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

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Studies on the Constituents of Impatiens noli-tangere L. (노랑물봉선의 성분에 관한 연구)

  • Choi, Bok-Ja;Kim, Chong-Won
    • Korean Journal of Pharmacognosy
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    • v.33 no.4 s.131
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    • pp.263-266
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    • 2002
  • From the herbs of this plant, six compounds were isolated and their structures were characterized as dieicosyl ether (1), scopoletin (2), ${\alpha}-spinasterol-3-O-{\beta}-D-glucopyranoside$ (3), kaempferol (4), quercetin (5), and quercetin 7, 3', 4'-trimethylether-3-O-rutinoside (6) by chemical and spectroscopic evidences. These compounds were isolated for the first time from this plant and compound 6 was first isolated from nature.

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.

Isolation and Characterization of Antioxidative Compounds from the Aerial Parts of Angelica keiskei

  • Kim, So-Joong;Cho, Jeong-Yong;Wee, Ji-Hyang;Jang, Mi-Young;Kim, Cheol;Rim, Yo-Sup;Shin, Soo-Cheol;Ma, Seung-Jin;Moon, Jae-Hak;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.14 no.1
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    • pp.58-63
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    • 2005
  • Ethyl acetate-soluble neutral fraction of hot water extracts from the aerial parts of Angelica keiskei showed a 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Six antioxidative compounds were purified and isolated by various chromatographic procedures. Based on the analyses of FAB-MS and NMR, the isolated compounds were structurally elucidated as luteolin 7-O-${\beta}$-D-glucopyranoside (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2), quercetin 3-O-${\beta}$-D-glucopyranoside (3), quercetin 3-O-${\alpha}$-D-arabinopyranoside (4), kaempferol 3-O-${\alpha}$-D-arabinopyranoside (5), and luteolin 7-O-rutinoside (6). The glycosides of flavonols and luteolin showed DPPH radical-scavenging activity. One molecule of 2, 3, 4, 6, 1, and 5 scavenged 4.2, 4.2, 4.1, 2.5, 2.2, and 1.4 molecules of DPPH radical, respectively.

Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

Effects of Temperature and UV Irradiation on Stability of Anthocyanin-Polyphenol Copigment Complex in Mulberry Fruits (오디에서 열처리와 자외선 조사가 Anthocyanin-Polyphenol Copigment Complex의 안전성에 미치는 효과)

  • Bang, In-Soo;Yu, Chang-Yeon;Lim, Jung-Dae
    • Korean Journal of Medicinal Crop Science
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    • v.18 no.3
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    • pp.191-200
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    • 2010
  • Anthocyanin and polyphenolic compounds present in fruits of mulberry (Morus alba L.) were determined and the influence of temperature and UV irradiation on stability of the anthocyanin-copigment complex were investigated. The copigmentation substance selected in non-anthocyanin fraction from mulberry for the study included: phenolic acid (hydroxybenzoic acid) and flavonoid (quercetin-3-O-$\beta$-D-glucopyranoside). The copigmentation effect increased with the copigment content. UV irradiation had a stronger degradation effect on the copigmentation complex than heating at $80^{\circ}C$. The non-anthocyanin fraction of mulberry and isolated flavonoid (quercetin-3-O-$\beta$-D-glucopyranoside) from mulberry fruit predominated over other copigment substances.

The Flavonoids from Caragana Chamlagu Leaves (골담초엽의 플라보노이드)

  • 마충운;함인혜;황완균
    • YAKHAK HOEJI
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    • v.43 no.2
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    • pp.143-149
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    • 1999
  • The phytochemical studies of the leaves of Caragana chamlagu were carried out as a sieries of the investigation of medicinal resources. The roots of Caragana chamlagu have been used as neuralgia, arthritis and migraine in the folk medicines of Korea. The methanolic extract of the leaves of Caragana chamlagu was suspended with water and then separated with chloroform. Compound I was isolated from precipitates of these water fraction by recrystalization. The aqueous fraction of MeOH extract was performed to column chromatography on Amberlite XAD-4 and Sephadex LH-20, and three compounds, compound II, compound III, and compound IV were isolated. The structures of the four compounds were elucidated by spectroscopic data of $^1H-NMR$, ^{13}C-NMR$, IR, and FAB-MS. Compound I-IV were tilianine ($acacetin-7-O-{\beta}-D-glycopyranoside$), rutin($quercetin-3-O-{\alpha}-L-rhamnopyranosy(1{\rightarrow}6)-{\beta}-D-glu-copyranoside$), $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-D-galactopyranoside$, and apigetrin, ($apigenin-7-O-{\beta}-D-glycopyranoside$), respectively.

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Anti-cancer Activity of Flavonoids from Aceriphyllum rossii (돌단풍(Aceriphyllum rossii)에서 분리한 플라보노이드의 항암활성)

  • Ahn, Eun-Mi;Han, Jae-Taek;Kwon, Byoung-Mog;Kim, Sung-Hoon;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.309-315
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    • 2008
  • The methanol extract from the aerial parts of Aceriphyllum rossii was fractionated into ethyl acetate, n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded five flavonol glycosides. They were identified as astragalin (1), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (2), rutin (3), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl 1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (4), and quercetin 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (5) on the basis of spectroscopic data. All of them showed an inhibition in farnesyl protein tranferase (FPTase) activity, and rutin (3) inhibited the growth of rat H-ras cell and the cell migration of human umbilical vein endothelial cells (HUVECs).

Antioxidant Activity of Anthraquinones and Flavonoids from Flower of Reynoutria sachalinensis

  • Zhang Xinfeng;Thuong Phuong Thien;Jin WenYi;Su Nguyen Duy;Sok Dai Eun;Bae KiHwan;Kang Sam Sik
    • Archives of Pharmacal Research
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    • v.28 no.1
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    • pp.22-27
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    • 2005
  • Bioassay-guided fractionation of methanol extract of Reynoutria sachalinensis flower using DPPH assay has led to the isolation of three anthraquinones and three flavonoids. Their structures were identified as emodin (1), emodin-8-O-$\beta$-D-glucopyranoside (2), physcion-8-O-$\beta$-D­glucopyranoside (3), quercetin-3-O-$\alpha$-L-arabinofuranoside (4), quercetin-3-O-$\beta$-D-galactopyra­noside (5), and quercetin-3-O-$\beta$-D-glucuronopyranoside (6) by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for antioxidant activities with free radical 1, 1-diphenyl-2-picrylhydrazyl (DPPH) scavenging, superoxide radical scavenging and $Cu^{2+}$-mediated low density lipoprotein (LDL) oxidation assay. The results demonstrated that three flavonoids, 4, 5, and 6 had remarkable antioxidant activities with the $IC_{50}$ values of 64.3, 54.7, and 46.2${\mu}M$ (DPPH scavenging), the $IC_{50}$ values of 6.0, 6.7, and $4.4{\mu}M$ (superoxide radical scavenging) and the $IC_{50}$ values of 3.8, 3.2, and 5.4${\mu}M$ against LDL oxidation, respectively.

Extractives from Pollen (화분의 추출성분)

  • 이상극;김진규;함연호;박재군;배영수
    • Journal of Korea Foresty Energy
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    • v.22 no.1
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    • pp.30-36
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    • 2003
  • 2kg of pollen extracted with EtOH(98%), concentrated, and fractionated with a series of hexane, CH$_2$Cl$_2$ EtOAc and $H_2O$ on a separately funnel. Each fraction was freeze dried to give dark-brown powder and EtOAc soluble portion of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol as eluents. Spectrometric analysis such as NMR and FAB-MS including TLC were performed to characterize the structures of isolated compounds. Pollen contained a small amount of flavonol derivatives such as quercetin-3-O-$\beta$-D-glucopyranoside and kaempferol-3-O-$\beta$-D-rutinoside in addition to a small amount of flavanonol compound such as aromadendrin-5-methyl ether and acid compound such as.

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Antioxidant Activity and Inhibition of MMP-9 by Isorhamnetin and Quercetin 3-O-$\beta$-D-Glucopyranosides Isolated from Salicornia herbacea in HT1080 Cells

  • Kong, Chang-Suk;Kim, You-Ah;Kim, Moon-Moo;Park, Jin-Sook;Kim, Se-Kwon;Lee, Burm-Jong;Nam, Taek-Jeong;Seo, Young-Wan
    • Food Science and Biotechnology
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    • v.17 no.5
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    • pp.983-989
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    • 2008
  • Two flavonoids, isorhamnetin 3-O-$\beta$-D-glucopyranoside (1) and quercetin 3-O-$\beta$-D-glucopyranoside (2), from slander glasswort (Salicornia herbacea, Korean name hamcho) were isolated. Antioxidative and matrix metalloproteinase-9(MMP-9) inhibitory effects of these compounds were investigated in HT 1080 cell lines. These compounds suppressed the electron spin resonance (ESR) signal intensity on generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical in a free-cellular system. Their scavenging effects on generation of intercellular reactive oxygen species (ROS) also exhibited similar trends with DPPH radical in the free cellular system. Also, a control group combined only with Fe(II)-$H_{2}O_2$ resulted in DNA apoptosis by oxidative stress, whereas treatments with these compounds suppressed radical-mediated DNA damage. Intracellular glutathione (GSH) levels were slightly increased in the presence of compound 1 and 2. Moreover, these compounds led to the reduction of the expression levels of MMP-9 without cytotoxic influence. These results suggest that these compounds have a potential as a valuable natural antioxidant and MMP inhibitor related to oxidative stress. Therefore, these compounds not only can be developed as a candidate for a therapeutic potential but also a source for use as ingredients of health foods or functional foods to prevent metastasis involving MMP-9, closely related to ROS.