Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
55 巻, 1 号
選択された号の論文の33件中1~33を表示しています
Regular Articles
  • Mohammad Abdul-Azim Mohammad, Nagwan Hamdy Zawilla, Fawzy Mohammad El- ...
    2007 年 55 巻 1 号 p. 1-6
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Three stability indicating assay methods are developed for the determination of norfloxacin (Nor) in the presence of its decarboxylated degradation product and in mixture with tinidazole (Tnd). The proposed methods are reversed phase ion pair liquid chromatography (LC), thin layer densitometry (TLC) and second derivative ratio spectra zero crossing spectrophotometry (2DD). Chromatographic separation was achieved on μ-Bondapack C18 column 5 μm (300 mm×3.9 mm, I.D.) and precoated silica gel TLC stationary phases for LC and TLC methods, respectively. Mobile phases consisting of phosphate buffer pH 3.2 : methanol (3 : 1, v/v) containing 0.005 M pentane sulfonic acid sodium salt and isopropanol : butanol : concentrated ammonia : water (25 : 50 : 5 : 25, v/v/v/v) were used for resolution of Nor and Tnd by both techniques, respectively. Detection was carried at 280 nm. In the ratio spectra method, detection of Nor was carried at 282 nm. Linearity, accuracy and precision were found to be acceptable over concentration ranges of 20—225 μg/ml, 0.8—4 μg/spot and 1—7 μg/ml for Nor by LC, TLC and 2DD methods and over concentration ranges of 37.5—375 μg/ml and 4.8—20 μg/spot for Tnd by LC and TLC methods respectively. The suggested methods were successfully applied for the determination of both drugs in bulk powder, laboratory prepared mixtures and in commercial samples. Statistical comparison between the results obtained by the proposed and the reference methods was carried out using Student t-test, F ratio and one way ANOVA.
  • Shigeki Kobayashi, Hidetaka Wakamatsu, Nahomi Atuchi, Rie Miyajima, Ay ...
    2007 年 55 巻 1 号 p. 7-14
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Our aim in this study is to elucidate the correlations between inhibition and chirality, especially, diastereomer, against cell proliferation of double-stranded peptides. In previous studies, we reported on the design, synthesis, and chemical properties on a series of novel double-stranded peptides, (y-AA–x-AA)2–spacer(S) (AA=amino acid, S=spacer, symbols x and y represent L- or D-forms, and (y-, x-) as represent of the symbol) conjugated with –y-AA–x-AA– and –z-AA–y-AA–x-AA– sequences to a spacer of carbon number n. The inhibition of A431 and srctsNRK cells growth by four diastereomers of the N1,N12-bis(y-Phe–x-Phe)dodecanediamines (n=12) increased in the following order: (L-, L-)<(D-, D-)<(L-, D-)<(D-, L-). A similar trend was seen in the order for the activity of (y-AA–x-AA)2–spacer(S) with a spacer of carbon number n=2, 3, 4, 5, 6, and 12 against the cell growth inhibition. To understand the mechanism of diasteromer selective cell growth inhibition, the correlations between chirality and cell growth inhibition were investigated from the measurement of the changes in cytosolic Ca2+ concentration (=[Ca2+]c) of A431 cells. Although less active N1,N12-bis(L-Phe–L-Phe)dodecanediamine increases cytosolic [Ca2+]c, more active diasteromers, N1,N12-bis(L-Phe–D-Phe)dodecanediamine and N1,N12-bis(D-Phe–L-Phe)dodecanediamine, decrease cytosolic [Ca2+]c in A431 cell. This study provides diastereomeric effected new insights—this controls the polarity of double-stranded peptides—into the control of tumor cell proliferation and design of the uptake by penetration through the cell membrane of drugs.
  • Zhi-Gang Yang, He-Ran Li, Li-Yan Wang, Yong-Hai Li, Shun-Guang Lu, Xiu ...
    2007 年 55 巻 1 号 p. 15-18
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    In our investigation on the chemical constituents of Hippophae rhamnoides L., the chloroform-soluble fraction of the 80% acetone extract of branch bark was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide and recombinant mouse interferon-γ-activated murine macrophage-like cell line, RAW 264.7 cells. Two new triterpenoids, 2-O-trans-p-coumaroyl maslinic acid (1) and 2-O-caffeoyl maslinic acid (2), and three known triterpenoids, oleanolic acid (3), 3-O-trans-p-coumaroyl oleanolic acid (4), and 3-O-caffeoyl oleanolic acid (5), and 6-methoxy-2H-1-benzopyran (6) and β-sitosterol (7) were isolated from the branch bark extract. Their inhibitory activities on the production of NO in RAW 264.7 cells and radical-scavenging activities were examined.
  • Naonobu Tanaka, Yoshihisa Takaishi
    2007 年 55 巻 1 号 p. 19-21
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Six new xanthones, 4,6-dihydroxy-2,3-dimethoxyxanthone (1), 2,6-dihydroxy-3,4-dimethoxyxanthone (2), 6-hydroxy-2,3,4-trimethoxyxanthone (3), 3,6-dihydroxy-1,2-dimethoxyxanthone (4), 4,7-dihydroxy-2,3-dimethoxyxanthone (5), and 3,7-dihydroxy-2,4-dimethoxyxanthone (6) were isolated from the stems of Hypericum chinense, together with four known xanthones. Their structures were established based on spectroscopic studies.
  • Elena Cartagena, Olga Álvarez Colom, Adriana Neske, Juan Carlos ...
    2007 年 55 巻 1 号 p. 22-25
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Sixteen plant sesquiterpene lactones, thirteen from four species of the Family Asteraceae, and three from a species of Hepaticae, as well as seven annonaceous acetogenins isolated from the seeds of the tropical tree Annona cherimolia (Family Annonaceae), were evaluated for their ability to inhibit or stimulate the production of biofilm by a strain of Pseudomonas aeruginosa. The tested compounds carry a γ-lactone moiety in their structures. This structural feature is similar to the lactone moiety present in N-acyl homoserine lactones, compounds that play the important role of “quorum sensors” in the mechanisms of biofilm formation observed in many gram-negative bacteria. A special assay was employed to evaluate the influence of the tested plant compounds to inhibit or stimulate the production of biofilm in a P. aeruginosa wild strain. Most of the tested compounds affected the biofilm formation mechanism. Six sesquiterpene lactones isolated from Acanthospermum hispidum and one from Enydra anagallis as well as an acetogenin from Annona cherimolia strongly inhibited (69—77%) the biofilm formation when incorporated to a bacterial culture at a concentration of 2.5 μg/ml. However, one of the acetogenins, squamocin, stimulated the biofilm formation even at a concentration of 0.25 μg/ml. The study of substances affecting the biofilm formation can lead to the design of new strategies to control P. aeruginosa infections.
  • Tian-Rong Li, Zheng-Yin Yang, Bao-Dui Wang
    2007 年 55 巻 1 号 p. 26-28
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    A new ligand, naringenin-2-hydroxy benzoyl hydrazone (H5L), was prepared by condensation of naringenin with 2-hydroxy benzoyl hydrazine. Its Cu(II), Ni(II), Zn(II) complexes have also been synthesized and characterized on the basis of 1H-NMR, IR, UV–Vis spectra, elemental analyses, molar conductivity and thermal analyses. The general formula of these complexes was M(H3L) [M=Cu(II), Ni(II) and Zn(II)]. In addition, the antioxidant activities (superoxide and hydroxyl radical) of the free ligand and its complexes were determined in vitro. These compounds were found to possess potent antioxidant activity and be better than standard antioxidants like vitamin C and mannitol. In particular, the Cu(II) complex displayed excellent activity on the superoxide radical.
  • Helena Nicklasson, Fridrun Podczeckb
    2007 年 55 巻 1 号 p. 29-33
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    The purpose of this study was to investigate the role of pores in the fracture of circular compacts and to predict compact properties and critical crack lengths. Four different particle size fractions of sucrose, ranging from 20 to 500 μm, were compressed into circular discs (i.e. flat tablets) and rectangular beam specimens of porosity between 30 and 14%. Modelling of the relationship between the tensile strength of the circular discs and the compact porosity indicated extensive fragmentation during compaction for particles in the size range of 250—500 μm, accompanied by a change in densification mechanism for very coarse particles (355—500 μm). When determining the critical stress intensity factor from rectangular single edge notched beam specimens by 3-point bending, an apparent influence of particle size on the values could be seen, whereby here the results indicated that the critical particle size for fragmentation to occur is about 20—40 μm. It was possible to predict the critical stress intensity factor of the compacts from the median pore size and the tensile strength of the circular disc specimens by interpolation of the critical crack length for propagation to occur. The results indicated that for sucrose compacts regardless of their porosity, the pores themselves acted as stress concentrators, not as sharp cracks. For sucrose compacts, crack propagation hence proceeds most likely along grain boundaries.
  • Naoko Kiyota, Kazushi Shingu, Koki Yamaguchi, Yasuyuki Yoshitake, Kazu ...
    2007 年 55 巻 1 号 p. 34-36
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Three new C28 steroidal glycosides, isotubocaposides A (1), B (2), and C (3), were isolated from the fruits of Tubocapsicum anomalum MAKINO. Their chemical structures were elucidated on the basis of spectroscopic and X-ray diffraction analysis of p-bromobenzoyl derivative (5) of isotubocaposigenin (4), the sapogenol derivative of these three glycosides. Isotubocaposides have the structural peculiarity of an unusual side chain carrying a C-21 bound to C-24 on the lactone ring.
  • Kazunari Sakagami, Toshihito Kumagai, Takeo Taguchi, Atsuro Nakazato
    2007 年 55 巻 1 号 p. 37-43
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    We successfully synthesized the potent and selective group II mGluR agonist (+)-1 (MGS0008) via a process incorporating the key step of efficient fluorination of epoxide (±)-5c. This method would be adaptable to large-scale synthesis to produce (+)-1 in multi-gram quantities.
  • Ponnurengam Malliappan Sivakumar, Sethu Kailasam Geetha Babu, Doble Mu ...
    2007 年 55 巻 1 号 p. 44-49
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Design of compounds having good anti-tubercular activity is gaining much importance in the field of tuberculosis research due to reemergence of antibiotic resistance strains. In this paper quantitative structure activity relationships (QSAR) were developed on chalcones, chalcone-like compounds, flavones and flavanones to understand the relationship between biological activity and structural features. Genetic function approximation (GFA) method was used to identify the descriptors that would lead to good regression equations. The best molecular descriptors identified were Jurs descriptors (Jurs charged partial surface area), hydrogen bond donor, principal moment of inertia, molecular energy, dipole magnetic, molecular area, absorption, distribution, metabolism and excretion (ADME) properties and Chi indices (Kier & Hall chi connectivity indices). Excellent statistically significant models were developed by this approach (r2=0.8—0.97) for the four groups of compounds. The cross validated r2 (XV r2) which is an indication of the predictive capability of the model for all the cases was also very good (=0.79—0.94).
  • Kun-Teng Wang, Lih-Geeng Chen, Ling-Ling Yang, Wei-Ming Ke, Hsing-Chan ...
    2007 年 55 巻 1 号 p. 50-56
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    In Asia, processed Atractylodis Rhizoma, the dried rhizome of Atractylodes ovata DE CANDOLLE (Compositae), is widely used as a tonic agent in herbal diets; stir-frying with soil is the most common processing method. In this study, we focused on determining variations in the function and concentrations of sesquiterpenoids in processed Atractylodis Rhizoma. Raw Atractylodis Rhizoma was processed by stir-frying it with different assistant substrates (i.e., red soil and burnt clay). The results indicated that there was less atractylon in stir-fried materials than in raw materials. However, there were higher levels of atractylenolides II and III in stir-fried materials than in raw materials. We also found that the heavy-metal content in burnt clay exceeded regulations set by the Taiwanese government. Moreover, commercial Atractylodis Rhizoma in Taiwan exhibited great differences in concentrations of the active components. In addition, atractylon showed stronger cytotoxicity than atractylenolides II and III in various cell lines. Therefore, we suggest that the toxic effects of atractylon are reduced following atractylon degradation to atractylenolides II and III. In conclusion, the toxicity of Atractylodis Rhizoma is reduced through processing.
  • Masayuki Yoshikawa, Toshio Morikawa, Seikou Nakamura, Ning Li, Xian Li ...
    2007 年 55 巻 1 号 p. 57-63
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Seven new acylated oleanane-type triterpene oligoglycosides, theasaponins A4 (1), A5 (2), C1 (3), E8 (4), E9 (5), G1 (6), and H1 (7), were isolated from the seeds of Japanese tea plant (Camellia sinensis). The structures of 1—7 were elucidated on the basis of chemical and physicochemical evidence.
  • Norbert Handler, Walter Jaeger, Helmut Puschacher, Klaus Leisser, Thom ...
    2007 年 55 巻 1 号 p. 64-71
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Curcumin, a major yellow pigment and active component of turmeric, has been shown to possess anti-inflammatory and anti-cancer activities. Recent studies have indicated that cyclooxygenase-1 (COX-1) plays an important role in inflammation and carcinogenesis. In order to find more selective COX-1 inhibitors a series of novel curcumin derivatives was synthesized and evaluated for their ability to inhibit this enzyme using in vitro inhibition assays for COX-1 and COX-2 by measuring PGE2 production. All curcumin analogues showed a higher rate of COX-1 inhibition. The most potent curcumin compounds were (1E,6E)-1,7-di-(2,3,4-trimethoxyphenyl)-1,6-heptadien-3,5-dione (4) (COX-1: IC50=0.06 μM, COX-2: IC50>100 μM, selectivity index>1666) and (1E,6E)-methyl 4-[7-(4-methoxycarbonyl)phenyl]-3,5-dioxo-1,6-heptadienyl]benzoate (6) (COX-1: IC50=0.05 μM, COX-2: IC50>100 μM, selectivity index>2000). Curcumin analogues therefore represent a novel class of highly selective COX-1 inhibitors and promising candidates for in vivo studies.
  • Love Kumar Soni, Satish Gopalrao Kaskhedikar
    2007 年 55 巻 1 号 p. 72-75
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Designing of a highly selective, potent and safe inhibitor of aldose reductase (ALR) capable of potentially blocking the excess glucose flux through the polyol pathway that prevails under diabetic condition has been a long standing challenge. In our study, we did quantitative structure–activity relationship (QSAR) analysis, based on Fujita–Ban and classical Hansch approach, on 5-[[2-(ω-carboxyalkoxy)aryl]methylene]-4-oxo-2-thioxothiazolidine derivatives. Study gave structural insight into the binding mode of the molecules to the aldose reductase enzyme. The Fujita–Ban approach revealed that benzylidene thiazolidine nucleus is more potent as compare to naphthyl-methylene thiazolidine analogs. The bulkierness of naphthyl-methylene might be inquisitive with receptor. Hansch approach suggested that electron-withdrawing groups are conducive to aldose reductase inhibitory activity.
  • Veerachamy Alagarsamy, Sankaranarayanan Murugesan
    2007 年 55 巻 1 号 p. 76-80
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    A variety of novel 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one with a variety of alkyl and aryl ketones. The starting material 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 4-methoxyaniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds 2-(1-methylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A1), 2-(1-ethylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A2) and 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent analgesic activity and the compound 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent anti-inflammatory activity when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to aspirin.
  • Kornvika Charupant, Khanit Suwanborirux, Surattana Amnuoypol, Emi Sait ...
    2007 年 55 巻 1 号 p. 81-86
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Jorunnamycins A—C (1a—c), three stabilized renieramycin-type bistetrahydroisoquinolines, were isolated from the mantles, the visceral organs, and the egg ribbons of the Thai nudibranch Jorunna funebris that was pretreated with potassium cyanide (KCN), along with five known compounds, renieramycins M (2m), N (2n), O (2o), and Q (2q) and mimosamycin (3). The structures of 1a—c were elucidated from spectroscopic data and by chemical conversion of renieramycin M (2m) into 1c via 1a. The chemical stability and the oxidative degradation generating simple isoquinoline alkaloids of a carbinolamine analog 1d, which was easily prepared by reacting 1c with silver nitrate in aqueous acetonitrile, are discussed. The results of cytotoxicity studies are also presented.
  • Yan Shi, Xiancheng Zhan, Lie Ma, Bing Lin, Linli Li, Chengrong Li, Nin ...
    2007 年 55 巻 1 号 p. 87-91
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    A drug stability experiment accelerated by compressed oxygen was established. The stability of 10% ascorbic acid solution as a model was studied and the kinetic parameters were obtained with the newly established experimental method. Because ascorbic acid degrades under both anaerobic and aerobic conditions, the total rate constant ktotal can be expressed as: ktotal=kanaerobic+kaerobic, where kanaerobic and kaerobic are the rate con-stants of anaerobic and aerobic degradations, respectively. The kanaerobic can be expressed as kanaerobic=Aanaerobic·exp(−Ea,anaerobic/RT) according to Arrhenius equation, and the kaerobic was found to be kaerobic=Aaerobic·exp(−Ea,aerobic/RTpO2 in our study.
  • Takafumi Nakatani, Katsuaki Jinpo, Naoki Noda
    2007 年 55 巻 1 号 p. 92-94
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Five cantharidin-related compounds were isolated from the Chinese blister beetle, Mylabris phalerate PALLAS (Meloidae). Their structures were determined based on spectroscopic and chemical evidence. Three of them were identified as cantharimide dimers, which consist of two units of cantharimide combined with a tri-, tetra-, or penta-methylene group.
  • Akikazu Kakehi, Hiroyuki Suga, Hirohide Isogai
    2007 年 55 巻 1 号 p. 95-101
    発行日: 2007年
    公開日: 2007/01/01
    ジャーナル フリー
    Various thieno[3,4-b]indolizine derivatives having an acylmethylthio or (3-ethoxycarbonyl-2-propenyl)thio group at the 3-position which could not be obtained by a conventional method were prepared by a new procedure using cyanoethyl group as a protecting group and their intramolecular arene–π interactions were investigated. In the 1H-NMR spectra of these thieno[3,4-b]indolizines, the low-field shifts (δ 0.10—0.33 ppm) for the 5-protons were observed in comparison with those of 3-(methylthio)thieno[3,4-b]indolizines as a standard. The UV spectra also exhibited a characteristic absorption band at 425—445 nm attributable to the arene–π interaction but their intensities were generally lower than those of 3-(arylmethylthio)thieno[3,4-b]indolizines. In their X-ray analyses, the anti conformation for 3-(acylmethylthio)thieno[3,4-b]indolizines and the gauche one for the 3-(3-ethoxycarbonyl-2-propenyl)thio derivatives were exhibited.
Notes
feedback
Top