Chemical and Pharmaceutical Bulletin

Regular Articles

An Experimental Approach to Study the Binding Properties of Vitamin E (α-Tocopherol) during Hairless Mouse Skin Permeation

Ae-Ri Cho LEE, Kakuji TOJO

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 659-663
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.659

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An experimental approach to study the binding properties of vitamin E has been developed. Total vitamin E solubility in the skin was determined by a partition study, followed by in vitro skin permeation studies with whole skin and stripped skin. The amount of freely diffusable vitamin E in the diffusion process was determined from the permeation profiles of whole skin and stripped skin by employing a bi-layer model. The concentrations of vitamin E in the stratum corneum and viable dermis were determined separately. By subtracting this amount from the total concentration of vitamin E in the skin, as determined by the solubility study, the amount of bound vitamin E was determined. After skin permeation reached a steady state, the donor solution was removed and the permeation study continued (desorption study). During the entire period of the desorption experiment, the amount of vitamin E in the receptor solution hardly increased and remained constant. After the desorption experiment, vitamin E still remaining in the skin was determined by extracting with tissue solubilizer, SOLABLE, and is considered as the amount of vitamin E strongly bound in the skin. The concentrations of bound vitamin E determined by permeation and desorption studies coincided relatively well. To further investigate skin binding of vitamin E, a differential scanning calorimetry study was performed. Vitamin E-treated stratum corneum showed phase transitions at 76 and 85 °C, associated with lipid transitions. The thermal transitions associated with the lipid transition suggested interactions of vitamin E with lipid components of the skin. During skin permeation, vitamin E forms a very strong reservoir in the skin tissue and this amount of vitamin E, about 30%, exists as a bound-form with the lipid components of the stratum corneum.

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Selective Flotation-Spectrophotometric Determination of Trace Copper(II) in Natural Waters, Human Blood and Drug Samples Using Phenanthraquinone Monophenylthiosemicarbazone

Magdi Ebrahiem KHALIFA, Magda Ali AKL, Shaban El-Sayed GHAZY

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 664-668
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.664

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Copper(II) forms 1:1 and 1:2 intense red complexes with phenanthraquinone monophenylthiosemicarbazone (PPT) at pH 3-3.5 and ≥6.5, respectively. These complexes exhibit maximal absorbance at 545 and 517 nm, the molar absorptivity being 2.3×10⁴ and 4.8×10⁴ l mol^-1cm^-1, respectively. However, the 1:1 complex was quantitatively floated with oleic acid (HOL) surfactant in the pH range 4.5-5.5, providing a highly selective and sensitive procedure for the spectrophotometric determination of Cu^II. The molar absorptivity of the floated Cu-PPT complex was 1.5×10⁵ l mol^-1cm^-1. Beer’s law was obeyed over the range 3-400 ppb at 545 nm. The analytical parameters affecting the flotation process and hence the determination of copper traces were reported. Also, the structure of the isolated solid complex and the mechanism of flotation were suggested. Moreover, the procedure was successfully applied to the analysis of Cu^II in natural waters, serum blood and some drug samples.

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Mechanistic Appraisal of the Charge-Transfer Complexes of Promethazine with Chloranil: A Modelling Approach

Michael U ADIKWU, Hans-Dieter HÖLTJE

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 669-674
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.669

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Various mechanisms are often used to explain the interaction between electron donors and acceptors. Commonly proposed mechanisms are those in which the acceptor interacts with the aromatic π-systems in the donor molecule or the acceptor forms a weak interaction of the Lewis acid with Lewis base type. In this study, the above mechanisms were examined as well as other possible mechanisms. Promethazine was chosen as the model drug containing aromatic systems capable of π-π interaction as well as N-methyl group capable of forming a complex with the weak Lewis acid, p-chloranil. Our modelling studies revealed that the situation where the p-chloranil interacts with a protonated N-methyl group is the most significant mechanism of interaction, based on the calculated energies for the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the Tripos force field energy terms and also the stability of the complexes during molecular dynamics simulations.

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Synthesis and Cytotoxic Activity of Benzopyranoxanthone Analogues of Benzo[b]acronycine and Psorospermine

Chavalit SITTISOMBUT, Nadine COSTES, Sylvie MICHEL, Michel KOCH, Fran& ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 675-679
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.675

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Condensation of 3-hydroxy-2-naphthalenecarboxylic acid with phloroglucinol afforded 1, 3-dihydroxy-12H-benzo[b]xanthen-12-one. Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to a series of benzo[b]pyrano[2, 3-i]xanthen-6-ones and benzo[b]pyrano[3, 2-h]xanthen-7-ones related to psorospermine and benzo[b]acronycine. In contrast with what is observed in the pyridoacridone and benzopyridoacridone series, the linear benzo[b]-pyrano[2, 3-i]xanthen-6-one derivatives were more potent than their angular benzo[b]pyrano[3, 2-h]xanthen-7-one isomers. cis-3, 4-Diacetoxy-5-methoxy-2, 2-dimethyl-3, 4-dihydro-2H, 6H-benzo[b]pyrano[2, 3-i]xanthen-6-one, the most active among the new compounds, was more potent than acronycine in inhibiting the proliferation of L1210 murine leukemia cells.

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Prediction of Endocrine Disruptors Based on a New Structure—Activity Relationship for Sex and Environmental Hormones Using Chemical Hardness Concept

Shigeki KOBAYASHI, Toshiya SUGAYA, Nobuo SAKATA, Masami UEBAYASI, Keii ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 680-688
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.680

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Classification of the relationship between electronic structures and biological activities of endocrine disruptors (so-called environmental hormones) was attempted using the parameters of absolute hardness (η), absolute electronegativity (χ), and global softness (S), approximately defined as η=1/2(ε_LUMO−ε_HOMO), χ=−1/2(ε_HOMO+ε_LUMO), and S=1/η, respectively, based on the hardness concept. The strength of binding affinity and toxicity of the chemicals were approximately proportional to the absolute hardness, and laterally toxic chlorinated PCDDs, PCBs, and DDTs are classified as chemically soft. Here we found that the electronic structures of environmental hormones can be classified into four main groups: 17β-estradiol type (group I), testosterone type (group II), thyroxine type (group III), and HCH (hexachlorocyclohexane) type (group IV). Therefore, if we can predict the coordinate (χ, η) of the electronic structure of one chemical on the η-χ activity diagram, we would be able to predict the receptor with which the chemicals (environmental hormones) interact. For instance, 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (2, 3, 7, 8-TCDD) is classified in group III, therefore, it would bind with the thyroid receptor more than the estrogen receptor (group I). It appears that dibutyl phthalate would not interact with estrogen receptor because it does not belong to group I. In addition, the coordinates of these four groups do not complementarily overlap with the electronic structures of 20 natural amino acid residues. The η-χ activity diagram is a new tool for the prediction of the toxicity and biological activity of environmental hormones.

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Novel Products from Oxidation of the Norditerpenoid Alkaloid Pseudaconine with HIO₄

Feng-Peng WANG, Qiao-Hong CHEN, Zheng-Bang LI, Bo-Gang LI

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 689-694
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.689

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Oxidation of pseudaconine 8, a norditerpenoid alkaloid, with HIO₄ led to a series of novel interesting products, depending greatly on reaction medium and work-up conditions. Treatment of 8 in MeOH-H₂O (1:1) with NaIO₄ gave compounds 10 and 11, but compound 12 was obtained quantitatively when the final reaction solution was alkalized with conc. NH₄OH. The imine 12 was also obtained in 100% yield by treating 8 in 5% HCl solution with NaIO₄ followed by alkalizing the reaction products to pH>9 with conc. NH₄OH. When the work up pH was 7-8, only N, O-mixed acetal-ketal 13 was formed in 96% yield, which was converted quantitatively to 12 by further alkalizing. When the reaction mixture was alkalized to pH 7-8 with Na₂CO₃, a hemiacetalketal 14 was afforded quantitatively, which was converted to 15 in 87% yield by further treatment with Na₂CO₃ or 5% NaOH methanol. Compound 15 could be converted back to 14 by treatment with 10% HCl solution. Acetylation of the imine 12 gave the compounds 16 and 17 in 15% and 19% yields, respectively. All of the new compounds were isolated and fully characterized.

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Constituents of Crinoidea. 2. Isolation and Structure of the Novel Type Gangliosides from the Feather Star Comanthus japonica

Kazuyoshi ARAO, Masanori INAGAKI, Ryuichi HIGUCHI

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 695-698
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.695

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Two novel type gangliosides CJP2 and CJP3 have been obtained from the feather star Comanthus japonica. On the basis of methylation linkage analysis combined with ammonolysis and other chemical and spectroscopic evidence, the chemical structures of CJP2 and CJP3 were determined to be α-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide and α-9-O-Me-NeuGc-(2→11)-α-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide, respectively. These gangliosides are unique in that they are inositolphosphoceramide derivatives possessing sialic acid; such gangliosides have not previously been identified. The presence of 9-O-methyl-N-glycolyl-neuraminosyl residues is also unique in naturally occurring gangliosides.

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An Iridoid Gentiobioside, a Benzophenone Glucoside and Acylated Flavone C-Glycosides from Tripterospermum japonicum (SIEB. et ZUCC.) MAXIM

Hideaki OTSUKA, Kaori KIJIMA

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 699-702
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.699

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From aerial parts of Tripterospermum japonicum, 6′-O-β-D-glucopyranosylmorroniside, benzophenone glucoside, named triptephenoside and 2′′′- and 4′′′-O-acetyl-2″-O-α-L-rhamnopyranosylisovitexins were isolated, along with known iridoid and secoiridoid glucosides, and C-glycosyl flavones.

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Synthesis and Azannulation of Pyridinylaminohexadienones

Maria Teresa COCCO, Cenzo CONGIU, Valentina ONNIS

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 703-706
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.703

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4-(2-Pyridinylamino)-1, 1, 1-trifluoro-3-penten-2-ones 3, obtained from the reaction of commercially available 2-aminopyridine derivatives and 4-methoxy-1, 1, 1-trifluoro-3-penten-2-one 2, were converted to 6-(dimethylamino)-4-(2-pyridinylamino)-3, 5-hexadien-2-ones 4 by treatment with dimethylformamide dimethyl acetal. Azannulation of hexadienones 4 afforded 4-(2-pyridinylamino)-2-trifluoromethylpyridines 5 and 2-(trifluoroacetylmethylene)pyrido[1, 2-a]pyrimidines 6, classes of compounds particularly interesting from a chemical and biological point of view.

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Farnesyl Hydroxybenzoic Acid Derivatives from Ferula kuhistanica

Bei CHEN, Yoshihisa TAKAISHI, Kazuyoshi KAWAZOE, Kimiko TAMEMOTO, Gish ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 707-710
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.707

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Four new farnesyl hydroxybenzoic acid derivatives, kuhistanols E-H (1-4), were isolated from the roots of the Uzbekistan medicinal plant Ferula kuhistanica. The structures of the new compounds were elucidated based on spectroscopic and chemical evidence.

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Studies on Chemical Modification of Monensin IX. Synthesis of 26-Substituted Monensins and Their Na⁺ Ion Transport Activity

Rie TANAKA, Akito NAGATSU, Hajime MIZUKAMI, Yukio OGIHARA, Jinsaku SAK ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 711-715
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.711

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The C-26 modified monensin derivatives, 26-O-benzoylmonensin (3), 26-O-benzylmonensin (4) and 26-phenylaminomonensin (5) were prepared from monensin (1). Na⁺ ion transport activity through biological membrane and antibacterial activity of 3-5 were evaluated and compared with the activities reported for a 26-phenylurethane derivative (2). Among these compounds, 5 showed the largest Na⁺ ion transport and antibacterial activities. In these compounds, the formation of head-to-tail hydrogen bonds was suggested to be an important factor for Na⁺ ion transport and antibacterial activities.

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Effects of Constituents from the Bark of Magnolia obovata on Nitric Oxide Production in Lipopolysaccharide-Activated Macrophages

Hisashi MATSUDA, Tadashi KAGEURA, Mamiko ODA, Toshio MORIKAWA, Yasuko ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 716-720
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.716

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The methanolic extract from a Japanese herbal medicine, the bark of Magnolia obovata, was found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages. By bioassay-guided separation, three neolignans (magnolol, honokiol, obovatol) and three sesquiterpenes (α-eudesmol, β-eudesmol, γ-eudesmol) were obtained as active constituents. A trineolignan (magnolianin), a phenylpropanoid glycoside (syringin), lignan glycosides (liriodendrin, (+)-syringaresinol 4′-O-β-D-glucopyranoside) and a sesquiterpene (caryophyllene oxide) did not show any activity. On the other hand, sesquiterpene-neolignans (eudesmagnolol, clovanemagnolol, caryolanemagnolol, eudeshonokiol A, eudesobovatol A) showed the strong cytotoxic effects. Active constituents (magnolol, honokiol, obovatol) showed weak inhibition for inducible NO synthase (iNOS) enzyme activity, but potent inhibition of iNOS induction and activation of nuclear factor-κB.

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Synthesis and Antimalarial Activity of Febrifugine Derivatives

Yasuo TAKEUCHI, Midori KOIKE, Kumiko AZUMA, Hiromi NISHIOKA, Hitoshi A ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 721-725
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.721

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The regiosomers (2a, b) of the piperidine ring of febrifugine (1a) and isofebrifugine (1b) were synthesized from 4-allyl-3-piperidone (5). Reduction of 5 afforded a mixture of the trans and cis alcohols (6a, b) without diastereoselectivity; this result differentiated it from the reduction of 2-allyl-3-piperidone (14). The antimalarial activity of 2a, b and related compounds was tested.

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Steroidal Glycosides from the Bulbs of Camassia leichtlinii and Their Cytotoxic Activities

Minpei KURODA, Yoshihiro MIMAKI, Fusako HASEGAWA, Akihito YOKOSUKA, Yu ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 726-731
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.726

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Phytochemical analysis of the bulbs of Camassia leichtlinii (Liliaceae) resulted in the isolation of six new spirostanol saponins, a new furostanol saponin, a cholestane glucoside, and four known steroidal saponins. The structures of the new saponins were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy, and by the results of hydrolytic cleavage. Cytotoxic activities of the isolated compounds against human oral squamous cell carcinoma (HSC-2) cells and normal human gingival fibroblasts (HGF) are also reported.

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Studies on the Constituents of Catalpa Species. VI. Monoterpene Glycosides from the Fallen Leaves of Catalpa ovata G. DON

Koichi MACHIDA, Megumi ANDO, Yasunori YAOITA, Rie KAKUDA, Masao KIKUCH ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 732-736
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.732

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Five new monoterpene glycosides, ovatolactone 7-O-(6′-O-p-hydroxybenzoyl)-β-D-glucopyranoside, ovatic acid methyl ester 7-O-(6′-O-p-hydroxybenzoyl)-β-D-glucopyranoside, 7-O-p-hydroxybenzoylovatol 1-O-(6′-O-p-hydroxybenzoyl)-β-D-glucopyranoside, 6′-O-p-hydroxybenzoylcatalposide and (2E, 6R)-2, 6-dimethyl-8-hydroxy-2-octenoic acid 8-O-[6′-O-(E)-p-coumaroyl]-β-D-glucopyranoside were isolated from the fallen leaves of Catalpa ovata G. DON. Their structures were determined by extensive spectroscopic studies and syntheses.

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Alkaloids, Diarylheptanoid and Naphthalene Carboxylic Acid Ester from Rhoiptelea chiliantha

Zhi-Hong JIANG, Takashi TANAKA, Chizuko INUTSUKA, Isao KOUNO

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 737-740
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.737

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Two pyrrolidine alkaloids (1, 2) were isolated from the fruits of Rhoiptelea chiliantha DIEL et HAND.-MAZZ. (Rhoipteleaceae). A diphenyl ether-type diarylheptanoid (3), and a naphthalene carboxylic acid methyl ester (4) which is biogenetically-related to juglone were isolated from the branches of the same plant. Their chemical structures were elucidated on the basis of spectroscopic analysis and chemical evidence.

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Bioactive Saponins and Glycosides. XVIII. Nortriterpene and Triterpene Oligoglycosides from the Fresh Leaves of Euptelea polyandra SIEB. et ZUCC. (2): Structures of Eupteleasaponins VI, VI Acetate, VII, VIII, IX, X, XI, and XII

Toshiyuki MURAKAMI, Hideo OOMINAMI, Hisashi MATSUDO, Masayuki YOSHIKAW ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 741-746
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.741

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Following the elucidation of eupteleasaponins I, II, III, IV, V, and V acetate, eupteleasaponins VI, VI acetate, VII, VIII, IX, X, XI, and XII were isolated from the fresh leaves of Euptelea polyandra SIEB. et ZUCC. The structures of eupteleasaponins VI-XII were determined on the basis of chemical and physicochemical evidence.

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Relationship of Electrochemical Oxidation of Catechins on Their Antioxidant Activity in Microsomal Lipid Peroxidation

Bin YANG, Akira KOTANI, Kensuke ARAI, Fumiyo KUSU

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 747-751
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.747

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The oxidation potentials of catechins were measured by employing flow-through column electrolysis. The oxidation potentials of catechins were shown to depend on their structures. At the same time, the antioxidant activity of catechins on NADPH-dependent lipid peroxidation in rat liver microsomes was evaluated. Catechins showed a 50% inhibition of lipid peroxidation in the concentration range of 10-51 μM. Among those studied, galloylated catechins exhibited stronger antioxidant activities than those of nongalloylated catechins. A quantitative relationship has been obtained to describe the antioxidant activity of catechins: log IC₅₀ (μM)=1.56+2.49E_1/2 (V)-0.29 logP (r=0.907), where IC₅₀ represents the concentration for 50% in hibition of lipid peroxidation, E_1/2 represents the half-wave potential of the first oxidation wave, and P represents the octanol/water partition coefficient. This relationship suggested two important characteristics determining catechin antioxidant activity, namely the ease of oxidation and the lipophilicity.

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Notes

Triterpenoid Saponins from Berries of Hedera colchica

Vakhtang MSHVILDADZE, Riad ELIAS, Robert FAURE, Laurent DEBRAUWER, Gen ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 752-754
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.752

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Fifteen triterpenoid saponins were isolated from the berries of Hedera colchica and their structures established on the basis of chemical and spectroscopic evidence. Among them, two are new compounds: colchiside A (3) and colchiside B (15) and four are described for the first time in the berries of Hedera colchica (compounds 1, 8, 9 and 11).

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Glucose and Lactate Biosensors Prepared by a Layer-by-Layer Deposition of Concanavalin A and Mannose-Labeled Enzymes: Electrochemical Response in the Presence of Electron Mediators

Yuka KOBAYASHI, Tomonori HOSHI, Jun-ichi ANZAI

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 755-757
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.755

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An electrochemical response of glucose and lactate biosensors which were prepared by coating a platinum electrode with a thin film composed of concanavalin A and mannose-labeled glucose oxidase (GOx) or lactate oxidase (LOx) was evaluated in the presence of ferrocene derivatives as electron mediator. Both glucose and lactate biosensors showed catalytic current to glucose and lactate, respectively, in cyclic voltammetry, suggesting that the ferrocene derivatives can mediate electron transport smoothly from the reduced forms of GOx and LOx in the thin films to the electrode. Among the three kinds of ferrocene derivatives used, ferrocenylmethanol was found to be the most suitable electron mediator because of its low oxidation potential. The glucose and lactate sensors gave useful calibration graphs, in which higher detection limits were reached as compared with those observed when the sensors were operated in the absence of electron mediator.

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New Triterpenoid Saponins from Maesa tenera

Kazuo KOIKE, Zhonghua JIA, Tamotsu NIKAIDO

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 758-761
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.758

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Two new triterpenoid saponins, maetenosides A and B were isolated from the aerial parts of Maesa tenera and were respectively defined as 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)][β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl camelliagenin A 22-O-angelate (1) and 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→3)][β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl camelliagenin A 22-O-angelate (2). Their structures were established on the basis of chemical and spectroscopic methods.

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Purification and Characterization of Anti-complementary Polysaccharide from Leaves of Thymus vulgaris L.

Hyug CHUN, Woo Jin JUN, Dong Hoon SHIN, Bum Shik HONG, Hong Yon CHO, H ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 762-764
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.762

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For the purification of the anti-complementary polysaccharide from Thymus vulgaris L., the hot-water extract of thyme leaves was successively fractionated by ethanol precipitation and ultra-filtration. The retentate with 300-kDa membrane cartridge showed a potent anti-complementary activity. It was further purified by open column chromatographies on DEAE-Toyopearl 650C, Butyl-Toyopearl 650M and Sephadex G-100, obtaining TV3-IIA-I, the purified anti-complementary polysaccharide. The anti-complementary polysaccharide exhibited the anti-complementary activity via both classical and alternative pathways. Based upon the methylation analysis and the reaction with β-glucosyl Yariv reagent, the anti-complementary polysaccharide from thyme might contain an arabinogalactan moiety, at least in part.

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Latifolosides K and L, Two New Triterpenoid Saponins from the Bark of Ilex latifolia

Jing HUANG, Xu WANG, Yukio OGIHARA, Noriko SHIMIZU, Toshiyuki AKIYAMA, ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 765-767
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.765

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Two new triterpenoid saponins, latifoloside K (1), 3-O-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)-]-α-L-arabinopyranosyl 3β-hydroxy-urs-12, 18-dien-28-oic acid 28-O-β-D-glucopyranosyl ester and latifoloside L (2), 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)-]-α-L-arabinopyranosyl 3β, 19α-dihydroxyursolic acid, were isolated from the bark of Ilex latifolia THUNB. Also isolated were two known compounds, ilekudinoside A (3) and kudinoside G (4). Structural assignments were established on the basis of spectroscopic data and chemical evidence.

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Three New Flavonol Malonylrhamnosides from Ribes alpinum

Katia GLUCHOFF-FIASSON, Bernard FENET, Jean-Claude LECLERC, Joël ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 768-770
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.768

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Three new flavonol malonylrhamnosides, 3-O-(4″-O-malonyl)-α-L-rhamnopyranosides of mearnsetin, myricetin and quercetin respectively, together with the corresponding mearnsitrin, myricitrin, quercitrin and the 4-O-methyl phloracetophenone 2-O-β-D-glucopyranoside, were isolated from the leaves of Ribes alpinum and fully characterized by spectrocopic methods including 2D NMR.

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A New Secoiridoid Glucoside, Amaronitidin, from the Peruvian Folk Medicine “Hercampuri” (Gentianella nitida)

Nobuo KAWAHARA, Kazuo MASUDA, Setsuko SEKITA, Motoyoshi SATAKE

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 771-772
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.771

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A new secoiridoid glucoside designated amaronitidin (1) was isolated from the Peruvian folk medicine “Hercampuri” (Gentianella nitida) along with three known secoiridoid glucosides. Their structures were determined by extensive spectroscopic investigation.

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Two New Podophyllotoxin Glucosides from Sinopodophyllum emodi (WALL.) YING

Changqi ZHAO, Jing HUANG, Akito NAGATSU, Yukio OGIHARA

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 773-775
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.773

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Two new aryltetralin-type lignans, isopodophyllotoxin 7′-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1) and 4-demethyl-picropodophyllotoxin 7′-O-β-D-glucopyranoside (2), along with eight known podophyllotoxin derivatives: 4-demethyl-podophyllotoxin 7′-O-β-D-glucopyranoside (3), podophyllotoxin 7′-O-β-D-glucopyranoside (4), deoxypodophyllotoxin (5), picropodophyllotoxin (6), podophyllotoxin (7), 4-demethyl-picropodophyllotoxin (8), 4-demethyl-podophyllotoxin (9), and 4-demethyl-deoxypodophyllotoxin (10), were isolated from the roots and rhizomes of Sinopodophyllum emodi (WALL.) YING (Berberidaceae). Their structures were identified based on NMR spectral data and chemical evidence.

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Medicinal Foodstuffs. XXIII.¹⁾ Structures of New Oleanane-Type Triterpene Oligoglycosides, Basellasaponins A, B, C, and D, from the Fresh Aerial Parts of Basella rubra L.

Toshiyuki MURAKAMI, Kazuhiro HIRANO, Masayuki YOSHIKAWA

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 776-779
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.776

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Basellasaponins A, B, C, and D, oleanane-type triterpene oligoglycosides having the dioxolane-type substituent, were isolated from the fresh aerial parts of Basella rubra L. together with betavulgaroside I, spinacoside C, and momordins IIb and IIc. The chemical structures of basellasaponins A, B, C, and D were determined from chemical and physicochemical evidence.

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Antioxidative Glucosides from the Fruits of Ligustrum lucidum

Zhen-Dan HE, Paul Pui-Hay BUT, Tak-Wah Dominic CHAN, Hui DONG, Hong-Xi ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 780-784
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.780

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The ethanol extract of the fruits of Ligustrum lucidum was shown to have inhibitory effects on the hemolysis of red blood cells induced by 2, 2′-azo-bis-(2-amidinopropane) dihydrochloride. Bioassay-guided analysis led to the isolation of ten secoiridoid glucosides. Two of them were new, lucidumosides C and D. Their structures were elucidated by spectroscopic methods. The other eight compounds were identified as oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, neonuezhenide, lucidumoside A and lucidumoside B. Five compounds, oleoside dimethyl ester, oleuropein, neonuezhenide, lucidumoside B and lucidumoside C, exhibited strong antioxidant effect against hemolysis of red blood cells induced by free radicals.

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Hopeafuran and a C-Glucosyl Resveratrol Isolated from Stem Wood of Hopea utilis

Toshiyuki TANAKA, Tetsuro ITO, Yoshimi IDO, Ken-ichi NAKAYA, Munekazu ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 785-787
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.785

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A new resveratrol dimer and a new C-glucosyl resveratrol were isolated from stem wood of Hopea utilis along with nine stilbenoid derivatives comprising bergenin and (+)-lyoniresinol. The structures have been elucidated on the basis of the spectroscopic evidence.

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An Improved Synthesis of Butyl 4-[(4-Amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)

Jun SAKAGUCHI, Taijiro HIGASHI, Takahiro AZUMA, Tomio SUZUKI, Nobuhiko ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 788-790
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.788

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A new and facile route for the synthesis of the novel gastrointestinal prokinetic butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (1b), which exhibited potent gastro- and colon-prokinetic activities by oral administration without significant side effects, was established. The key intermediate, butyl 4-amino-1-piperidineacetate (16), was prepared from commercially available 4-amino-1-benzylpiperidine (2) in a high yield with four steps. Compound 1b was prepared by condensation of commercially available 4-amino-5-chloro-2-methoxybenzoic acid (7) with 16 in 84% yield. This improved synthetic route was appropriate for large-scale synthesis of 1b.

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α-Glucosidase Inhibitors with a 4, 5, 6, 7-Tetrachlorophthalimide Skeleton Pendanted with a Cycloalkyl or Dicarba-closo-dodecaborane Group

Sonei SOU, Hiroyasu TAKAHASHI, Ryu YAMASAKI, Hiroyuki KAGECHIKA, Yasuy ...

Article type: scientific monograph
2001 Volume 49 Issue 6 Pages 791-793
Published: 2001
Released on J-STAGE: April 26, 2002

DOIhttps://doi.org/10.1248/cpb.49.791

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Previous studies of α-glucosidase inhibitors derived from thalidomide revealed that 4, 5, 6, 7-tetrachloro-N-alkylphthalimide derivatives are superior lead compounds. Structure-activity relationship studies indicated that a hydrophobic group at the N(2) position is mandatory for potent activity. Accordingly, we have designed and synthesized some 4, 5, 6, 7-tetrachloro-N-cycloalkylphthalimide and 4, 5, 6, 7-tetrachloro-N-dicarba-closo-dodecaborane derivatives. The prepared compounds exhibited potent α-glucosidase-inhibitory activity. Among them, 4, 5, 6, 7-tetrachloro-N-cycloheptylphthalimide (9) showed the most potent activity, being approximately 30 times more active than the classical inhibitor, 1-deoxynojirimycin (1).

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