• Biomolecules & Therapeutics
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• v.6 no.3
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• pp.242-246
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• 1998

The inhibitory activities of Amberlite active fraction, which was obtained from methanol soluble fraction of freeze dried slikworm urine, on the rat intestinal glycosidase-catalyzed enzymatic reaction were examined in in viro and in vivo experiments. Amberlite active fraction showed significant inhibitory effects on the hydrolysis of o-glycosidic bond, especially $\alpha$-1,4 bond. On the other hand, the inhibition on the hydrolysis of $\beta$-glycosidic bond was very weak. Oral administration of Amberlite active fraction resulted in a dose-dependent decrease in the blood glucose after an oral maltose load, and postprandial hyperglycemia in carbohydrate-loaded mice was suppressed by Amberlite active fraction at 60 mgHg in decreasing order of maltose, starch, sucrose and lactose. 60 mg/kg of Amberlite active fraction lowered the blood glucose level markedly after 18, 35, and 60 min after an oral maltose load and the antihyperglycemic activity was maintained upto 90 min. In alloxan-induced hyperglycemic mice, Amberlite active fraction at a dose of 100 mg/kg also significantly lowered blood glucose after an oral maltose load, and its efficacy was almost equivalent to that of acarbowe.

• BMB Reports
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• v.34 no.4
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• pp.347-354
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• 2001

$\alpha$-Glucosidase of an extreme thermophile, Thermus caldophilus GK24 (TcaAG), was purified 80-fold from cells to a homogeneous state and characterized. The enzyme exhibited optimum activity at pH 6.5 and $90^{\circ}C$, and was stable from pH 6.0 to 85 and up to $90^{\circ}C$. The enzyme had a half-life of 85 minutes at $90^{\circ}C$. An analysis of the substrate specificity showed that the enzyme hydrolyzed the non-reducing terminal unit of $\alpha$-1,6-glucosidic linkages of isomaltosaccharides and panose, $\alpha$-1,3-glycosidic bond of nigerose and turanose, and $\alpha$-1,2-glycosidic bond of sucrose. The gene encoding the TcaAG was cloned, sequenced, and sequenced in E. coli. The nucleotide sequence of the gene encoded a 530 amino acid polypeptide and had a G+C content of 68.4% with a strong bias for G or C in the third position of the codons (93.6%). A sequence analysis revealed that TcaAG belonged to the $\alpha$-amylase family. We suggest that this monomeric, thermostable, and broad-acting $\alpha$-glucosidase is a departure from previously exhibited specificities. It is, therefore, a novel $\alpha$-glucosidase.

• Bulletin of the Korean Chemical Society
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• v.19 no.5
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• pp.569-575
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• 1998

Investigation of the structure of the gangliosides has proven to be very important in the understanding of their biological roles. We have determined the tertiary structure of asialoganglioside GM1 $(GA_1)$ using NMR spectroscopy and distance geometry calculations. All of the structures are very similar except the glycosidic torsion angles in the ring IV and ring III linkages. There are two low-energy structures for GA1, G1 and G2. G1 differs from G2 only in the IV-III glycosidic linkages and the orientation of acetamido group in ring III. There is a stable intramolecular hydrogen bond between the third hydroxyl group in ring I and the ring oxygen atom in ring II. Also, there may be a weak hydrogen bond between the second hydroxyl group in ring IV and the acetamido group in ring III. Small coupling constants of $^3J_{IH3,IOH3}\; and\; ^3J_{IVH2,IVOH2}$ support this result. Overall structural features of $(GA_1)$ are very similar to those of $(GM_1)$. It implicates that specificities of the sugar moieties in GM1 are caused not by their tertiary foldings, but mainly by the electrostatic interactions between the polar sialic acid and its receptors. Since it is evident that $(GA_1)$ is more hydrophobic than $(GA_1)$, a receptor with a hydrophobic binding site can recognize the $(GA_1)$ better than $(GA_1)$. Studies on the conformational properties of $(GA_1)$ may lead to a better understanding of the molecular basis of its functions.

• Journal of Microbiology and Biotechnology
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• v.33 no.12
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• pp.1606-1614
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• 2023

Biochemical gut metabolism of dietary bioactive compounds is of great significance in elucidating health-related issues at the molecular level. In this study, a human gut bacterium cleaving C-C glycosidic bond was screened from puerarin conversion to daidzein, and a new, gram-positive C-glycoside-deglycosylating strain, Dorea sp. MRG-IFC3, was isolated from human fecal sample under anaerobic conditions. Though MRG-IFC3 biotransformed isoflavone C-glycoside, it could not metabolize other C-glycosides, such as vitexin, bergenin, and aloin. As evident from the production of the corresponding aglycons from various 7-O-glucosides, MRG-IFC3 strain also showed 7-O-glycoside cleavage activity; however, flavone 3-O-glucoside icariside II was not metabolized. In addition, for mechanism study, C-glycosyl bond cleavage of puerarin by MRG-IFC3 strain was performed in D₂O GAM medium. The complete deuterium enrichment on C-8 position of daidzein was confirmed by ¹H NMR spectroscopy, and the result clearly proved for the first time that daidzein is produced from puerarin. Two possible reaction intermediates, the quinoids and 8-dehydrodaidzein anion, were proposed for the production of daidzein-8d. These results will provide the basis for the mechanism study of stable C-glycosidic bond cleavage at the molecular level.

• Bulletin of the Korean Chemical Society
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• v.22 no.3
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• pp.293-297
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• 2001

The purpose of this paper is to introduce the simplified linkage position determination method using tandem mass spectrometry combined with molecular modeling study. Using low energy tandem mass spectrometric experiments and molecular modeling, it has been suggested that significant differences in glycosidic bond cleavage may occur due not only to ionic considerations but also may have contributions from steric hindrance of the absorbance of collision energy, leading to a statistically higher bond cleavage for sterically crowded linkages. Permethylated derivatives of the linkage-isomeric trisaccharides give useful fragmentation ratios and productions, including a 3-linkage specific ion. The ratios of fragment ions are related to the ability of each linkage position in the oligosaccharide to absorb collisional energy.

• Korean Journal of Food Science and Technology
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• v.31 no.1
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• pp.189-195
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• 1999

Isoflavones of soy milk were mainly present as sugar conjugates such as genistin and daidzin which a glucosyl residue was attached to their aglycones, genistein and daidzein through ${\beta}-glycosidic$ bond, respectively. When soy milk containing sucrose as a sugar source was fermented with lactic acid bacteria, small amount of lactic acid $(0.16{\sim}0.29%)$ was produced but isoflavone conjugates were fully hydrolyzed. Supplementation of glucose or lactose was required for normal lactic acid production and affected the hydrolysis of isoflavone conjugates in some lactic acid bacteria. In the case of Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047, glycosidic bond of isoflavone was fully hydrolyzed regardless of glucose supplementation. But only $25{\sim}40%$ of daidzin and $65{\sim}80%$ of genistin was hydrolyzed when glucose was added into soy milk in the other lactic acid bacteria, Lactobacillus bulgaricus KCTC 3188, Lactobacillus casei KCTC 3109, Lactobacillus delbrueckii subsp lactis KCTC 1058, Lactobacillus lactis KCTC 2181. The hydrolyzing enzyme, ${\beta}-glucosidase$ produced by lactic acid bacteria except Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047 could be considered as inducible in the fermentation of soy milk and its production was decreased when glucose was added.

• Journal of the Korean Society of Clothing and Textiles
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• v.18 no.1
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• pp.15-22
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• 1994

The formation of carbonyl group was dominant to other functional groups. Concentrations of both carboxyl and peroxide groups were found to rapidly reach low steady state values that increased slightly with increa-sing temperature and relatice humidity. Since the deg-radation of cellulose samples was in the initial stage and the conversion of glycosidic bonds and hydroxyl groups were very small, it was found that changes in the physical and chemical properties could be fitted to a first-order reaction model.

• Journal of the Korean Wood Science and Technology
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• v.20 no.1
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• pp.23-27
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• 1992

81.9% of the cellulose delignified by acetosolv process was hydrolyzed in HCl-$AlCl_3$ hydrolysis system when $AlCl_3$ was used as catalyst in breaking down of glycosidic bond of cellulose. It was well compared that the HCl hydrolysis system without $AlCl_3$ as catalyst showed only 60~61% of the hydrolyzed yield. Also monosaccharide yield including glucose clearly increased when $AlCl_3$ was use. When concentration of HCl and $AlCl_3$ was increased, the hydrolyzed monosaccharide was increased within certain range. The monosaccharid yield out of the hydrolyzed reached 55.4% at optimum conditions which were identified as 20% of Hel solution, 0.03 Mol of $AlCl_3$, $120^{\circ}C$ of reaction temperature and 7 hours of reaction time employed in this study.

• Microbiology and Biotechnology Letters
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• v.22 no.3
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• pp.252-258
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• 1994

Transglycosylation of stevioside in the attrition coupled heterogeneous reaction system using raw starch as a glycosyl donor has significant advantages over conventional reaction systems using liquefied starch as a donor. The transglycosylation of stevioside under the presence of organic solvent showed that transglycosylation reaction occurs via two steps ; initially from raw starch to cyclodextrin(CD), and then followed by transglycosylation of produced CD. Comparison of the transglycosylation efficiency of c$\alpha $-, $\beta $, $\gamma $-CDs indicated that $\alpha $-, $\beta $-CD are mainly utilized as a glycosyl donor for following reaction. The reaction mechanism of transglycosylation between stevioside and CD proceeded according to random sequential bireactant mechanism. The equilibrium constant of transglycosylation reaction of cyclodextrin glucanotransferase wase also evaluated. The structure of transglycosylated stevioside was confirmed by TLC, and it was found that glycosyl group(G$_{1}, $ ~ G$_{4}$-glycosidic bond.

• Mycobiology
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• v.34 no.4
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• pp.230-235
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• 2006

Fruiting bodies of Phellinus linteus were extracted by hot water and alkali methods. Sugar contents of PL-H (hot water extract) and PL-A (alkali water extract) were 81.1%, 37.4% and protein contents were 6.2%, 21.8%, respectively. Amino acid pattern showed that two extracts contained large amount of aspartic acid and alanine. Two extracts showed characteristic IR absorption pattern for glycosidic bond at $890\;cm^{-1}$. PL-H was divided two fractions by gel filtration chromatography and the molecular weights of each fraction were estimated to be about 10 kD and 225 kD, respectively and also PL-A was estimated 10 kD. Two extracts showed strong antitumor, immunomodulating and antioxidant activities, and were compared with commercialized glycopeptide anticancer drugs.