• 제목/요약/키워드: glycosidic bond

검색결과 29건 처리시간 0.02초

잠뇨의 흰쥐 소장내 glycosidase 저해활성 (Inhibitory Effect of Silkworm Urine on the Rat Intestinal Glycosidase)

  • 송주경;정성현
    • Biomolecules & Therapeutics
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    • 제6권3호
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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.

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Novel $\alpha$-Glucosidase from Extreme Thermophile Thermus caldophilus GK24

  • Nashiru, Oyekanmi;Koh, Suk-Hoon;Lee, Se-Yong;Lee, Dae-Sil
    • BMB Reports
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    • 제34권4호
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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.

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Tertiary Structure of Ganglioside $G_{A1}$ as Determined by NMR Spectroscopy

  • 이경익;이상원;전길자;김양미
    • Bulletin of the Korean Chemical Society
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    • 제19권5호
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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.

C-Glycoside-Metabolizing Human Gut Bacterium, Dorea sp. MRG-IFC3

  • Huynh Thi Ngoc Mi;Santipap Chaiyasarn;Heji Kim;Jaehong Han
    • Journal of Microbiology and Biotechnology
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    • 제33권12호
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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.

A Conformational Study of Oligosaccharides Investigated by Tandem Mass Spectrometry and Molecular Modeling

  • Eunsun Yoo Yoon
    • Bulletin of the Korean Chemical Society
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    • 제22권3호
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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.

대두 요구르트 제조에서 이소플라본 배당체의 가수분해 (Hydrolysis of ${\beta}-glycosidic$ Bonds of Isoflavone Conjugates in the Lactic Acid Fermentation of Soy Milk)

  • 최연배;우제구;노완섭
    • 한국식품과학회지
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    • 제31권1호
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    • pp.189-195
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    • 1999
  • 두유에 존재하는 이소플라본은 주로 포도당 잔기가 aglycone인 genistein과 daidzein에 ${\beta}-glycoside$ 결합을 하고 있는 배당체인 genistin과 daidzin이다. 두유에 설탕을 첨가하여 유산균으로 대두 요구르트로 발효를 시키면 젖산의 생성은 매우 낮아 약 $0.16{\sim}0.29%$에 불과하였지만 대부분의 이소플라본 배당체가 가수분해되어 aglycone으로 전환되었다. 포도당이나 젖당을 첨가하여 발효시키면 정상적인 젖산발효는 일어났지만 이소플라본 배당체의 가수분해는 균주에 따라 변하였다. Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047은 당의 첨가와 무관하게 이소플라본 배당체를 완전히 가수분해시켰다. 그 밖의 균주는 daidzin은 약 $25{\sim}40%$, genistin은 약 $65{\sim}80%$ 정도만을 가수분해시켜 이들 당에 의해 가수분해가 감소하였다. 즉 Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047을 제외한 Lactobacillus bulgaricus KCTC 3188, Lactobacillus casei KCTC 3109, Lactobacillus delbrueckii subsp lactis KCTC 1058, Lactobacillus lactis KCTC 2181과 같은 균주의 경우 이소플라본 배당체의 가수분해에 관여하는 효소인 ${\beta}-glucosidase$가 유도 효소로 포도당이나 젖당에 의해 생산이 저해되었을 것으로 예상된다. 또한 MRS 배지에서 배양하였을 때에도 Lactobacillus delbrueckii subsp. delbrueckii KCTC 1047만이 이 효소를 생산하였다.

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Cellulose의 광분해에 관한 연구(II) - 광조사된 면섬유의 화학적 성질을 중심으로 - (Photodegradation of Cellulosics(Part II) - Chemical Properties of Irradiated Cotton -)

  • 전경숙
    • 한국의류학회지
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    • 제18권1호
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    • pp.15-22
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    • 1994
  • 본 연구에서는 면시험포와 cellophane film을 이용하여 xenon arc lamp 를 사용한 인공기후조 안에서 광선의 파장에 따른 강도의 변화와 변색을 조사하였다. Pyrex와 quartz filter를 사용하여 광선의 파장이 섬유의 성질을 변화시키는 중요한 요인임을 밝히고 first-order kinetic model을 사용하여 반응속도를 측정하였다. 또 면섬유의 황변현상을 화학적으로분석하여 파장이 긴 자외선과 가시광선의 영역에서는 황변과 동시에 표백효과가 있음을 알게 되었고 그 속도를 측정하였다. 세가지의 중요한 말단기분석을 통해 carbonyl기의 양이 제일 많고 carboxyl기와 peroxide기도 존재함을 분석하였고 또 이들의 양은 온도와 습도에 따라 변화하는 것으로 나타났다 Cellulose chain의 중합도를 측정하고 이를 cellulose bond scission과 연결시켜서 중합도와 섬유의 강도저하와의 관계를 연구하였다.

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염산(鹽酸)과 촉매 AlCl3의 농도가 볏짚 Cellulose의 산가수분해(酸加水分解)에 미치는 영향 (The Effect of HCl-AlCl3(Catalyst) Concentrations on Acid Hydrolysis of Ricestraw Cellulose)

  • 이병근
    • Journal of the Korean Wood Science and Technology
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    • 제20권1호
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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.

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생전분을 당공여체로 한 분쇄마찰매체 함유 효소반응계에서의 Stevioside의 당전이 반응 기작 (Reaction Mechanism of Transglycosylation of Stevioside in the Attrition Coupled Reaction System Using Raw Starch as a Glycosyl Donor)

  • 백승걸;박동찬;허태린;이용현
    • 한국미생물·생명공학회지
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    • 제22권3호
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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.

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Antitumor and Antioxidant Activities of the Extracts from Fruiting Body of Phellinus linteus

  • Lee, June-Woo;Baek, Seong-Jin;Bae, Woo-Chul;Park, Jeong-Min;Kim, Yong-Seok
    • Mycobiology
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    • 제34권4호
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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.