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Biomedical subjects

Jun Kawabata

Publications and source records attributed to Jun Kawabata.

At least 19 recordsLinked to original sources
PubMed2006

Alpha-glucosidase inhibitory effect of mulberry (Morus alba) leaves on Caco-2.

The effects of brewing time on dry weight content and alpha-glucosidase inhibitory active component released from mulberry (Morus alba) tea were studied. Different tea products showed significant differences in inhibitory activity against both sucrase and maltase. The most effective enzyme inhibition was observed when 3 to 5 min brewing time was applied in tea preparation. In a Caco-2 cell culture experiment the tea reduced the liberated glucose contents in both apical and basal sides of the cell monolayers. It can be concluded that hot water extract of mulberry leaves does have inhibitory effect against alpha-glucosidases, sucrase and maltase enzymes, and has a potential to be consumed as antidiabetic herb tea.

Beverages↗
PubMed2006

Agesamides A and B, bromopyrrole alkaloids from sponge Agelas species: application of DOSY for chemical screening of new metabolites.

Diffusion-ordered NMR spectroscopy (DOSY) is a versatile and powerful NMR technique and a noninvasive analytical method for mixture analysis that does not require prior physical separation of the analytes. In our search for new metabolites from natural resources, DOSY was applied for constituent analysis of crude bromopyrrole fractions separated from an Okinawan marine sponge Agelas sp. so that two new bromopyrrole alkaloids, agesamides A (1) and B (2), have been isolated. The structures and relative stereochemistry of 1 and 2 were elucidated from spectroscopic data.

Animals↗
PubMed2006

Structural analysis of a novel saccharide isolated from fermented beverage of plant extract.

Fermented beverage of plant extract was prepared from about 50 kinds of vegetables and fruits. Natural fermentation was carried out mainly by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.). Three kinds of saccharides have been found in this beverage and produced by fermentation. The saccharides isolated from the beverage using carbon-Celite column chromatography and preparative HPLC, were identified as a new saccharide, beta-d-fructopyranosyl-(2-->6)-d-glucopyranose, laminaribiose and maltose by examination of constituted sugars, GLC and GC-MS analyses of methyl derivatives and MALDI-TOF-MS and NMR measurements of the saccharides.

Beverages↗
PubMed2006

Application of 1D BIRD or X-filtered DEPT long-range C-C relay for detection of proton and carbon via four bonds and measuring long-range 13C-13C coupling constants.

We propose the 13C-detecting 1D DEPT long-range C-C relay to detect super long-range H-C connectivity via four bonds (1H-13C-X-X-13C, X represents 12C or heteronuclear). It is derived from the DEPT C-C relay which detects the H-C correlations via two bonds (1H-13C-13C) by setting the delays for J(CC) in the C-C relay sequence to the (LR)J(CC). This sequence gives correlation signals split by small (LR)J(CC), which seriously suffers from residual center signal. The unwanted signal is due to long-range C-H couplings ((LR)J(CH)). The expected relayed magnetization transfer 1J(CH) --> (LR)J(CC) occurs in the 1H-13C-X-(X)-13C isotopomer, whereas the unwanted signal of (LR)J(CH) comes from 1H-12C-(X)-13C isotopomers, whose population is 100 times larger than that of the 1H-13C-X-(X)-13C isotopomer. The large dispersive line of this unwanted center signal would be a fatal problem in the case of detecting small (LR)J(CC) couplings. This central signal could be removed by an insertion of BIRD pulse or X-filter. DEPT spectrum editing solved a signal overlapping problem and enabled accurate determination of particular (LR)J(CC) values. We demonstrate here the examples of structure determination using connectivity between 1H and 13C via four bonds, and the application of long-range C-C coupling constants to discrimination of stereochemical assignments.

Animals↗
PubMed2006

DPPH radical scavenging reaction of hydroxy- and methoxychalcones.

The DPPH radical scavenging activity of 2',4',6'-trihydroxy- and 2'-hydroxy-4',6'-dimethoxychalcones carrying a 2,3- and 3,4-dihydroxylated, and 3,4,5-trihydroxylated B-ring was evaluated in alcoholic and non-alcoholic solvents. All test compounds scavenged more than two equivalent of radicals by a possible conversion to the corresponding B-ring quinones and in most cases subsequently underwent cyclization to aurones and flavanones, these being identified in the reaction solutions by an in situ NMR analysis. Interestingly, the reaction between 2',3,4-trihydroxy-4',6'-dimethoxychalcone and the DPPH radical was significantly affected by the solvent used, which might be accounted for by the difference in readiness for cyclization to an aurone.

Biphenyl Compounds↗
PubMed2005

Absolute stereochemistry of citrinadins a and B from marine-derived fungus.

[Structure: see text]. Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of 1 with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).

Alkaloids↗
PubMed2005

Radical scavenging activity of dicaffeoyloxycyclohexanes: contribution of an intramolecular interaction of two caffeoyl residues.

Six regio- and stereoisomers of dicaffeoyloxycyclohexanes and 2,4-di-O-caffeoyl-1,6-anhydro-beta-D-glucose were synthesized as model compounds of dicaffeoylquinic acids, and their radical scavenging activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt) radical scavenging tests. Both DPPH and ABTS radical scavenging reactions of these compounds consisted of two different steps. In the first step, catechol moieties of the caffeoyl residues were rapidly converted to o-quinone structures and no significant difference in the reactivity was observed among the tested compounds. In the second step, however, the rate of the reaction increased as the intramolecular distance of the two caffeoyl residues decreased. A novel intramolecular coupling product, which could scavenge additional radicals, was isolated from the reaction mixture of trans-1,2-dicaffeoyloxycyclohexane and DPPH radical. The result suggests that the second step of the radical scavenging reaction is arising from an intramolecular interaction between the two caffeoquinone residues to regenerate catechol structures, and that the closer their distance is, the more rapidly they react. The radical scavenging activity of natural dicaffeoylquinic acids in a biological aqueous system might also depend on the positions of caffeoyl ester groups.

Benzothiazoles↗
PubMed2005

Lambertellol C, a labile and novel biosynthetic congener of lambertellols A and B.

Lambertellol C (1), a labile biosynthetic congener of lambertellols A and B, was isolated from a fermentation broth of Lambertella sp. 1346 based on the diagnostic isotope patterns in the mass spectrum of a highly labeled sample. The CD spectrum of 1 indicated that this lambertellol analogue exists as a racemate. The mechanism for this racemization is discussed.

Chromatography, High Pressure Liquid↗
PubMed2005

alpha-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as alpha-glucosidase inhibitors.

The SAR studies suggested that the C-ring of baicalein (1) was not necessary for the activity, and validated the importance of 2,3,4-trihydroxybenzoyl structure of 1. Thus, a series of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs were investigated for the alpha-glucosidase inhibitory activity. The results indicated that 5,6,7-trihydroxy-2-phenyl-4-quinolone (2) and 5,6,7-trihydroxyflavanone (4) showed the comparable activity to 1, while 3,5,6,7-tetrahydroxyflavone (7), 5,6,7-trihydroxyisoflavone (8), and 6-hydroxygenistein (9) showed moderate alpha-glucosidase inhibitory activity. In addition, it was found that 6-amino-5,7-dihydroxyflavone (16) was a more potent and specific rat intestinal alpha-glucosidase inhibitor than 1, and showed the comparable activity to acarbose. This is the first report on mammalian intestinal alpha-glucosidase inhibitory activity of 6-aminoflavones. Kinetic studies revealed that 16 inhibited both sucrose- and maltose-hydrolyzing activities of rat intestinal alpha-glucosidase uncompetitively.

Animals↗
PubMed2005

Bitterness and toxicity in wild yam (Dioscorea spp.) tubers of Nepal.

Wild yams make a significant contribution to diets of tribal people in Nepal. However, these wild tubers are unpalatable, taste bitter, produce inflammation and show occasional toxicity. Four wild yam species, which are eaten after primary treatment by Nepali aborigines, were analyzed for bitter and toxic principles. Bitter components were identified as furanoid norditerpenes (diosbulbins A and B). Diosbulbins A and B were found in the range of 0.023-0.046 and 0.151-0.442 g kg(-1), respectively. Results demonstrated that diosbulbin B, with an average value of 0.314 g kg(-1), was the principal bitter compound as compared to diosbulbin A (0.037 g kg(-1)). The toxic alkaloid, dioscorine and histamine (an allergen) were not detected in these tubers, whereas cyanogens (as HCN equivalent) content were found ranging from 3.2 to 6.0 ppm. Our results revealed that Nepali wild yam tubers are not toxic varieties, as they do not contain either toxic dioscorine or histamine and cyanogens contents were satisfactorily below the safety limits. The inflammation and occasional toxicity observed could possibly be due to the presence of high level of oxalate in these tubers. Domestic cooking methods were found to be very efficient in removing bitterness, thus making the bitter yams palatable.

Consumer Product Safety↗
PubMed2005

Gastric colonization of Candida albicans differs in mice fed commercial and purified diets.

It has been difficult to produce persistent colonization by Candida albicans in the gastrointestinal tract of adult mice without the use of antibiotics and immunosuppressants. We hypothesized that diet influences the colonization of C. albicans and tested the hypothesis. BALB/c mice fed either a commercial rodent diet or a nutritionally adequate mixture of purified ingredients were inoculated i.g. with C. albicans (5 x 10(7) cells). Gastrointestinal colonization was examined by fecal culture, tissue culture, and histology. Mice fed the purified diet had a high fecal recovery of C. albicans [5-6log(10) colony forming units (cfu)/g feces] throughout the experimental period (6 wk), and the major site of colonization was the stomach. C. albicans was undetectable in the feces of mice fed the commercial diet 2 wk after inoculation. Immunosuppressants induced systemic dissemination of C. albicans in mice fed the purified diet. The number of lactobacilli and the concentration of organic acids in the stomach were significantly lower in mice fed the purified diet than in those fed the commercial diet. In vitro culture experiments revealed that acetic and lactic acids suppressed the growth of C. albicans. These results suggest that a reduction in lactobacilli in the stomach of mice fed the purified diet contributed to sustained gastric candidiasis. We therefore propose a novel model of sustained gastric candidiasis by a single i.g. inoculation of C. albicans in healthy adult mice fed a purified diet.

Animal Feed↗
PubMed2005

Allergic airway eosinophilia is suppressed in ovalbumin-sensitized Brown Norway rats fed raffinose and alpha-linked galactooligosaccharide.

We recently found that dietary raffinose suppressed allergic airway eosinophilia in ovalbumin-sensitized Brown Norway rats. Using this model in the present study, we compared the efficacy of other oligosaccharides with that of raffinose. Brown Norway rats were immunized s.c. with ovalbumin on d 0 and exposed to aerosolized ovalbumin on d 20; broncho-alveolar lavage fluid was obtained on d 21. In Expt. 1, rats were fed a control diet or diets supplemented with different oligosaccharides (50 g/kg diet, raffinose, alpha-linked galactooligosaccharide, fructooligosaccharide, and xylooligosaccharide). The number of eosinophils in the fluid was significantly lower in rats fed raffinose and alpha-linked galactooligosaccharide diets than in those fed the control diet. Dietary fructooligosaccharide and xylooligosaccharide did not affect airway eosinophilia. In Expt. 2, i.p. administration of raffinose and alpha-linked galactooligosaccharide, but not fructooligosaccharide and xylooligosaccharide, suppressed airway eosinophilia in rats fed the control diet. In Expt. 3, suppression of airway eosinophilia by dietary alpha-linked galactooligosaccharide occurred in cecectomized rats administered neomycin. Reduced levels of interleukin (IL)-4 and IL-5 mRNA in lung tissue were associated with the suppression of airway eosinophilia. We propose that indigestible oligosaccharides differ in their suppressive effect on allergic airway eosinophilia in ovalbumin-sensitized Brown Norway rats and that the effect appears not to be mediated by intestinal microflora.

Animals↗
PubMed2005

Oral administration of freeze-dried kefir reduces intestinal permeation of and oral sensitization to ovalbumin in mice.

An increase in plasma ovalbumin concentrations after intragastric administration of ovalbumin was suppressed by concomitant freeze-dried kefir in BALB/c mice. Serum levels of ovalbumin-specific immunoglobulin G and proliferation of splenic mononuclear cells in mice immunized orally with ovalbumin were suppressed by feeding freeze-dried kefir. We propose that kefir reduces intestinal permeation of food antigen, which contributes to suppression of oral sensitization.

Administration, Oral↗
PubMed2004

Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid.

DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity of protocatechuic acid and its structural analogues (methyl protocatechuate, 3',4'-dihydroxyacetophenone, 3,4-dihydroxybenzaldehyde, and 3,4-dihydroxybenzonitrile) were examined in aprotic and protic solvents. In aprotic acetonitrile, all test compounds scavenged two radicals. In protic methanol, however, these compounds rapidly scavenged five radicals except for protocatechuic acid, which consumed only two radicals. The result indicated that higher radical scavenging activity in methanol than in acetonitrile was due to a nucleophilic addition of the methanol molecule on the oxidized quinones, which led to a regeneration of catechol structures. To investigate the importance of the nucleophilic addition on the quinones for the high radical scavenging activity, DPPH radical scavenging activity of protocatechuic acid and its analogues was examined in the presence of a variety of nucleophiles. The addition of a strong nucleophile such as a cysteine derivative significantly increased the radical scavenging equivalence. Furthermore, thiol adducts at C-2 and C-2,5 of protocatechuic acid and its analogues were isolated from the reaction mixtures. These results strongly suggest that the quinone of protocatechuic acid and its analogues undergo a nucleophilic attack at C-2 to yield 2-substituted-3,4-diols. Then, a regenerated catechol moiety of adducts scavenge two additional radicals by reoxidation into quinones, which undergo the second nucleophilic attack at the C-5. This mechanism demonstrates a possibility of synergistic effects of various nucleophiles on the radical scavenging ability of plant polyphenols containing a 3,4-dihydroxy substructure like protocatechuic acid and its analogues.

Amines↗
PubMed2004

Biosynthesis of lambertellols based on the high specific incorporation of the 13C-labeled acetates and their biological properties.

Biosyntheses of lambertellols A (1) and B (2) as well as lambertellin (3) were investigated by isotope labeling experiments. Nearly 40% of specific incorporation of [1,2-(13)C(2)]acetate was achieved, and all the carbons in 1 and 2 were labeled. This high incorporation of the labeled acetate was realized by providing INADEQUATE spectra by employing only 0.4 and 0.7 mg of 1 and 2, respectively. Our studies revealed that 1-3 are biogenetically synthesized via loss of two carbons from octameric acetate. A biological assay against Monilinia fructicola revealed those remarkably inhibited hyphal germinations. However, neither of them killed the spores immediately, even in high concentration. These conditions induced the formation of microconidia.

Acetates↗
PubMed2004

Radical scavenging mechanism of phenol carboxylic acids: reaction of protocatechuic esters.

Solvent-dependency of the antiradical reaction of protocatechuic acid (3,4-dihydroxybenzoic acid, PA) and its esters has been investigated. In aprotic solvents, methyl protocatechuate (PAMe) was readily oxidized by two molar equivalents of DPPH radical and converted to protocatechuquinone methyl ester (PQMe). On the other hand, in alcoholic solvents such as methanol, PAMe rapidly consumed five radicals in 30 min and changed to complex oxidized mixtures. A 1H-NMR analysis of the reaction mixture of PAMe and DPPH radical in methanol showed that PAMe was rapidly converted to PQMe and its 3-hemiacetal. In addition, a signal of 2-methoxy-PQMe 3-hemiacetal was also detected in the reaction mixture. The results suggested that PQMe undergoes a nucleophilic attack by the solvent alcohol molecule at the C-2 of the ring in methanol, leading to a regeneration of catechol structure, which accounts well for the higher DPPH radical scavenging activity of PAMe in alcohols than in aprotic solvents.

Biphenyl Compounds↗