• Title/Summary/Keyword: stilbene

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POTENT INHIBITION OF HUMAN CYTOCHROME P450 1 ENZYMES BY DIMETHOXYPHENYL VINYL THIOPHENE.

  • Lee, Sangk wang;Kim, Sanghee;Kim, Mie young;Chun, Young-Jin
    • Proceedings of the Korean Society of Toxicology Conference
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    • 2002.05a
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    • pp.92-92
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    • 2002
  • Recently we have reported that various hydroxystilbenes show strong inhibition of human P450 1 activity. A series of synthetic trans-stilbene derivatives were prepared and their inhibitory potentials were evaluated with the bacterial membrane of recombinant human P450 1A1, 1A2 or 1B1 coexpressed with human P450/NADPH-450 reductase to find new candidates for cancer chemoprevention.(omitted)

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Phytochemical Constituents of Bletilla striata and Their Cytotoxic Activity

  • Woo, Kyeong Wan;Park, Jong Eel;Choi, Sang Un;Kim, Ki Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.91-94
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    • 2014
  • Column chromatographic separation of the MeOH extract from the tubers of Bletilla striata yielded seven phenolic components including four phenanthrenes, 3,7-dihydroxy-2,4-dimethoxyphenanthrene (1), 3,7-dihydroxy-2,4,8-trimethoxyphenanthrene (2), 9,10-dihydro-4,7-dimethoxyphenanthrene-2,8-diol (3), and 9,10-dihydro-1-(4'-hydroxybenzyl)-4,7-dimethoxyphenanthrene-2,8-diol (4) and three stilbenes, gigantol (5), 3',4"-dihydroxy-5',3",5"-trimethoxybibenzyl (6), and batatasin III (7). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 2, 3, and 6 were reported for the first time from this plant. The isolated compounds (1-7) were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.

Stilbenoids of Korean Pine (Pinus koraiensis) Inner Bark

  • Kwon, Dong-Joo;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.37 no.5
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    • pp.474-479
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    • 2009
  • Pinus koraiensis inner bark was collected and extracted with 95% ethanol. The extracts were concentrated and then sequentially fractionated using n-hexane, $CH_2Cl_2$, EtOAc, and $H_2O$ to be freeze dried. A portion of EtOAc fraction (6.6 g) was chromatographed on a Sephadex LH-20 column using aqueous methanol to isolate (+)-catechin (1), (-)-epicatechin (2), and trans-pinostilbenoside (3). Resveratrol (4) and trans-pinostilbene (5) were isolated by column chromatography using EtOH-hexane mixture after purification with aqueous methanol. The structures of these stilbenosides and flavans were characterized by spectroscopic tools using NMR and MS.

MODULATION OF CELL CYCLE-RELATED PROTEIN EXPRESSION BY RESVERATROL IN HUMAN LUNG CANCER CELLS

  • Kim, Young-Ae;Kong, Kyu-Ri;Lee, Won-Ho;Park, Kun-Young;Rhee, Suk-Hee;Park, Yung-Hyun
    • Proceedings of the Korean Society of Toxicology Conference
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    • 2001.10a
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    • pp.149-149
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    • 2001
  • Resveratrol (3,5,4'-trihydroxy-trans-stilbene), a phytoalexin found in grapes and wines is a potent antioxidant with cancer-preventive properties, the mechanism by which resveratrol imparts cancer chemopreventive effect is poorly defined. The aim of the present study was to further elucidate the possible mechanisms by which resveratrol exerts its anti-proliferative action in cultured human lung cancer cells.(omitted)

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Photochemical Reduction of trans-1,2-Bispyrazylethylene (트란스-1,2-비스피라질에틸렌의 광화학적 환원)

  • Sang Chul Shim;Jeong Seok Chae
    • Journal of the Korean Chemical Society
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    • v.21 no.2
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    • pp.102-107
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    • 1977
  • Photochemical reduction of 1,2-bispyrazylethylene,a stilbene like heterocompound, was studied in hydrogen donating solvents and reduction product, 1, 2-bispyrazylethane, was identified. Salt and solvent effects on the quantum yields of the reduction, sensitization and quenching studies showed that the reactive state for the photochemical reduction of the compound is $(n,{\pi}^*)^1$ state rather than $({\pi},{\pi}^*)^1$ state.

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Epoxidation of Simple Alkenes with O2 and Isobutyraldehyde Catalyzed by Ni Catalysts Deposited on Nanoporous Carbon

  • Lim, So-Young;Kang, Min;Kim, Ji-Man;Lee, Ik-Mo
    • Bulletin of the Korean Chemical Society
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    • v.26 no.6
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    • pp.887-891
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    • 2005
  • Novel nickel catalyst deposited on nanoporous carbon was found to be an efficient catalyst for the epoxidation of simple alkenes with $O_2$ and isobutyraldehyde under mild conditions. Alkenes exhibited different reactivities towards Ni-catalyst and epoxidation with stilbene proceeds stereospecifically. This may be rationalized with the mechanism involving coordinated acylperoxy radical intermediate. Nickel contents depend on the preparative methods and the KNI-3 catalyst, which was synthesized by wet impregnation of $Ni(NO_3)_2$ into nanoporous carbon, shows the highest activity. The activity of the catalyst is well correlated with contents of nickel. Recycled catalysts suffer considerable loss of activity due to leaching of catalytic active species, nickel.

Solid-Phase Synthesis of Unfunctionalized Arenes Via the Traceless Cleavage of Sulfonate Linkers

  • Kim, Chul-Bae;Cho, Chul-Hee;Jo, Min-Jy;Park, Kwang-Yong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.10
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    • pp.3655-3659
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    • 2011
  • The hydrogenolysis of polymer-bound arenesulfonates by 2-propylmagnesium chloride was performed through reductive cleavage of the C-S bond in the presence of a nickel catalyst. The reaction underwent in the highest efficiency by adding 15 equiv of the nucleophile in two additions with $dppfNiCl_2$ in THF. Various unfunctionalized naphthalene, biphenyl, and stilbene derivatives were produced in good yields by the traceless sulfonate linker system at room temperature.

Inhibition of Nitric Oxide Production by Stilbenes from Polygonum cuspidatum (호장으로부터 분리한 스틸벤류의 Nitric Oxide 저해활성)

  • Joo, Si Mong;Hong, Yun Jung;Yang, Ki Sook
    • YAKHAK HOEJI
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    • v.58 no.1
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    • pp.12-15
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    • 2014
  • Polygonum cuspidatum which is widely distributed in Korea has been used as treatments of dermatitis, gonorrhea, favus athlete's foot, hyperlipidemia and inflammation in traditional medicine. We examined anti-oxidant and antiinflammatory activity by measuring DPPH radical scavenging activity and the inhibition of IFN-${\gamma}$ and LPS-induced NO production in RAW 264.7 murine macrophage cells. We isolated and characterized resveratrol (1), trans-resveratrol 3-O-${\beta}$-Dglucopyranoside (2). Compounds 1 and 2 showed potent activities compared with L-NMMA ($N^G$-monomethyl-L-arginine). These results suggested that the stilbene compounds isolated from Polygonum cuspidatum might be used as antiinflammatory agents.

Photocyclization of 1,2-Bispyrazylethylene and 2-Styrylpyrazine

  • Sang-Chul Shim;Suk-Kyu Lee
    • Bulletin of the Korean Chemical Society
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    • v.1 no.2
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    • pp.68-70
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    • 1980
  • 1,4,5,8-Tetraazaphenanthrene, a new tetraazaheteroaromatic compound, has been synthesized photochemically in 90 % yield and quantum yield of $5.1{\times}10^{-2}$ from dilute benzene solutions of 1,2-bispyrazyl ethylene(BPE) in the presence of oxygen as an oxidant. Iodine was not appropriate oxidant because of strong complexing with BPE and also enhanced intersystem crossing of BPE and thereby decreasing the photocyclization of BPE. Salt effect, solvent effect, and quenching and sensitization studies on the photocyclization of BPE have shown that ($^l(n, {\pi}^*$) is the reactive state for the cyclization in comparison to ($^1{\pi}, {\pi}^*$) state for the ordinary stilbene derivatives.

Five New Stilbenes from the Stem Bark of Artocarpus communis

  • Chan, Susanna T.S.;Popplewell, Wendy L.;Bokesch, Heidi R.;McKee, Tawnya C.;Gustafson, Kirk R.
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.266-271
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    • 2018
  • Five new prenylated stilbenes (1 - 5), along with the known compounds cudraflavone C, trans-4-isopentenyl-3,5,2',4'-terahydroxystilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2',4'-tetrahydroxystilbene, pannokin G, cycloartobiloxanthone, artonin P, morusin, artocarpin, artonin E, kuwanon C, artobiloxanthone, and artoindonesianin C (6 - 17) were isolated from the stem bark of the tropical tree Artocarpus communis. The structures were established by NMR spectroscopic analysis, MS studies, and comparison with spectral data reported in the literature.