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Biomedical subjects

Jun Kawabata

Publications and source records attributed to Jun Kawabata.

At least 37 records · Page 2Linked to original sources
PubMed2004

Effects of alcoholic solvents on antiradical abilities of protocatechuic acid and its alkyl esters.

DPPH radical scavenging reactions of protocatechuic acid and its methyl ester were investigated in various solvents. In alcoholic solvents, methyl protocatechuate rapidly scavenged more than four equivalents of the radical, whereas approximately two equivalents were consumed in aprotic solvents. Methyl, ethyl, butyl, isopropyl, and tert-butyl protocatechuates were examined for their DPPH radical scavenging abilities in methanol or ethanol. As a result, the radical scavenging equivalence of sterically bulky esters tended to decrease compared to that of methyl or ethyl ester. The ABTS radical scavenging ability of those esters in water also showed the same tendency. Since 2-methoxy derivatives were detected in the reaction mixture of methyl protocatechuate and DPPH radical in methanol, a nucleophilic attack of an alcoholic molecule on the o-quinone intermediate, which is sensitive to steric hindrance from alkyl groups of both esters and alcoholic solvents, must be crucial for total radical scavenging abilities.

Alcohols↗
PubMed2004

Importance of the B ring and its substitution on the alpha-glucosidase inhibitory activity of baicalein, 5,6,7-trihydroxyflavone.

Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent alpha-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4'-hydroxy-, 3',4'-dihydroxy-, and 3',4',5'-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4'-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

Animals↗
PubMed2004

A novel method for producing a foodstuff from defatted black sesame seed that inhibits allergen absorption.

A method is proposed to produce a foodstuff that inhibits allergen absorption through the intestinal tract. Defatted black sesame (Sesamum indicum) seeds as a starting material were hydrolyzed with a crude preparation of trypsin at 40 degrees C and pH 8 for 3 hrs while gently stirring to generate an active peptide. The resulting hydrolysate was heated to inactivate the trypsin and make the active components soluble. An extract was obtained by centrifugation and then freeze-dried. Ser-Asn-Ala-Leu-Val-Ser-Pro-Asp-Trp-Ser-Met-Thr-Gly-His (compound 1) as an active peptide, and sesamino1 2'-O-beta-glucopyranosyl-(1-->2)-O-[beta-glucopyranosyl(1-->6)]-O-beta-glucopyranoside (compound 2) and sesamino1 2'-O-beta-glucopyranosyl (1-->2)-O-beta-glucopyranoside (compound 3) were identified as active lignan glycosides in an in vitro model by using Caco-2 cells. Compound 1 was active at 10(-7) M and compounds 2 and 3 at 10(-5) M.

Absorption↗
PubMed2004

Structure-activity relationships for alpha-glucosidase inhibition of baicalein, 5,6,7-trihydroxyflavone: the effect of A-ring substitution.

In order to estimate the effects of the A-ring hydroxyl group of baicalein (5,6,7-trihydroxyflavone, 1) on rat intestinal alpha-glucosidase inhibition, flavone, monohydroxyflavones, dihydroxyflavones, and methylated derivatives of 5,6,7-trihydroxyflavone were used for the structure-activity relationship (SAR) study. The importance of the 6-hydroxyl group of baicalein was validated for an exertion of the activity. And also, the tested flavones which lacked a hydroxyl substituent on any of positions 5, 6, or 7, showed no activity. Hence, the 5,6,7-trihydroxyflavone structure was concluded to be crucial for the potent inhibitory activity. In addition, an introduction of electron-withdrawing or electron-donating groups at position 8 of baicalein led to a dramatic decrease for activity, except for 8-fluoro-5,6,7-trihydroxyflavone, which carried a less bulky substituent on position 8. Hence, this result suggested that a sterically bulky substituent on C-8 of baicalein was detrimental for the activity regardless of its electronic nature. Through examining the inhibitory mechanism of baicalein against rat intestinal alpha-glucosidase, it was suggested to be a mixed type inhibition.

Animals↗
PubMed2004

Isolation of tryptophan as an inhibitor of ovalbumin permeation and analysis of its suppressive effect on oral sensitization.

Tryptophan was isolated from rat feces as an active compound against ovalbumin permeation in an in vitro Caco-2 cell model. Tryptophan dose-dependently inhibited ovalbumin permeation with accompanying increase in transepithelial electric resistance, and its inhibitory activity reached a plateau at 10 mM. Brown Norway rats were sensitized by intragastric administration of ovalbumin together with or without tryptophan. Antibody levels specific to ovalbumin in the sera and proliferative responses of spleen mononuclear cells to ovalbumin were significantly lower in rats administered ovalbumin plus tryptophan than those administered ovalbumin alone. These results suggest that tryptophan suppresses oral sensitization to ovalbumin, probably via suppression of ovalbumin absorption from the intestinal tract.

Administration, Oral↗
PubMed2003

Amphidinolide Y, a novel 17-membered macrolide from dinoflagellate Amphidinium sp.: plausible biogenetic precursor of amphidinolide X.

A novel cytotoxic 17-membered macrolide, amphidinolide Y (1), has been isolated from a marine dinoflagellate Amphidinium sp., and it was elucidated to exist as a 9:1 equilibrium mixture of 6-keto- and 6(9)-hemiacetal forms (1a and 1b, respectively) on the basis of 2D NMR data and chemical means. The feeding experiments with (13)C-labeled acetates suggested that amphidinolide Y (1) may be a biogenetic precursor of 16-membered macrodiolide, amphidinolide X (2).

Animals↗
PubMed2003

Amphidinolide X, a novel 16-membered macrodiolide from dinoflagellate Amphidinium sp.

A novel cytotoxic 16-membered macrodiolide, amphidinolide X (1), has been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42). The gross structure of 1 was elucidated on the basis of spectroscopic data including one-bond and long-range (13)C-(13)C correlations. The relative and absolute stereochemistries were determined by combined analyses of NOESY data and (1)H-(1)H and (1)H-(13)C coupling constants of 1 and NMR data of the degradation products. Amphidinolide X (1) is the first macrodiolide consisting of polyketide-derived diacid and diol units from natural sources. The biosynthetic origins of 1 were investigated by means of feeding experiments with (13)C-labeled acetates.

Animals↗
PubMed2003

Synthesis and structural analysis of five novel oligosaccharides prepared by glucosyltransfer from beta-D-glucose 1-phosphate to isokestose and nystose using Thermoanaerobacter brockii kojibiose phosphorylase.

Five novel oligosaccharides (tetra-, penta- and hexa-saccharides) were synthesized by glucosyltransfer from beta-D-glucose 1-phosphate to isokestose (O-beta-D-fructofuranosyl-(2-->1)-O-beta-D-fructofuranosyl-(2-->1)-alpha-D-glucopyranoside) or nystose (O-beta-D-fructofuranosyl-(2-->1)-O-beta-D-fructofuranosyl-(2-->1)-O-beta-D-fructofuranosyl-(2-->1)-alpha-D-glucopyranoside) using Thermoanaerobacter brockii kojibiose phosphorylase. The oligosaccharides were identified as 2(2-alpha-D-glucopyranosyl)(m)isokestose; [O-alpha-D-glucopyranosyl-(1-->2)](m)-O-[beta-D-fructofuranosyl-(2-->1)](2)-alpha-D-glucopyranoside: m=1, 2, and 3, and 2(2-alpha-D-glucopyranosyl)(n)nystose; [O-alpha-D-glucopyranosyl-(1-->2)](n)-O-[beta-D-fructofuranosyl-(2-->1)](3)-alpha-D-glucopyranoside: n=1 and 2 using gas liquid chromatography analysis of the methyl derivatives, and MALDI-TOF-MS and NMR measurements of the newly formed oligosaccharides. 1H, 13C NMR signals of each saccharide were assigned using 2D-NMR techniques, including COSY, HSQC, HSQC-TOCSY, HMBC, CH(2)-selected E-HSQC, and CH(2)-selected E-HSQC-TOCSY.

Bacteria, Anaerobic↗
PubMed2003

Novel oxidative dimer from caffeic acid.

The novel Diels-Alder adduct, dicaffeoyl quinone as its hydrate, was formed from the oxidation of 3,4-dihydroxycinnamic acid (caffeic acid) with NaIO4. The structure of this hydrate was determined by spectroscopic methods.

Caffeic Acids↗
PubMed2003

Polyphenols from some foodstuffs as inhibitors of ovalbumin permeation through caco-2 cell monolayers.

Some spices showed high inhibitory activity against ovalbumin permeation through Caco-2 cell monolayers. Pimentol from allspice, rosmarinic acid and luteolin-7-O-beta-glucuronide from thyme, quercetin-3-O-beta-glucuronide from coriander and rutin from tarragon were identified as the active principles. A structure-activity relationship study among the active isolates and their related compounds indicated that the presence of a catechol structure played an important role in the inhibitory activity of each compound.

Anti-Allergic Agents↗
PubMed2003

Activin A induces phosphorylation of Smad2 but not complex formation of Smad2 with Smad4 in human colon cancer cell line HT-29.

Western blotting coupled with immunoprecipitation showed that activin A treatment induced phosphorylation of Smad2 but not complex formation of Smad2/4 in human colon cancer-derived HT-29 cells. Because HT-29 cells expressed neither Smad4 mRNA nor Smad4 protein, it is suggested that deletion of Smad4 leads to a defect of formation of Smad2/4 complex upon activin A stimulation in HT-29 cells.

Activins↗
PubMed2003

Effect of enzymatic modification of dietary wheat flour for reducing its allergenicity on oral sensitization to and intestinal absorption of ovalbumin.

Increase in plasma immunoglobulin G specific to orally administered ovalbumin in Brown Norway rats was retarded by feeding enzyme-treated wheat flour when compared with untreated flour. Because plasma ovalbumin concentrations after feeding ovalbumin tended to be lower in mice fed enzyme-treated flour than in those fed untreated flour, suppression of ovalbumin absorption may be relevant to retarded sensitization observed in rats.

Allergens↗
PubMed2003

6-hydroxyflavonoids as alpha-glucosidase inhibitors from marjoram (Origanum majorana) leaves.

A methanol extract of marjoram leaves strongly inhibited rat intestinal alpha-glucosidase. Five 6-hydroxyflavonoids, 6-hydroxyapigenin (scutellarein; IC50 for sucrose hydrolysis by rat intestinal alpha-glucosidase, 12 microM), 6-hydroxyapigenin-7-O-beta-D-glucopyranoside (> 500 microM), 6-hydroxyluteolin-7-O-beta-D-glucopyranoside (300 microM), 6-hydroxyapigenin-7-O-(6-O-feruloyl)-beta-D-glucopyranoside (>500 microM), and 6-hydroxyluteolin-7-O-(6-O-feruloyl)-beta-D-glucopyranoside (> 500 microM), were isolated as active principles and related compounds. The two feruloylglucosides are novel compounds.

Animals↗
PubMed2002

Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction.

DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging reactions of protocatechuic and gallic acids, and their methyl esters, have been investigated by NMR. In acetone, methyl protocatechuate was gradually converted to a Diels-Alder adduct of two molecules of the intermediate quinone in the reaction with DPPH radical, whereas methyl gallate rapidly gave a symmetrical dimer via a putative quinone precursor. Both dimers are rather unstable and their structures have been deduced by in situ NMR measurements of the reaction mixtures. Gallic acid also gave a corresponding symmetrical dimer in the same reaction as methyl gallate, although protocatechuquinone produced from protocatechuic acid did not yield a Diels-Alder adduct, unlike its methyl ester. Interestingly, these dimer formations were not observed in methanol solution.

Acetone↗
PubMed2002

Isolation and measurement of quercetin glucosides in flower buds of Japanese butterbur (Petasites japonicus subsp. gigantea Kitam.).

Three quercetin glucosides were isolated from flower buds of Japanese butterbur (Petasites japonicus subsp. gigantea Kitam.) together with caffeic acid as the ingredients that had DPPH radical scavenging activity, using the DPPH-HPLC method for measuring the radical scavenging activity. These quercetin glucosides were identified as quercetin 3-O-beta-D-glucoside, quercetin 3-O-beta-D-6''-O-acetylglucoside, and rutin, and the amounts of the glucosides in flower buds were also examined by HPLC. The flower buds were harvested from four different sites, the total amount of quercetin glucosides in each site was 100-170 mg/100 g fr. wt., and there were no great differences of the amounts between growing fields.

Antioxidants↗
PubMed2002

An active compound against allergen absorption in hypoallergenic wheat flour produced by enzymatic modification.

Hypoallergenic wheat flour produced by modification with cellulase and actinase showed inhibitory activity against ovalbumin permeation in an in vitro model by using the Caco-2 cell monolayer. The activity was found in the cellulase preparation used for producing the flour. An active compound was isolated by HPLC and identified as Trp-Ser-Asn-Ser-Gly-Asn-Phe-Val-Gly-Gly-Lys by 1H-NMR data and Edman degradation. The undecapeptide, some oligopeptides with the N-terminal sequences and Trp ethyl ester showed activity at 10(-7) M, acetyl Trp being active at 10(-2) M. These data suggest that the Trp residue without a free carboxyl group would be required for the inhibitory activity of ovalbumin absorption through the intestinal tract.

Absorption↗
PubMed2002

Subulatin, an antioxidic caffeic acid derivative isolated from the in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta.

The new caffeic acid derivative, subulatin (1), was isolated from in vitro cultured liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta. The structure of 1 involved two caffeic acids, D-glucose, and 2-carboxy-6-(1,2-dihydroxy-ethyl)-4,5-dihydroxy-5,6-dihydro-4H-pyran. The connectivity of those and the absolute stereochemistry of 1 were elucidated on the basis of spectroscopic evidence. The antioxidative activity of 1 was comparable to that of alpha-tocopherol. (2'R)-Phaselic acid (2a) and (-)-9,2''-epiphylloyl-L-malic acid (4) were also isolated from J. subulata and L. heterophylla, respectively. A chiral HPLC analysis of the p-bromobenzoyl-malic acids derived from 2a showed that 2a from J. subulata was unusual (+)-trans-caffeoyl-D-malic acid.

Antioxidants↗