• Title/Summary/Keyword: Quercetin-3-O-glucoside

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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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Component Analysis and Study on Anti-elastase Activity of Equisetum arvense Extracts(II) (쇠뜨기 추출물의 성분 분석과 엘라스타제 활성 저해 효과 연구(II))

  • Park, Soo-Nam;Yang, Hee-Jung
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.33 no.3
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    • pp.139-144
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    • 2007
  • In the previous study, we reported the antioxidative activity of Equisetum arvense extracts. In this study, its inhibitory effect on elastase and components were investigated. Aglycone fractions obtained from the deglycosylation reaction of ethylacetate fraction among the Equisetum arvense extracts, showed 4 bands and 4 peaks in TLC and HPLC experiments, respectively. Four components were identified as luteolin(composition ratio, 19.12%), quercetin(12.87), apigenin(15.81) and kaempferol(52.20). TLC chromatogram of ethylacetate fraction of Equisetum arvense extract revealed 7 bands and HPLC chromatogram showed 8 peaks, which were identified as kaempferol-3,7-O-diglucoside(composition ratio, 15.74%), luteolin-5-O-glucoside(galuteolin, 11.91), apigenin-5-O-glucoside(12.91), kaempferol-3-O-glucoside(astragalin, 27.94), quercetin-glycoside(10.81, structure was not determined), kaempferol-glycoside (12.33, structure was not determined), luteolin(3.72) and apigenin(4.62) in the order of elution time. The inhibitory effect of aglycone fraction on elastase($IC_{50}$, $9.8{\mu}g/mL$) was very high. But ethylacetate fraction(flavonoid glycosides) rarely exhibited the inhibitory activity on elastase. Combined with the previous results of the antioxidative activity of Equisetum arvense extracts, it is concluded that the inhibitory activity on elastase of the aglycone fraction could be applicable to new functional cosmetics for smoothing wrinkles.

A Novel Benzoyl Glucoside and Phenolic Compounds from the Leaves of Camellia japonica

  • Cho, Jeong-Yong;Ji, Soo-Hyun;Moon, Jae-Hak;Lee, Kye-Han;Jung, Kyung-Hee;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.17 no.5
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    • pp.1060-1065
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    • 2008
  • A novel benzoyl glucoside (4) and 13 known phenolic compounds were isolated from the leaves of Camellia japonica by a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The structure of 4 was determined to be 4-hydroxy-2-methoxyphenol 1-O-$\beta$-D-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (camelliadiphenoside). The 13 known compounds were identified as (E)-coniferyl alcohol (1), (-)-epicatechin (2), 4-hydroxyphenol 1-O-$\beta$-D-(6-O-p-hydroxybenzoyl) glucopyranoside (3), naringenin 7-O-$\beta$-D-glucopyranoside (5), quercetin 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (6), kaempferol 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (7), (+)-catechin (8), 1,6-di-O-p-hydroxybenzoyl-$\beta$-D-glucopyranoside (9), phloretin 2'-O-$\beta$-D-glucopyranoside (10), quercetin 3-O-$\beta$-D-glucopyranoside (11), quercetin 3-O-$\beta$-D-galactopyranoside (12), kaempferol 3-O-$\beta$-D-galactopyranoside (13), and kaempferol 3-O-$\beta$-D-glucopyranoside (14). Their chemical structures were determined by the spectroscopic data of fast atom bondardment mass spectrometry (FABMS) and nuclear magnetic resonance (NMR). Flavonoids having the catechol moiety showed significantly higher DPPH radical scavenging activity than other isolated compounds having monohydroxy phenyl group.

Phenolic Compounds from Orostachys japonicus having Anti-HIV-1 Protease Activity

  • Park, Ju-Gwon;Park, Jong-Cheol;Hur, Jong-Moon;Park, Sung-Jong;Choi, Da-Rae;Shin, Dong-Young;Park, Ky-Young;Cho, Hyun-Wook;Kim, Moon-Sung
    • Natural Product Sciences
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    • v.6 no.3
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    • pp.117-121
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    • 2000
  • The water extract of the aerial parts of Orostachys japonicus A. Berger showed the inhibitory activity against HIV-1 protease. From the same parts of O. Japanicus, 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, gallic acid and methyl gallate, together with flavonoids, kaempferol, quercetin, kaempferol $3-O-{\beta}-D-glucoside$, kaempferol $3-O-{\beta}-D-galactoside$ and quercetin $3-O-{\beta}-D-glucoside$ were isolated and characterized by spectral data.

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Comparison of Flavonoid Characteristics between Blueberry (Vaccinium corymbosum) and Black Raspberry (Rubus coreanus) Cultivated in Korea using UPLC-DAD-QTOF/MS (UPLC-DAD-QTOF/MS를 이용한 국내 재배 블루베리(Vaccinium corymbosum)와 복분자(Rubus coreanus)의 플라보노이드 특성 비교)

  • Jin, Young;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Jang, Hwan-Hee;Hwang, Yu-Jin;Choe, Jeong-Sook;Lee, Sung-Hyun;Cha, Youn-Soo;Kim, Jung-Bon
    • Korean Journal of Environmental Agriculture
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    • v.36 no.2
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    • pp.87-96
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    • 2017
  • BACKGROUND: The objective of this study was to identify and compare the main phenolic compounds (anthocyanins, flavonoids, phenolic acids) in blueberry and black raspberry cultivated in Korea using ultra-performance liquid chromatography diode array detection-quadrupole time-of-flight mass spectrometry (UPLC-DAD-QTOF/MS). METHODS AND RESULTS: Twenty-nine flavonoids were identified by comparison of ultraviolet and mass spectra with data in a chemical library and published data. Blueberry contained flavonols including kaempferol, quercetin, isorhamnetin, myricetin, and syringetin aglycones. Isorhamnetin 3-O-robinobioside, kaempferol 3-O-(6"-O-acetyl)glucoside, quercetin, quercetin 3-O-arabinofuranoside (avicularin), quercetin 3-O-(6''-O-malonyl) glucoside, and quercetin 3-O-robinobioside were detected for the first time in blueberry. The flavonoids in raspberry consisted of quercetin aglycone and its glycosides. The mean total flavonoid content in blueberry [143.0 mg/100 g dry weight (DW)] was 1.5-times that in raspberry (95.4 mg/100 g DW). The most abundant flavonoid in blueberry was quercetin 3-O-galactoside (hyperoside, up to 76.1 mg/100 g DW) and that in raspberry was quercetin 3-O-glucuronide (miquelianin, up to 55.5 mg/100 g DW). Miquelianin was not detected in blueberry. CONCLUSION: Flavonol glycosides were the main flavonoids in blueberry and black raspberry cultivated in Korea. The composition and contents of flavonoids differed between blueberry and black raspberry, and may be affected by the cultivar and cultivation conditions.

Flavonoid chemistry of Fallopia sect. Reynoutria (Polygonaceae) in Korea (한국산 닭의덩굴속 호장근절(마디풀과)의 화학분류학적 연구)

  • Park, Jin Hee;Moon, Hye-Kyoung;Park, Chong-Wook
    • Korean Journal of Plant Taxonomy
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    • v.41 no.1
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    • pp.10-15
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    • 2011
  • Fifteen populations comprising three taxa and a putative hybrid of Fallopia sect. Reynoutria in Korea were examined for their leaf flavonoid constituents. Nineteen flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols quercetin and kaempferol, and of the flavones apigenin and luteolin. Among them, quercetin 3-O-galactoside and quercetin 3-O-glucoside were major flavonoid constituents, and present in all taxa. The flavonoid data appear to be very useful for taxon delimitation, and all taxa examined are readily distinguished by their flavonoid profiles. In addition, the flavonoid data suggest that the Nonsan population may be of hybrid origin involving F. japonica var. japonica, F. forbesii, and F. sachalinensis. In F. japonica var. japonica, there is no apparent correlation between their levels of polyploidy and flavonoid chemistry, but geographical variation of the flavonoid profiles among some populations was detected.

Antioxidative and Radical Scavenging Properties of the Constituents Isolated from Cosmos caudatus Kunth

  • Abas, Faridah;Shaari, Khozirah;Lajis, N.H.;Israf, D.A.;Kalsom, Y. Umi
    • Natural Product Sciences
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    • v.9 no.4
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    • pp.245-248
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    • 2003
  • A phytochemical investigation on the methanolic extract of Cosmos caudatus has led to the isolation of quercetin $3-O-{\beta}-D-arabinofuranoside$ (1), quercetin $3-O-{\beta}-D-rhamnoside$ (2), quercetin $3-O-{\alpha]-D-glucoside$ (3) and quercetin (4). These compounds were shown to be the antioxidative constituents of the plant when evaluated using the ferric thiocyanate (FTC) and thiobarbituric acid (TBA), and radical scavengers based on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assays.

Triterpenoids and Flavonoids Isolated from the Leaves of Alnus firma (사방오리 잎의 Triterpenoid 및 Flavonoid 화합물)

  • Yu, Young-Beob;Nakamura, Norio;Miyashiro, Hirotsugu;Hattori, Masao;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • v.38 no.1
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    • pp.76-83
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    • 2007
  • In this study, three triterpenoids, two steroids and nine flavonoids were isolated from the leaves of Alnus firma Sieb. et Zucc. On the basis of spectroscopic evidences, the structures of these compounds were established as ${\beta}$-amyrin acetate, ${\beta}$-amyrin, ${\beta}$-sitosterol, alnustic acid methyl ester, ${\beta}$-sitosterol glucoside, pinocembrin, alnustinol, quercetin, quercetin-3-O-${\alpha}$-L-arabinofuranoside, quercetin-3-O-${\alpha}$-L -rhamnopyranoside, quercetin-3-O-${\beta}$-D-glucopyranoside, myricetin-3-O-${\beta}$-D-galac-topyranoside, (+)-catechin and (-)-epicatechin.

Hybridization of Quercus aliena Blume and Q. serrata Murray in Korea - Analyses of Morphological variation and Flavonoid chemistry -

  • Park, Jin Hee;Park, Chong-Wook
    • Korean Journal of Environment and Ecology
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    • v.29 no.2
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    • pp.145-161
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    • 2015
  • This research was conducted in order to understand the hybridization between Quercus aliena Blume and Q. serrata Murray in Korea which show wide range of morphological variations within species and interspecific variations of diverse overlapping characteristics caused by hybridization. Morphological analysis (principal components analysis; PCA) of 116 individuals representing two species and their intermediates were performed. As a result, two species were clearly distinguished in terms of morphology, and intermediate morpho-types assumed to be hybrids between the two species were mostly located in the middle of each parent species in the plot of the principal components analysis. There was a clear distinction between two species in trichome distribution pattern which is an important diagnostic character in taxonomy of genus Quercus, whereas intermediate morpho-types showed intermediate state between two species' trichome distributions. Forty-two individuals representing two species and their intermediates were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified: They were glycosylated derivatives of flavonols, kaempferol, quercetin, isorhamnetin and myricetin. The flavonoid constituents of Q. aliena were five glycosylated derivatives: kaempferol 3-O-galactoside, kaempferol 3-O-glucoside, quercetin 3-O-galactoside, quercetin 3-O-glucoside, and Isorhamnetin 3-O-glucoside. The flavonoid constituents of Q. serrata had 20 diverse flavonol compounds including five flavonoid compounds found in Q. aliena. It was found that there is a clear difference in flavonoid constituents of Q. aliena and Q. serrata. Flavonoid chemistry is very useful in recognizing each species and putative hybrids. The flavonoid constituents of intermediates were a mixture of the two species' constituents and they generally showed similar characteristics to morpho-types. The hybrids between Q. aliena and Q. serrata showed morphologically and chemically diverse characteristics and it is assumed that there are frequent interspecific hybridization and introgression.

Inhibitory Effects of Methanol Extract, Phenolic Acids and Flavonoids from the Leaves of Eucalyptus darylmpleana against 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Park, Jong-Cheol;Park, Ju-Gwon;Hur, Jae-Seoun;Choi, Myeong-Rak;Yoo, Eun-Jeong;Kim, Sung-Hwan;Son, Jin-Chang;Kim, Moon-Sung
    • Natural Product Sciences
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    • v.10 no.5
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    • pp.244-247
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    • 2004
  • The inhibitory effects of the leaves of Eucalyptus darylmpleana (Myrtaceae) on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was examined. The scavenging effect of the ethyl acetate fraction of Eucalyptus darylmpleana leaves on DPPH radical was stronger than the other fractions, and further purified by silica gel and Sephadex LH-20 column chromatography. 3,4-Dihydroxybenzoic acid, gallic acid, quercetin, quercetin $3-O-{\alpha}-_L-rhamnoside$, quercetin $3-O-{\beta}-_D-glucoside$ and quercetin 3-O-rutinoside were isolated and elucidated by spectroscopic data. Among these components, gallic acid and quercetin $3-O-{\alpha}-_L-rhamnoside$ exhibited potent scavenging activities on DPPH radical with $IC_{50}$ values of 6.02 and $5.54\;{\mu}M$, respectively.