• 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.

• 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.

• 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.

• Archives of Pharmacal Research
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• 제27권7호
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• pp.751-756
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• 2004

Flavonoids have been demonstrated to exhibit a wide range of biological activities including anti-inflammatory and neuroprotective actions. Although a significant amount of flavonoids has been identified to be present as glycosides in medicinal plants, determinations of the biological activities of flavonoids were mainly carried out with aglycones of flavonoids. Therefore, the exact role of the glycosidation of flavonoid aglycones needs to be established. In an attempt to understand the possible role of glycosidation on the modulation of the biological activities of flavonoids, diverse glycosides of kaempferol, quercetin, and aromadendrin were examined in terms of their anti-inflammatory activity determined with the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglial cells. The results indicated that glycosidation of aglycones attenuated the suppressive activity of aglycones on LPS-induced NO production. Although attenuated, some of glycosides, depending on the position and degree of glycosidation, maintained the inhibitory capability of LPS-induced NO production. These findings suggest that glycosidation of flavonoid aglycones should be considered as an important modulator of the biological activities of flavonoids.

• 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.

• 한국식품저장유통학회지
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• 제23권7호
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• pp.1004-1011
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• 2016

본 연구에서는 국내산 대추나무의 잎과 열매의 flavonoid 배당체를 조사하기 위하여 선행 연구된 인용문헌을 바탕으로 대추나무, 묏대추나무, 야생대추나무 등 대추나무속(Zizyphus)에 따른 flavonoid의 화학적 정보 수집 및 정리하여 대추나무속의 flavonoid 라이브러리를 제작하였다. 각 flavonoid 개별성분은 UPLC-DAD-QTOF-ESI/MS를 사용하여 분석하였으며 제작된 라이브러리의 정보를 이용하여 국내산 대추나무로부터 총 6종의 flavonoid를 확인하였다. 이를 통하여 국내산 대추나무 잎의 주요 성분은 quercetin 배당체인 rutin임을 확인하였고, 특히 quercetin 3-O-robinobioside 및 isoquercitrin는 구축된 라이브러리를 바탕으로 대추나무 잎에서는 처음 확인된 것을 알 수 있었다. 본 연구와 같이 대추나무속 flavonoid의 화합물 정보를 포함하여 제작한 라이브러리는 선행된 연구와의 차이점 판단을 가능하게 할 것으로 사료된다.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1998년도 Proceedings of UNESCO-internetwork Cooperative Regional Seminar and Workshop on Bioassay Guided Isolation of Bioactive Substances from Natural Products and Microbial Products
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• pp.186-186
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• 1998

Persicaria lapathifolia Gray (Polygonaceae) is a common weed in Korea. This plant and other Persicaria species including P. orientale and P. pubescens have been used as an analgesic and stomachic as well as for the treatment of rheumatoid arthritis and malaria. During the screening program of plant extracts, MeOH extract of P. scabrum showed anticomplement activity and the MeOH extract was partitioned with hexane, chloroform, ethyl acetate, and buthanol. EtOAc fraction showed strong activity and activity guided separation yielded eight flavonoids. Two known galloylated and a novel ferulloylated flavonoid glycosides showed strong anticomplement activity. Other flavonoid glycosides, kaempferol 3-O-${\alpha}$-$\sub$L/-arabinopyranoside, kaempferol 3-O-${\beta}$-$\sub$D/-glucopyranoside, kaempferol 3-O-${\beta}$-$\sub$D/-galactopyranoside, quercetin 3-O-${\alpha}$-$\sub$L/-arabinopyranoside, quercetin 3-O-${\beta}$-$\sub$D/-glucopyranoside, quercetin O-${\beta}$-$\sub$D/-galactopyranoside did not showed anicomplement activity.

• 생명과학회지
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• 제29권12호
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• pp.1371-1377
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• 2019

뇌에서 과량의 reactive oxygen species (ROS) 생성에 의해 유발되는 산화적 스트레스는 알츠하이머 질환과 같은 신경퇴행성 질환의 원인으로 알려져 있다. 본 연구에서는 kaempferol, kaempferol-3-O-glucoside, quercetin, quercetin-3-β-D-glucoside와 같은 flavonoid와 그 배당체의 H₂O₂ 유도 산화적 스트레스에 대한 C6 신경교세포보호 효과를 확인하였다. H₂O₂만을 처리한 control군은 아무것도 처리하지 않은 normal군에 비해 세포 생존율 감소와 ROS 생성 증가를 통해 C6 신경교세포의 산화적 손상이 유도되었음을 확인하였다. 반면 4가지 flavonoid를 각각 처리한 군의 경우, H₂O₂를 처리한 control군에 비해 세포 생존율 증가와 ROS 생성 감소를 통해 산화적 손상 억제를 통한 신경교세포 보호 효과를 확인하였다. Flavonoid의 신경교세포 보호 작용 메커니즘을 규명하기 위해, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and interleukine (IL)-1β 등의 염증 관련 단백질 발현을 측정하였다. H₂O₂를 처리한 control군은 normal군에 비해 iNOS, COX-2, IL-1β 단백질 발현 증가와 IκB-α 발현 감소를 통해 신경교세포의 산화적 손상으로 인한 염증 반응을 확인하였다. 반면, 4가지 flavonoid를 각각 처리한 군의 경우 iNOS, COX-2, IL-1β 단백질 발현 감소와 IκB-α 발현 증가를 나타내어, 염증 반응 개선을 통한 신경교세포 보호 효과를 확인하였다. 특히, quercetin과 그 배당체인 quercetin-3-β-D-glucoside를 처리한 군은 kaempferol과 그 배당체인 kaempferol-3-O-glucoside를 처리한 군에 비해 우수한 신경교세포 보호 효과를 나타내었다. 본 연구는 4가지 flavonoid가 신경교세포에서 산화적 스트레스 억제를 통해 신경퇴행성 질환을 예방 및 치료할 수 있을 것으로 사료된다.

• Archives of Pharmacal Research
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• 제25권3호
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• pp.313-319
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• 2002

A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

• Preventive Nutrition and Food Science
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• 제10권1호
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• pp.1-5
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• 2005

Eight flavonoids, apigenin-6-C-β-D-glucopyranosy l-8-C-β-D-glucopyranoside (AGG), quercetin 7-O-β-D­glucopyranoside (QG), luteolin 7-O-β-D-glucopyranoside (LG), quercetin 7-O-(6'-O-acetyl)-β-D-glucopyranoside (QAG), luteolin 7-O-(6'-O-acetyl)-β-D-glucopyranoside(LAG), quercetin (Q), luteolin (L) and acacetin 7-O-β­D-glucuronide (AG) were determined by HPLC in the safflower (Carthamus tinctorius L.) leaf during growth and processing. During growth, levels of five flavonoid glycosides (AGG, QG, LG, QAG, & LAG) in the leaf increased progressively at over time according to growth stages, reached a maximum before June 11, and then decreased sharply, while those of three flavonoid aglycones (Q, L, & AG) increased greatly at the early stage of growth, reached a peak before May 28, and then decreased rapidly. During the steaming process, contents of five flavonoid glycosides increased rapidly with increased steaming time, reached a maximum after 5 min of steaming, and then decreased, whereas those of flavonoid aglycones except for AG decreased sharply with increased steaming time. During the roasting process, contents of three flavonoid glycosides decreased rapidly with increased roasting time, whereas those of two acetylflavonoid glycosides (QAG & LAG) and three flavonoid aglycones increased progressively with increased roasting time, reached a maximum after 3 min of roasting, and then decreased. These results suggest that appropriate steamed and roasted safflower leaves are a rich source of flavonoids, and may be a good source of bioactive components as a functional leaf tea.