• Title/Summary/Keyword: N-Glycoside

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Influence of Isolation Method on the Composition of Apricot (Prunus armeniaca var. ansu Max.) Flavor (살구의 휘발성 성분 조성에 대한 분리방법의 영향)

  • Kim, Young-Hoi;Kwag, Jai-Jin;Kwon, Young-Ju;Yang, Kwang-Kyu
    • Korean Journal of Food Science and Technology
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    • v.22 no.5
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    • pp.543-548
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    • 1990
  • Volatile components of fresh apricot (Prunus armeniaca var. ansu Max.) were isolated by simultaneous distillation-extraction at two different pH values of 3.1 and 7.0 and by headspace trapping method. The volatiles were analyzed by GC and GC-MS. A total of 80 components were identified in the three aroma concentrates, including 9 naphthalene derivatives that were not previously reported in apricot. Of components identified in native pH (3.1) sample, the major components were aliphatic $C_6$ aldehydes and alcohols, monoterpene alcohols, benzyl alcohol, ${\beta}-phenylethyl$ alcohol and naphthalene derivatives, while those in neutral pH(7.0) sample and headspace volatiles were aliphatic $C_6$ aldehydes and alcohols. Simultaneous distillation-extraction at pH 3.1 was significantly increased the concentration of n-hexanal, trans-2-hexenal, cis-3-hexen-1-ol, linalool oxide, linalool, ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol, ${\beta}-phenylethyl$ alcohol and naphthalene derivatives. These results demonstrate that above the components are present in glycosidically bound forms in apricot.

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Flavonol glycosides from the flowers of Carthamus tinctorius and their anti-diabetic activity (잇꽃(Carthamus tinctorius)으로부터 Flavonol glycoside 화합물들의 분리 및 항당뇨 효과)

  • Bo-Ram Choi;Hyoung-Geun Kim;Yoon Hee Nam;Dahye Yoon;Woo Cheol Shin;Jin-Kyu Jang;Yunji Lee;Tong Ho Kang;Nam-In Baek;Dae Young Lee
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.477-483
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    • 2023
  • The flowers of Carthamus tinctorius (Safflower) were extracted with 80% aqueous methanol (CTex) and the concentrates were partitioned into EtOAc (CTE), n-BuOH (CTB), and H2O (CTW) fractions. Repeated silica gel (SiO2) and octadecyl silica gel column chromatographies for the EtOAc and n-BuOH fractions led to isolation of four flavonol glycosides. Nuclear magnetic resornance, infrarad spectroscopy, and mass spectroscopy revealed the chemical structure of the isolated compounds, astragalin (1), isoquercetin (2), nicotiflorin (3), and rutin (4). Quantitative analysis of four isolated compounds in CTex was performed by HPLC. CTex was found to contain 1 at 0.107, 2 at 0.367, 3 at 6.752, and 4 at 0.991 mg/g, respectively. Through this study, an experiment was conducted to evaluate the protective effect on pancreatic islets of the extract, solvent fractions, and all isolated compounds using a zebrafish larvae damaged by alloxan. Pancreatic islet size treated with EtOAc (CTE), n-BuOH (CTB), and H2O (CTW) fractions and compounds 1-4 significantly increased compared to the alloxan-induced group. These results indicate that C. tinctorius flowers and its isolated compounds are used as potential anti-diabetic agents.

Ginsenoside Rh2 Induces Apoptosis via Activation of Caspase-1 and -3 and Up-Regulation of Bax in Human Neuroblastoma

  • Kim, Young-Soak;Jin, Sung-Ha
    • Archives of Pharmacal Research
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    • v.27 no.8
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    • pp.834-839
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    • 2004
  • In human neuroblastoma SK-N-BE(2) cells undergoing apoptotic death induced by ginsenos-ide Rh2, a dammarane glycoside that was isolated from Panax ginseng C. A. Meyer, caspase-1 and caspase-3 were activated. The expression of Bax was increased in the cells treated with ginsenoside Rh2, whereas Bcl-2 expression was not altered. Treatment with caspase-1 inhibi-tor, Ac-YVAD-CMK, or caspase-3 inhibitor, Z-DEVD-FMK, partially inhibited ginsenoside Rh2-induced cell death but almost suppressed the cleavage of the 116 kDa PARP into a 85 kDa fragment. When the levels of p53 were examined in this process, p53 accumulated rapidly in the cells treated early with ginsenoside Rh2. These results suggest that activation of caspase-1 and -3 and the up-regulation of Bax are required in order for apoptotic death of SK-N-BE(2) cells to be induced by ginsenoside Rh2, and p53 plays an important role in the pathways to promote apoptosis.

Pharmaco-Constituents of Korean Cultivated Rhubarb Leaves -The Flavonoids from Leaves- (한국산 재배대황엽의 약효성분 -엽의 후라보노이드-)

  • Ham, In-Hye;Oh, In-Se;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • YAKHAK HOEJI
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    • v.38 no.4
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    • pp.469-475
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    • 1994
  • As the continued studies for Korean cultivated rhubarb, MeOH extract of the leaves was fractionated with ether, ethylacetate, and n-butanol. From the ethyl acetate fraction of MeOH extract, one flavone glycoside, apigenin-8-${\beta}$-D-glucopyranoside(vitexin, $C_{21}H_{20}O_{10}$) and from the n-BuOH fraction of MeOH extract, two flavonol glycosids, kaempferol-3-O-(2,6-di-O-rhamnopyranosyl)-${\beta}$-D-galactopyranoside$(C_{33}H_{40}O_{19})$and quercetin-3-O-rutinoside(rutin, $C_{27}H_{30}O_{16}$) were isolated and identified through the physico-chemical properties and spectroscopic evidences(UV, IR, NMR, Mass) respectively.

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Studies on the Seasonal Variation of the Polyalcohols and the Free Reducing Sugars in the Leaves of Syringa dilatata $N_{AKAI}$ (수수꽃다리 잎중의 다가 알코올과 유리 환원당의 소장에 관한 연구)

  • Kim, Chang-Min;Ryu, Kyung-Soo
    • Korean Journal of Pharmacognosy
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    • v.1 no.2
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    • pp.23-28
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    • 1970
  • One of the indigeneous plants to this country, Syringa dilatata $N_{AKAI}$ (Oleaceae) is known in commerce as 'Ya-Jung-Hyang' (野丁香) and has been known to be of effect as bitter stomachics. Seasonal variations in the content of polyalcohols and free reducing sugars in leaves of this plant which contains syringin glycoside, mannitol and free reducing sugars etc. were studied. Application of chromotropic acid to formaldehyde which was obtained from polyalcohols and reducing sugars by treatment with periodic acid results in reddish violet coloration and the solution has absorption maximum at wave length $570m\;{\mu}$. By the use of ionic exchange resin chromatography, poyalcohols were separated from the above mixture. The content of polyalcohols of this plant was plentiful in the growing season while that of free reducing sugars was decreasing vice versa.

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Flavonol Glycosides from Parthenocissus tricuspidata Leaves (담쟁이덩굴엽의 플라보놀 배당체)

  • 황현경;성환길;황완균;김일혁
    • YAKHAK HOEJI
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    • v.39 no.3
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    • pp.289-296
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    • 1995
  • For the investigation of medicinal resources the studies were carried out to evaluated the pharmaco-constituents in the Leaves of Parthenocissus tricuspidata(Vitaceae), of which leaves have been used in Korea as folk remedies for the treatments of arthritis, jaundice, toothache, neuralgia, and etc. From 1-butanol fraction of the MeOH extract, Compound I ($C_{21}H_{18}O_{13}$, Quercetin-3-O-$\beta$-D-glucuronopyranoside), Compound II ($C_{21}H_{20}O_{12}$, Quercetin-3-O-$\beta$-D-glucopyranoside) and Compound III ($C_{25}H_{28}O_{12}$, Quercetin-3-O-(6"-n-butyl)-$\beta$-D-glucuronopyranoside) were isolated by column chromatographic separation using Sephadex LH-20 and ODS gel. Their structures were elucidated through instrumental analyses, such as $^{1}H$-NMR, $^{13}C$-NMR, IR, UV, El-Mass, FAB-Mass and GC. Especially compound III was Flavonol glycoside and named parthenosin.

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Isolation and quantitative analysis of metabolites from Scrophularia buergeriana and their hepatoprotective effects against HepG2 Cells (현삼 (Scrophularia buergeriana)에서 분리한 화합물의 함량분석 및 간세포 보호 효과)

  • Na, Hyeon Seon;Oh, Seon Min;Shin, Woo Cheol;Bo, Jeon Hwang;Kim, Hyoung-Geun;Yoon, Dahye;Yang, Seung Hwan;Lee, Young-Seob;Kim, Geum-Soog;Baek, Nam-In;Lee, Moon-Soon;Lee, Dae Young
    • Journal of Applied Biological Chemistry
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    • v.62 no.4
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    • pp.399-406
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    • 2019
  • The roots of Scrophularia buergeriana were extracted with 80% aqueous Methanol and the concentrates were partitioned into EtOAc, n-BuOH, and H2O fractions. The repeated silica gel or octadecyl SiO2column, and medium pressure liquid chromatographies for the n-BuOH fraction led to isolation of phenylethanoid glycosides and iridoid glycosides. The chemical structures of these compounds were determined as harpagoside (1), angoroside C (2), aucubin (3) and acetoside (4) based on spectroscopic analyses including nuclear magnetic resonance and MS. A simple and efficient HPLC with UV detection method for the simultaneous determination of the four compounds (1-4) has been developed and applied to their content determination in the S. buergeriana. The roots were extracted by 80% methanol, and the contents of 1, 2, 3, and 4 were determined to 11.5, 7.6, 41.2, and 4.8 mg/g, respectively. Additionally, angoroside C (2) and acetoside (4) exhibited hepatoprotective effect against ethanol-induced hepatotoxicity in HepG2 cell line.

Isolations of Flavonoids and a Higher Alcohol from the Aerial Parts of Brassica juncea (갓 지상부에서 플라보노이드와 고급 알콜 화합물의 분리)

  • Ahn, Byoung-Gwan;Hur, Jong-Moon;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • v.38 no.3 s.150
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    • pp.254-257
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    • 2007
  • The aerial parts of Brassica juncea (Cruciferae) called by brown or oriental mustard have been widely used as a spice in food and also traditional folk medicine as stimulant, diuretic and expectorant agent. And Gatkimchi made of the aerial parts of this plant are very popular in Korea. The aerial parts of this plant was refluxed with MeOH and then fractionationed with $CH_2Cl_2$, EtOAc, n-BuOH and $H_2O$, successively. One higher alcohol compound and three flavonoids were isolated from the EtOAc fraction through silica gel and Sephadex LH-20 column chromatographies. Their structures were elucidated as n-hexacosanol(1), kaempferol(2), isorhamnetin $3-O-{\beta}-D-glucopyranoside(3)$ and isorhamnetin $3-O-(6'-O-acetyl)-{\beta}-D-glucopyranoside(4)$ by comparison of spectral data with those in references. And compounds 1 and 4 were firstly isolated from this plant.

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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Fractionnement des produits de $r{\acute{e}}action$ de Maillard par $diff{\acute{e}}rentes$ techniques et observation $d'activit{\acute{e}}$ fermentaire do ces fractions -II. Fractionnement par chromatographie de partage- (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) -II. 분배(分配)크로마토고라피에 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.101-104
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    • 1969
  • Partition chromatography의 방법(方法)으로는 우선 cellulose powder colume을 시도해 보았으나 이는 얻어진 fraction의 용매제거의 난점(難點)이 있으므로 결국(結局) paper chromatography 방법(方法)만을 사용(使用)하였다. 연구결과(硏究結果)로는 우선 갈색색소의 fraction에 있어서 발효초기(醱酵初期)에 약간의 활성(活性)을 관찰(觀察)할수 있었으며 glycine이 함유된 fraction 에서는 발효초기에 벌써 상당한 활성을 보였으며 이는 또한 발효의 진행(進行)에 따라 점차 증가되었다. 그리고 N-glycoside의 fraction에서는 발효초기에 미약(微弱)한 활성(活性)을 관찰할 수 있었다. 그러나 paper chromatography의 방법(方法)은 본실험(本實驗)에 적합하지 않다고 생각되며 그 이유(理由)는 일회(一回)에 fractionation 할수있는 시료(試料)의 양(量)이 극(極)히 제한되어 있다는 점(點)과 또 fractionation 도중에 타물질(他物質)의 오염으로 인(因)해서 시료(試料)의 정확(正確)한 발효 활성(活性)을 측정(測定)할수 없다는 것이다.

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