Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 51, Issue 2
Displaying 1-28 of 28 articles from this issue
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Regular Articles
  • Anti-tack Action of Polyvinylpyrrolidone on Hydroxypropylmethylcellulose Solution
    Lai Wah Chan, Tin Wui Wong, Pih Chng Chua, Peter York, Paul Wan Sia He ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 107-112
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.107
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    The anti-tack action of polyvinylpyrrolidone (PVP) on hydroxypropylmethylcellulose (HPMC) solution was elucidated using a probe test method. The influence of PVP of varying molecular weights at various PVP concentrations and solution temperatures on the tackiness of HPMC solution was studied. The viscosity, surface tension, cloud point and solution spectroscopy of HPMC solutions and glass transition temperature of HPMC films, with and without PVP, were investigated. The tackiness of HPMC solutions in response to the addition of PVP, at different concentrations of HPMC and using HPMC with varying contents of hydroxypropyl/methoxyl substitution, was also evaluated. PVP is a commonly used binder and adhesive. However, it reduced the tack of the HPMC solution when used at low concentrations, without affecting the state of hydration of HPMC. Lower molecular weight PVP was more effective as an anti-tack agent owing to suitable hydrodynamic size to intersperse among the HPMC chains. The degree of reduction in tack values was more pronounced for HPMC that showed a greater extent of interaction between polymer chains such as when high concentration of HPMC or low solution temperature was employed. This indicated that the tack reduction property of PVP relied on its ability to interact with the HPMC chains. The profile of reduction in tack values was affected by the contents of HPMC substitution and was a result of net reduction in the extent of hydrogen bonding between HPMC chains. It was significantly correlated to the changes of viscosity and surface tension of the HPMC solutions but not to the glass transition temperatures of the polymers prepared as solid films. The results suggested that the anti-tack action of PVP was attributed to its ability to interact with HPMC chains in the aqueous medium and consequently to reduce the extent of HPMC–HPMC bonding.
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  • Development of 5-[(3-Aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one as a Novel Whitening Agent
    Duck Hee Kim, Jae-Sung Hwang, Heung Soo Baek, Kil-Joong Kim, Byeong Go ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 113-116
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.113
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    A stable derivative of kojic acid, 5-[(3-aminopropyl)phosphinooxy]-2-(hydroxymethyl)-4H-pyran-4-one (Kojyl-APPA), was synthesized in good yield. The effects of Kojyl-APPA on tyrosinase activity and melanin synthesis were investigated. Kojyl-APPA showed tyrosinase inhibition effect (30%) in situ, but not in vitro. Kojyl-APPA inhibited tyrosinase activity significantly at 24 h after treatment in normal human melanocytes. It means that Kojyl-APPA is not a direct inhibitor of tyrosinase itself, but it is converted to a potential inhibitor kojic acid enzymatically in cells. In addition, Kojyl-APPA decreased melanin content to 75% of control in melanoma cells and decreased neomelanin synthesis to 43% of control in normal human melanocytes. Its permeation through skin increased by about 8 times as compared with kojic acid.
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  • Synthesis of Potent and Selective Inhibitors against the Proliferation of Human Coronary Artery Smooth Muscle Cells
    Haruhisa Ogita, Yoshiaki Isobe, Haruo Takaku, Rena Sekine, Yuso Goto, ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 117-121
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.117
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    A series of diarylamide urea derivatives were synthesized and evaluated for their inhibitory activities against human coronary artery smooth muscle cells (SMCs) and human coronary artery endothelial cells (ECs). Compound 2h was much superior to Tranilast, in terms of both the potency of its inhibitory activity toward the proliferation of SMCs and the cell selectivity.
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  • Synthesis of Eosinophil Infiltration Inhibitors with Antihistaminic Activity
    Michiyo Gyoten, Hideaki Nagaya, Shigeru Fukuda, Yasuko Ashida, Yasuhik ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 122-133
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.122
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    A series of [1, 2, 4]triazolo[1, 5-b]pyridazines (5) and imidazo[1, 2-b]pyridazines (6) having cyclic amines was synthesized and evaluated for antihistaminic activity and inhibitory effect on eosinophil infiltration. When a piperidine or a piperazine containing a benzhydryl group and a suitable spacer was incorporated at the 6-position, the fused pyridazines were found to exhibit both antihistaminic activity and an inhibitory effect on eosinophil chemotaxis. Above all, 6a showed potent antihistaminic activity, but little blockade of central H1 receptors in contrast with its complete blockade of peripheral H1 receptors as determined by an ex vivo binding assay. Furthermore, 6a inhibited eosinophil infiltration of the skin caused by a topical antigen challenge in sensitized guinea pigs, while an antihistamine terfenadine was not effective. After the pharmacokinetic study, 6a was found to be rapidly hydrolyzed to 6o, which was also orally active. Compound 6o, 2-[6-[[3-[4-(diphenylmethoxy)piperidino]propyl]amino]imidazo[1, 2-b]pyridazin-2-yl]-2-methylpropionic acid dihydrate (TAK-427), having both antihistaminic and antiinflammatory activity, is currently undergoing clinical trials as a therapeutic agent for atopic dermatitis and allergic rhinitis.
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  • Pentacyclic Triterpenoids from the Aerial Parts of Lantana camara
    Sabira Begum, Aneela Wahab, Bina Shaheen Siddiqui
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 134-137
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.134
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    Three new pentacyclic triterpenoids, camaryolic acid (1), methylcamaralate (2) and camangeloyl acid (3) and six known compounds β-sitosterol 3-O-β-D-glucopyranoside (4), octadecanoic acid (5), docosanoic acid (6), palmitic acid (7), camaric acid (8) and lantanolic acid (9) were isolated from the aerial parts of Lantana camara. Structures of the new compounds were elucidated by spectroscopic and chemical methods.
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  • Studies on Non-Thiazolidinedione Antidiabetic Agents. 2. Novel Oxyiminoalkanoic Acid Derivatives as Potent Glucose and Lipid Lowering Agents
    Hiroshi Imoto, Yasuo Sugiyama, Hiroyuki Kimura, Yu Momose
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 138-151
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.138
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    We previously reported that (Z)-2-{4-[(5-methyl-2-phenyl-1, 3-oxazol-4-yl)methoxy]benzyloxyimino}-2-(4-phenoxyphenyl)acetic acid (3) showed potent glucose and lipid lowering effects in genetically obese and diabetic mice, KKAy. This compound also showed transcriptional activity for peroxisome proliferator-activated receptor (PPAR)-γ. We expanded on the structure–activity relationships of oxyiminoalkanoic acid derivatives based on this transcriptional activity (in vitro). Insertion of a carbon chain between the imino carbon and the carboxyl moiety of (Z)-2-{4-[(5-methyl-2-phenyl-1, 3-oxazol-4-yl)methoxy]benzyloxyimino}-2-phenylacetic acid (2) resulted in a marked increase in transcriptional activity at PPARγ. In vivo potencies of synthesized compounds, which showed strong functional activity at PPARγ, were tested using KKAy mice. Among these compounds, (E)-4-{4-[(5-methyl-2-phenyl-1, 3-oxazol-4-yl)methoxy]benzyloxyimino}-4-phenylbutyric acid (27) exhibited marked glucose and lipid lowering activity while showing no significant body weight gain. Compound (27) (TAK-559) showed favorable pharmacokinetic properties with good absorption and duration, and was considered as an attractive candidate for further evaluation.
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  • Glycosides of Atractylodes japonica
    Junichi Kitajima, Akane Kamoshita, Toru Ishikawa, Akihito Takano, Tats ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 152-157
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.152
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    From the water-soluble portion of the methanol extract of the fresh rhizome of Atractylodes japonica, five new sesquiterpenoid glycosides, including a compound having a secoguaiane skeleton, and a new aromatic compound glycoside were isolated together with ten known compounds. Their structures were clarified by spectral investigation.
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  • Quantitative Analysis of Bilobalide and Ginkgolides from Ginkgo biloba Leaves and Ginkgo Products Using 1H-NMR
    Young Hae Choi, Hyung-Kyoon Choi, Arno Hazekamp, Paloma Bermejo, Yvonn ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 158-161
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.158
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    1H-NMR spectrometry was applied to the quantitative analysis of the bilobalide, ginkgolides A, B, and C in Ginkgo biloba leaves and six kinds of commercial Ginkgo products without any chromatographic purification. The experiment was performed by the analysis of each singlet H-12, which were well separated in the range of δ 6.0—7.0 in the 1H-NMR spectrum. However, the H-12 protons of bilobalide and ginkgolides may have overlapped with H-6 or H-8 protons of the Ginkgo flavonoids. Therefore, the optimum 1H-NMR solvent for the analysis of the compound was selected through the evaluation of solvent effects on the resolution of these signals from the compounds. Acetone-d6–benzene-d6 (50 : 50) was found to be the best one among the solvents evaluated. The quantity of the compounds was calculated by the relative ratio of the intensity of each compound to the known amount of internal standard (25 μg/ml), phloroglucinol. This method allows rapid and simple quantitation of underivatized bilobalide and ginkgolides in 5 min without any pre-purification steps.
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  • Pharmacological Evaluation of Some New 6-Amino/Methyl Pyridine Derivatives
    Inguva Ravlee, Ramaiah Sivakumar, Nithyanantham Muruganantham, Navanee ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 162-170
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.162
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    In the present study, a series of 2-substituted-pyridines were synthesized and characterized by IR, 1H-NMR and Elemental Analysis. The compounds were assayed against seizures induced by maximal electro shock (MES) and pentylenetetrazole (scMet). Neurologic deficit was evaluated by the rotarod test. The decrease in the elevated motor activity by introceptive chemical stimuli (amphetamine antagonistic activity) was studied at the dose level of 25 and 50 mg/kg, antihistaminic and cardiac activity were also studied. All the compounds exhibited significant anticonvulsant activity. Compounds 2-(2-hydroxy-3-piperazinopropylamino)-6-aminopyridine, 2-[2-hydroxy-3-(1-imidazolyl)propylamino]-6-aminopyridine, 2-[2-(1-imidazolyl)ethylamino]-6-methylpyridine and 2-[2-(methylamino)ethylamino]-6-methylpyridine were most active of the series against MES-induced seizures. Compounds 2-[2-(phenylamino)ethylamino]-6-aminopyridine, 2-[2-[bis(2-hydroxyethyl)amino]ethylamino]-6-aminopyridine, 2-[2-(diethylamino)ethylamino]-6-methylpyridine and 2-[2-hydroxy-3-(1-imidazolyl)propylamino]-6-methylpyridine exhibited significant decrease in the elevated motor activity at the dose of 50 mg/kg. Remarkable sympathetic blocking activity was observed with 2-(2-hydroxy-3-piperazinopropylamino)-6-aminopyridine, 2-(2-hydroxy-3-morpholinopropylamino)-6-methylpyridine and 2-(2-hydroxy-3-piperazinopropylamino)-6-methylpyridine only. Compounds 2-[2-(diethylamino)ethylamino]-6-aminopyridine, 2-[2-[bis(2-hydroxyethyl)amino]ethylamino]-6-aminopyridine, and 2-[2-(diethylamino)ethylamino]-6-methylpyridine exhibited significant blocking of histamine induced contraction on guinea pig ileum.
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  • Nanoparticle Formation of Poorly Water-Soluble Drugs from Ternary Ground Mixtures with PVP and SDS
    Koichi Itoh, Adchara Pongpeerapat, Yuichi Tozuka, Toshio Oguchi, Keiji ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 171-174
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.171
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    Poorly water-soluble drugs N-5159, griseofulvin (GFV), glibenclamide (GBM) and nifedipine (NFP) were ground in a dry process with polyvinylpyrrolidone (PVP) and sodium dodecyl sulfate (SDS). Different crystallinity behavior of each drug during grinding was shown in the ternary Drug/PVP/SDS system. However, when each ternary Drug/PVP/SDS ground mixture was added to distilled water, crystalline nanoparticles which were 200 nm or less in size were formed and had excellent stability. Zeta potential measurement suggested that the nanoparticles had a structure where SDS was adsorbed onto the particles that were formed by the adsorption of PVP on the surface of drug crystals. Stable existence of crystalline nanoparticles was attributable to the inhibition of aggregation caused by the adsorption of PVP and SDS on the surface of drug crystals. Furthermore, the electrostatic repulsion due to the negative charge of SDS on a shell of nanoparticles could be assumed to contribute to the stable dispersion.
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  • Synthesis and Characterization of 6-O-Acyl-2-O-α-D-glucopyranosyl-L-ascorbic Acids with a Branched-acyl Chain
    Akihiro Tai, Daisuke Kawasaki, Kenji Sasaki, Eiichi Gohda, Itaru Yamam ...
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 175-180
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.175
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    We previously reported the chemical synthesis of a series of novel monoacylated vitamin C derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) possessing a straight-acyl chain of varying length from C4 to C18, as effective skin antioxidants. In this paper, we describe branched type of 6-Acyl-AA-2G derivatives (6-bAcyl-AA-2G) synthesized by use of a 2-branched-chain fatty acid anhydride as an acyl donor. The stability of 6-bAcyl-AA-2G in neutral solution was much higher than that of 6-Acyl-AA-2G, while they were susceptible to enzymatic hydrolysis for exerting vitamin C effect. These branched derivatives as well as 6-Acyl-AA-2G increased the radical scavenging activity against 1, 1-diphenyl-2-picrylhydrazyl and the lipophilicity in octanol/water-partitioning systems with increasing length of their acyl group. In addition, the 6-bAcyl-AA-2G derivative with an acyl chain of C12, 6-bDode-AA-2G had the excellent solubility to various solvents, suggesting easy handling in cosmetic use. These characteristics of 6-bAcyl-AA-2G may be available for skin care application as an effective antioxidant.
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  • The First Example of α-Thiomagnesiums Generated from Dithioacetal Monoxides with Grignard Reagent; Their Properties and Some Synthetic Applications
    Tsuyoshi Satoh, Kiyoshi Akita
    Article type: Regular Article
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 181-186
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.181
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    Dithioacetal monoxides were synthesized from aldehydes and cyclohexanone, and reaction of the dithioacetal monoxides with Grignard reagents was investigated. The dithioacetal monoxide synthesized from alkylaldehyde and 4-chlorobenzenethiol reacted with i-PrMgCl to afford the desired α-thiomagnesium in high yield. The generated α-thiomagnesium was found to be stable at room temperature and to be useful in organic synthesis. In contrast to this, the dithioacetal monoxides derived from benzaldehyde and cyclohexanone did not give satisfactory results.
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Notes
  • Studies on the Chemical Constituents of Stem Bark of Millettia leucantha: Isolation of New Chalcones with Cytotoxic, Anti-herpes Simplex Virus and Anti-inflammatory Activities
    Ampai Phrutivorapongkul, Vimolmas Lipipun, Nijsiri Ruangrungsi, Kanyaw ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 187-190
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.187
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    Four new chalcone derivatives (1, 4, 7, 10) were isolated from the stem bark of Millettia leucantha KURZ (Leguminosae) along with two known ones (2, 6) and five known flavones (3, 5, 8, 9, 11). Structure elucidation and unambiguous assignment of the isolates were achieved with the aid of 1D and 2D NMR extensive studies. Correlation of 10 to 4 was successfully done by reduction with Et3SiH/CF3CO2H. Moderate cytotoxic activity was observed in chalcones (1, 10), whereas dihydrochalcones (4, 6) showed moderate anti-Herpes Simplex Virus (HSV) activity. Interestingly, flavone 8 showed significant anti-inflammatory effects inhibiting both cyclooxygenase (COX)-1 and -2.
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  • Two New Flavonoids from Andrographis rothii
    Muntha Kesava Reddy, Mopuru Vijaya Bhaskar Reddy, Galla Jayakrishna, D ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 191-193
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.191
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    Two new flavonoids, 5, 7, 2′, 5′-tetramethoxyflavanone (1) and 5-hydroxy-7, 2′-dimethoxyflavone (2), together with two known flavones, skullcapflavone I (3) and echioidin (4) were isolated from the whole plant of Andrographis rothii. The structures of the new compounds were established by extensive one- and two-dimensional (1D- and 2D-) NMR spectral studies.
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  • A New Coumestan from Tephrosia calophylla
    Pennaka Hari Kishore, Mopuru Vijaya Bhaskar Reddy, Duvvuru Gunasekar, ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 194-196
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.194
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    A new coumestan, tephcalostan (1) has been isolated from the whole plant of Tephrosia calophylla BEDD. together with two known flavonoids, 7-O-methylglabranin (2) and kaempferol 3-O-β-D-glucopyranoside (3). The structure of tephcalostan was elucidated as 5′-(R)-8, 9-methylenedioxy-5′-isopropenyl-4′, 5′-dihydrofurano[2′, 3′:2, 3]coumestan by extensive one-and two-dimensional (1D- and 2D-)-NMR techniques including 1H–1H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser enhancement spectroscopy (NOESY) experiments.
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  • A New ent-Clerodane Diterpene from the Aerial Parts of Baccharis gaudichaudiana
    Shihori Akaike, Megumi Sumino, Toshikazu Sekine, Shujiro Seo, Nobuhito ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 197-199
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.197
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    A new ent-clerodane diterpene, named bacchariol (1) was isolated from the aerial parts of Baccharis gaudichaudiana DC. (Compositae), together with known ent-clerodane diterpenes (2, 3), eight known flavonoids (4—11) and 3, 5-dicaffeoylquinic acid (12). Their structures were determined by spectroscopic analyses. Flavonoids (7, 8, 11) and 12 showed moderate scavenging activities toward 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals.
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  • A New Triterpene Glucosyl Ester from the Fruit of the Blackberry (Rubus allegheniensis)
    Masateru Ono, Michiko Tateishi, Chikako Masuoka, Hiromasa Kobayashi, K ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 200-202
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.200
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    A new triterpene glucosyl ester, rubusside A, has been isolated from the fruit of the blackberry (Rubus allegheniensis PORT.) along with a known triterpene glucosyl ester, niga-ichigoside F1. The chemical structure of rubusside A was determined on the basis of spectroscopic data as well as chemical evidence.
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  • O-Demethylation and Sulfation of 7-Methoxylated Flavanones by Cunninghamella elegans
    Abdel-Rahim Sayed Ibrahim, Ahmed Mohamed Galal, Mohammed Shamim Ahmed, ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 203-206
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.203
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    Metabolism of 7-O-methylnaringenin (sakuranetin) by Cunninghamella elegans NRRL 1392 yielded naringenin and naringenin-4′-sulfate. C. elegans also converted 5, 3′, 4′-trihydroxy-7-methoxyflavanone into eriodictyol-4′-sulfate. Furthermore, incubation of 5, 4′-dihydroxy-7, 3′-dimethoxyflavanone with the same fungus gave homoeriodictyol (5, 7, 4′-trihydroxy-3′-methoxyflavanone) and homoeriodicytol-7-sulfate. The structures of the new metabolites were established by spectral analysis including 2D-NMR, HR-ESI-FT-MS beside hydrolysis by acid.
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  • Diterpenoids from Amazonian Crude Drug of Fabaceae
    Tadashi Kido, Masahiko Taniguchi, Kimiye Baba
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 207-208
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.207
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    A new cassane diterpene was isolated from Amazonian crude drug, “Acapu, ” the wood of Vouacapoua americana, together with two known cassane furanoditerpenes, (+)-vouacapenic acid and (+)-methyl vouacapenate. The structure was characterized as cassa-13(14), 15-dien-19-oic acid on the basis of spectroscopic evidence.
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  • Synthesis of Granulatimide Positional Analogues
    Takuji Yoshida, Masakazu Nishiyachi, Nobuyuki Nakashima, Masayuki Mura ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 209-214
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.209
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    The Stille coupling reaction of the stannylindole 13 with the 5-iodoimidazole derivative 14 (or 27) in the presence of PdCl2(PPh3)2 gave the corresponding indole-imidazole coupling product 15 (or 28), thereby affording a synthetic approach to 10-methylgranulatimide (7), 15-methylgranulatimide (11), and 10, 15-dimethylgranulatimide (12), as well as 10-methylisogranulatimide B (5).
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  • Bacopasides III—V: Three New Triterpenoid Glycosides from Bacopa monniera
    Ajit Kumar Chakravarty, Saraswati Garai, Kazuo Masuda, Takahisa Nakane ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 215-217
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.215
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    Three new saponins, designated as bacopasides III, IV and V have been isolated from Bacopa monniera WETTST. and their structures have been elucidated as 3-O-α-L-arabinofuranosyl (1→2)-β-D-glucopyranosyl jujubogenin (1), 3-O-β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl jujubogenin (2) and 3-O-β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl pseudojujubogenin (3) mainly on the basis of two dimensional (2D) NMR and other spectral analyses.
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  • Effects of Natural Polysaccharide Addition on Drug Release from Calcium-Induced Alginate Gel Beads
    Yoshifumi Murata, Kumiko Tsumoto, Kyoko Kofuji, Susumu Kawashima
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 218-220
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.218
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    Calcium-induced alginate gel beads (Alg-Ca) containing various polysaccharides, including an alginate hydrolysate, were prepared and the drug release profiles were investigated. Hydrocortisone (HC) was gradually released from Alg-Ca into the mimic gastric fluid, while in intestinal fluid, it was quickly released with the dissolution of Alg-Ca. However, with Alg-Ca containing 5% chitin (CT), dissolution of Alg-Ca was not observed, and release of HC showed apparent zero-order kinetics. Furthermore, addition of the alginate hydrolysate altered the HC-release profile for Alg-Ca.
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  • Asymmetric Borane Reduction of Prochiral Ketone Using Chiral Bis(α, α-diphenyl-2-pyrrolidinemethanol) Carbonate
    Takashi Yanagi, Ken Kikuchi, Hideki Takeuchi, Takehiro Ishikawa, Toshi ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 221-223
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.221
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    Chiral bis(α, α-diphenyl-2-pyrrolidinemethanol) carbonate (DPP2·H2CO3) is a useful asymmetric auxiliary for the asymmetric borane reduction of prochiral ketones. Chiral DPP2·H2CO3 is recoverable from the reaction and directly reusable for the reaction. The intermediate of KUR-1246, which we are developing as a new uterine relaxant, was synthesized using the methodology.
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  • Steric-Control for the Enantioselective Hydrolysis of Amino Acid Esters in Hybrid Membrane Systems
    Osamu Tanoue, Hideaki Ichihara, Koichi Goto, Yoko Matsumoto, Ryuichi U ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 224-226
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.224
    JOURNAL FREE ACCESS
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    The enantioselective hydrolysis of the amino acid esters, p-nitrophenyl-N-dodecanoyl-D(L)-phenylalaninates (C12-D(L)-Phe-PNP) catalyzed by active tripeptide, N-(benzyloxycarbonyl)-L-phenylalanyl-L-histidyl-L-leucine (Z-PheHisLeu) in the presence of coaggregates (hybrid membranes) composed of native phospholipid, L-α-dimyristoylphosphatidylcholine (DMPC) and nonionic surfactant, polyoxyethylene (8) lauryl ether (C12(EO)8) was easily controlled by regulating the reaction temperature and changing the composition of coaggregates. Furthermore, excellent correlations were observed between the enantioselectivity in the hydrolysis of C12-D(L)-Phe-PNP catalyzed by Z-PheHisLeu in the presence of coaggregates and physical properties of hybrid membranes. It is assumed that catalytic activities of tripeptide catalyst in hybrid membranes should be regulated by changing the microenvironments of reaction fields.
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  • Novel Channel Structure of Bile Acid-Guest Inclusion Complex Formed between Ursodeoxycholic Acid and Phenanthrene
    Toshiro Fukami, Kentaro Yamaguchi, Yuichi Tozuka, Kunikazu Moribe, Tos ...
    Article type: Note
    Subject area: [not specified]
    2003 Volume 51 Issue 2 Pages 227-229
    Published: 2003
    Released on J-STAGE: February 01, 2003
    DOIhttps://doi.org/10.1248/cpb.51.227
    JOURNAL FREE ACCESS
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    The crystal structure of inclusion complex between ursodeoxycholic acid (UDCA), and phenanthrene has been determined. UDCA molecules formed hydrogen bond network to provide the channel structure along b axis, and phenanthrene molecules were accommodated in the cavity with a stoichiometry of 1 : 1 molar ratio. The channel structure observed in the UDCA-phenanthrene complex was significantly different from that of inclusion complex previously reported for deoxycholic acid (DCA) and cholic acid (CA). Because of the mesh-like hydrogen bond network, channel framework of UDCA could have less flexibility than that of DCA and CA. The difference of molecular state of phenanthrene was clearly observed in solid-state fluorescence measurement.
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