• 제목/요약/키워드: quercetin-3-O-${\beta}$-D-glucopyranoside

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별날개골풀의 페놀성 성분 (Phenolic Constituents from Juncus diastrophanthus)

  • 도초;형명명;안달래;이은별;이소연;김반지;이재혁;박정숙;배종진;김대근
    • 생약학회지
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    • 제44권4호
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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.

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

  • 남정환;조인숙;김수정;남춘우;서종택;유동림;김원배;유승열;이응호;김민영;유영민;박희준;정현주
    • Applied Biological Chemistry
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    • 제51권2호
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    • pp.136-141
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    • 2008
  • 곧은 나무이끼의 전초에서 물질을 분리 및 동정하기 위해 곧은 나무이끼의 MeOH 추출물을 $CHCl_3$, EtOAc 및 BuOH로 용매 분획하였다. $CHCl_3$ 분획으로부터 2-chromenone(coumarin)을 분리 하였고 EtOAc 분획에서 3,4-dihydroxy-cinnamic acid (caffeic acid), 3,3',4',5,7-pentahydroxy-2-phenyl-chromen-4-one (quercetin)과 kaemperol-3-O-${\beta}$-D-glucopyranoside(astragalin)을 분리하였다. BuOH 분획으로부터 3-[[3-(3,4-Dihydr oxyphenyi)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid(chlorogenic acid)와 quercetin-3-O-rutinoside(rutin)를 분리하여 IR, UV, Mass, NMR과 이화학적인 방법으로 그 구조를 규명하였다. 곧은 나무이끼에서 이 물질들이 분리된 것은 처음으로 보고되는 것이다.

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

  • 임현우;심재걸;최형균;이민원
    • 생약학회지
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    • 제36권3호통권142호
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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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    • 제20권3호
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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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    • 제11권2호
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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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    • 제23권2호
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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
    • 한국약용작물학회지
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    • 제14권5호
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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.

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

  • 이상원;이유건;조정용;김영출;이상현;김월수;문제학
    • 한국식품과학회지
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    • 제47권2호
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    • pp.170-175
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    • 2015
  • 본 연구에서는 국산배의 기능학적 우수성 증명을 위해 국산배로부터 생리활성 화합물을 밝히고자 하였다. 이에 배 과피 MeOH 추출물을 용매분획하여 얻은 EtOAc-산성획분을 대상으로 Sephadex LH-20 column chromatography와 ODS-HPLC를 이용하여 순차적으로 정제를 행하여 2종의 화합물을 단리하였다. 단리된 화합물 1과 2는 MS 및 NMR 분석을 통하여 각각 quercetin 3-O-${\beta}$-Dglucopyranoside(화합물 1)와 3,5,6,7,8,3',4'-heptahydroxyflavan [(-)-dulcisflavan, 화합물 2)]으로 동정되었다. 단리된 화합물 1은 동양배로부터, 그리고 화합물 2는 배로부터 처음 동정된 화합물이다. 본 연구결과가 국산배의 기능학적 우수성 증명을 위한 기초자료로 활용되길 기대한다.

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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    • 제18권2호
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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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    • 제28권4호
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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 $166.6 {\mu}g/mL$.