• 한국식품위생안전성학회지
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• 제11권2호
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• pp.115-121
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• 1996

In order to compare the suppressive effect of quercetin and several its glycosides, such as quercitrin (quercetin-3-rhamnoside), isoquercitrin (quercetin-3-glucoside), hyperin (quercetin-3-galactoside) and tutin (quercetin-3-rhamnosyl glucoside), on the genotoxicity by N-methyl-N-nitrosourea(MNU), in vitro sister chromatid exchange(SCE) test using mouse spleen lymphocytes and in vivo micronucleus test using mouse peripheral blood were performed. MNU-induced SCEs in vitro were not decreased by the simultaneous treatment of test compounds. Among them, quercetin and hyperin showed significant suppressive effects at high dose(10-5M). On the other hand, MNU-induced micronucleated reticulocytes(MNRETS) in vivo were significantly decreased with good dose-dependent manner in all compound tested. However, there were not significant differences between quercetin aglycone and its glycosides in the suppressive aglycone and its glycosides may act as an antigenotoxic agent in vivo and may be useful as a chemopreventive agent of alkylating agent.

• Biomolecules & Therapeutics
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• 제24권4호
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• pp.410-417
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• 2016

Quercetin is a flavonoid usually found in fruits and vegetables. Aside from its antioxidative effects, quercetin, like other flavonoids, has a various neuropharmacological actions. Quercetin-3-O-rhamnoside (Rham1), quercetin-3-O-rutinoside (Rutin), and quercetin-3-(2(G)-rhamnosylrutinoside (Rham2) are mono-, di-, and tri-glycosylated forms of quercetin, respectively. In a previous study, we showed that quercetin can enhance ${\alpha}7$ nicotinic acetylcholine receptor (${\alpha}7$ nAChR)-mediated ion currents. However, the role of the carbohydrates attached to quercetin in the regulation of ${\alpha}7$ nAChR channel activity has not been determined. In the present study, we investigated the effects of quercetin glycosides on the acetylcholine induced peak inward current ($I_{ACh}$) in Xenopus oocytes expressing the ${\alpha}7$ nAChR. $I_{ACh}$ was measured with a two-electrode voltage clamp technique. In oocytes injected with ${\alpha}7$ nAChR copy RNA, quercetin enhanced $I_{ACh}$, whereas quercetin glycosides inhibited $I_{ACh}$. Quercetin glycosides mediated an inhibition of $I_{ACh}$, which increased when they were pre-applied and the inhibitory effects were concentration dependent. The order of $I_{ACh}$ inhibition by quercetin glycosides was Rutin${\geq}$Rham1>Rham2. Quercetin glycosides-mediated $I_{ACh}$ enhancement was not affected by ACh concentration and appeared voltage-independent. Furthermore, quercetin-mediated $I_{ACh}$ inhibition can be attenuated when quercetin is co-applied with Rham1 and Rutin, indicating that quercetin glycosides could interfere with quercetin-mediated ${\alpha}7$ nAChR regulation and that the number of carbohydrates in the quercetin glycoside plays a key role in the interruption of quercetin action. These results show that quercetin and quercetin glycosides regulate the ${\alpha}7$ nAChR in a differential manner.

• 한국환경성돌연변이발암원학회지
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• 제19권2호
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• pp.116-121
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• 1999

Quercetin and its glycosides showed a strong free radical scavenging effect to DPPH radical generation. However, there were not big differences between quercetin aglycone and glycosides under experimental condition of this study. On the other hand, quercetin had pro-oxidant effect in bleomycin-dependent DNA assay. Quercetin aglycone and its glycosides, quercitrin inhibited $H_2$$O_2$- induced DNA damage in CHL cells. They also have an anticlastogenicity toward DNA breakage agent by radical generation like bleomycin. These results indicate that quercetin aglycone and its glycosides are capable of protecting the free radical generation induced by reactive oxygen species like $H_2$$O_2$. The mechanism of inhibition in hydrogen peroxide-induced genotoxicity may be due to their free radical scavenging properties. Therefore, quercetin aglycone and its glycosides may be useful chemopreventive agents by protecting of free radical generation which are involved in carcinogenesis and aging. However, quercetin and its glycosides must also carefully examined for pro-oxidant properties before being proposed for use in vivo.

• 약학회지
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• 제42권4호
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• pp.414-421
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• 1998

In order to compare the suppressive effect of quercetin and its glycosides, such as quercitrin (quercetin-3-rhamnoside), isoquercitrin (quercetin-3-glucoside), hyperin (querceti n-3-galactoside)and rutin (quercetin-3-rhamnosyl glucoside), on the genotocicity by benzo(a)pyrene(B(a)P), in vitro sister chromatid exchange(SCE) test using mouse spleen lymphocytes and in vivo micronucleus test using mouse peripheral blood were performed. B(a)P-induced SCEs in vitro were slightly decreased by the simultaneous treatment of quercetin and its glycosides, although there was no significant decrease. On the other hand, MNU induced micronucleated reticulocytes(MNRL7s) in vivo were significantly decreased with a dose-dependent manner in all compounds tested. However, there were no differences between quercetin aglycone and glycosides in the suppressive effects under experimental condition of this study. To elucidate, the action mechanism of quercetin aglycone and its glycosides against B(a)P-induced genotoxicity, the assay of DNA binding with B(a)P was studied. Quercetin aglycone and its glycosides inhibited B(a)P metabolism in the presence of S-9 mix and decreased the B(a)P/DNA binding in the calf thymus DNA with S-9 mix. These results suggest that antigenotoxicity of quercetin antiglycosides on B(a)P-induced genotoxicity is due to decrease of DNA binding with B(a)P through the inhibition of metabolism with B(a)P in the calf thymus DNA. Therefore, quercetin and its glycosides may act as an antigenotoxicity agent and may be useful as a chemopreventive agent of polycyclic aromaic hydrocarbons like B(a)P.

• Horticulture, Environment, and Biotechnology : HEB
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• 제59권6호
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• pp.909-917
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• 2018

Quercetin and its glycoside derivatives were identified and quantified using high-performance liquid chromatograph (HPLC) and liquid chromatograph/mass spectrometer/mass spectrometer (LC/MS/MS) in the leaves, flowers, and fruits of 22 Malus genotypes. In all genotypes, small amounts of quercetin aglycone were present, with water-soluble glycoside forms were the most abundant in different Malus plant tissues, including quercetin-3-galactoside, quercetin-3-rutinoside, quercetin-3-glucoside, quercetin-3-xyloside, quercetin-3-arabinoside, and quercetin-3-rhamnoside. Among these six quercetin glycosides, quercetin-3-galactoside was the common form in Malus plants, except in the leaves and flowers of M. ceracifolia and M. magdeburgensis, and in the fruits of M. micromalus 'Haihong Fruit', where there was a higher concentration of quercetin3-glucoside. Among the different tissues tested, leaves contained the highest concentration of quercetin and its glycosides, while fruits contained the lowest concentrations of these compounds. Among the genotypes we analyzed, no specific genotype consistently contained the highest concentration of quercetin and its glycoside derivatives. M. domestica 'Honeycrisp' had the highest total compound concentration (approximately $1600mg\;kg^{-1}$), whereas M. hupehensis contained the lowest in its fruits. In contrast, the concentration of total quercetin and its glycosides was more than $5000mg\;kg^{-1}$ in the leaves of eight genotypes and greater than $2500mg\;kg^{-1}$ in the flowers of seven species. In general, the concentration of quercetin and its glycoside derivatives depended on the species and tissue type. These results may provide useful information for the evaluation and selection of edible Malus fruits and the materials for quercetin glycoside extraction.

• Natural Product Sciences
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• 제8권3호
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• pp.77-82
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• 2002

An investigation of the methanolic extract of Maesa lanceolata leaves has led to the isolation of four novel flavonol glycosides characterised as myricetin 3-0-2', 3', 4'-triacetylxylopyranoside (1), quercetin $3-O-{\beta}-3'$, $6'-diacetylglucopyranosyl-(1{\longrightarrow}4)-{\alpha}-2'$, 3'-diacetylrhamnopyranoside (2), myricetin $3-O-xylopyranosyl-(1{\to}3)-{\alpha}-rhamnopyranoside$ (3) and quercetin $3-O-{\beta}-ga1actopyranosyl-(1{\to}4)-{\alpha}-rhamnopyranoside-7-O-{\beta}-galactopyranoside$ (4). Also isolated from the same extract were known flavonols; quercetin (5), myricetin (6), quercetin 3-O-xylopyranoside (7), quercetin $3-O-{\alpha}-rhamnopyranoside$ (8), myricetin $3-O-{\alpha}-rhamnopyranoside$ (9), myricetin $3-O-{\beta}-galactopyranoside$ (10) and quercetin 3-O-rutinoside (11).

• Archives of Pharmacal Research
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• 제22권4호
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• pp.423-427
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• 1999

A study was carried out to evaluate flavonol glycosides in leaves of Symplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, Kaempferol-3-O-$\beta$-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, quercetin-3-O-$\beta$-D-glucopyranosy-1-($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses a quercetin-3-O-$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, isorhamnetin-3-O-$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranosdie, and quercetin-3-O$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glycopyranosyl-7-O-($6^{IIII}$-trans-caffeoyl)-$\beta$-D-glucopyranoside.

• 생약학회지
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• 제24권1호
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• pp.47-53
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• 1993

The seasonal variations of the major six flavonol glycosides(kaempferol 2,6-dirhamnosyl glucoside, quercetin 3-O-rutinoside, kaempferol 3-O-rutinoside, isorhamnetin 3-O-rutinoside, quercetin 3-O-coumaroyl glucorhamnoside and kaempferol 3-O-coumaroyl glucorhamnoside) in Ginkgo biloba leaves were investigated. The contents were determined by HPLC on reversed phase $C_{18}$ column. This result showed that the percentage of six flavonol glycosides decreased during the season from 1.57% in May to 0.39% in November. The content of each flavonol glycoside indicated a similar tendency to decrease. However, the contents of rutinosides of kaempferol, quercetin and isorhamnetin fluctuated markedly than those of coumaroyl glucorhamnosides of kaempferol and quercetin and kaempferol 2,6-dirhamnosyl glucoside.

• 한국식품과학회지
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• 제54권2호
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• pp.115-125
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• 2022

열풍건조로 제조된 껍질을 포함한 적양파 분말은 강력한 항산화제인 플라보노이드 함량이 생양파즙에 비해 약 22배로 고농도로 농축되어 있으며, 60-70% ethanol 농도에서 70℃, 2시간 추출시 가장 높은 수율을 나타내었다. 이때 추출된 플라보노이드의 함량은 DPPH radical 소거능과 상관계수 0.877의 높은 상관관계를 나타내었다. 적양파 분말의 플라보이드는 주로 quercetin 배당체인 Q3,4'G, Q4'G와 QA로 이루어져 있으며, 15:39:47의 비율로 구성되어 있었다. 염산, 젖산, 초산 등 다양한 종류의 산처리에 의해 적양파 분말 속 quercetin 배당체는 QA로 전환될 수 있었으며 저농도 초산용액에서 QA로 전환되는 비율이 높았다. 이는 적양파 분말에 포함된 glucosidase가 저농도 산용액에서 활성화되면서 일어나는 반응으로 사료되었다. 초산 처리초기에는 diglycoside인 Q3,4'G의 de-glycosylation이 급격히 일어났으며, 초산처리 6시간 이후에는 Q4'G의 분해와 함께 QA가 증가하여 24시간 경과 후에 최대 QA의 함량에 도달하였으며, QA의 증가는 DPPH radical 소거능과 유의적인 상관성(r=0.90)을 나타내어 생리활성의 증가를 나타내었다. 본 연구결과, 양파의 주요 플라보노이드인 quercetin 배당체는 저농도 초산 처리로 빠르고 간편하게 QA로 전환이 가능하였으며, 이와 더불어 생리활성의 증가도 도모할 수 있었다. 적양파 분말을 이용하여 저농도 산처리를 통하여 QA로의 전환률을 높이면, 고농도의 quercetin을 함유한 양파 소재의 개발이 가능할 것이며, 이를 통해 기능성 양파 가공품의 개발로 이어질 수 있을 것이다.

• 약학회지
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• 제50권6호
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• pp.351-357
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• 2006

Polygoni Radix (Polygonaceae) has been used as renal disoder hematopoietic, menstrual irregularity and antiaging in Korean folk medicine. Specially aerial parts has been used for insomnia and sedative agent. In order to investigate the efficacy of antioxidant activity on these aerial parts, the bio-activity guided fraction and isolation of physiologically active substance were performed. H$_2$O, 30%, 60%, 100% MeOH were examined antioxidant activity by DPPH method. It was revealed that 30%, 60% MeOH fractions have significantly antioxidant activity. From 60% MeOH fraction, six known flavonoid glycosides (quercetin, quercetin 3-O-${\beta}$-D-galactopyranosyl-4'-O-glucopyrano side-3'-methyl ether, quercetin 3-O-${\alpha}$-L-rhannopyranoside, quercetin 3-O- ${\alpha}$-L-rhamnopyranoside-4'-methylethor, quorcetin 3-O-${\beta}$-D-galactopyranoside, quercetin 3-O-${\beta}$-D-galactopyranoside) and 3,4-Oihydrocinnarnic acid were isolated. To investigate the antioxidant activities of each com-pounds, we measured radical scavening activity with DPPH method and anti-lipid peroxidative efficacy on low density lipo-protein (LDL) with TBARS assay and anti-acetylcholinestrase activity with Ellman's Test. Four compounds (ll, IV Vl, Vll) of quercetin glycosides showed significant activity.