Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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51 巻, 5 号
選択された号の論文の28件中1～28を表示しています
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Regular Articles
  • Further Bisabolenes and Dammarane Triterpenes of Commiphora kua Resin
    Lawrence Onyango Arot Manguro, Ivar Ugi, Peter Lemmen
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 479-482
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.479
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    From the resins of Commiphora kua a novel bisabolene; 6-hydroxy-2-methyl-5-(5′-hydroxy-1′(R),5′-dimethylhex-3′-enyl)-phenol together with two new dammarane triterpenes, 3β,16β,20(S),25-tetrahydroxydammar-23-ene and 3β-acetoxy-16β,20(S),25-trihydroxydammar-23-ene, have been isolated. In addition, being reported are known compounds identified as 2-methyl-5-(4′(S)-hydroxy-1′(R),5′-dimethylhex-5′-enyl)-phenol, 2-acetoxyfuranodienone, 2-methoxyfuranodienone, 3β,16β,20(R)-trihydroxydammar-24-ene and its acetate derivative, 3β-acetoxy-16β,20(R)-dihydroxydammar-24-ene, and β-amyrin and its acetate derivative. 2-Methyl-5-(4′(S)-hydroxy-1′(R),5′-dimethylhex-5′-enyl)-phenol displayed fungicidal activity against Cladosporium cucumernum on TLC assay.
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  • Dammarane Triterpenes of Commiphora confusa Resin
    Lawrence Onyango Arot Manguro, Ivar Ugi, Peter Lemmen
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 483-486
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.483
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    Fractionation of a steam distilled residue of Commiphora confusa resin has yielded four novel dammarane triterpenes characterised as (20S)-3β-acetoxy-12β,16β-trihydroxydammar-24-ene, (20S)-12β,16β-trihydroxydammar-24-ene-3β-O-β-glucopyranoside, (20S)-3β-acetoxy-12β,16β,25-tetrahydroxydammar-23-ene, and (20S)-3β,12β,16β,25-pentahydroxydammar-23-ene. The known compounds β-amyrin, 3β-amyrinacetate, 2-methoxyfuranodienone, 2-acetoxyfuranodienone, (20R)-3β-acetoxy-16β-dihydroxydammar-24-ene, (20R)-3β,16β-trihydroxydammar-24-ene, 3β-acetoxy-16β-hydroxydammar-24-ene, 3β-hydroxydammar-24-ene, 3β-acetoxydammar-24-ene, and β-sistosterol were also isolated from the same extract. The structures of the compounds were determined using spectroscopic, physical, and chemical methods.
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  • Effect of Crystallization Behavior of Polyethylene Glycol 6000 on the Properties of Granules Prepared by Fluidized Hot-Melt Granulation (FHMG)
    Motonori Kidokoro, Kaoru Sasaki, Yasuo Haramiishi, Norio Matahira
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 487-493
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.487
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    The objective of this study was to investigate the effect of the crystallization behavior of Macrogol 6000 (polyethylene glycol 6000; PEG 6000), used as a binder, during the solidification process on the properties of mononucleic granules prepared by the fluidized hot-melt granulation (FHMG) technique. Crystallization of PEG 6000 from molten liquid was investigated using differential scanning calorimetry (DSC) and hot stage microscopy. The results obtained from the measurement of isothermal crystallization demonstrated that crystallization of PEG 6000 was either slow or rapid. Analysis based on solid-state decomposition showed that slow crystallization was due to the two-dimensional growth of nuclei mechanism, while rapid crystallization was due to the three-dimensional growth of nuclei mechanism. Observation of the crystallization of PEG 6000 by hot stage microscopy supported the existence of two different crystallization mechanisms. Granules containing PEG 6000 that underwent rapid crystallization during FHMG showed a significantly higher fraction powder under 150 μm in diameter. This was caused by the loss of powder particles from the surface of mononucleic granules during the solidification process, because many cracks were observed after crystallization of PEG 6000 with a short isothermal crystallization time (ICT) due to the reduced of sticking of particles. The results of this study suggested that the crystallization behavior of the binder during the solidification process of FHMG can influence the properties of the resultant granules, such as particle size distribution, content uniformity or taste masking. It was also indicated that measuring the ICT using DSC was a useful method to classify PEG 6000.
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  • Synthesis, Characterization, and Antibacterial Activities of Some Rare Earth Metal Complexes of Pipemidic Acid
    Lin Yang, Dongliang Tao, Xiaoli Yang, Yongfang Li, Yuming Guo
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 494-498
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.494
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    Eight new solid complexes of pipemidic acid (PPA) with trichlorizated rare earth metals LaCl3, CeCl3, PrCl3, NdCl3, SmCl3, TbCl3, DyCl3, and YCl3 have been synthesized. The complexes were characterized by elemental analyses, IR, NMR, and molar conductance measurements. The general formulas of the complexes are [M(PPA)4]Cl3 (M=Ce(III), Pr(III), Nd(III), Sm(III), Tb(III), Dy(III), Y(III)), and [La(PPA)4Cl]Cl2. At the same time, the antibacterial activities of PPA and four of its complexes were tested. The results show that PPA and its complexes all have inhibitory action against bacteria of Escherichia coli, Bacillus subtilis, Streptococcus pneumoniae, and Pseudomonas aeruginosa but not Staphylococcus aureus. We compared their antibacterial activities and found that the antibacterial activity of [La(PPA)4Cl]Cl2 against S. pneumoniae is much stronger than that of PPA and the other complexes.
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  • Sinodielides E—H, four New Guaianolides, from the Root of Sinodielsia yunnanensis
    Nian-He Wang, Masahiko Taniguchi, Daisuke Tsuji, Kimiye Baba
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 499-501
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.499
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    Four new guaianolides, sinodielides E—H (1—4), were isolated from the root of Sinodielsia yunnanensis WOLFF. Their structures were established by spectral evidence.
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  • Dioxopyrrolines. LXII. Diels–Alder Reaction of 1-Aryl-4- and 5-methoxycarbonyl-1H-pyrrole-2,3-diones with Various 1,3-Dienes
    Kunihiko Mohri, Katsumi Yokoyama, Hiroaki Komiya, Yuhya Watanabe, Yuki ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 502-507
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.502
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    Two new dioxopyrrolines (1-aryl-4-methoxycarbonyl-1H-pyrrole-2,3-dione 6 and the 5-methoxycarbonyl isomer 8) behaved as good dienophiles to some kind of 1,3-dienes examined. In most cases, the products were explained by the reaction where the largest lobe of HOMO of dienes reacted to the larger LUMO of dienophiles in an expected cis-endo manner. However, in the reactions of 8 with alkylbutadienes, piperylene and isoprene, abnormality in the reaction was observed, which was well explained by taking account of steric factors.
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  • Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol
    Li-Hua Xie, Teruaki Akao, Kenjiro Hamasaki, Takeshi Deyama, Masao Hatt ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 508-515
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.508
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    By anaerobic incubation of pinoresinol diglucoside (1) from the bark of Eucommia ulmoides with a fecal suspension of humans, eleven metabolites were formed, and their structures were identified as (+)-pinoresinol (2), (+)-lariciresinol (3), 3′-demethyl-(+)-lariciresinol (4), (−)-secoisolariciresinol (5), (−)-3-(3″, 4″-dihydroxybenzyl)-2-(4′-hydroxy-3′-methoxybenzyl)butane-1, 4-diol (6), 2-(3′, 4′-dihydroxybenzyl)-3-(3″, 4″-dihydroxybenzyl)butane-1, 4-diol (7), 3-(3″-hydroxybenzyl)-2-(4′-hydroxy-3′-methoxybenzyl)butane-1, 4-diol (8), 2-(3′, 4′-dihydroxybenzyl)-3-(3″-hydroxybenzyl)butane-1, 4-diol (9), (−)-enterodiol (10), (−)-(2R, 3R)-3-(3″, 4″-dihydroxybenzyl)-2-(4′-hydroxy-3′-methoxybenzyl)butyrolactone (11), (−)-(2R, 3R)-2-(3′, 4′-dihydroxybenzyl)-3-(3″, 4″-dihydroxybenzyl)butyrolactone (12), (−)-(2R, 3R)-3-(3″-hydroxybenzyl)-2-(4′-hydroxy-3′-methoxybenzyl)butyrolactone (13), 2-(3′, 4′-dihydroxybenzyl)-3-(3″-hydroxybenzyl)butyrolactone (14), 2-(3′-hydroxybenzyl)-3-(3″, 4″-dihydroxybenzyl)butyrolactone (15) and (−)-(2R, 3R)-enterolactone (16) by various spectroscopic means, including two dimensional (2D)-NMR, mass spectrometry and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and time course experiments monitored by thin-layer chromatography. Furthermore, a bacterial strain responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol was isolated from a human fecal suspension and identified as Enterococcus faecalis strain PDG-1.
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  • Comparative Molecular Field Analysis Study of Stilbene Derivatives Active against A549 Lung Carcinoma
    Sanghee Kim, Sun Young Min, Sang Kook Lee, Won-Jea Cho
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 516-521
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.516
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    A series of 43 stilbene derivatives that showed cytotoxicity against human lung carcinoma (A549) was analyzed using comparative molecular field analysis (CoMFA) for defining the hypothetic pharmacophore model. The polyoxylated stilbenes were found to be active inhibitors of tubulin polymerization. Several cis-stilbenes are structurally similar to combretastatins. However, the trans-stilbenes are assumed to be close to resveratrol found in grapes and have been reported to be potential cancer chemopreventive agents by modulating the initiation, promotion, and progression of the carcinogenic process. With several synthesized compounds that were evaluated for antitumor cytotoxicity against human lung tumor cells (A549), the stilbene derivatives were subjected to CoMFA. To perform systematic molecular modeling of these compounds, a conformational search was carried out based on the precise dihedral angle analysis of the lead compound (1p). The X-ray crystallographic structure of combretastatin A-1 was also used for defining the active conformers of the compounds. After determining the energy-minimized conformers of the lead compound (1p), CoMFA was performed using five different alignments. The three dimensional (3D)-quantitative structure–activity relationship study resulted in reasonable cross-validated, conventional r2 values equal to 0.640 and 0.958, respectively.
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  • Synthesis, Conformational Analysis and Free Radical Scavenging Activity of Some New Spiropyranoquinolinones
    Vassiliki Panteleon, Panagiotis Marakos, Nicole Pouli, Emmanuel Mikros ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 522-529
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.522
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    A series of novel spiroadamantyl- and spirocyclical substituted pyranoquinolin-2-ones were synthesized and the conformation of the pyran ring was investigated. The free radical scavenging activity of the synthesized compounds was determined by their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH). All compounds tested scavenged the DPPH radical and among them derivatives possessing extended conjugation showed the highest activity.
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  • Minor Withanolides from Physalis philadelphica: Structures, Quinone Reductase Induction Activities, and Liquid Chromatography (LC)-MS-MS Investigation as Artifacts
    Jian-Qiao Gu, Wenkui Li, Young-Hwa Kang, Bao-Ning Su, Harry H. S. Fong ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 530-539
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.530
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    As a result of a bioactivity-guided search for novel, plant-derived cancer chemopreventive agents, ixocarpalactone A (5) was isolated previously as a potent quinone reductase inducer from the leaves and stems of Physalis philadelphica. In the present study, this promising lead compound was reisolated in gram quantities for in vivo biological testing. During the course of this work, four additional minor new withanolides were also obtained and characterized, namely, 2,3-dihydro-3β-methoxyixocarpalactone A (1), 2,3-dihydro-3β-methoxyixocarpalactone B (2), 2,3-dihydroixocarpalactone B (3), and 4β,7β,20R-trihydroxy-1-oxowitha-2,5-dien-22,26-olide (4). However, compounds 1 and 2 were determined using liquid chromatography (LC)-MS-MS to be artifacts generated during the extraction and isolation procedure. Ixocarpalactone A was detected in the fresh fruits (tomatillos) of P. philadelphica by LC-MS-MS analysis at a concentration of 143±4.53 ppb.
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  • Diastereoselective Solid-Phase Radical Addition to Oxime Ether Anchored to Polymer Support
    Hideto Miyabe, Chihiro Konishi, Takeaki Naito
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 540-544
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.540
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    Stereocontrol in radical reactions of oxime ether anchored to polymer support was studied. Highly diastereoselective solid-phase radical reaction was achieved by using triethylborane and diethylzinc as a radical initiator at low reaction temperature, providing a novel method for the synthesis of the α-amino acid derivatives with excellent diastereoselectivities.
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  • Five New Sesquiterpenoids and a New Diterpenoid from Erigeron annuus (L.) PERS., Erigeron philadelphicus L. and Erigeron sumatrensis RETZ.
    Takeyoshi Iijima, Yasunori Yaoita, Masao Kikuchi
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 545-549
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.545
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    The aerial parts of Erigeron annuus (L.) PERS., E. philadelphicus L. and E. sumatrensis RETZ. (Compositae) have been investigated chemically. A new sesquiterpenoid, 6β,14-epoxyeudesm-4(15)-en-1β-ol (1), and a new diterpenoid, philadelphinone (6), have been isolated from E. philadelphicus. Four new sesquiterpenoids, (7R*)-opposit-4(15)-ene-1β,7-diol (2), 11-methoxyopposit-4(15)-en-1β-ol (3), 15-methoxyisodauc-3-ene-1β,5α-diol (4) and 10α-hydroxycadin-4-en-15-al (5), have been isolated from E. annuus. Compounds 2 and 4 were also isolated from E. sumatrensis. The structures of the new compounds were elucidated on the basis of their spectral data.
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  • Analysis of the Peptides (Prp106—126, MSI-78A, and Oxaldie 1) with the Same Biological Activity by Discrete Fourier Transform: Toward a Selection Rule in Ligand–Receptor Interaction
    Naganori Numao, Hisashi Fujii, Yoshiyuki Fukazawa, Ken Yoshioka, Mayum ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 550-559
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.550
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    Here, we first report a novel method in which the “desired cross-spectrum” of the peptides Prp106—126, MSI-78A, and oxaldie 1 with the same biological activities is obtained by the multiplication of two cross-spectra derived from the RNA sequence and from the cognate amino acid sequence by discrete Fourier transform (DFT), respectively. Based on a well-known method reported previously, we investigated the cross-spectrum by the multiplication of two of three desired cross-spectra. As a result, we found that one prominent peak occurring in the three cross-spectra showed the same frequency when a binary scale was used as a parameter of nucleotide or amino acid in the analysis. Moreover, we examined the relationship between a binary scale and other physicochemical ones. Almost the same results could be reproduced when the absolute elctronegativity scale (or the absolute hardness one) was used, but not in the case of the hydrophobic or electron–ion interacting potential scale reported previously. This indicates that either the absolute electronegativity scale (or the absolute hardness one) or a binary scale, or both is very useful in extracting the information desired for various proteins by the present method from the amino acid and the RNA sequence.
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  • Four New 2-(2-Phenylethyl)chromone Derivatives from Withered Wood of Aquilaria sinensis
    Toru Yagura, Michiho Ito, Fumiyuki Kiuchi, Gisho Honda, Yasuo Shimada
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 560-564
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.560
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    Four new chromone derivatives, 5-hydroxy-6-methoxy-2-(2-phenylethyl)chromone (1), 6-hydroxy-2-(2-hydroxy-2-phenylethyl)chromone (2), 8-chloro-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydrochromone (3), 6,7-dihydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone (4) were isolated from the MeOH extract of withered wood of Aquilaria sinensis, together with seven known constituents of agarwood.
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  • Synthesis and Biological Activity of Novel 5-(ω-Aryloxyalkyl)oxazole Derivatives as Brain-Derived Neurotrophic Factor Inducers
    Tsuyoshi Maekawa, Nozomu Sakai, Hiroyuki Tawada, Katsuhito Murase, Mas ...
    原稿種別: Regular Article
    専門分野: [not specified]
    2003 年 51 巻 5 号 p. 565-573
    発行日: 2003年
    公開日: 2003/05/01
    DOIhttps://doi.org/10.1248/cpb.51.565
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    A novel series of 5-(ω-aryloxyalkyl)oxazole derivatives was prepared and their effects on brain-derived neurotrophic factor (BDNF) production were evaluated in human neuroblastoma (SK-N-SH) cells. Syntheses were performed by construction of an oxazole ring as a key reaction. Most of the 5-(ω-aryloxyalkyl)oxazole derivatives markedly increased BDNF production in SK-N-SH cells. 4-(4-Chlorophenyl)-2-(2-methyl-1H-imidazol-1-yl)-5-[3-(2-methoxyphenoxy)propyl]-1, 3-oxazole, one of the most promising compounds, showed potent activity (EC50=7.9 μM) and the improvement of the motor nerve conduction velocity and the tail-flick response accompanied by a recovery of the brain-derived neurotrophic factor level in the sciatic nerve of streptozotocin (STZ)-diabetic rats.
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