• Title/Summary/Keyword: lignan compound

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Analgesic Constituent from the Herba of Saururus chinensis ($L_{OUR.})B_{AILL.}$ (삼백초의 진통성분)

  • Park, Si-Kyung;Oh, Gab-Jin;Kim, Hyun-Tae;Kim, Hyun-Jong;Chung, Sun-Gan;Cho, Eui-Hwan
    • YAKHAK HOEJI
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    • v.42 no.3
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    • pp.238-242
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    • 1998
  • For the investigation of bioactive natural products with analgesic activity, we have evaluated various extracts of Saururi Herba (Saururaceae), which has been used in traditiona l medicine for edema, beriberi, jaundice, turbid urine, carbuncle and furuncle. The diethylether extract of this plant was found to show a significant analgesic effect on writhing syndrome in mice. Using bioactivity-guided separation of the diethylether extract, analgesic constituent, (8S, 8`R, 7R, 6`R)-2'-oxo-4,5: 4',5'-bis(methylenedioxy)-${\Delta}^{1,3,5,3'}$-8.8', 7.6', 2.O.5'-neolignan(sauchinone) was isolated and structurally identified by physico-chemical properties and spectroscopic evidences. This compound has good analgesic activity with lower toxicity, as compared to other antipyretic-analgesic drug(acetaminophen).

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Isolation and Quantitative Analysis of Acanthoside D from Acanthopanacis Cortex (오가피로부터 Acanthoside D의 분리 및 함량분석)

  • Hong, Sung-Su;Hwang, Ji-Sang;Lee, Seon-A;Hwang, Bang-Yeon;Ha, Kwan-Won;Ze, Keum-Ryon;Seung, Rack-Seun;Ro, Jai-Seup;Lee, Kyong-Soon
    • Korean Journal of Pharmacognosy
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    • v.32 no.4 s.127
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    • pp.316-321
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    • 2001
  • The Acanthopanax genus belonging to the Araliaceae family is widely used as a traditional medicine having tonic and sedative effects. For the quality control of Acanthopanacis Cortex, lignan compound, acanthoside D, was isolated from the MeOH extract of Acanthopanax sessiliforum Seeman. (Araliaceae) and identified by the spectroscopic analysis. A quantitative analysis of acanthoside D using HPLC method showed that the average contents were $0.081{\pm}0.058%$ in 39 samples collected throughout the regions of Korea.

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Whitening Activity of Phenolic Compounds from Rhizome of Phragmites communis

  • Choi, Sun Eun;Yoon, Jung-Hye;Park, Kwan Hee;Kim, Kyoung Young;Song, Yu Jin;Jin, Hye Young;Lee, Min Won
    • Natural Product Sciences
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    • v.20 no.4
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    • pp.269-273
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    • 2014
  • Activity guided phytochemical examination of the rhizome of Phragmites communis has led to the isolation of two phenolic acids and two lignans. Structures of these compounds were elucidated as methyl gallate (1), ${\rho}$ -hydroxy cinnamic acid (2), (+) -lyoniresinol (3), (+)-lyoniresinol-9'-O-${\beta}$-D-glucopyranoside (4) by comparisons with previously reported spectral data. To investigate the melanogenesis inhibitory effects of these compounds, the melanin level and tyrosinase activity were examined in B16F10 melanoma cell. Each compound inhibited both tyrosinase activity and melanin synthesis compared with positive control, kojic acid and arbutin. These results suggest that the phenolic compounds from Phragmites communis might be developed as a potent skin whitenting cosmeceuticals.

Antioxidant Compounds Isolated from the Roots of Phlomis umbrosa Turcz.

  • Nguyen, Duc Hung;Le, Duc Dat;Zhao, Bing Tian;Ma, Eun Sook;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.119-124
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    • 2018
  • Two triterpenoids, arjunolic acid (1), belleric acid (2), five phenylethanoids, martynoside (3), orobanchoside (4), 3,4-dihydroxyphenethylalcohol-6-O-caffeoyl-${\beta}$-$\text\tiny{D}$-glucoside (5), leucosceptoside B (6), lunariifolioside (7), four phenolic acids, ferulic acid (8), syringic acid (9), vanillic acid (10), 4-hydroxybenzoic acid (11), and one lignan, (+)-syringaresinol-${\beta}$-$\text\tiny{D}$-glucoside (12), were isolated from the roots of P. umbrosa. All isolated compounds were explored for their antioxidant potential in the DPPH and ABTS assays. In DPPH assay, compound 5 showed high antioxidant capacity. Compounds 3, 4, 6, and 7 displayed considerable antioxidant activities. In addition, compounds 5-7 exhibited potential antioxidant capacities in the ABTS assay.

Isolation and identification of lignans as Antioxidant from loaves of Catalpa ovata G. $D_{ON}$ (개오동나무 잎으로부터 항산화 활성을 갖는 lignan 화합물의 분리 및 동정)

  • 국주희;마승진;문제학;박근형
    • KSBB Journal
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    • v.18 no.6
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    • pp.511-516
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    • 2003
  • The methanol extract from leaves of Catalpa ovata 6. DoN showed DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging activity, and its antioxidative compounds were studied. The ethyl acetate-soluble neutral fraction from the methanol extract was successively purified with silica gel adsorption column chromatography, Sephadex LH-20 column chromatography and HPLC. Three antioxidative compounds were isolated and identified as piperitol, pinoresinol and lariciresinol by HR-MS and NMR spectroscopic analyses. The DPPH radical-scavenging activity of the identified compounds decreased in the order of lariciresinol > pinoresinol > piperitol.

Polyphenol mixture of a native Korean variety of Artemisia argyi H. (Seomae mugwort) and its anti-inflammatory effects

  • Seong Min Kim;Soo Jung Lee;Venu Venkatarame;Gowda Saralamma;Sang Eun Ha;Preethi Vetrivel;Kebede Taye Desta;Jin Young Choi;Won Sup Lee;Sung Chul Shin;Gon-Sup Kim
    • International Journal of Molecular Medicine
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    • v.44 no.5
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    • pp.1741-1752
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    • 2019
  • In the present study, a polyphenolic mixture was isolated from Seomae mugwort (SM; a native Korean variety of Artemisia argyi H.) via extraction with aqueous 70% methanol followed by the elution of ethyl acetate over a silica gel column. Each polyphenolic compound was analyzed using high-performance liquid chromatography coupled with tandem mass spectrometry, and compared with the literature. In addition to the 14 characterized components, one hydroxycinnamate, six flavonoids, and one lignan were reported for the first time, to the best our knowledge, in Artemisia argyi H. The anti-inflammatory properties of SM polyphenols were studied in lipopolysaccharide-treated RAW 264.7 macrophage cells. The SM polyphenols attenuated the activation of macrophages via the inhibition of nitric oxide production, nuclear factor-κB activation, the mRNA expression of inducible nitric oxide synthase, tumor necrosis factor α and interleukin-1β, and the phosphorylation of mitogen-activated protein kinase. Our results suggested that SM polyphenols may have therapeutic potential for the treatment of inflammatory-related diseases.

The Antiproliferative Effects of Compounds Isolated from Schisandra chinensis (오미자로부터 분리된 화합물의 암세포 증식 억제 효과)

  • Suh, Won-Se;Park, So Yeon;Min, Byung Sun;Kim, Sea Hyun;Song, Jeong Ho;Shim, Sang Hee
    • Korean Journal of Food Science and Technology
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    • v.46 no.6
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    • pp.665-670
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    • 2014
  • We isolated twelve lignans and three terpenoids were isolated from the n-hexane fraction of Schisandra chinensis extract. Using spectroscopic data and comparison with available literature, the following compounds were identified: (1) wuweizisu C, (2) gomisin N, (3) deoxyschisandrin, (4) gomisin A, (5) schisandrin, (6) chamigrenal, (7) schisanlactone D, (8) methylgomisin O, (9) angeloylgomisin O, (10) (-)-gomisin $L_2$, (11) schisandronic acid, (12) (-)-gomisin $L_1$, (13) (+)-gomisin $K_3$, (14) gomisin J, and (15) tigloylgomisin H. Notably, this was the first finding that compound (8) was isolated from this plant. Each compound was evaluated for its in vitro cytotoxic activities toward HL-60 (human leukemia), HeLa (human cervical carcinoma), and MCF-7 (breast cancer) cell lines. Compounds (7), (8), and (9) exhibited strong cytotoxic effects on HL-60 ($IC_{50}$ 7.37, 6.60, and $8.00{\mu}M$, respectively), whereas compound (6) exhibited weak cytotoxicity towards MCF-7 ($IC_{50}$ $30.50{\mu}M$). In addition, compound (8) showed the strongest activity towards HeLa cells ($IC_{50}$ $1.46{\mu}M$).

Isolation of Antimicrobial Substance from Schizandra chinensis Baillon and Antimicrobial Effect (오미자로부터 항균활성 물질의 분리 및 항균효과)

  • Lee, Ju-Yeun;Min, Young-Kyoo;Kim, Hee-Yun
    • Korean Journal of Food Science and Technology
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    • v.33 no.3
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    • pp.389-394
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    • 2001
  • In order to isolate antimicrobial substances from Schizandra chinensis, the dried fruits were extracted with the methanol and the extract showed a strong antimicrobial activity. Also, the methanol exract was further fractionated with hexane, dichloromethane, ethylacetate and buthanol. The ethyl acetate-soluble fraction showed the strongest antimicrobial activity. These fraction were further separated by using various chromatographic methods including thin layer chromatography, silicagel open column chromatography and prep. HPLC. A major component S-EA-5-T1 and S-EA-5-T3 from the ethyl acetate fraction, which showed a strong antimicrobial activity was identified by Mass and NMR spectrometry. Two compounds were isolated and identified as trimethylcitrate and the essential oil of Schizandra chinensis and was estimated as gomisin C, respectively. The growth of S. typhimurium was also inhibited about 1.65 to 2.86 log cycle in minced pork by the addition 1% of Schizandra chinensis extract for 12 days at $4^{\circ}C$. These results suggested that these compounds have a strong potential as a natual food preservatives.

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Inhibition of Phospholipase $C{\Upsilon}1$ and Cancer Cell Proliferation by Lignans and Flavans from Machilus thunbergii

  • Lee, Ji-Suk;Kim, Jin-Woong;Yu, Young-Uck;Kim , Young-Choong
    • Archives of Pharmacal Research
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    • v.27 no.10
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    • pp.1043-1047
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    • 2004
  • Thirteen compounds were isolated from the $CH_2Cl_2$ fraction of Machilus thunbergii as phospholipase $C{\Upsilon}1\;(PLC{\Upsilon}1)$ inhibitors. These compounds were identified as nine lignans, two neolignans, and two flavans by spectroscopic analysis. Of these, 5,7-di-O-methyl-3',4'-methylenated (-)-epicatechin (12) and 5,7,3'-tri-O-methyl (-)-epicatechin (13) have not been reported previously in this plant. In addition, seven compounds, machilin A (1), (-)-sesamin (3), machilin G (5), (+)-galbacin (9), licarin A (10), (-)-acuminatin (11) and compound 12 showed dose-dependent potent inhibitory activities against $PLC{\Upsilon}1$ in vitro with $IC_{50}$ values ranging from 8.8 to 26.0 ${\mu}M$. These lignans, neolignans, and flavans are presented as a new class of $PLC{\Upsilon}1$ inhibitors. The brief study of the structure activity relationship of these compounds suggested that the benzene ring with the methylene dioxy group is responsible for the expression of inhibitory activities against $PLC{\Upsilon}1$. Moreover, it is suggested that inhibition of $PLC{\Upsilon}1$ may be an important mechanism for an antiproliferative effect on the human cancer cells. Therefore, these inhibitors may be utilized as cancer chemotherapeutic and chemopreventive agents.

$PPAR_{\gamma}$ Ligand-binding Activity of Fragrin A Isolated from Mace (the Aril of Myristica fragrans Houtt.)

  • Lee, Jae-Young;Kim, Ba-Reum;Oh, Hyun-In;Shen, Lingai;Kim, Naeung-Bae;Hwang, Jae-Kwan
    • Food Science and Biotechnology
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    • v.17 no.6
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    • pp.1146-1150
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    • 2008
  • Peroxisome proliferator-activated receptor-gamma ($PPAR_{\gamma}$), a member of the nuclear receptor of ligand-activated transcription factors, plays a key role in lipid and glucose metabolism or adipocytes differentiation. A lignan compound was isolated from mace (the aril of Myristica fragrans Houtt.) as a $PPAR_{\gamma}$ ligand, which was identified as fragrin A or 2-(4-allyl-2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)-propane. To ascertain whether fragrin A has $PPAR_{\gamma}$ ligand-binding activity, it was performed that GAL-4/$PPAR_{\gamma}$ transactivation assay. $PPAR_{\gamma}$ ligand-binding activity of fragrin A increased 4.7, 6.6, and 7.3-fold at 3, 5, and $10{\mu}M$, respectively, when compared with a vehicle control. Fragrin A also enhanced adipocytes differentiation and increased the expression of $PPAR_{\gamma}$ target genes such as adipocytes fatty acid-binding protein (aP2), lipoprotein lipase (LPL), and phosphoenol pyruvate carboxykinase (PEPCK). Furthermore, it significantly increased the expression level of glucose transporter 4 (GLUT4). These results indicate that fragrin A can be developed as a $PPAR_{\gamma}$ agonist for the improvement of insulin resistance associated with type 2 diabetes.