• Title/Summary/Keyword: N-Glycoside

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Identification of a Neolignan Glycoside from the Pine Tree, Pinus densiflora Showed Antithrombotic Activity (Pinus densiflora 유래의 항트롬빈 활성을 나타내는 Neolignan Glycoside의 동정)

  • Seo, Min-Jeong;Kang, Byoung-Won;Jeong, Yong-Kee
    • Journal of Life Science
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    • v.24 no.8
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    • pp.873-879
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    • 2014
  • The constituents from the needles of the pine tree, Pinus densiflora, were purified and investigated for antithrombotic activity. The needles were initially extracted three times with 70% ethanol, and the extract was sequentially fractionated with chloroform and n-butanol. The aqueous layer formed after n-butanol fractionation was subjected to purification by medium pressure and high pressure liquid chromatography. The two neolignans, 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl -3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside (a neolignan glycoside) and 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$) were identified by $^1H$ and $^{13}C$ NMR spectra. The effect of the purified compounds, the neolignan glycoside and icariside $E_4$ on thrombin inhibition were investigated by measuring thrombin clotting time in plasma. As a result, the clotting of the neolignan glycoside was delayed four times compared to that of icariside $E_4$. In addition, an analysis of the inhibition effect by changing the concentration showed that the clotting time was delayed in accordance with an increase in the concentration of the neolignan glycoside. Furthermore, we examined the interaction of thrombin and fibrinogen to clarify the action mechanism. As a result, the delay of clotting time in the response of thrombin and pure fibrinogen may indicate that neolignan glycosides inhibit the thrombin action in a direct manner, leading to the suppression of fibrin generation.

Antitumor and Antiinflammatory Constituents from Celtis sinensis

  • Kim Dae Keun;Lim Jong Pil;Kim Jin Wook;Park Hee Wook;Eun Jae Soon
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.39-43
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    • 2005
  • Eight compounds were isolated from the methanolic extract of the twigs of Celtis sinensis through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as two triterpenoids, germanicol and epifriedelanol, two amide compounds, trans-N-caffeoyltyramine and cis-N-coumaroyltyramine, two lignan glycoside, pinoresinol glycoside and pinoresinol rutinoside, and two steroids by spectroscopic analysis.

Iridoid Glycoside(VI) -Studies on the Iridoid Glycoside of Ajuga multiflora Bunge- (이리도이드 배당체(配糖體)(VI) -조개나물의 이리도이드 배당체-)

  • Chung, Bo-Sup;Yoo, Woan-Keun
    • Korean Journal of Pharmacognosy
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    • v.16 no.3
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    • pp.160-164
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    • 1985
  • Ajuga multiflora Bunge is a perennial herb in the family of Labiatae. The iridoid glycoside was isolated from the ethylacetate fraction and the n-butanol fraction of the plant. The structure of the substance was identified as 8-O-acetylharpagide by UV, IR, NMR spectra and several chemical reactions.

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The Stability and Mutagenecity of $\beta$-Sitosterol Glycoside, Antimicrobial Compound from Schima wallichii sp. liukiuensis (Schima wallichii sp. liukiuensis로부터 분리된 $\beta$-Sitosterol Glycoside 항균물질의 안정성 및 돌연변이원성)

  • Choi, Myung-Suk;Shin, Keum;Rhee, Dong-Kwon;Kwon, Oh-Woung;Son, Sung-Ho
    • Biomolecules & Therapeutics
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    • v.7 no.3
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    • pp.205-209
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    • 1999
  • Stability of the $\beta$-sitosterol glycoside from Schima wallichii sp. at various physical conditions were investigated, mutagenecity of the steroid saponin was determined by Ames test. When exposed in pH 3 to pH 8, the $\beta$-sitosterol glycoside was stable on antimicrobial activity against yeasts. The antimicrobial activity of the $\beta$-sitosterol glycoside also stable in high temperature, $N_2$, $O_2$ gas and light exposure, and metal ion. Ames test result revealed that $\beta$-sitosterol glycoside did not have any mutagenic activity. These results suggest that the $\beta$-sitosterol glycoside might be a promising candidate as a natural antimicrobial compound.

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Anti-inflammatory Activity of a Flavonol Glycoside from Tephrosia Spinosa

  • Chakradhar, V.;Babu, Y. Hari;Ganapaty, S.;Prasad, Y. Rajendra;Rao, N. Koteswara
    • Natural Product Sciences
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    • v.11 no.2
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    • pp.63-66
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    • 2005
  • A rare flavonol glycoside identified as $eupalitin-3-O-{\beta}-D-glucoside$ (I) was isolated from Tephrosia spinosa (Leguminosae) and its anti-inflammatory activity was evaluated against carrageenin induced paw edema. The compound exhibited significant activity when compared to the standard drug indomethacin.

Fractionnement des prodiuts de $r{\acute{e}}action$ de Maillard par $diff{\acute{e}}rentes$ techniques et observation $d'activit{\acute{e}}$ fermentaire de ces fractions -I. Fractionnement sur ${\acute{e}}changeur$ de cation- (여러가지 방법(方法)에 의(依)한 Premelanoidin의 분획(分劃)과 그 분획물(分劃物)의 발효활성(醱酵活性)에 관(關)한 관찰(觀察) -I. 양(陽)이온 교환수지(交換樹脂)에 의(依)한 분획(分劃)-)

  • Lee, Yang-Hee;Petit, Leon;Fittes, Eliane
    • Applied Biological Chemistry
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    • v.11
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    • pp.95-100
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    • 1969
  • 마이야르반응(反應) 생성물(生成物)인 Premelanoidin 중(中) 주정발효(酒精醱酵)의 속도(速度)를 촉진(促進)하는 물질(物質)을 분리(分離)하기 위(爲)하여 양(陽)이온 교환수지를 이용(利用)하여 Premelanoidin을 fractionation하고 얻어진 각(各) fraction의 주정발효(酒精醱酵)의 활성(活性)여부를 시험(試驗)하였다. 양(湯)이온 교환수지로는 Dowex $50{\times}8$, 50-100을 사용(使用)하고 elution solvent로는 $2N-NH_4OH$ 용액(溶液)을 사용(使用)하였으며 얻어진 각(各) 5ml의 fraction은 냉동건조(冷凍乾操)해서 다시 본래(本來) 시료(試料)의 농도(濃度)(0.2N)로 희석하여 활성시험(活性試驗)에 사용(使用)하였다. Fractionation의 결과(結果)는 water filtrate 구(區)에 glucose, 5-HMF 및 소량(少量)의 갈색색소의 fraction을 얻었고 ammoniacal eluate 구(區)에 대부분(大部分)의 갈색색소와 glycine N-glycoside의 fraction을 얻을 수 있었다. 주정발효(酒精醱酵)의 활성(活性)은 glucose, 갈색색소 및 glycine-N-glycoside 구획에서 관찰할 수 있었으나 glucose 는 전(前) 실험(實驗)에서 활성(活性)이 없는 물질(物質)로 인정(認定)되었으며 본(本) 실험(實驗)에 나타난 활성(活性)은 Dowex 50에 의(依)한 fractionation 과정중 glucose 자체(自體)의 변질(變質)에 의(依)한 것으로 추측된다. 결국(結局) 활성물질(活性物質)이 존재(存在)하는 fraction은 Ammoniacal eluate 구(區)의 갈색색소 fraction과 glycine 및 N-glycoside를 함유하는 fraction이라고 인정(認定)된다.

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Biological Active Components of Fruits of Poncirus trifoliata (지실의 생리활성성분)

  • Youn, Whang-Geum;Kim, Dong-Hyun;Kim, Nam-Jae;Hong, Nam-Doo
    • YAKHAK HOEJI
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    • v.36 no.6
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    • pp.548-555
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    • 1992
  • The biological activities of fruits of Poncirus trifoliata have been studied. 70% Ethanol extract of Ponciri Fructus was fractionated with ether, ethyl acetate and n-butanol by turns. The ether fraction showed antibacterial activity on Staphylococcus aureus and inhibited the contractability of the isolated mice ileum. The ethyl acetate and n-butanol fractions showed the anti-edematous effect on the carrageenin-induced edema of rat hindpaw. From the n-butanol fraction, one of the flavonoid glycoside was isolated and identified as poncirin. Ponciri Fructus contained about 6% poncirin which was 5,7-dihydroxy-4´-methoxy flavanone rhamnoglucoside and poncirin showed antiinflammatory activities. Poncirin was considered as the major effective component of Ponciri Fructus.

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Spinoside, New Coumaroyl Flavone Glycoside from Amaranthus spinosus

  • Azhar-ul-Haq,;Malik, Abdul;Khan, Anwar-ul-Haq Sher Bahadar;Shah, Muhammad Raza;Muhammad, Pir
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1216-1219
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    • 2004
  • Spinoside, new coumaroyl flavone glycoside was isolated from the n-butanol fraction of the mathanolic extract of the whole plant of Amaranthus spinosus and assigned the structure 7-pcoumaroyl apigenin 4-O-${\beta}$ -D-glucopyranoside (1) on the basis of spectroscopic techniques including 1D and 2D NMR spectroscopy. In addition ${\alpha}$ - xylofuranosyl uracil (2), ${\beta}$ -D-ribofuranosyl adenine (3) and ${\beta}$ -sitosterol glucoside (4) have also been isolated for the first time from this species.

A New Stereoisomeric Monoterpene Glycoside from Clematis heracleifolia leaves

  • Kim, Mi Ae;Yang, Heejung;Kim, Myong Jo;Chun, Wanjoo;Kwon, Yongsoo
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.107-110
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    • 2016
  • A new stereoisomeric monoterpene glycoside and five already-known compounds were isolated from the n-BuOH soluble fraction of Clematis heracleifolia leaves. On the basis of spectral data, the structures of the isolated compounds were identified as protocatechuic acid (1), ferulic acid (2), caffeic acid (3), aesculin (4), (6Z)-9-hydroxylinaloyl glucoside (5), and 9-hydroxylinaloyl glucoside (6) and these were isolated for the first time from this plant. Among these compounds, (6Z)-9-hydroxylinaloyl glucoside (5) is a newly isolated from plant source.