• Title/Summary/Keyword: glycoside

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Quantitative Determination of Bioactive Compounds in Some Artemisia capillaris by High-Performance Liquid Chromatography

  • Kim, Sang-Won;Kim, Hyeong-Woo;Woo, Mi-Hee;Lee, Jae-Hyun;Choi, Jae-Sue;Min, Byung-Sun
    • Natural Product Sciences
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    • v.16 no.4
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    • pp.233-238
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    • 2010
  • In order to facilitate the quality control of Artemisia capillaris, a simple, accurate and reliable HPLC method was developed for the simultaneous determination of the six bioactive compounds: scopolin (1), chlorogenic acid (2), 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside (3), hyperoside (4), isorhamnetin 3-Orobinobioside (5), and scoparone (6), which were selected as the chemical markers of A. capillaris. Separation was achieved on an Agilent Eclipse XDB-C18 column with a gradient solvent system of 0.1% trifluoroacetic acid aqueous-acetonitrile at a flow-rate of 1.0 mL/min and detected at 254 nm. All six calibration curves showed good linearity ($R^2$ > 0.998). A simple reversed phase HPLC method was developed for extracting pharmacologically active compounds scopolin, chlorogenic acid, 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside, hyperoside, isorhamnetin 3-O-robinobioside, and scoparone from A. capillaris using a binary gradient of acetonitrile : 0.1% trifluoroacetic acid with UV detection at 254 nm. The scopolin (1), chlorogenic acid (2), 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside (3), hyperoside (4), isorhamnetin 3-O-robinobioside (5), and scoparone (6) contents of the herb of A. capillaris collected from fifteen district markets in Korea were 0.00~0.90 mg/g, 0.06~7.29 mg/g, 0.06~0.91 mg/g, 0.07~5.05 mg/g, 0.42~13.11 mg/g, and 1.11~29.82 mg/g, respectively. The results demonstrated that this method is simple and reliable for the quality control of A. capillaris.

Isolation of Flavone Glycoside from Circium japonicum var ussuriense and Biological Activity on the Cardiovascular System (엉겅퀴 지상부의 심혈관 작용활성 및 후라본 배당체의 분리)

  • Lim, Sang-Sun;Lee, Jong-Ho;Park, Jong-Cheol
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.26 no.2
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    • pp.242-247
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    • 1997
  • A flavone glycoside was separated from the aerial part of Circium japonicum var ussuriense Kitamura and the effect on cardiovascular system was investigated. The cadiovascular contractility of this compound was observed in the artria and aortae from normal rats. It increased the spontancous beat in right atria and the contractile force in left atria, and caused the contraction of thoracic aortae. For the blood pressure, it had ascending effect. The effective component, which acted on stimulation and contraction in the artria and aortae of rats was fractionated with n-BuOH, separated and identified by column chromatography, UV, IR, $^1H-NMR$ and $^{13}C-NMR$. The chemical structure for this component was determined to be $hispidulin-7-{\alpha}-rhamnopyranosyl(1{\rightarrow}2)-{\beta}-D-glucopyranoside$.

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The Preventive and Curative Effect of Cyanidin-3β-D-Glycoside and Its Metabolite Protocatechuic Acid Against TNBS-induced Colitis in Mice

  • Jang, Se-Eun;Choi, Jong-Ryul;Han, Myung Joo;Kim, Dong-Hyun
    • Natural Product Sciences
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    • v.22 no.4
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    • pp.282-286
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    • 2016
  • Cyanidin-$3{\beta}$-D-glycoside (C3G), which is widely distributed in herbal medicines and functional foods, exhibits anti-inflammatory, anti-oxidant, and anti-scratching behavioral effects. Orally administered C3G is metabolized to protocatechuic acid (PA) by gut microbiota. Therefore, we compared the anti-colitic effect of C3G to that of PA in mice with 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis. Orally administered C3G and PA preventively and curatively ameliorated TNBS-induced colitis parameters, including macroscopic colitis score, colon shortening, and increase of myeloperoxidase activity. Treatment with C3G or PA also inhibited the expression of cyclooxygenase-2, inducible NO synthatase, $IL-1{\beta}$, IL-6, and $TNF-{\alpha}$ and the activation of $NF-{\kappa}B$ in the colon of mice with TNBS-induced colitis. Furthermore, these also inhibited lipopolysaccharide-induced $NF-{\kappa}B$ activation and $TNF-{\alpha}$ expression in peritoneal macrophages. The anti-colitic effect of PA was more effective than C3G. Orally administered PA more potently attenuate colitis than C3G by inhibiting $NF-{\kappa}B$ activation and the anti-colitic efficacy of C3G may be dependent on the biotransformation of C3G to PA by gut microbiota.

Isolation, Identification, and Characterization of Pichia guilliermondii K123-1 and Candida fermentati SI, Producing Isoflavone β-Glycosidase to Hydrolyze Isoflavone Glycoside Efficiently, from the Korean Traditional Soybean Paste

  • Kim, Won-Chan;So, Jai-Hyun;Kim, Sang-In;Shin, Jae-Ho;Song, Kyung-Sik;Yu, Choon-Bal;Kho, Yung-Hee;Rhee, In-Koo
    • Journal of Applied Biological Chemistry
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    • v.52 no.4
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    • pp.163-169
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    • 2009
  • A total of 155 microbial strains were isolated from the Korean traditional soybean paste based on their morphological features on the growth of agar plate. Among the isolated strains, a total of 28 strains were capable of hydrolyzing isoflavone glycoside to isoflavone aglycone efficiently in the soybean paste. Finally, two strains, K123-1 and SI, were selected because of their resistance to 15% NaCl and ability to convert isoflavone glycoside to isoflavone aglycone efficiently during the fermentation of soybean paste. The isolated strains K123-1 and SI were identified to be Pichia guilliermondii and Candida fermentati, respectively, using the partial 26S rDNA sequence analysis and phylogenic analysis. Pichia guilliermondii K123-1 and Candida fermentati SI converted daidzin to daidzein up to 96% and 95%, respectively, and genistin to genistein up to 92% when soybean pastes were fermented at $30^{\circ}C$ for 20 days with a single isolated strain. Pichia guilliermondii K123-1 and Candida fermentati SI were able to grow in the presence of 15% NaCl on both liquid medium and agar plate. We think that Pichia guilliermondii K123-1 and Candida fermentati SI might be one of good candidates for making functional soybean paste because they are isolated from the Korean traditional soybean paste and have a good ability to convert isoflavone glycosides to isoflavone aglycones and a high salt tolerance.

Study on Inhibition of Platelet Aggregation of Bioactive Constituents from Paeonia lactiflora (작약의 혈소판 응집억제작용에 관한 연구)

  • 박관혁;서범석;손동주;박영현;장성근
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.4 no.4
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    • pp.357-360
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    • 2003
  • Methanol extracts from Paeonia lactiflora showed a strong inhibition against platelet aggregation on platelet activation test. Therefore, the bioactive constituents from Paeonia lactiflora were prepared using chromatography methods and were analyzed by NMR and reference data. Compound 1b was confirmed a same structure with henzoyloxypaeoniflorin, compound 2e was a same structure with paeoniflorin; main product of Paeonia lactiflora. Analytical data of compound 3a were not consistent with any known paeoniflorin soucture, but showed the souctural similarity with it. And also the aggregation inhibition activity of compound 3a showed a strong inhibition($\geq$ 90%) induced by collagen. Therefore it suggested that the structure of compound 3a may be the similar structure of benzoyloxypaeoflorin with a functional group in place of benzoyl group and/or a different functional group in stead of Rl. We suggested that benzoyl group of benzoyloxypaeoniflorin substitued instead of 5-carbon OH group on glycoside moiety paeoniflorin played role of the metabolite in case of a platelet aggregation inhibition activity. Paeoniflorin showed more strong inhibition by thrombin than collagen. Therefore, it may be destructed a calcium metabolite as a forming $Ca^2+$ chelate. Compound 3a may be that other functional group instead of OH group of 5-carbon on glycoside moiety of paeoniflorin and/or OH group of benzoyl moiety of paeoniflorin played role of the metabolite in a platelet aggregation inhibition.

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Isolation and Characterization of Antioxidative Compounds from the Aerial Parts of Angelica keiskei

  • Kim, So-Joong;Cho, Jeong-Yong;Wee, Ji-Hyang;Jang, Mi-Young;Kim, Cheol;Rim, Yo-Sup;Shin, Soo-Cheol;Ma, Seung-Jin;Moon, Jae-Hak;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.14 no.1
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    • pp.58-63
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    • 2005
  • Ethyl acetate-soluble neutral fraction of hot water extracts from the aerial parts of Angelica keiskei showed a 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Six antioxidative compounds were purified and isolated by various chromatographic procedures. Based on the analyses of FAB-MS and NMR, the isolated compounds were structurally elucidated as luteolin 7-O-${\beta}$-D-glucopyranoside (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2), quercetin 3-O-${\beta}$-D-glucopyranoside (3), quercetin 3-O-${\alpha}$-D-arabinopyranoside (4), kaempferol 3-O-${\alpha}$-D-arabinopyranoside (5), and luteolin 7-O-rutinoside (6). The glycosides of flavonols and luteolin showed DPPH radical-scavenging activity. One molecule of 2, 3, 4, 6, 1, and 5 scavenged 4.2, 4.2, 4.1, 2.5, 2.2, and 1.4 molecules of DPPH radical, respectively.

Effects of Cooking and Drying Methods on the Polar Lipids Composition of Shrimp (가열 및 건조방법이 새우의 극성지방질 조성에 미치는 영향)

  • Kim, Hyun-Ku;Jo, Kil-Suk;Shin, Hyo-Sun
    • Korean Journal of Food Science and Technology
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    • v.21 no.1
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    • pp.25-30
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    • 1989
  • Effects of cooking and drying methods on the composition of glycolipids and phospholipids of shrimp, Metapenaeus joyneri, were investigated. Major components of the glycolipids were esterified steryl glycosides, monogalactosyl diglycerides and steryl glycosides. Hot air drying enhanced the esterified steryl glycosides content substantially with the reduction of the monogalactosyl diglycerides content. However, reversed pattern was shown for freeze drying. Main components of the phospholipids were phosphatidyl ethanolamines, phosphatidyl cholines, phosphatidic acids, phosphatidyl inositols and phosphatidyl serines. Phosphatidic acids content for hot air and freeze dried shrimp without tooting was 8.3% and 5.9%, respectively. On the other hand, freeze dried shrimp with microwave heating was higher in phosphatidyl ethanolamines contents but lower in phosphatidyl cholines contents than hot air dried shrimp. Major fatty acids of the glycolipids and phospholipids fractions were pentadecanoic acid, palmitic acid, oleic acid, nervonic acid and eicosapentaenoic acid in fresh shrimp.

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Saponins of Korean Ginseng Panax ginseng C.A. Meyer [Part I] - Determination of Saponins Fractions - (한국인삼(韓國人蔘)의 Saponin에 관(關)한 연구(硏究) [제1보(第一報)] - Saponin fraction별(別) 정량방법(定量方法)에 관(關)하여 -)

  • Cho, Sung-Hwan;Cho, Han-Ok;Kim, Ze-Uook
    • Applied Biological Chemistry
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    • v.19 no.4
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    • pp.233-242
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    • 1976
  • In this paper, new methods for the determination of the total and the individual saponin glucosides were proposed. One of them was a colorimetric method following Two-dimensional Thin layer chromatography. And the method employing Thinchrograph TFG-10 or Densitorol DMU-33C followed the separation of the saponins by means of a preparative thin layer chromatography. In accordance with the density of the chromatogram of each saponin, Thinchrogram or Densitogram of the individual saponin fraction was plotted and determined.

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Effect of Aqueous Extract of Guava (Psidium guajava L.) Leaves on the Oral Glucose Tolerance Test and Inhibition of Glycoside Hydrolase (구아바 잎 열수추출물의 당류분해효소 저해 효과 및 OGTT에 미치는 효과)

  • Choi, Su-Min;Kim, Joong-Hark;Chung, Ji-Sang;Kim, Hwa-Young;Chang, Hye-Eun;Hwang, Sung-Joo;Hong, Seong-Gil
    • Korean Journal of Medicinal Crop Science
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    • v.20 no.2
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    • pp.94-100
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    • 2012
  • Guava ($Psidium$ $guajava$) contain a great deal of polyphenol compound and work on the treatment of $Diabetes$ $mellitus$ effectively. In this study, the bioactivities of aqueous extract (GLEx) of guava leaf were investigated. Total phenolic contents of GLEx was 266.9 mg tan/g. The effects of GLEx on digestive enzymes, ${\alpha}$-amylase, maltase and sucrase were investigated. $IC_{50}$ values of GLEx against ${\alpha}$-amylase, maltase and sucrase were 0.65 mg/$m{\ell}$, 2.0 mg/$m{\ell}$ and 3.5 mg/$m{\ell}$ respectively. The effect of GLEx on oral glucose tolerance test (OGTT) was performed in normal ICR mouse, control (dstilled water) and GLEx (aqueous extract of Guava leaf) were co-administered orally with glucose, showed reducing effect on the blood glucose level. The guava is likely to useful for prevention or improvement of hyperglycemia by lowering the blood glucose level and inhibiting glycoside hydrolase activity.

PspAG97A: A Halophilic α-Glucoside Hydrolase with Wide Substrate Specificity from Glycoside Hydrolase Family 97

  • Li, Wei;Fan, Han;He, Chao;Zhang, Xuecheng;Wang, Xiaotang;Yuan, Jing;Fang, Zemin;Fang, Wei;Xiao, Yazhong
    • Journal of Microbiology and Biotechnology
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    • v.26 no.11
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    • pp.1933-1942
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    • 2016
  • A novel ${\alpha}-glucoside$ hydrolase (named PspAG97A) from glycoside hydrolase family 97 (GH97) was cloned from the deep-sea bacterium Pseudoalteromonas sp. K8, which was screened from the sediment of Kongsfjorden. Sequence analysis showed that PspAG97A belonged to GH97, and shared 41% sequence identity with the characterized ${\alpha}-glucoside$ BtGH97a. PspAG97A possessed three key catalytically related glutamate residues. Mutation of the glutamate residues indicated that PspAG97A belonged to the inverting subfamily of GH97. PspAG97A showed significant reversibility against changes in salt concentration. It exhibited halophilic ability and improved thermostability in NaCl solution, with maximal activity at 1.0 M NaCl/KCl, and retained more than 80% activity at NaCl concentrations ranging from 0.8 to 2.0 M for over 50 h. Furthermore, PspAG97A hydrolyzed not only ${\alpha}-1,4-glucosidic$ linkage, but also ${\alpha}-1,6-$ and ${\alpha}-1,2-glucosidic$ linkages. Interestingly, PspAG97A possessed high catalytic efficiency for long-chain substrates with ${\alpha}-1,6-linkage$. These characteristics are clearly different from other known ${\alpha}-glucoside$ hydrolases in GH97, implying that PspAG97A is a unique ${\alpha}-glucoside$ hydrolase of GH97.