• Title/Summary/Keyword: Glycoside

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Effects of Dammarane Glycosides of Panax ginseng on Cholinergic Neurons in Primary Cultured Chicken Embryonic Brain Cells (일차배양한 계배 뇌세포 내의 콜린성 신경에 대한 인삼 Dammarane계 Glycosides의 작용)

  • Kim, So-Ra;Park, Mi-Jung;Huh, Hoon;Lee, Heum-Sook;Kim, Young-Choong
    • YAKHAK HOEJI
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    • v.38 no.4
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    • pp.401-409
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    • 1994
  • The cholinergic activity of dammarane glycosides of Panax ginseng was examined both morphologically and chemically on primary cultures of chicken embryonic brain cells. When primary cultured chicken embryonic cells were treated with $50\;{\mu}g/ml$ of total dammarane glycosides of Panax ginseng followed by the exposure to 10mM atropine for 48 hr, lactate dehydrogenase levels within the cells remained at 36% of untreated control values while atropine-treated controls fell to 0% lactate dehydrogenase. It was found that cholinergic activity was mainly exerted by the panaxadiol glycosides. The treatment of the cells with $50\;{\mu}g/ml$ of panaxadiol glycosides followed by the exposure to atropine, lactate dehydrogenase levels within the cells remained at 60% of untreated control values. Ginsenoside $Rb_1$, a component of panaxadiol glycosides, was found to exert the cholinergic activity keeping the lactate dehydrogenase levels within the cells at 70% of untreated control values. The cholinergic activity of ginsenoside $Rb_1$ seems to be exerted through acting on the $Ca^{2+}$ channel in cultured brain cells.

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Inactivation of human pleural fluid phospholipase $A_2$ by dioscin

  • Beak, Suk-Hwan;Kim, Sung-Hwan;Son, Kun-Ho;Chung, Kyu-Charn;Chang, Hyeun-Wook
    • Archives of Pharmacal Research
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    • v.17 no.4
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    • pp.218-222
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    • 1994
  • The natural product, spirostanol glycoside dioscin, was shown to directly inactivate human pleural fluid phospholipase $A_2{\;}(PLA_2)$ Inactivation was dose, and time dependent. The $IC_{50}$ was estimated at 18 .mu.M and virtually complete inactivation of the enzyme occurred at 50 .mu.M. Using Michaelis-Menten kinetics, dioscin inactivated the enzyme by a competitive inhibitory manner, the apparent Ki value was $6.9{\times}10_{-4}$. Reversibility was studied directly by dialysis method, the inhibition was reversible. Additioin of excess $Ca^{2+}$ concentration up to 8 mM did not antagonize the inhibitory activity of dioscin. Inactivation of several kinds of $PLA_2$ by dioscin is due to interaction with the active site of $PLA_2$ and may be a useful adjunt in the theraphy of inflammatory diseases.

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Structure-Activity Relationship of Triterpenoids Isolated from Mitragyna stipulosa on Cytotoxicity

  • Tapondjou, Leon Azefack;Lontsi, David;Sondengam, Beiham Luc;Choudhary, Muhammad Iqbal;Park, Hee-Juhn;Choi, Jong-Won;Lee, Kyung-Tae
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.270-274
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    • 2002
  • Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

Ginsenoside $Rb_1$: the Anti-Ulcer Constituent from the Head of Panax ginseng

  • Jeong, Choon-Sik;Hyun, Jin-Ee;Kim, Yeong-Shik
    • Archives of Pharmacal Research
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    • v.26 no.11
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    • pp.906-911
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    • 2003
  • We previously reported that the butanol (BuOH) fraction of the head of Panax ginseng exhibited gastroprotective activity in peptic and chronic ulcer models. In order to identify the active constituent, an activity-guided isolation of the BuOH faction was conducted with a HCI$.$ethanol-induced gastric lesion model. The BuOH fraction was passed through a silica-gel column using a chloroform-methanol gradient solvent system, and six fractions (frs. 1-6) were obtained. The active fr. 5 was further separated by silica-gel column, to yield 6 subfractions (subfrs. a-f). Subfr. d was composed of ginsenosides Re, Rc and $Rb_1$. The most active constituent was ginsenoside $Rb_1$ ($GRb_1$), a protopanaxadiol glycoside, which was investigated for its anti-ulcer effect. Gastric injury induced by HCI$.$ethanol, indomethacin and pyloric ligation (Shay ulcer) was apparently reduced with oral $GRb_1$ doses of 150 and 300 mg/kg. $GRb_1$ at these dosage significantly increased the amount of mucus secretion in an ethanol-induced model. The anti-ulcer effects were consistent with the result of histological examination. These results suggest that the major active constituent in the head of Panax ginseng is $GRb_1$ and that anti-ulcer effect is produced through an increase in mucus secretion.

In Vitro Antimutagenic Effects of Alaternin and Isorubrofusarin Gentiobioside from roasted Cassia tora

  • Choi, Jae-Sue;Lee, Hee-Jung;Park, Kun-Young;Jung, Gun-Ok
    • Natural Product Sciences
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    • v.4 no.2
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    • pp.100-104
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    • 1998
  • The antimutagenic activity of a methanol extract of roasted Cassia tora seed against aflatoxin $B_1(AFB_1)$ was demonstrated with the Salmonella typhimurium assay. The numbers of revertants per plate decreased significantly when this extract was added to the assay system using Salmonella typhimurium TA100 and or TA98. The MeOH extract was then sequentially partitioned with $CH_2Cl_2$, EtOAc, n-BuOH, and $H_2O$. The $CH_2Cl_2$ and n-BuOH fractions possessed antimutagenic activity, but the EtOAc and $H_2O$ fractions were inactive. Both the MeOH extract and its fractions were capable of inhibiting the indirect-acting mutagen $AFB_1$, suggesting that these fractions may prevent the metabolic activation of $AFB_1$, or scavenge the electrophilic intermediate capable of inducing mutations. Column chromatography using silica gel yielded pure alaternin from the $CH_2Cl_2$ a fraction, and adenosine and isorubrofusarin gentiobioside from the n-BuOH fraction. Alaternin and isorubrofusarin gentiobioside demonstrated significant antimutagenic activities.

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Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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Isolation of Flavone-7-O-Glycosides from the Aerial Parts of Angelica keiskei and Anti-hyperlipidemic Effect (Angelica keiskei의 고지혈증 개선효과 및 2종의 플라본 7-O-배당체의 분리)

  • Park, Jong-Cheol;Cho, Young-Sook;Park, Seok-Kyu;Park, Jeong-Ro;Chun, Soon-Sil;Ok, Kwang-Dae;Choi, Jong-Won
    • Korean Journal of Pharmacognosy
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    • v.26 no.4
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    • pp.337-343
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    • 1995
  • Two flavone glycosides were isolated from the aerial part of Angelica keiskei Koidz and identified by means of spectral analysis as luteolin-$7-O-{\beta}-{_D}-glucoside$ and Iuteolin-7-O-rutinoside. Intraperitoneal administration of methanolic extract(100mg/kg) and $luteolin-7-O-{\beta}-{_D}-glucoside(5mg/kg)$ isolated from this plant produced a significant hypolipemic activity.

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A Novel Cellulase of the Mulberry Longicorn Beetle, Apriona germari, Dependent on N-Glycosylation for Enzymatic Activity

  • Lee, Seong-Jin;Kim, Seong-Ryul;Yoon, Hyung-Joo;Kim, IK-Soo;Lee, Kwang-Sik;Je, Yeon-Ho;Lee, Sang-Mong;Seo, Sook-Jae;Sohn, Hung-Dae;Jin, Byung-Rae
    • Proceedings of the Korean Society of Sericultural Science Conference
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    • 2003.04a
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    • pp.77-78
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    • 2003
  • A novel -1, 4-endoglucanase (EGase, EC 3.2.1.4) cDNA belonging to glycoside hydrolase family (GHF) 45 was cloned from the mulberry longicorn beetle, Apriona germari. The cDNA encoding EGase of A. germari (Ag-EGase) is 711 base pairs long with an open reading frame of 237 amino acid residues. The deduced protein sequence of Ag-EGase showed 54% and 48% identity to phytophagous beetle Phaedon cochleariae and termite Reticulitermes speratus hindgut symbiont, respectively. (omitted)

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Structural Characterization of a Flavonoid Compound Scavenging Superoxide Anion Radical Isolated from Capsella bursa-pastoris

  • Kweon, Mee-Hyang;Kwak, Jae-Hyock;Ra, Kyung-Soo;Sung, Ha-Chin;Yang, Han-Chul
    • BMB Reports
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    • v.29 no.5
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    • pp.423-428
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    • 1996
  • A superoxide anion radical scavenger isolated from Capsella bursa-pastoris was characterized by infrared (IR) spectroscopy, sugar analysis, ultraviolet (UV) spectroscopy, $^{1}H$ and $^{13}C$ nuclear magnetic resonance (NMR) spectroscopies, and fast atom bombardment (FAB) mass analysis. The compound was assumed to be a flavonoid-O-glycoside from IR spectrum and UV absorption maxima. When the sugar composition of the compound was examined by thin layer chromatography (TLC) and gas chromatography (GC) of the acid hydrolysate, only glucose was detected. According to the results of UV spectrotroscopy by using shift reagents, the compound was supposed to be luteolin (5,7,3',4'-tetrahydroxy flavone) or chrysoeriol (5,7,4'-trihydroxy-3'-methoxy flavone) with glucose. Based on $^{1}H$- and $^{13}C-NMR$ spectroscopies, the compound was deduced as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone. In FAB mass analysis the compound was finally characterized as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone ($C_{29}H_{34}O_{16}$, M.W.=638).

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Purification and Some Properties of Rutinosidase from Arthrobacter sp. (Arthrobacter sp.가 생산하는 Rutinosidase의 정제 및 특성)

  • ;Toshio Omori;Tohru Kodama
    • Microbiology and Biotechnology Letters
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    • v.18 no.4
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    • pp.360-367
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    • 1990
  • The several glycoside hydrolysing enzymes related to rutin degradation are found to be rhamnosidase, glucosidase and rutinosidase. Rutinosidase was purified to electrophoretic homogeneity from cell extracts of rutin-degrading strain, MT-57, which was identified as a Arthrobacter sp. Its molecular weight was estimated to be 42, 000 by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and 40, 000 by gel filtration. The optimum pH for enzyme was found to be 7.5, and relatively stable in alkaline solution. The optimum temperature for enzyme was $45^{\circ}C$, being stable up to $50^{\circ}C$ for 20 min. The Bm value of enzyme for rutin was 0.5 $\mu \textrm m$. The enzyme activity was increased by the chelating agent such as EDTA, $NaN_3$, and 8-hydroxyquinoline, was strongly inhibited by $CO_{2+}, Ni^{2+}$, and $Cu^{2+}$. The enzyme had high substrate specificity in the rutinoside.

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