研究者詳細 - 木村　幸敬

論文 - 木村　幸敬

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Hydrolysis of disaccharides containing glucose residue in subcritical water 査読

T Oomori, SH Khajavi, Y Kimura, S Adachi, R Matsuno

BIOCHEMICAL ENGINEERING JOURNAL 18 ( 2 ) 143 - 147 2004年5月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELSEVIER SCIENCE SA

The hydrolysis of disaccharides consisting of two glucose residues or of glucose and fructose or galactose residues in subcritical water was measured using a tubular reactor at 10 MPa and 180-260 degreesC. The relationship between the fraction of remaining disaccharide and the residence time could be expressed by the Weibull equation for all the disaccharides tested at any temperature. The susceptibility to hydrolysis largely depended on the type of disaccharide, and it was found that the electrostatic potential charge of a glucosidic oxygen atom was an indication for the susceptibility of disaccharide to the hydrolysis. It was also shown that the enthalpy-entropy compensation held for the hydrolysis of disaccharides in subcritical water. (C) 2003 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.bej.2003.08.002

Relationship between structure and permeability of dipeptide derivatives containing tryptophan and related compounds across human intestinal epithelial (Caco-2) cells 査読

R Ano, Y Kimura, M Urakami, M Shima, R Matsuno, T Ueno, M Akamatsu

BIOORGANIC & MEDICINAL CHEMISTRY 12 ( 1 ) 249 - 255 2004年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

The permeability of dipeptide derivatives containing tryptophans and indole derivatives through Caco-2 cells was used as an in vitro intestinal absorption model in order to clarify structural factors which influence their intestinal epithelial permeation and metabolism. Most peptide derivatives were hydrolysed not only by the cytosolic enzymes in Caco-2 cells during permeation but also by enzymes released to the apical. solution before cell permeation. The N-terminal blocked dipeptides were more resistant to hydrolases expressed in the Caco-2 cells and indole derivatives were not entirely degraded. Based on compound concentration dependency and comparison of permeability coefficients in apical-to-basolateral and basolateral-to-apical directions, the main absorption mechanism of compounds were determined. Compounds were then classified into three groups; (1) passively transported compounds, (2) actively transported compounds and (3) compounds excreted by P-glycoprotein. (C) 2003 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2003.10.001

Preparation of fine W/O/W emulsion through membrane filtration of coarse W/O/W emulsion and disappearance of the inclusion of outer phase solution 査読

M Shima, Y Kobayashi, T Fujii, M Tanaka, Y Kimura, S Adachi, R Matsuno

FOOD HYDROCOLLOIDS 18 ( 1 ) 61 - 70 2004年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELSEVIER SCI LTD

A water-in-oil-in-water (W/O/W) emulsion was prepared as a carrier system for the daily uptake of a bioactive compound using decaglycerol monolaurate and hexaglyceryl condensed ricinolate as hydrophilic and lipophilic surfactants, respectively. 1,3,6,8-Pyrenetetrasulfonic acid tetrasodium salt (PTSA) was used as a hydrophilic model compound of a bioactive substance. Membrane filtration of a coarse W/O/W emulsion prepared with a rotor/stator homogenizer produced a fine emulsion which had a mean oil-droplet diameter of < 1 mum. The emulsions were stable for I week at 4 degreesC. The encapsulation efficiency of PTSA was > 90%. Microscopic observations revealed that the fluorescent material in the outer-phase solution was included into the oil phase during rotor/stator homogenization. It was suggested that because the rotor/stator homogenizer was used to produce both O/W and W/O/W emulsions, some part of the outer phase solution would be included in the oil phase during the second homogenization. The fluorescence shown in the oil droplets of the coarse W/O/W emulsion was diminished after membrane emulsification. This phenomenon suggested that the included outer-phase solution was released to the outer-phase solution from the interior of the W/O/W oil droplets during the membrane emulsification. (C) 2003 Elsevier Ltd. All rights reserved.

DOI： 10.1016/S0268-005X(03)00042-0

Decomposition kinetics of maltose in subcritical water 査読

SH Khajavi, Y Kimura, T Oomori, R Matsuno, S Adachi

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 68 ( 1 ) 91 - 95 2004年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

The decomposition process of maltose in subcritical water was studied using a tubular reactor in the temperature range of 180 to 260degreesC and at 10 MPa. The formation of glucose and 5-hydroxymethyl-2-furaldehyde during the maltose decomposition was also observed. The decomposition rate of maltose was faster at higher temperatures. The rate was approximated by first-order kinetics during the early stage of the decomposition, but was accelerated and deviated from these kinetics at the later stage. The effluent pH decreased as the residence time in the reactor increased and the decrease of pH affected the maltose decomposition rate and glucose formation. Low pH of a feed solution accelerated maltose decomposition. A good correlation was obtained between the pH of the effluent and the rate constant of the first-order kinetics.

DOI： 10.1271/bbb.68.91

Hydrolysis of the oil phase of a W/O/W emulsion by pancreatic lipase 査読

M Shima, M Tanaka, Y Kimura, S Adachi, R Matsuno

JOURNAL OF CONTROLLED RELEASE 94 ( 1 ) 53 - 61 2004年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：ELSEVIER SCIENCE BV

W/O/W emulsions are expected to protect bioactive substances from degradation by pancreatic enzymes. We investigated the enzymatic hydrolysis of the oil phase and release of a marker substance from the inner-aqueous phase to the outer-aqueous phase using an artificial digestive fluid. Octanoic acid triacylglycerol (C8TG) was used as the oil phase. W/O/W emulsions were prepared by two-step homogenization and succeeding membrane filtration. When the artificial digestive fluid containing lipase and gall was added to the emulsion, release of the marker substance from the inner-phase solution, oil-phase hydrolysis, and emulsion coalescence occurred in that order. When a coarse emulsion and 0.2- and 0.8-mum membrane-filtered fine emulsions were treated with the fluid for 1 h, the degrees of C8TG hydrolysis were 3.8%, 55% and 57%, the fractions of the marker substance released from the inner-water phase were 2.7%, 89% and 72%, and the median diameters of the oil droplets were changed from 32 to 23 mum, 0.71 to 27 mum, and from 2.2 to 26 mum, respectively. These results suggested that the diameter of the oil droplets in the W/O/W emulsion significantly affected the release profile of the marker loaded in the inner-water phase of the emulsion. (C) 2003 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.conrel.2003.09.008

Relationships between structure and high-throughput screening permeability of peptide derivatives and related compounds with artificial membranes: application to prediction of Caco-2 cell permeability 査読

R Ano, Y Kimura, M Shima, R Matsuno, T Ueno, M Akamatsu

BIOORGANIC & MEDICINAL CHEMISTRY 12 ( 1 ) 257 - 264 2004年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

To evaluate absorption of compounds across the membrane via a transcellular route, the permeability of peptide derivatives and related compounds was measured by the parallel artificial membrane permeation assay (PAMPA). The permeability coefficients by PAMPA were analyzed quantitatively using classical QSAR and Volsurf approaches with the physicochemical parameters. The results from both approaches showed that hydrogen bonding ability of molecules in addition to hydrophobicity at a particular pH were significant in determining variations in PAMPA permeability coefficients. The relationship between Caco-2 cell permeability and artificial lipid membrane permeability was then determined. The compounds were sorted according to their absorption pathway in the plot of the Caco-2 cell and PAMPA permeability coefficients. (C) 2003 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2003.10.002

Kinetics on Disaccharide Decomposition in Subcritical Water

Kimura Yukitaka, Khajavi Shabnam Haghighat, Oomori Toshinobu, Matsuno Ryuichi, Adachi Shuji

アジア・太平洋化学工学会議発表論文要旨集 2004 374 - 374 2004年

記述言語：英語出版者・発行元：公益社団法人化学工学会

Decomposition of disaccharides consisting of two glucose residues or glucose and fructose or galactose residues was measured using a tubular reactor at various residence time under the condition of 160 to 260°C and 10 MPa. The decomposition processes were expressed by the Weibull equation for all the disaccharides at any temperature. The susceptibility to decomposition depended on the type of glucosidic bond and was related to an electrostatic potential charge on the oxygen atom in the bond. Detail studies for decomposition kinetics were performed for maltose and sucrose. A change of pH during the decomposition intensively affected the decomposition rate, which could be also expressed by autocatalytic equation for sucrose decomposition.

DOI： 10.11491/apcche.2004.0.374.0

Anti-oxidant activity of acyl ascorbates in intestinal epithelial cells 査読

Y Kimura, H Kanatani, M Shima, S Adachi, R Matsuno

BIOTECHNOLOGY LETTERS 25 ( 20 ) 1723 - 1727 2003年10月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：KLUWER ACADEMIC PUBL

The anti-oxidant activity of acyl ascorbates, with acyl chain lengths of 10 to 18, was measured in an intestinal epithelial cell line. All the acyl ascorbates exhibited the activity for the oxidization induced by three different types of oxidants, at levels higher than ascorbic acid. Myristoyl ascorbate was the most effective and showed activity at 3 x 10(-12) to 3 x 10(-6) M. Incubation with myristoyl ascorbate for more than 3 h was needed to sufficiently suppress the oxidization of the intestinal cell monolayers.

DOI： 10.1023/A:1026098519848

Relationship between structure and permeability of tryptophan derivatives across human intestinal epithelial (Caco-2) cells 査読

M Urakami, R Ano, Y Kimura, M Shima, R Matsuno, T Ueno, M Akamatsu

ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES 58 ( 1-2 ) 135 - 142 2003年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：VERLAG Z NATURFORSCH

L-Trp and its derivatives were used as model compounds to clarify structural factors which influence the intestinal epithelial permeation and metabolism of amino-acid derivatives. Permeability of model compounds through Caco-2 cells was used as an in vitro absorption model for human intestinal epithelial cells. The influence of compound concentration, the effects of various transporter substrates on permeability coefficients, and pH dependency of permeability coefficients were investigated. The transcellular permeability of Trp and Trp-NH2 in the direction from the apical side to the basolateral side, in which nutrients and drugs were ordinarily absorbed, declined with increasing concentration and saturated at more than 1 and 0.4 mm, respectively. The permeability coefficients for N-terminal protected Trp derivatives and Ac-Trp-NH2 showed similar and constant values in both from the apical-to-basolateral and basolateral-to-apical directions. In addition, significant inhibition of the apical-to-basolateral permeation of Trp by Leu and Phe was observed. The permeability coefficient ratio at pH 6.3 to that at pH 7.3 was explained by the ratio of the ionic form to the neutral form of the compounds. Based upon these results and the partition coefficients in the 1-octanol/water system, possible absorption mechanism of Trp and its derivatives across Caco-2 cells was proposed.

Effects of medium-chain fatty acids on intracellular calcium levels and the cytoskeleton in human intestinal (Caco-2) cell monolayers 査読

Y Kimura, Y Hosoda, M Yamaguchi, H Nagano, M Shima, S Adachi, R Matsuno

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 65 ( 4 ) 743 - 751 2001年4月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

The effects of medium-chain fatty acids (M(IFA) on intracellular calcium (Ca2+) levels and actin filaments in the Caco-2 monolayer were investigated, A site-dependent increase in intracellular Ca2+ levels caused by decanoic acid (C10) at 13 mM was observed by confocal laser scanning microscopy. The area in which the intracellular Ca2+ levels was increased was measured by image analysis, and increased to 11% of the total area of the monolayer within 1 minute, This was maintained far 5 minutes, and decreased thereafter, The other Ca2+FAs did not significantly increase the intracellular Ca2+ levels, Obvious morphological changes of actin filaments were induced by only C10 among C8-C14. The area in which actin filaments were depleted was also quantified, and the increase in area became significant after 40 minutes. The area of the actin-depleted spot corresponded to the area occupied by 5 to 10 cells as sell as that in which the intracellular Ca2+ level was increased. The effectiveness of only C10 suggested that the mechanism of the absorption enhancement by C10 a would be different from that by the other MCFAs, or that C10 has some additional physiological functions although the mechanism of the enhancement is the same as for:he other MGFAs.

DOI： 10.1271/bbb.65.743

Recovery of Caco-2 cell monolayers to normal from the transport-enhanced state induced by capric acid sodium salt an its monoacylglycerol 査読

M Shima, Y Kimura, S Adachi, R Matsuno

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 63 ( 4 ) 680 - 687 1999年4月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

Caco-2 cell monolayers were used as a model of the intestinal epithelium to investigate the recovery profile from the transport-enhanced state induced by the transport enhancers, capric acid sodium salt (C10FANa) and capric acid monoacylglycerol (C10MG), The transepithelial electrical resistance, MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide) assay, and lactate dehydrogenase (LDH) release rate were investigated. The cell monolayer recovered depending on the concentration of the enhancer and on the exposure time, The MTT assay revealed that the cells recovered their mitochondrial dehydrogenase activity without proliferation. The cell monolayer exposed to C10FANa released LDH to both the apical and basolateral sides, but to C10MG, only to the apical side, The results were compared with those for SDS and taurocholic acid sodium salt, and the effect of C10FANa was found to be different. These results suggest that the damage by MCFA compounds is recoverable and that the recovery can be assessed by an MTT assay, but that the LDH-release behavior is different among the enhancers.

DOI： 10.1271/bbb.63.680

Physico-chemical properties of fatty acids for assessing the threshold concentration to enhance the absorption of a hydrophilic substance 査読

Y Kimura, Y Hosoda, M Shima, S Adachi, R Matsuno

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 62 ( 3 ) 443 - 447 1998年3月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

The effects of natural and non-natural fatty acids on enhancing the absorption of a hydrophilic marker through a human epithelial cell (Caco-2) monolayer were measured to elucidate the properties of the fatty acids. Fatty acids from C9 to C14 enhanced the absorption depending on the concentration and the carbon chain length. Those fatty acids with longer chains gave a higher permeability coefficient at low concentrations and a lower toxicity than those with shorter chains. The surface energy lowering coefficient (SELC), an intrinsic physico-chemical property, and the critical micellar concentration (CMC) were good criteria for identifying the threshold concentrations of a fatty acid to significantly enhance absorption.

DOI： 10.1271/bbb.62.443

Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells 査読

T Lindmark, Y Kimura, P Artursson

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS 284 ( 1 ) 362 - 369 1998年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：AMER SOC PHARMACOLOGY EXPERIMENTAL THERAPEUTICS

Medium chain fatty acids (MCFAs) are used to enhance the permeability of mucosal tissues to hydrophilic drugs, but their mechanism of action is largely unknown, In this study, the absorption-enhancing effects of the sodium salts of two MCFAs, capric acid (C10) and lauric acid (C12), were studied in monolayers of human intestinal epithelial Caco-2 cells, Both MCFAs induced a rapid increase in epithelial permeability to the hydrophilic marker molecule sodium fluorescein. Inhibition of phospholipase C and inhibition or activation of various kinases and buffering of intracellular calcium indicated that the effects on epithelial permeability were mediated through phospholipase C-dependent inositol triphosphate/diacylglycerol pathways. Surprisingly, the inositol triphosphate and diacylglycerol pathways were found to have opposing effects on paracellular permeability. Exposure to the MCFAs also resulted in a concentration dependent reduction of cellular dehydrogenase activity and ATP levels. C10, but not C12, induced redistribution of the tight junction proteins ZO-1 and occludin. These results indicate that the two MCFAs have partially different and more complex mechanisms than previously recognized, which has important implications for their use in vivo.

The relationship between transport-enhancement effects and cell viability by capric acid sodium salt, monocaprin, and dicaproin 査読

M Shima, Y Kimura, S Adachi, R Matsuno

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 62 ( 1 ) 83 - 86 1998年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

Using Caco-2 cell monolayers and MTT assay, the relationship between cell viability (a) and transport-enhancement effect of 1,2-dicaproin (C6DG), monocaprin (C10MG), and capric acid sodium salt (C10FANa) was examined, Transport enhancement effect was assessed by apparent permeability (P-app) of penicillin V. There was a linear relationship between (P-app-aS(a)) and (1-a) values, where S-a, was the apparent permeability for the viable cells. The apparent permeability for the damaged cells (Sd) was evaluated from the slope of the line, Each of the enhancer compounds gave a different S-d value 2.00 x 10(-4), 0.82 x 10(-4), and 0.10 x 10(-4)cm/s for C6DG, C10MG, and C10FANa, respectively, but the value was independent of its concentration for C10MG and C10FANa. C6DG would be the safest enhancer among the three compounds because of its high Sd value at the low level of cell damage. Sd could be used as a criterion for estimating the safety of enhancers.

DOI： 10.1271/bbb.62.83

Effects of medium-chain fatty acids and their acylglycerols on the transport of penicillin V across Caco-2 cell monolayers 査読

M Shima, K Yohdoh, M Yamaguchi, Y Kimura, S Adachi, R Matsuno

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 61 ( 7 ) 1150 - 1155 1997年7月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

The transport-enhancing effects of medium-chain fatty acids (caproic, caprylic, and capric acids) and their acylglycerols (mono-, di-, triacylglycerols) were investigated by using Caco-2 cell monolayers as a model of the human intestinal epithelium. Penicillin V was used as a model for a hydrophilic bioactive compound. Among the fatty acids and acylglycerols tested, 1,2-dicaproin, monocaprin, monocaprylin, and capric acid sodium salt effectively enhanced the transport rate, whereas other substances enhanced the rate only slightly or not at all. With each of these four substance, the rate of enhancement was proportional to the concentration at low concentrations, but leveled off at high concentrations. The transport-enhancing effects were well correlated with the reduction in surface tension and with a physico-chemical parameter, denoted by the surface energy-lowering coefficient, characterizing the surface activity of a substance.

DOI： 10.1271/bbb.61.1150

EFFECTS OF A PEPTIDE MIXTURE WITH A HIGH FISCHERS RATIO ON SERUM AND CEREBRAL-CORTEX AMINO-ACID LEVELS AND ON CEREBRAL-CORTEX MONOAMINE LEVELS, COMPARED WITH AN AMINO-ACID MIXTURE WITH A HIGH FISCHERS RATIO 査読

CH ODAGIMA, Y KIMURA, S ADACHI, R MATSUNO, H YOKOGOSHI

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 59 ( 4 ) 731 - 734 1995年4月

記述言語：英語出版者・発行元：TAYLOR & FRANCIS LTD

Peptide mixtures with high and low Fischer's ratios (i.e., the ratio of branched-chain amino acids to aromatic amino acids), obtained from an enzymatic hydrolysate of casein, and the corresponding amino acid mixtures were intragastrically force-fed to rats. Cerebral cortex monoamines vr ere more influenced by the ingestion of the peptide than that of the amino acid mixture.

DOI： 10.1271/bbb.59.731

EQUILIBRIUM YIELD OF N-ALKYL-BETA-D-GLUCOSIDE THROUGH CONDENSATION OF GLUCOSE AND N-ALCOHOL BY BETA-GLUCOSIDASE IN A BIPHASIC SYSTEM 査読

C PANINTRARUX, S ADACHI, Y ARAKI, Y KIMURA, R MATSUNO

ENZYME AND MICROBIAL TECHNOLOGY 17 ( 1 ) 32 - 40 1995年1月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：BUTTERWORTH-HEINEMANN

The beta-glucosidase-catalyzed synthesis of n-alkyl-beta-D-glucosides through the condensation of glucose and n-alcohols with alkyl chain lengths of 6 to 12 was carried out in a biphasic system, where the organic phase consisted only of an alcohol substrate. All the alcohols tested were condensed with glucose to give the corresponding n-alkyl-beta-D-glucosides. An equation was formula ted to predict the equilibrium yields of n-alkyl-beta-D-glucosides under various conditions, and its validity was experimentally verified. The equilibrium constant for the formation of n-alkyl-beta-D-glucosides was independent of the alkyl chain length and was 1.90 at 60 degrees C. The volume ratio of the organic to the aqueous phase was a factor significantly affecting the equilibrium yield. It was also shown that the synthesis at lower initial glucose concentrations effectively yielded alkylglucosides with less beta-glucobiose formation.

DOI： 10.1016/0141-0229(94)00082-3

Trypsin-catalyzed synthesis of oligopeptides containing hydrophilic and essential amino acid, L-lysine. 査読

Y Kimura, M Shima, T Notsu, S Adachi, R Matsuno

DEVELOPMENTS IN FOOD ENGINEERING, PTS 1 AND 2 582 - 584 1994年

Separation of Alkyl β-D-Glucosides and n-Alcohols by Using a Porous Tnmethylolpropane Trimethacrylate Homopolymer Gel 査読

Shuji Adachi, Chaiya Panintrarux, Yoichi Araki, Yukitaka Kimura, Ryuichi Matsuno

Bioscience, Biotechnology, and Biochemistry 58 ( 9 ) 1558 - 1563 1994年

記述言語：英語掲載種別：研究論文（学術雑誌）

Alkyl β-D-glucosides and /i-alcohols were separated by high-performance liquid chromatography on a porou gel of a trimethylolpropane trimethacrylate homopolymer, using a mixture of water with methanol or acetonitrile as the eluent. The effect of the methanol and acetonitrile concentrations on the separability was examined, and the optimum concentration of each to separate alkyl glucosides and alcohols with alkyl chain lengths of six to twelve was determined. A model for analyzing the elution characteristics of the solutes for various levels of methanol or acetonitrile is proposed, based upon the chemical potential of the solutes and eluent at the interface between the gel and eluent phases. Conventional column chromatographic separation of an alkyl glucoside and an alcohol was also performed by using gel with a larger particle diameter. © 1994, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.

DOI： 10.1271/bbb.58.1558

Preperation of peptide mixture with High Fischer ratio from protein hydrolysate by adsorption on activated carbon 査読

Bioseparation 3 227 - 232 1993年

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