Chemical and Pharmaceutical Bulletin
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Volume 52, Issue 11
Displaying 1-33 of 33 articles from this issue
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Regular Articles
  • Enzymes Inhibiting Lignans from Vitex negundo
    Azhar-Ul-Haq, Abdul Malik, Itrat Anis, Sher Bahadar Khan, Ejaz Ahmed, ...
    2004 Volume 52 Issue 11 Pages 1269-1272
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1269
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    Two new lignans trivially named negundins A (1) and B (2), were isolated along with (+)-diasyringaresinol (3), (+)-lyoniresinol (4), vitrofolal E (5) and vitrofolal F (6), reported for the first time from this species. The structures of the new compounds were established through spectral studies. Compound 2 showed potent inhibitory activity against lipoxygenase enzyme, while 5 showed moderate activity against butyryl-cholinesterase.
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  • Influence of the Homogenisation Procedure on the Physicochemical Properties of PLGA Nanoparticles
    Jo. Vandervoort, Krassimira Yoncheva, Annick Ludwig
    2004 Volume 52 Issue 11 Pages 1273-1279
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1273
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    Pilocarpine HCl-loaded PLGA nanoparticles were prepared by emulsification solvent evaporation. Three different stabilisers, polyvinylalcohol (PVA), Carbopol and Poloxamer were used, as well as mixtures thereof. The influence of the homogenisation pressure and number of cycles on the properties of nanoparticles were studied. Particle size was shown to depend on the stabiliser used. An increase of the homogenisation pressure or the number of cycles resulted in a decrease in particle size. The zeta potential value was influenced mainly by the nature of the stabiliser. Particles stabilised with poloxamer or PVA showed a slightly negative zeta potential value, while samples stabilised with carbopol posessed a more negative zeta potential, which became less negative after homogenisation. Drug encapsulation depended strongly on the stabiliser used. The higher drug entrapment of the carbopol-stabilised particles could be explained by an electrostatic interaction between the negatively charged carboxyl groups of carbopol and the positively charged, protonated pilocarpine. The drug release patterns of the particles prepared were quite similar. Differences between the release patterns of the homogenised particles could be attributed both to differences in size as well as drug encapsulation. Turbidimetric measurements suggested an interaction between mucin and PLGA nanoparticles exclusively stabilised with Carbopol.
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  • Equilibrium Studies on Chromium(III) Complexes of Salicylic Acid and Salicylic Acid Derivatives in Aqueous Solution
    Mehmet Suat Aksoy, Ulviye Özer
    2004 Volume 52 Issue 11 Pages 1280-1284
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1280
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    The complexes of chromium(III) ion formed by salicylic acid, SA(H2L), and its derivatives (H2L): 5-nitrosalicylic acid (5-NSA), 5-sulphosalicylic acid (5-SSA) were investigated by means of potentiometry and spectroscopy, at 25 °C and in ionic strength of 0.1 M KNO3 and 0.1 M KCl, respectively. Over the acidic pH range, the coordination of Cr(III) ion to SA and its derivatives in 1 : 1 mole ratio occurs, CrL+ type complex is formed. In the excess of ligand, the coordination of the second ligand molecule is somewhat hindered; as a result CrL(HL) type complex occurs. Their existences were verified and their formation constants were determined. At near neutral pH, CrL(OH) and CrL(HL)(OH)− type hydroxo complexes formed by hydrolytic equilibria and their formation constants were also defined. The stabilities of Cr(III) complexes of SA and its derivatives decrease in the following order: SA>5-SSA>5-NSA. The formation constants of Cr(III) complexes of SA and its derivatives are in comparable ranges with the corresponding complexes of the 2,x-dihydroxybenzoic acid (2,x-DHBA) of Cr(III) ion. The stabilities of SA complexes for V(IV), Cr(III) and Fe(III) ions that have similar ionic radii, increase in the order VOL<CrL+<FeL+. It is worthwhile noting that the binding ability of Cr(III) to salicylate ion is four orders of magnitude higher than to transferin, which is a blood serum protein and is associated with insulin action.
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  • Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives
    Masao Tsukayama, Hironari Wada, Yasuhiko Kawamura, Kazuyo Yamashita, M ...
    2004 Volume 52 Issue 11 Pages 1285-1289
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1285
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    The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone derivative, which was hydrogenated to give 6-alkylhydroxyisoflavone (luteone hydrate) (2). Dehydration of 2 gave 2′,4′,5,7-tetrahydroxy-6-prenylisoflavone (luteone) (1). Wighteone hydrate (3) was also synthesized from 6-iodotris(benzyloxy)isoflavone in a similar manner. 6-Alkyl-4′5,7-trihydroxy-coumaronochromone (4) was synthesized by oxidative cyclization of 2 with o-chloranil.
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  • A Pharmacokinetic Model for Ocular Drug Delivery
    Kakuji Tojo
    2004 Volume 52 Issue 11 Pages 1290-1294
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1290
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    A pharmacokinetic model of ocular drug delivery has been developed for describing the elimination and distribution of ocular drugs in the eye. The model, based on Fick's second law of diffusion, assumes a modified cylindrical eye with three pathways for drug transport across the surface of the eye: the anterior aqueous chamber, the posterior aqueous chamber and the retina/choroids/scleral membrane covering the vitreous body. The model parameters such as the diffusion coefficient and the partition coefficient in various eye tissues can be evaluated from the in vitro membrane penetration experiments using a side-by-side diffusion cell system. The diffusion coefficient for a drug is also predicted by taking account of the effect of the molecular weight of model compounds. The present ocular pharmacokinetic model, which can predict the local concentration distribution in the eye, has well described the in vivo concentration profile in the various eye tissues, the lens, the aqueous humor and the vitreous body, following not only topical eye drop instillation but systemic administration as well. The present model also simulates the effects of binding and metabolism in the eye as well as the individual difference in ocular functions and structure such as cataract surgery and vitreous fluidity on the distribution and elimination of drug molecules in the eye.
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  • Phytochemical Analysis of Anti-atherogenic Constituents of Xue-Fu-Zhu-Yu-Tang Using HPLC-DAD-ESI-MS
    Li Liu, Yiyu Cheng, Haijiang Zhang
    2004 Volume 52 Issue 11 Pages 1295-1301
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1295
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    Xue-Fu-Zhu-Yu-Tang is a famous traditional Chinese medicine (TCM) formula for treating cardiovascular disease and related ailments in China for centuries. To profile the phytochemical constituents of the formula, an HPLC-DAD-ESI-MS analytical method has been developed to separate and determinate the medium- or non-polar fraction of the decoction, which has been demonstrated potency to lower the serum total triglyceride concentration, strongly decrease the TXA2/PGI2 ratio and attenuate production of proinflammatory cytokines in high cholesterol-fed rats. By comparing their retention time, UV and MS data with those obtained from the authentic compounds, ferulic acid (1), naringin (2), neohesperindin (3), naringenin (8), marmin (13), senkyunolide A (14), dehydrosafynol (16), safynol (17) and Z-ligustlide (18) are unequivocally determined. Moreover, additional thirteen compounds are tentatively identified as senkyunolide I (4), senkyunolide H (5), poncirin (7), benzoylpaeoniflorin (10), (Z)-6,7-epoxyligustilide (11), senkyunolide G (12), 2-methoxy-safynol (15), cnidilide (19), tangeritin (20), saikosaponin b2 (21), 29-O-acetylsaikosaponin b2 (22), saikosaponin b1 (23) and auraptene (24), according to the comparison of their UV and MS data with the published data. The present study provides an approach to rapidly characterize bioactive constituents in TCM formulae.
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  • Mechanochemical Solid-State Polymerization (XI): Effect of Water-Insoluble Pharmaceutical Aids on Drug Release from Mechanically Synthesized Polymeric Prodrugs
    Shin-ichi Kondo, Shouichi Hosaka, Yasushi Sasai, Masayuki Kuzuya
    2004 Volume 52 Issue 11 Pages 1302-1306
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1302
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    We discuss here the effect of water-insoluble pharmaceutical aids on the nature of drug release from composite polymeric prodrugs synthesized by mechanochemical solid-state polymerization. Magnesium stearate (Mgst) and hydrogen castor oil (HCO) were used as water-insoluble pharmaceutical aids. Composite polymeric prodrugs were synthesized by the mechanochemical solid-state polymerization of a vinyl monomer of 5-fluorouracil (I) in the presence of Mgst or HCO. The molecular weight of the resulting polymeric prodrugs increased with increasing the content of Mgst or HCO. Prodrug hydrolysis was carried out in a heterogeneous system in phosphate buffer at pH 6.8 and 37 °C. The rate of drug release from the composite polymeric prodrug containing Mgst (Poly-Mgst) was faster than that from polymeric prodrug containing no pharmaceutical aids (Poly-Non), while hydrolysis of the composite polymeric prodrug containing HCO (Poly-HCO) was slower than Poly-Non. Scanning electron microscope (SEM) photos showed the surface of Poly-HCO was smoother than that of Poly-Non and Poly-Mgst. It was suggested that the slower drug release from Poly-HCO may be responsible for the smaller specific surface area than that of Poly-Non. It was also shown that the rate of drug release from the composite polymeric prodrugs decreases with increasing the content of Mgst or HCO. Hence, novel composite polymeric prodrugs with a variety of drug release rates can be prepared by mechanochemical solid-state polymerization in a totally dry process.
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  • Constituents of Crinoidea, 4. Isolation and Structure of Ceramides and Glucocerebrosides from the Feather Star Comanthus japonica
    Masanori Inagaki, Akemi Oyama, Kazuyoshi Arao, Ryuichi Higuchi
    2004 Volume 52 Issue 11 Pages 1307-1311
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1307
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    Five ceramides, JC-1—JC-5, and four glucocerebrosides, JCer-1—JCer-4, have been isolated from their parent ceramide and glucocerebroside molecular species JC and JCer obtained from the less polar lipid fraction of the chloroform/methanol extract of the feather star Comanthus japonica. The structures of these sphingolipids have been determined on the basis of chemical and spectroscopic evidence. Reversed-phase HPLC was effective at isolating these sphingolipids, revealing very close resemblance in their structures. JC-1, JC-3, JC-4, JC-5 and JCer-2, JCer-4 are newly found ceramides and glucocerebrosides, respectively.
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  • Simultaneous Comparison of Relative Reactivities of Twelve Major Anthocyanins in Bilberry towards Reactive Nitrogen Species
    Takashi Ichiyanagi, Yoshihiko Hatano, Seiichi Matsuo, Tetsuya Konishi
    2004 Volume 52 Issue 11 Pages 1312-1315
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1312
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    The reactivities of twelve major anthocyanins identified in bilberry extracts towards nitric oxide (NO·) and peroxynitrite (ONOO−) were studied in vitro using capillary zone electrophoresis (CZE). The reactivities of the anthocyanins towards NO· were slightly weak compared with that of (+)-catechin as a reference antioxidant under anaerobic conditions except delphinidin glycosides (Dp3glys). The reactivities of other anthocyanins were not significantly affected by either the aglycon structure or the type of sugar moiety. Under aerobic conditions, all anthocyanins and catechin showed significant enhancement of the reactivity, indicating that they reacted with other reactive species secondarily generated from NO·. Dp3glys showed rather extraordinally high reactivity towards ONOO− compared to other anthocyanins which showed approximately two times low reactivity than catechin when compared with IC50. Structural divergence in the reactivity was also small for all these anthocyanins.
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  • Preparation of New Nitrogen-Bridged Heterocycles. 56. Syntheses and Reactions of 1-[2,2-Bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium Salts
    Akikazu Kakehi, Hiroyuki Suga, Yuuya Yamauchi, Katsuaki Yasuraoka, Tom ...
    2004 Volume 52 Issue 11 Pages 1316-1321
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1316
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    The title compounds, readily available from the S-alkylation of pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides with alkyl halides or alkyl bromoacetates, were treated with a base and then a dehydrogenating agent to provide some unique products such as 3-[bis(alkylthio)methylene]-2(3H)-indolizinones and dialkyl 7-methyl-4-oxo-1,4,8,8a-tetrahydro-1,4-thiazino[3,4,5-cd]indolizine-1,5-dicarboxylates. On the other hand, similar reaction of these pyridinium salts in the absence of the dehydrogenating agent afforded alkyl 2-hydroxyindlizine-3-carboxythiolates, whose yields were increased by adding trifluoroacetic acid to the reaction mixture. The structures of some products were confirmed by the X-ray analyses.
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  • Application of LC-NMR for Characterization of Rat Urinary Metabolites of Zonampanel Monohydrate (YM872)
    Kin-ya Sohda, Tsuyoshi Minematsu, Tadashi Hashimoto, Ken-ichi Suzumura ...
    2004 Volume 52 Issue 11 Pages 1322-1325
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1322
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    Zonampanel monohydrate (YM872) has a potent and selective antagonistic effect on the glutamate receptor subtype, α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA) receptor. Metabolic fingerprinting in rat urine after a single intravenous administration of 14C-labeled YM872 (14C-YM872) revealed the presence of two metabolites, R1 and R2. The two metabolites were semi-purified by preparative HPLC from rat urine after a single intravenous administration of non-labeled YM872, and their structures were elucidated by various instrumental analyses involving LC-NMR. The results showed that R1 and R2 have a hydroxyamino group and an amino group at the C-7 position of the quinoxalinedione skeleton, respectively. Therefore, the proposed metabolic pathway of YM872 in rats involves the reduction of the nitro group to a hydroxyamino group and then subsequent reduction to an amino group.
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  • Antiallergic Agents from Natural Sources 9. Inhibition of Nitric Oxide Production by Novel Chalcone Derivatives from Mallotus philippinensis (Euphorbiaceae)
    Akihiro Daikonya, Shigeki Katsuki, Susumu Kitanaka
    2004 Volume 52 Issue 11 Pages 1326-1329
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1326
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    Three novel chalcone derivatives, mallotophilippens C (1), D (2) and E (3) were isolated from the fruits of Mallotus philippinensis MUELL. ARG. These compounds were identified, using chemical and spectral data, as 1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-(4-hydroxy-phenyl)-propenone, 3-(3,4-dihydroxy-phenyl)-1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-propenone and 1-[5,7-dihydroxy-2-methyl-6-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-2H-chromen-8-yl]-3-(3,4-dihydroxy-phenyl)-propenone, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ). Furthermore, they downregulated cyclooxygenase-2 (COX-2) gene, interleukin-6 (IL-6) gene and interleukin-1β (IL-1β) gene expression. These results suggest that they have anti-inflammatory and immunoregulatory effects.
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  • Synthesis and Pharmacological Evaluation of Novel Arylpiperazine Derivatives as Nonsteroidal Androgen Receptor Antagonists
    Isao Kinoyama, Nobuaki Taniguchi, Toru Yoden, Hiroshi Koutoku, Takashi ...
    2004 Volume 52 Issue 11 Pages 1330-1333
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1330
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    The search for novel antiandrogens by high-throughput screening (HTS) of the Yamanouchi chemical library led to the discovery of the lead compound (5), which possesses an arylmorpholine moiety. Through the optimization of the lead compound (5), we have found a series of novel arylpiperazine derivatives. Among them, 4-[4-cyano-(3-trifluoromethyl)phenyl]-N-(4-fluorophenyl)piperazine-1-carboxamide (22; YM-92088) exhibited a potent AR antagonistic activity with an IC50 value of 0.47 μM in the reporter assay, which is more potent than bicalutamide (4) which has an IC50 value of 0.89 μM.
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  • Synthesis of Unnatural 1-Methyl-2-quinolone Derivatives
    Motoki Asahara, Taku Katayama, Yasuo Tohda, Nagatoshi Nishiwaki, Masah ...
    2004 Volume 52 Issue 11 Pages 1334-1338
    Published: 2004
    Released on J-STAGE: November 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1334
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    Unnatural 1-methyl-2-quinolone derivatives were synthesized by regioselective C–C bond formation. When 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) was treated with enamines, nucleophilic addition readily occurred at the 4-position, and succeeding hydrolysis of enamine moiety followed by elimination of nitrous acid furnished 4-acylmethyl-1-methyl-6,8-dinitro-2-quinolones. The same products could be prepared by the reaction of TNQ with ketones in the presence of triethylamine. The present reaction enabled the introduction of various kinds of acylmethyl groups substituted with alkyl, aryl or hetaryl groups.
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Notes
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