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

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Phenolic Constituents from Juncus diastrophanthus (별날개골풀의 페놀성 성분)

  • Tao, Chao;Xing, Ming Ming;Ahn, Dalrae;Lee, Eun Byeol;Lee, So Yeon;Kim, Ban Ji;Lee, Jae Hyeok;Park, Jeong-Suk;Bae, Jong Jin;Kim, Dae Keun
    • Korean Journal of Pharmacognosy
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    • v.44 no.4
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    • pp.368-371
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    • 2013
  • Five phenolic compounds were isolated from the whole plants of Juncus diastrophanthus (Juncaceae) through repeated column chromatography. Their chemical structures were elucidated as methyl 3,5-di-O-caffeoylquinate (1), luteolin-7-O-${\beta}$-D-glucopyranoside (2), methyl 4,5-di-O-caffeoylquinate (3), quercetin-3-O-${\beta}$-D-arabinopyranoside (4), and methyl 3,4-di-O-caffeoylquinate (5) by spectroscopic techniques. These compounds were isolated for the first time from this plant.

Phytochemical Constituents of Climacium dendroides (곧은 나무이끼(Climacium dendroides)의 식물 화학적 성분연구)

  • Nam, Jung-Hwan;Cho, In-Sook;Kim, Su-Jeong;Nam, Chun-Woo;Seo, Jong-Taek;Yoo, Dong-Lim;Kim, Won-Bae;Ryu, Seung-Yeol;Lee, Eung-Ho;Kim, Min-Young;Yoo, Young-Min;Park, Hee-Juhn;Jung, Hyun-Ju
    • Applied Biological Chemistry
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    • v.51 no.2
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    • pp.136-141
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    • 2008
  • The chromatographic separation of organic solvent extracts of liverwort led to the isolation of six compounds. 2-Chromenone (1), 3, 4-dihydroxy-cinnamic acid (2), 3, 3', 4', 5, 7-pentahydroxy-2-phenylchromen-4-one (3), kaemperol-3-O-${\beta}$-D-glucopyranoside (4), 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1, 4, 5-trihydroxycyclohexane carboxylic acid (5) and quercetin-3-O-rutinoside (6) were isolated from the methanolic extracts of the all part of Climacium dendroides. Their structure were established by chemical and spectroscopic methods. All compounds were isolated for the first time from this plant Climacium dendroides.

Phenolic Compounds from Barks of Actinidia arguta Planchon Growing in Korea and its Anti-Oxidative and Nitric Oxide Production Inhibitory Activities (국내산 다래나무 수피의 페놀성 화합물의 항산화 및 Nitric Oxide 생성 억제 활성)

  • Lim, Hyun-Woo;Shim, Jae-Geul;Choi, Hyung-Kyoon;Lee, Min-Won
    • Korean Journal of Pharmacognosy
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    • v.36 no.3 s.142
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    • pp.245-251
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    • 2005
  • Phytochemical examination of the barks of Actinidia arguta led to the isolation of five flavonoids. Structures of compounds were elucidated as catechin (1), (-)-epicatechin (2), quercetin (3), $quercetin-3-O-{\beta}-D-glucopyranoside$ (4), $quercetin-3-O-{\beta}-D-galactopyranoside$ (5) by comparison with previously reported spectral evidences. To investigate the anti-oxidative effect and nitric oxide (NO) production inhibitory activity of these compounds, DPPH radical scavenging activity and nitric oxide production inhibitory activity in $IFN-{\gamma}$, LPS stimulated RAW 264.7 cell were examined. The $IC_{50}s$ were determinied as follows : $1\;$IC_{50}=26.61\;{\mu}g/ml$, $2\;IC_{50}=25.30\;{\mu}g/ml$, $3\;IC_{50}=20.41\;{\mu}g/ml$, $4\;IC_{50}=18.23\;{\mu}g/ml$ , $5\;IC_{50}=30.46\;{\mu}g/ml$, $6\;IC_{50}=28.0;{\mu}g/ml$, $7\;IC_{50}=27.24\;{\mu}/ml$. These NO production inhibitory effects were significantly different compared with the positive control, L-NMMA $(IC_{50}=20.77\;{\mu}g/ml)$, respectively. Compound $1\;(IC_{50}=6.19\;{\mu}g/ml)$, $2\;(IC_{50}=8.98\;{\mu}g/ml)$, $3\;(IC_{50}=7.30\;{\mu}g/ml)$ and $4\;(IC_{50}=7.64\;{\mu}g/ml)$ also showed potent antioxidative activities similar level to ascorbic acid $(IC_{50}=9.22\;{\mu}g/ml)$. These results suggest that barks of A. arguta have a potent anti-oxidative and anti-inflammatory activity.

Flavonoid Glycosides as Acetylcholinesterase Inhibitors from the Whole Plants of Persicaria thunbergii

  • Kim, Se Young;Park, Jun Young;Park, Pil Sung;Bang, Sang Ho;Lee, Kyung Min;Lee, Yu Ra;Jang, Yong Hyun;Kim, Myong Jo;Chun, Wanjoo;Heo, Moon Young;Kwon, Yongsoo
    • Natural Product Sciences
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    • v.20 no.3
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    • pp.191-195
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    • 2014
  • The n-BuOH soluble fraction of the whole plant of Persicaria thungergii showed acetylcholinesterase inhibitory activity. Four flavonoid glycosides and a flavonoid were isolated from this fraction, and identified as quercitrin (1), luteolin-4'-O-${\beta}$-D-glucopyranoside (2), quercetin (3), quercetin-3-O-glucuronide (4), and isorahmnetin-3-O-glucuronid (5), by chromatographed and spectral data, respectively. All isolated compounds were showed acetylcholinesterase inhibitory activity, with $IC_{50}$ values of 243.1, 10.5, 39.1, 8.2 and $23.2{\mu}M$, respectively.

The Chemical Constituents and their Antioxidant Activity of the Stem of Rhododendron mucronulatum

  • Lee, Jin-Hoon;Jeon, Wan-Joo;Yoo, Eun-Sook;Kim, Chang-Min;Kwon, Yong-Soo
    • Natural Product Sciences
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    • v.11 no.2
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    • pp.97-102
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    • 2005
  • From the n-BuOH soluble traction of the 70% aqueous acetone extract of Rhododendron mucronulatum stem, twelve compounds were isolated. On the basis of spectral data, they were identified as scopoletin (1), (+)-taxifolin (2), quercetin (3), (-)-catechin (4), (+)-epicatechin (5), scopolin (6), lyoniside (7), ssioriside (8), fraxin (9), $(+)-lyoniresinol-3{\alpha}-O-{\beta}-D-glucopyranoside$ (10), $(+)-taxifolin-3-O-{\alpha}-L-arabinopyranoside$ (11), and astragalin (12), respectively. All isolated compounds were tested antioxidant activity against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. Compounds 2 and 3 showed the potent antioxidant activity, and compounds 5, 8, and 11 showed moderate activity.

Lipid Peroxidation Inhibitory Activity of Some Constituents isolated from the Stem Bark of Eucalyptus globulus

  • Yun, Bong-Sik;Lee, In-Kyoung;Kim, Jong-Pyung;Chung, Sung-Hyun;Shim, Gyu-Seop;Yoo, Ick-Dong
    • Archives of Pharmacal Research
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    • v.23 no.2
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    • pp.147-150
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    • 2000
  • Twelve compounds with lipid peroxidation inhibitory activity were isolated from the stem bark of E. globulus. Their structures were assigned as a new aromatic monoterpene (1) and eleven known compounds, pinoresinol (2), vomifoliol (3), 3,4,5-trimethoxyphenol 1-O-$\beta$-D-(6'-O-galloyl)glucopyranoside (4), methyl gallate (5), rhamnazin (6), rhamnetin (7), eriodictyol (8), quercetin (9), taxifolin (10), engelitin (11), and catechin (12) on the basis of UV, mass, and NMR spectroscopic analyses. These compounds except vomifoliol significantly inhibited lipid peroxidation in rat liver microsome.

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Antioxidant Constituents from the Leaves of Cedrela sinensis A. Juss

  • Lee, Ik-Soo;Wei, Chun-Hua;Thoung, Phuong Thien;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.267-272
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    • 2006
  • Phytochemical study on the EtOAc fraction from the MeOH extract of the leaves of Cedrela sinensis led to the isolation of five known phenolic compounds (1-5), whose structures were identified as (+)-catechin (1), $kaempferol-3-0-{\alpha}- L-rhamnopyranoside$ (2), quercetin (3), $quercetin-3-O-{\alpha}-L-rhamnopyranoside$ (4), and $quercetin-3-O-{\beta}-D-glucopyranoside$ (5), respectively, by comparing their spectral $(uv,\;JR,\;IH\;and\;^{13}C-NMR,\;and\;ESI-MS)$ and physicochemical data with those reported in the literature. Among the isolated compounds (1-5), compounds 1 and 3-5 exhibited significant DPPH radical scavenging effects with $IC{_50}$ values ranging from $21.3{\pm}1.4\;to\;38.1{\pm}3.2 {\mu}M$ as well as superoxide anion radical scavenging effects with $IC{_50}$ values ranging from $9.4{\pm}0.7\;to\;21.2{\pm}3.6 {\mu}M$. Furthermore, compounds 1 and 3-5 also exhibited considerable inhibitory effects on LDL peroxidation induced by either $CU^{2+}$ or AAPH with $IC{_50}$ values ranging from $1.4{\pm}0.4\;to\;11.9{\pm}1.4\;{\mu}M$. These results indicated that flavonoids are the major constituents of C. sinensis and considered to be antioxidant principles of this plant.

Isolation and Identification of Two Flavonoids from Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) Fruit Peel (추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 2종의 Flavonoids의 단리·동정)

  • Lee, Sang Won;Lee, Yu Geon;Cho, Jeong-Yong;Kim, Young Chool;Lee, Sang-Hyun;Kim, Wol-Soo;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.47 no.2
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    • pp.170-175
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    • 2015
  • The methanol extract of Asian pear (Pyrus pyrifolia N. cv. Chuhwangbae) fruit peel was purified using solvent fractionation, Sephadex LH-20 column chromatography, and octadecylsilane high performance liquid chromatography. Based on the electrospray ionization mass spectrometry and nuclear magnetic resonance data, the two isolated compounds were identified as quercetin 3-O-${\beta}$-D-glucopyranoside (1) and 3,5,6,7,8,3',4'-heptahydroxyflavan [(-)-dulcisflavan, 2]. Compounds 1 and 2 were isolated and identified for the first time from Asian pears and pears, respectively.

Isolation and Structural Determination of Free Radical Scavenging Compounds from Korean Fermented Red Pepper Paste (Kochujang)

  • Chung, Jin-Ho;Shin, Heung-Chule;Cho, Jeong-Yong;Kang, Seong-Koo;Lee, Hyoung-Jae;Shin, Soo-Cheol;Park, Keun-Hyung;Moon, Jae-Hak
    • Food Science and Biotechnology
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    • v.18 no.2
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    • pp.463-470
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    • 2009
  • Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

Antiinflammatory Constituents from the Roots of Smilax bockii warb.

  • Xu Jing;Li Xian;Zhang Peng;Li Zhan-Lin;Wang Yi
    • Archives of Pharmacal Research
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    • v.28 no.4
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    • pp.395-399
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    • 2005
  • From $70\%$ ethanol extract of the roots of Smilax bockii warb., seven flavonoids, kaempferol (1), $kaempferol-7-O-\beta-D-glucopyranoside$ (2), quercetin (3), isorhamnetin (4), (+)-dihydro­kaempferol (5), engeletin (6), isoengeletin (7), and $n-butyl-\beta-D-fructopyranoside$ (8), caffeic acid n-butyl ester (9) were isolated and identified by means of chemical and spectroscopic. Compounds 2, 4, and 6-9 were isolated for the first time from the roots of S. bockii and compounds 2, 8, and 9 were firstly isolated from the genus Smilax. In addition, using the SEAP (Secreted alkaline phosphatase) assay system, we investigated the in vitro anti-inflammatory activity of the $70\%$ ethanol extract of the roots of S. bockii, which showed moderate activity in inhibiting $TNF-\alpha-induced NF-{\kappa}B$ activation with an $IC_{50}$ value of $166.6 {\mu}g/mL$.