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941.
Nobuhiko Fushimi Hirotaka Teranishi Kazuo Shimizu Shigeru Yonekubo Kohsuke Ohno Takashi Miyagi Fumiaki Itoh Toshihide Shibazaki Masaki Tomae Yukiko Ishikawa-Takemura Takeshi Nakabayashi Noboru Kamada Yuji Yamauchi Susumu Kobayashi Masayuki Isaji 《Bioorganic & medicinal chemistry》2013,21(3):748-765
Sodium glucose co-transporter 1 (SGLT1) plays a dominant role in the absorption of glucose in the gut and is considered a promising target in the development of therapeutic options for postprandial hyperglycemia. Previously, we reported potent and selective SGLT1 inhibitors 1 and 2 showing efficacy in oral carbohydrate tolerance tests in diabetic rat models. In a pharmacokinetic (PK) study of 2, excessive systemic exposure to metabolites of 2 was observed, presumably due to the high permeability of its aglycone (2a). To further improve SGLT1 inhibitory activity and reduce aglycone permeability, a series of 4-benzyl-5-isopropyl-1H-pyrazol-3-yl β-d-glycopyranoside derivatives bearing novel hydrophilic substitution groups on the phenyl ring were synthesized and their inhibitory activity toward SGLTs was evaluated. Optimized compound 14c showed an improved profile satisfying both higher activity and lower permeability of its aglycone (22f) compared with initial leads 1 and 2. Moreover, the superior efficacy of 14c in various carbohydrate tolerance tests in diabetic rat models was confirmed compared with acarbose, an α-glucosidase inhibitor (α-GI) widely used in the clinic. 相似文献
942.
Choemon Kanno Kunio Yamauchi Tomokichi Tsugo 《Bioscience, biotechnology, and biochemistry》2013,77(12):2067-2073
The polar lipid material which contains most of unsaponiriable matter of milk fat was collected by means of neutral alumina column chromatography. After saponification of the polar lipid material, the unsaponiriable matter was purified by repeated Florisil and neutral alumina column chromatography and the total tocopherol fraction was obtained. It was found that the total tocopherol fraction isolated from milk fat contained 6 of the known naturally occurring tocopherols, that is, α-, β-, γ-, and δ-tocopherols and α- and γ-tocotrienols. These were identified by two-dimensional thin-layer and gas-liquid chromatography before and after hydrogenation. 相似文献
943.
Makoto Shimizu Takamoto Kamiya Kunio Yamauchi 《Bioscience, biotechnology, and biochemistry》2013,77(11):2491-2496
Whey proteins adsorbed on fat globule surfaces during emulsification with coconut oil at pH 3 ~ 9 were examined. The amount of proteins adsorbed on the fat surface was dependent on the pH during emulsification. At any pH examined here, however, tightly-adsorbed proteins which were not extracted from the fat surface with urea or guanidine-HCl were 2 ~ 3 mg/m2. Marked selectivities in the adsorption of individual whey proteins were observed at any pH. No correlation between the adsorbabilities and the surface hydrophobicities of individual whey proteins was observed. Whey proteins adsorbed on the emulsified fat were much more easily digested with proteases compared to the native whey proteins, indicating that conformational changes of whey proteins occurred at the fat surface. The results suggested that conformational properties, such as flexibility of the structure, of whey proteins are important in the adsorption and possibly affect their emulsifying ability. 相似文献
944.
Tatsimori Yamagishi Mutsuko Takaya Futoshi Ebina Fumio Yamauchi 《Bioscience, biotechnology, and biochemistry》2013,77(2):537-539
The optical isomers of ten kinds of insecticidal 1,3,2-oxazaphospholidine 2-sulfides (OS) and two kinds of 1,3,2-benzodioxaphosphorin 2-sulfides (BS), including the commercial insecticide salithion, were synthesized in high optical purity by using two optically active aryl methyl phosphorochloridothionates (AMPC) as chiral two-step phosphorylating reagents. Their con-figurations were assigned according to the reaction mechanisms and supported by proton NMR information. 相似文献
945.
Makoto Miura Fumio Yamauchi Yasushi Ogawa Kazuo Shibasaki 《Bioscience, biotechnology, and biochemistry》2013,77(6):1631-1637
A proteolipid was isolated from the chloroform–methanol (2:1, by vol.) extract of defatted soybean meals by a modified Folch method. The proteolipid gave a yield of 0.05% of the defatted meals, and the ratio of protein and lipid was neary 3:4. The complex gave a single band containing both protein and lipid on polyacrylamide gel electrophoresis. TLC analysis of the lipid moiety showed that the major components were glycolipids and phospholipids. The protein moiety contained more hydrophobic amino acids and less acidic amino acids in comparison with the amino acid composition of soybean globulin. The protein moiety contained two kinds of protein component (I and II) which have molecular weights of 13,000 (I) and 15,000 (II) on SDS-urea polyacrylamide gel electrophoresis, and N-terminal amino acids of alanine (I) and glutamic acid (II). The apoprotein is a new protein and different from the whey proteins or globulins of soybean. 相似文献
946.
When Leuconostoc mesenteroides NRRL B-1299 was grown on a medium containing sucrose and lactose, a trisaccharide named ‘Lactsucrose’ (O-β-d-galactopyranosyl- (l→4) -O-α-d-glucopyranosyl- (l→2) -β-d-fructofuranoside) was produced. This sugar was obtained as a crystalline acetyl derivative and its structure was identified by the methods of paper chromatography, paper ionophoresis, hydrolysis with acid or enzymes and periodate oxidation. 相似文献
947.
Soo Won Lee Makoto Shimizu Shuichi Kaminogawa Kunio Yamauchi 《Bioscience, biotechnology, and biochemistry》2013,77(6):1535-1540
β-CN(f193–209), a hydrophobic peptide of 17 residues obtained from the chymosin hydrolyzate of β-casein, had little emulsifying activity (EA) at a neutral pH. When mixed with a hydrophilic glycomacropeptide (GMP) derived from κ-casein however, the EA of β-CN(f193-209) increased greatly. The mixing ratio of the peptides affected the EA as well as the adsorption of the peptides to oil droplets. Scanning electron microscopy indicated that the peptide film surrounding the emulsified oil droplets was thick and rough compared to the protein film. An amphipathic structure formed by some interaction between the hydrophilic GMP and the hydrophobic β-CN(f193-209) might contribute to the formation of the thick peptide film and stabilize the emulsified oil. 相似文献
948.
Choemon Kanno Hiroyuki Hattori Kunio Yamauchi 《Bioscience, biotechnology, and biochemistry》2013,77(5):1325-1332
Properties of proteins in the light (<d 1.03 on Ficoll and then <d 1.14 on sucrose) and heavy (d 1.03/1.05 on Ficoll and then <d 1.14 on sucrose) plasma membranes (PM) isolated from lactating bovine mammary gland were investigated. The PMs consisted of 57 ~ 62% of protein and 38 ~ 43% lipid. The lipid/protein ratio was 0.77 in the light PM and higher than 0.61 of the heavy PM. However, no appreciable differences were found between the light and heavy PMs with respect to polypeptide, amino acid, and carbohydrate compositions. The protein moiety contained approximate 5 ~ 6% carbohydrate: fucose 8 ~ 9, mannose 11 ~ 12, galactose 16, N-acetylglucosamine 32,N-acetylgalactosamine 12 ~ 15, and sialic acid 17~20 mol%. PM protein was high in the content of aspartic acid, glutamic acid, and leucine and low in proline, cystine, methionine, and histidine. On double immunodiffusion both PMs formed precipitin lines against milk fat globule membrane (MFGM) antiserum. Electrophoretic analysis on sodium dodecyl sulfate-polyacrylamide gel revealed the presence of many minor polypeptides and three major glycopeptides (PAS-I, II, and III) of molecular weights of 115,000, 94,000, and 82,000. The glycoprotein profiles of the PMs were different from those of MFGM, except that PAS-II and -III of PM corresponded to PAS-3 and -4 of MFGM, respectively. 相似文献
949.
Tatsunori Yamagishi Fumio Yamauchi Kazuo Shibasaki 《Bioscience, biotechnology, and biochemistry》2013,77(7):1575-1582
Heat denaturation of soybean 11S globulin was examined at 70° and 100°C in phosphate buffer (pH 7.6), at 0.01 and 0.5 ionic strength. Gel electrophoresis (Davis system) indicated that heat-denatured soybean 11S globulin contained two major components (buffer-soluble form). But they were not identified at 70°C-0.5 ionic strength. Gel filtration followed by SDS-gel electrophoresis showed that the major components were composed of a monomer and at least three of kinds of oligomers containing only an acidic subunit. Gel filtration of the precipitate formed at 100°C at 0.5 ionic strength gave two peaks. SDS-gel electrophoresis indicated that the first peak contained aggregates of highly polymerized subunits, and the second peak contained a monomer of basic subunit and seven kinds of oligomers with various proportions of basic subunits to an acidic subunit. 相似文献
950.
The quenching effect of α-, γ- and δ-tocopherols on the methylene blue sensitized photo- oxidation of methyl linoleate was investigated, and the 1O2. quenching ability of tocopherols was determined. The 1O2 quenching rate constants for α-, γ- and δ-tocopherols in ethanol were estimated to be 2.6 × 108 m?1 sec?1, 1.8 × 108 m?1 sec?1 and 1.0 × 108 m?1 sec?1, respectively. And the rate constants for the chemical reaction between each tocopherol and 1O2 were 6.6 × 106 m?1 sec?1, 2.6 × 106 m?1 sec?1 and 0.7 × 106 m?1 sec?1 for α-, γ- and δ-tocopherols, respectively. The results show that α-tocopherol is the most effective compound toward 1O2 among the three tocopherols. The photooxidation of each tocopherol produced two peroxides which, after chemical reduction, were identified to be tocopherol hydroquinone by gas chromatography-mass spectrometry analysis. The photooxidation mechanism of these tocopherols was assumed to be different from that of autoxidation. 相似文献