• Title/Summary/Keyword: $quercetin-3-O-{\beta}-D-galactopyranoside$

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Isolation of Compounds having Inhibitory Activity toward Tyrosinase from Receptaculum Nelumbinis (연방(蓮房)의 티로시나제 저해 활성을 보이는 성분분리)

  • Cho, Hyun Woo;Jung, Won Seok;An, Byeong Gwan;Cho, Jung Hee;Jung, Su Young
    • Korean Journal of Pharmacognosy
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    • v.44 no.1
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    • pp.1-5
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    • 2013
  • Nelnumbo nucifera Gaerth. (Nymphaeaceae) has been used in a korean traditional medicine to treat fever, sunstroke and dizziness. The receptaculums of this plant were refluxed with MeOH, and then fractionated with organic solvents ($CH_2Cl_2$, EtOAc and n-BuOH) to screen whitening activity using tyrosinase inhibitory activity. EtOAc ($IC_{50}$, 45.23 ${\mu}g/ml$) fractions showed a good tyrosinase inhibitory activity. Column chromatographic separation of $CH_2Cl_2$ and EtOAc fractions of Receptaculum nelumbinis led to the isolation 3 compounds. Their chemical structures were characterized as ${\beta}$-sitosterol (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2) and kaempferol 3-O-${\beta}$-D-glucopyranoside (3) by comparison NMR spectral data and with those in references, respectively. Isolated compounds 1 and 3 were firstly isolated from Receptaculums nelumbinis. Compounds 2 and 3 showed potent whitening activities.

Constituents of Crataegus Pinnatifida Var. psilosa Leaves (II) -Flavonoide from BuOH Fraction-

  • Oh, In-Se;Whang, Wan-Kyun;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.17 no.5
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    • pp.314-317
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    • 1994
  • The studies were camied out to evaluate the constituents in the leaves of Crataegus pinnatifida var. psilosa (Rosaceae) continuously. From the BuOH fraction of the MeOH extract, four flavonoid compounds, hyperoside (1), vitexin (2), 3"-O-rhamnosylvitexin (3) and $quercetin-3-O-{\alpha}-L-rhamnopyranoslyl-(1{\rightarrow}6)-{\beta}$-D-galactopyranoside (4) were isolated and identified on the basis of their physico-chemical properties and spectroscopic evidences by comparison with authentic samples.

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Isolation of a New Quercetin 3-O-trisaccharide from the Leaves of Rubus crataegifolius

  • Nam, Jung-Hwan;Jung, Hyun-Ju;Kim, Won-Bae;Park, Jong-Hee;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.13 no.3
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    • pp.225-228
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    • 2007
  • A new quercetin 3-O-trisaccharide was isolated from the leaves of Rubus crataegifolius (Rosaceae). The structure of this compound was determined as quercetin $3-O-{\alpha}-L-arabinofuranosyl-(1{\rightarrow}2)-{\beta}-D-xylopyranosyl-(1{\rightarrow}2)-{\beta}-D-galactopyranoside$ on the basis of 2D-NMR spectroscopic data. This flavonol glycoside was isolated for the first time from a natural source.

Isolation of Anti-oxidant from Domestic Crataegus pinnatifida Bunge Leaves (국산 산사나무 잎으로부터 항산화 활성성분의 분리)

  • Kang, In-Ho;Cha, Ja-Hyun;Han, Jeong-Hun;Lee, Seong-Wan;Kim, Hon-Jin;Kwon, Suck-Hyung;Ham, In-Hye;Hwang, Bo-Sik;Whang, Wan-Kyunn
    • Korean Journal of Pharmacognosy
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    • v.36 no.2 s.141
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    • pp.121-128
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    • 2005
  • In order to find the antioxidative compounds, fractionation of the MeOH extract of the leaves of Crataegus pinnatifida guided by DPPH scavenging test furnished seven phenolic compounds, $quercetin-3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), myricetin-3-O-rhamnose (2), $quercetin-3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-galctopyranoside$ (3), $quercetin-3-O-{\beta}-D-galactopyranoside$ (4), quercetin (5), $apigenin-8-C-{\beta}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (2'-O-rhamnosylvitexin) (6) and (-)-epicatechin (7). All of isolated compounds showed the significant antioxidative effect on DPPH free radical scavenging test and TBARS assay.

Isolation and NMR Assignment of a Pennogenin Glycoside from Dioscorea bulbifera L. var sativa

  • Teponno, Remy Bertrand;Tapondjou, Azefack Leon;Djoukeng, Jules Desire;Abou-Mansour, Eliane;Tabacci, Raphael;Tane, Pierre;Lontsi, David;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.12 no.1
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    • pp.62-66
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    • 2006
  • A steroidal saponin, $3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}3)]-{\beta}-D-glucopyranosylpennogenin$ ;(1, spiroconazole A) was isolated from the tubers of Dioscorea bulbifera L. var sativa and $^1H-and\;^{13}C-NMR$ assignment was completed using HMBC correlation. In addition, four phenolic substances, 2,7-dihydroxy-4-methoxyphenanthrene (2), quercetin (3), $quercetin-3-O-{\beta}-D-glucopyranoside$ (4), and $quercetin-3-O-{\beta}-D-galactopyranoside$ (5) were also isolated.

Flavonoids from the Stem of Rhamnus taquetii (좀 갈매나무 줄기의 플라보노이드)

  • Hwang, Wan-Gyun;Jeong, Hye-Jin;Go, Seong-Gwon;Lee, Mu-Taek;Kim, Il-Hyeok
    • YAKHAK HOEJI
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    • v.40 no.4
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    • pp.394-399
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    • 1996
  • As a series of the studies on the specific and indigenous plants of Mt. Halla, the constituents from stem of Rhamnus taquetii (Rhamnaceae) were investigated. From the water fraction of the MeOH extract, a new flavonol glycoside, kaempferide-3-O-${\alpha}$-L-rhamnopyranosyl(1->3)-${\alpha}$-L-rhamnopyranosyl(1-6)-${\beta}$-D-galactopyranoside, was isolated with three known compounds, quercetin, quercetin-3-methylether, kaempferol, by column chromatographic separation using Amberlite XAD-2, ODS-gel and Sephadex LH-20 and elucidated physico-chemical evidences($^1H-NMR,\;^{13}C-NMR$,IR, EI-Mass, FAB-Mass, and G.C.),respectively.

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Inhibitory Effects of Flavonoids Isolated from the Leaves of Stewartia koreana on Nitric-oxide Production in LPS-stimulated RAW 264.7 Cells (노각나무 잎에서 분리된 플라보노이드에 의한 대식세포에서 산화질소 생성 억제효과)

  • Lee, Seung-Su;Bang, Myun-Ho;Park, Se-Ho;Chung, Dae-kyun;Yang, Seun-Ah
    • Journal of Life Science
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    • v.28 no.5
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    • pp.509-516
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    • 2018
  • Five phenolic compounds were isolated from the ethyl acetate fraction of leaves from Stewartia koreana, and their nitric-oxide (NO) inhibitory activities were measured to identify the major active constituents responsible for the efficacy of the extract against inflammatory reactions. These five compounds were quercetin (1), quercitrin (2), hyperin (3), quercetin-3-O-(6"-O-galloyl)-${\beta}$-D-galactopyranoside (4), and kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside (5). Among the separated compounds in the EtOAc fraction, compounds 4 and 5 were isolated for the first time, and no study has yet reported their anti-inflammatory effects. The compounds were identified by spectroscopic analysis, and the isolated compounds showed significant NO inhibitory effects in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Compound 5 showed the most potent inhibitory effect (63.35% inhibition) against LPS-induced NO production compared to that of compound 1 (17.17%), compound 2 (5.0%), compound 3 (3.92%), and compound 4 (6.32%) at $10{\mu}g/ml$ concentration. NO production was inhibited by suppressing the protein expression of inducible nitric-oxide synthase in LPS-stimulated RAW 264.7 macrophages. These results indicate that kaempferol 3-O-[2",6"-di-O-(trans-p-coumaroyl)]-${\beta}$-D-glucopyranoside might be the major active compound responsible for the anti-inflammatory effects of S. koreana.

Phenolic Components from the Aerial Parts of Bromus japonicus Thunb. (참새귀리 지상부의 페놀성 성분)

  • Tao, Chao;Ahn, Dal-Rae;Xing, Ming Ming;Lee, Eun-Byeol;Kim, Dae-Keun
    • Korean Journal of Pharmacognosy
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    • v.43 no.3
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    • pp.213-216
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    • 2012
  • Six phenolic compounds were isolated from the aerial parts of Bromus japonicus (Gramineae) through repeated column chromatography. Their chemical structures were elucidated as luteolin (1), caffeic acid (2), luteolin-7-O-${\beta}$-D-glucopyranoside (3), quercetin-3-O-${\beta}$-D-galactopyranoside (4), quercetin-3-O-${\beta}$-D-glucopyranoside (5), and luteolin-4'-O-${\beta}$-D-glucopyranoside (6), respectively, by spectroscopic analysis. These compounds were isolated for the first time from this plant.

A New Flavonol Glycoside from Tristemma hirtum (Melastomataceae)

  • Kenfack, Joseph Nandjou;Ponou, Beaudelaire Kemvoufo;Kuhlborn, Jonas;Teponno, Remy Bertrand;Nono, Raymond Ngansop;Fouedjou, Romuald Tematio;Opatz, Till;Park, Hee Juhn;Tapondjou, Leon Azefack
    • Natural Product Sciences
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    • v.24 no.3
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    • pp.213-218
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    • 2018
  • Chemical investigation of the plant Tristemma hirtum P. Beauv (Melastomataceae) resulted to the isolation of a new flavonol glycoside named quercetin-7-O-${\alpha}$-D-arabinofuranoside (1), together with nine known compounds including 3'-hexadecanoyl-2'-(9aZ)-tetradecanoyl-glycerol 1'-O-[${\beta}$-D-galactopyranosyl-(1'' ${\rightarrow}$ 6'')-${\alpha}$-D-galactopyranoside] (2), arjunolic acid (3), ${\beta}$-sitosterol-3-O-${\beta}$-D-glucopyranoside (4), terminolic acid (5), quercetin (6), asiatic acid (7), maslinic acid (8), $1{\beta}$-O-galloylpedunculagin (9) and 6-hydroxyapigenin 7-O-${\beta}$-D-glucopyranoside (10) from the methanol extract using normal and reversed phase column chromatography. The structures of these compounds were determined by comprehensive interpretation of their spectral data mainly including 1D- 2D-NMR ($^1H-^1H$ COSY, HSQC, and HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis.

Flavonoids from the Seeds of Astragalus sinicus Linne

  • Yeom, Seung-Hwan;Kim, Min-Kee;Kim, Hyun-Jung;Shim, Jae-Geul;Lee, Jae-Hee;Lee, Min-Won
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.258.3-258.3
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    • 2003
  • The Seeds of Astragalus sinicus(Leguminosae) is used for the treatment of excretion of urine, circulation of blood and the throat inflammation in Korean traditional medicine. Eight flavonoids were isolated from 80% Acetone extracts. The structure were elucidated as Quercetin 3-O-${\beta}$-D-Xylopyranosyl-(1\longrightarrow2)-${\beta}$-D-galactopyranoside, ampelopsin and myricetin by phytochemical and spectral evidences. The other compounds are understudied by 2D-NMR.

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