuki Oyama, Yoshikazu Tomisugi, ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 899-903
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    A series of tentacle porphyrins having four aminoalkyl groups at the periphery was synthesized, and the DNA binding properties were investigated by absorption and circular dichroism (CD) spectroscopic methods. The aminopropyl chain was found to facilitate binding, and bisignate induced CD spectra revealed that the porphyrins are self-stacked on the DNA surface. The photonuclease activity of the tentacle porphyrins was also studied, and the aminopropylporphyrin showed the highest activity. The activity increased in proportion to the porphyrin load, but higher loads resulted in the decrease of activity. This inhibitory step corresponded to aggregation of the porphyrin. Thus, the aggregation was suggested to shield the inner porphyrin from the solvent, the production of active oxygen species being suppressed.
  • Yorinobu Yonezawa, Sumio Ishida, Hisakazu Sunada
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 904-908
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    To obtain basic and clear release properties, wax matrix tablets were prepared from a physical mixture of drug and wax powder at a fixed mixing ratio. Properties of release from the single flat-faced surface, curved side surface, and/or whole surface of the wax matrix tablet were examined. Then tortuosity and the applicability of Higuchi's square-root time law equation were examined. The Higuchi equation well analyzed the release processes of different release manners. However, the region fitted to the Higuchi equation differed with the release manner. Tortuosity obtained with release from the single flat-faced surface and curved side surface was comparable with that obtained with the release from a reservoir device tablet, whereas tortuosity obtained with release from the whole surface was larger. As the wax matrix tablets were prepared at a fixed mixing ratio, their internal structures should be similar. Therefore changes in the matrix volume or volume fraction with release were examined, and an extra volume where dissolved drug stray becomes large with release time in the case of release from the whole surface. These factors should be taken into account for evaluation of applicability and release properties. Furthermore, the entire release process should be analyzed using a combination of the square-root time law and other suitable equations in accordance with release manner or condition.
  • Kinzo Watanabe, Miyuki Sekine, Kazuo Iguchi
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 909-913
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Three marine prostanoids, 1, 2, and 3, were isolated from the extract of the Okinawan soft coral Clavularia viridis. The structures of these compounds were assigned based on the results of spectroscopic analysis. Compound 1 was shown to be preclavulone-A methyl ester, and this is the first isolation of the ester of preclavulone-A as a natural product. Preclavulone-A is proposed to be the key intermediate in the biosynthesis of marine prostanoids exemplified by clavulones in C. viridis. The new prostanoid 3 was suggested to be a biosynthetic intermediate from preclavulone-A to clavulones, and a possible biogenetic pathway via 3 is proposed.
  • Laura Ribeiro, Thorsteinn Loftsson, Domingos Ferreira, Francisco Veiga
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 914-922
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    The purpose of this study was to investigate the interactions between vinpocetine (VP), sulfobutyl ether beta-cyclodextrin (SBEβCD) and the water-soluble polymers polyvinylpyrrolidone (PVP) and hydroxypropyl methylcellulose (HPMC). The water-soluble polymers were shown to improve the complexation efficiency of SBEβCD, and thus less SBEβCD was needed to prepare solid VP–SBEβCD complexes in the presence of the polymers. The interactions between VP and SBEβCD, with or without PVP or HPMC, were thoroughly investigated in aqueous solutions using the phase-solubility method as well as in the solid state. The amount of VP solubilized in water or aqueous polymer solution increased linearly with increasing SBEβCD concentration, demonstrating AL-type plots. We estimated the apparent stability constant (Kc) at room temperature of VP–SBEβCD binary complex to be 340 M−1 and this value increased to 490 M−1 or 390 M−1, respectively, with the addition of PVP and HPMC, assuming a 1 : 1 VP–SBEβCD molar ratio. Improvement in the Kc values for ternary complexes clearly confirmed the benefit of the addition of water-soluble polymers to promote higher complexation efficiency. Solid VP–SBEβCD binary and ternary systems were prepared by physical mixing, kneading, coevaporation, and lyophilization methods and fully characterized by scanning electron microscopy, differential scanning calorimetry, and X-ray diffractometry. The results obtained suggest that coevaporation and lyophilization methods yield a higher degree of amorphous entities and indicated formation of VP–SBEβCD binary and ternary complexes.
  • Hiroyuki Nojima, Mayuko Takeda-Shitaka, Youji Kurihara, Kenshu Kamiya, ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 923-928
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Class II major histocompatibility complex (MHC) has tolerance for binding longer antigen peptides than those bound by class I MHC. In this paper, a normal mode analysis on HLA-DR1 class II MHC involving an antigen peptide indicated that the peptide-binding groove had some different dynamic characteristics from that of HLA-A2 class I MHC. The dynamic changes in the class I groove with removal of the bound peptide were limited primarily to the central region and the C-terminal side (corresponding to the C-terminal side of the bound peptide) of the groove, while the dynamic changes in the class II groove with removal of the bound peptide extended to the whole of the groove, and were especially remarkable around a strand located in the N-terminal side (corresponding to the N-terminal side of the bound peptide) of the groove. These results suggest that the N-terminal side of the class II groove is more flexible than the same side of the class I groove, and this flexibility may allow some N-terminal residues of the bound peptide to extend outside the class II groove. Definite anti-correlative motions with removal of the bound peptide appeared between two α-helical regions of class II MHC as in the case of class I MHC. These motions of the class II groove may play an important role in obtaining “a flexible dynamic fit” against diverse longer peptides both of whose terminals extend outside the groove.
  • María Luisa Jimeno, Ibon Alkorta, Carolina Cano, Nadine Jagerov ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 929-934
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    The oxalate salts and free bases of fentanyl and N-[1-(2-phenylethyl)-4-piperidyl]-N-(1-phenyl-4-pyrazolyl)propanamide, a new lead compound for long-acting analgesia, have been characterized by 1H- and 13C-NMR spectroscopy. The crystal structure of the hydrochloride of N-[1-(2-phenylethyl)-4-piperidyl]-N-(1-phenyl-4-pyrazolyl)propanamide monohydrate has been determined. Two centrosymmetrically related cations, joined through C(phenyl)-H…π contacts, encapsulate a large void that contains pairs of anions and bridged water molecules into a zero-dimensional (0D) supramolecular motif. The cations are linked to this framework via N+H…Cl contacts. GIAO/B3LYP calculations have been carried out to compare the experimental 13C chemical shifts with the absolute shieldings thus calculated. The protonation of both molecules takes place on the piperidine ring (axial protonation), as has been verified both in the solid state (X-ray) and in solution (NMR).
  • Li-Yan Wang, Nai-Li Wang, Xin-Sheng Yao, Syohei Miyata, Susumu Kitanak ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 935-941
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Four new ingenane-type diterpenes, 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-O-acetylingenol (1), 3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoyl-20-deoxyingenol (2), 3-O-(2E,4Z-decadienoyl)-20-deoxyingenol (3), and 3-O-(2E,4E-decadienoyl)-20-deoxyingenol (4), two new jatrophane-type diterpenes, kansuinins D (9) and E (10), and four known ingenane-type diterpenes were isolated from the root of Euphorbia kansui. Their structures were elucidated by spectroscopic and chemical analysis, and individual Xenopus cells at the blastular stage were cultured with the diterpenes to test for biological activity. 20-Deoxyingenol diterpenes 3 and 4 induced the greatest cell cleavage arrest (0.5 μg/ml of each compound resulted in >75% cleavage arrest), but cell cleavage inhibitory activity became weak when C-16 had an acyl residue. In contrast, the jatrophane diterpene kansuinin D (9) showed no activity.
  • Toshihiro Shimizu, Yoshinori Nakano, Shuji Morimoto, Tetsuro Tabata, N ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 942-947
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Lansoprazole fast-disintegrating tablet (LFDT) is a new patient-friendly formulation of lansoprazole. Since lansoprazole is an antiulcer agent and is unstable under acidic conditions, we have developed LFDT as an orally disintegrating tablet containing enteric-coated microgranules. The effect of compression on dissolution behavior was investigated, as compression affected cleavage and crushing of the enteric layer. To decrease cleavage and crushing of the enteric layer, the effects of the combined ratio of methacrylic acid copolymer dispersion to ethyl acrylate–methyl methacrylate copolymer dispersion and the concentration of triethyl citrate on the dissolution in the acid stage and the dissolution in the buffer stage were evaluated. By adjusting the ratio of methacrylic acid copolymer dispersion to ethyl acrylate–methyl methacrylate copolymer dispersion to 9 : 1 and adding a 20% triethyl citrate concentration, sufficient flexibility of the enteric layer and sufficient stability against compression forces were achieved. Agglomeration of enteric-coated microgranules during the coating process was decreased at the optimized concentration of triethyl citrate and glyceryl monostearate. We compared the absorption properties of LFDT and lansoprazole capsules in dogs. The absorption profiles of LFDT were similar to those of lansoprazole capsules.
  • Tian-Shung Wu, Dau-Min Lin, Li-Shian Shi, Amooru Gangaiah Damu, Ping-C ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 948-950
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    From the stems of Rubia wallichiana DECNE, thirty-four structurally related compounds were isolated and identified. Three of them, namely rubiawallin-A (1), -B (2), and -C (3), constitute the first report of their occurrence from the natural source. Their structures were determined by comprehensive analyses of their 1D and 2D NMR, and electron impact (EI) mass spectral data. Furthermore, an in vitro screening of cytotoxicity of the isolated compounds was also evaluated. Among the testing compounds, 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone (4) demonstrated most effective cytotoxicity towards Hepa-3B and Colo-205 cells.
  • Takashi Itoh, Kazuhiro Nagata, Masashi Yokoya, Michiko Miyazaki, Keiko ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 951-955
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine (9) in good yields and high stereoselectivity. The corresponding chiral allyl derivative of isoquinoline was transformed to a pyrrolidinoisoquinoline (16) in a highly enantioselective manner.
  • Makiko Nishida, Hitoshi Yoshimitsu, Masafumi Okawa, Toshihiro Nohara
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 956-959
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Four new cycloartane glycosides, named aquilegiosides G—J, were isolated from the dried aerial parts of Aquilegia vulgaris. Their structures were determined by spectroscopic analysis and chemical evidence.
  • Yoshihiro Mimaki, Minpei Kuroda, Akihito Yokosuka, Hiroshi Harada, Mas ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 960-965
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    To characterize the stems of Akebia trifoliata chemically, a detailed phytochemical examination was carried out on A. trifoliata stems, with particular attention to the triterpene and triterpene saponin constituents, and resulted in the isolation of three new triterpenes (1—3) and three new triterpene saponins (11—13), together with seven known triterpenes (4—10) and 12 known triterpene saponins (14—25). The structures of the new compounds were determined on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic data, and the results of hydrolysis. Four saponins (22—25), which were obtained in good yields and were not isolated from Akebia quinata stems, are concluded to be applicable as marker compounds in chemically distinguishing between A. trifoliata and A. quinata by conventional TLC examination. To the best our knowledge, the current work is the first chemical investigation of A. trifoliata.
  • Tsuyoshi Satoh, Tatsuya Sakamoto, Masanori Watanabe, Koji Takano
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 8 号 p. 966-970
    発行日: 2003年
    公開日: 2003/08/01
    ジャーナル フリー
    Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from ketones and chloromethyl p-tolyl sulfoxide, with ethylmagnesium chloride or isopropylmagnesium chloride at below −78 °C gave magnesium alkylidene carbenoids in about 90% yields. The reaction of the generated carbenoids with lithium α-sulfonyl carbanions was found to afford tri- and tetra-substituted allenes. Both cyclic ketones and acyclic ketones were useful in this procedure. However, the 1-chlorovinyl p-tolyl sulfoxides derived from aldehydes gave only rearranged products, acetylenes, under the reaction conditions. The magnesium alkylidene carbenoid derived from an optically active 1-chlorovinyl p-tolyl sulfoxide was treated with lithium α-carbanion of 1-naphthyl phenyl sulfone; however, the obtained allene was found to be racemic. The mechanism of this reaction is also discussed.
Notes
feedback
Top