Two-mode Analysis by High-performance Liquid Chromatography of<i>ρ</i>-Aminobenzoic Ethyl Ester-derivatized Monosaccharides

Yasuno, Shoichi; Murata, Takeomi; Kokubo, Kazuko; Yamaguchi, Takashi; Kamei, Masugu

doi:10.1271/bbb.61.1944

Cited by 87 publications

(44 citation statements)

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“…A chromatographic analysis [15][16][17] of sugar components after hydrolysis was performed for qniumucin extracted from different types of jellyfish. As shown in Table 2, the results were rather complicated because the sugar components fluctuated depending on the species of jellyfishes, as well as each fraction of the ion-exchange chromatography.…”

Section: Resultsmentioning

confidence: 99%

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Mucin (Qniumucin), a Glycoprotein from Jellyfish, and Determination of Its Main Chain Structure

et al. 2007

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We extracted a novel glycoprotein, a member of the mucin family, from five species of jellyfish with high yields (1%-3% dry weight, 0.02%-0.1% wet weight) and determined its main chain structure and molecular mass. The glycoprotein contains unique tandem repeats of eight amino acids, of which two threonine residues are probably glycosylated by N-acetyl-D-galactosamine (GalNAc). We named this substance, which is common in jellyfish and similar to the human mucin MUC5AC, "qniumucin" and suggested the utilization of this compound as a new marine resource.

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Section: Resultsmentioning

confidence: 99%

“…× 75 mm) from J-Oil Mills Inc., 0.2 M potassium borate buffer (pH 8.9) containing 7% CH 3CN, and a standard kit from J-Oil Mills Inc. containing 11 monosaccharides. 15,16 …”

Section: Methodsmentioning

confidence: 99%

Mucin (Qniumucin), a Glycoprotein from Jellyfish, and Determination of Its Main Chain Structure

et al. 2007

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“…Sugar Composition Analysis-Sugar compositions were determined as described previously (38). Briefly, the purified lectin (200 g) was dissolved in 20 l of distilled water in a test tube to which 4 M trifluoroacetic acid (20 l for neutral sugars) or 8 M HCl (20 l for amino sugars) was added.…”

Section: Amino Acid Composition Analysis and N-terminal Sequence Analmentioning

confidence: 99%

Purification, Characterization, and Sugar Binding Specificity of an N-Glycolylneuraminic Acid-specific Lectin from the Mushroom Chlorophyllum molybdites

Kobayashi

Umehara

et al. 2004

Journal of Biological Chemistry

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A carbohydrate-binding protein was isolated from the carpophores of the mushrooms and designated the Chlorophyllum molybdites lectin (CML) based on its origin. The molecular mass of CML was 32 kDa, and it was composed of two 16-kDa monomers with no disulfide bonds. Monosaccharide analysis indicated that 12% of the mass of CML was carbohydrate and consisted of GlcNAc:GalNAc:Gal:Man:L-Fuc in a molar ratio of 1.5:1.9: 4.4:4.8:1.0. In the hemagglutination inhibition assay, CML exhibited the strongest binding specificity toward N-glycolylneuraminic acid (NeuGc) among the monosaccharides tested, whereas NeuAc did not inhibit the hemagglutination at all. GalNAc and Me␣-GalNAc were also inhibitory at much higher concentrations than NeuGc. Among the glycoproteins, asialobovine submaxillary mucin (BSM) and porcine stomach mucin (PSM) showed strong inhibitory effects. In surface plasmon resonance analysis, asialo-BSM and PSM exhibited the strongest binding affinity. After co-injection of CML and NeuGc or GalNAc onto the asialo-BSM-or PSM-immobilized chip, the dissociation of CML from the immobilized PSM was accelerated by NeuGc and GalNAc, but the dissociation of CML from the immobilized asialo-BSM was only promoted by GalNAc. These results and the other surface plasmon resonance experiments allowed us to conclude that the binding of asialo-BSM to CML was because of an interaction between the lectin and the GalNAc residues of asialo-BSM, and both the NeuGc and GalNAc residues were responsible for the binding of PSM to CML. The results also suggested that CML had two different carbohydrate binding domains, one specific for NeuGc and the other for GalNAc.

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“…An amount of the saccharide was determined by HPLC with p aminobenzoic acid ethyl ester (ABEE) conversion method. 5,6) The formation of the saccharide was significantly slow at the beginning of fermentation. The production of the saccharide reached its maximum after 48 days' fermentation.…”

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“…The same experiment was done with 1.5 mL of culture of Streptococcus mutans JCM 5705 (1.6×10 6 CFU mL) instead of sa- Saccharide 1 produced during the fermentation was assessed by HPLC with the ABEE conversion method. 4,5) A 10 µL of plant extract was added to an ABEE reagent solution (40 µL). The mixture was incubated at 80 C for 1 h. Distilled water (0.2 mL) and chloroform (0.2 mL) were added and the mixture was centrifuged at 10,000 rpm for 1 min.…”

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Characteristics of O-.BETA.-D-Fructopyranosyl-(2.RAR.6)-D-glucopyranose Isolated from Fermented Beverage of Plant Extract

Okada¹,

Kawazoe²,

Yamamori³

et al. 2008

J. Appl. Glycosci.

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The extract from fifty kinds of fruits and vegetables was fermented to produce a new beverage. The fermented beverage showed scavenging activity against 1,1´ diphenyl 2 picrylhydrazyl (DPPH) radical, and reduced significantly the ethanol induced damage of gastric mucosa in rats. 1)We have previously examined the production of novel saccharides in a fermented beverage of plant extract, suchFurthermore, these saccharides have been confirmed to be produced by fermentation.Palatinose is known as a disaccharide composed of glucose and fructose as well as O β D fructopyranosyl (2 6) D glucopyranose. Palatinose is about half as sweet as sucrose, and is hydrolyzed by isomaltase. 4) In the present work, we investigated some characteristics of O β D fructopyranosyl (2 6) D glucopyranose (saccharide 1) from a fermented beverage of plant extract to compare with those of palatinose.Preparation of the beverage was described previously. 1)In brief, plant juice extracted by sucrose was incubated for 7 days at 37 C in darkness by using yeast and lactic acid bacteria. Then, the fermented extract was kept at 37 C during 6 to 10 months for additional maturation and aging. The time course of the formation of saccharide 1 by fermentation was measured (Fig. 1). An amount of the saccharide was determined by HPLC with p aminobenzoic acid ethyl ester (ABEE) conversion method. 5,6) The formation of the saccharide was significantly slow at the beginning of fermentation. The production of the saccharide reached its maximum after 48 days' fermentation. Then, the amount of the saccharide gradually decreased. Saccharide 1 was considered to be used as the substrate for production of other saccharides, which have higher degrees of polymerization.Isolation of saccharide 1 was carried out according to the method of a previous paper.2) The plant extract (100 g) was loaded onto a carbon Celite column. These chromatographic procedures were carried out ten times. Subsequently, the saccharide was successfully purified repeatedly using a preparative HPLC system (Tosoh, Tokyo, Japan) equipped with an Amide 80 column (Fig. 2) and ODS 80Ts column. Finally, purified saccharide 1 (980 mg) was obtained as a white powder. The structure of the isolated saccharide was confirmed by MALDI TOF MS and NMR measurements (data not shown). The yield and purity of saccharide 1 were 49 and 98%, respectively.The degree of sweetness was measured according to the method of Takenaka et al .7) The degree of sweetness of sucrose solutions ranging from 1.0 to 2.5% (w v) concentration at intervals of 0.5% was compared at room temperature with that of 10% saccharide 1 by 8 panelists.At the degree of sweetness corresponding to 10% (w v) saccharide 1, two panelists chose 1.5% sucrose, four panelists chose 2.0% sucrose and two panelists chose 2.5% sucrose. Therefore, saccharide 1 had about 0.2 times the sweetness of sucrose.Stability during heating was investigated as follows: a 50 mM acetate buffer (pH 3, 4 and 5) containing 4% (w J. Appl. Glycosci., 55, 179 182 (2008) ! C 2008 The ...

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Two-mode Analysis by High-performance Liquid Chromatography ofρ-Aminobenzoic Ethyl Ester-derivatized Monosaccharides

Cited by 87 publications

References 3 publications

Mucin (Qniumucin), a Glycoprotein from Jellyfish, and Determination of Its Main Chain Structure

Mucin (Qniumucin), a Glycoprotein from Jellyfish, and Determination of Its Main Chain Structure

Purification, Characterization, and Sugar Binding Specificity of an N-Glycolylneuraminic Acid-specific Lectin from the Mushroom Chlorophyllum molybdites

Characteristics of O-.BETA.-D-Fructopyranosyl-(2.RAR.6)-D-glucopyranose Isolated from Fermented Beverage of Plant Extract

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