• Title/Summary/Keyword: 2-D NMR

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Compounds from the Seeds of Myristica fragrans and Their Cytotoxic Activity

  • Cuong, To Dao;Lim, Chae-Jin;Trang, Tran Thi Thu;Bae, Yoon-Ho;Thu, Nguyen Van;Tung, Nguyen The;Hung, Tran Manh;Woo, Mi-Hee;Choi, Jae-Sue;Min, Byung-Sun
    • Natural Product Sciences
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    • v.18 no.2
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    • pp.97-101
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    • 2012
  • Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7'-(3',4'-methylenedioxyphenyl)-8,8'-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

Hematopoietic Characteristics of the Ethylacetate Fraction of Panax ginseng and Identification of the Chemical Constituents (인삼의 에칠아세테이트 추출분획의 조혈활성 특성 및 구성 성분 동정)

  • Park, Jong-Dae;Wee, Jae-Joon;Kim, Man-Wook;Lee, Hyong-Joo
    • Applied Biological Chemistry
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    • v.32 no.2
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    • pp.137-142
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    • 1989
  • The ethylacetate soluble fraction of Panax ginseng extract, which has been reported to exhibit hematopoietic effect, was divided into three subfractions, i.e., Fr. I, Fr. II and Fr. III by silica gel column chromatography. The hematopoietic effect of each subfraction was examined in rats treated with anticancer agent, Ara-C($1-{\beta}-D-arabinofuranosylcytosine)$). Among them, Fr. III showed 90% recovery of leucocyte and erythrocyte counts in bonemarrow cell depleted rats, suggesting it to be hematopoietic fraction. From Fr. III, two major compounds were isolated and identified as ginsenoside $Rh_1$ and $Rg_2$ by $^{13}C-NMR$ and degradation method.

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Synthesis and Characterization of Perylene-based Pyrrolopyrone Derivative for Organic Thin Film Transistor

  • Kim, Hyung-Sun;Jung, Sung-Ouk;Kim, Yun-Hi;Do, Lee-Mi;Kwon, Soon-Ki
    • Journal of Information Display
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    • v.6 no.4
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    • pp.1-5
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    • 2005
  • Perylene-based pyrrolopyrone derivative (PPD) was synthesized via condensation reaction with perylenetetracarboxylic dianhydride and 1,2-phenylenediarnine as n-type channel material. The structure of PPD was characterized by spectroscopic methods such FT-IR and $^1H$-NMR. PPD exhibited high thermal stability ($T_{d5wt%}: 560^{\circ}C$) and was found to be soluble only in protonic solvents with high acidity such as methane sulfonic acid and trifluoroacetic acid. The PPD solution showed maximum absorption and emission at 601 and 628 nm, respectively. Thin film transistors were fabricated by vacuum deposition and solution casting method. The electron mobilities of the devices were achieved as high as $0.17{\times}10^{-6}cm^2/Vs$ for vacuum deposited device and $0.4{\times}10^{-6}cm^2/Vs$ for spin coated device, respectively.

Mercury recovery from aqueous solutions by polymer-enhanced ultrafiltration using a sulfate derivative of chitosan

  • Carreon, Jose;Saucedo, Imelda;Navarro, Ricardo;Maldonado, Maria;Guerra, Ricardo;Guibal, Eric
    • Membrane and Water Treatment
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    • v.1 no.4
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    • pp.231-251
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    • 2010
  • The sulfatation of chitosan, by reaction with chlorosulfonic acid under controlled conditions, allowed increasing the pH range of chitosan solubility. The biopolymer was characterized using FTIR and $^{13}C$-NMR spectroscopy, elemental analysis and titration analysis and it was tested for mercury recovery by polymer enhanced ultrafiltration (PEUF). In slightly alkaline conditions (i.e., pH 8) mercury recovery was possible and at saturation of the polymer the molar ratio $-NH_2$/Hg(II) tended to 2.6. Polymer recycling was possible changing the pH to 2 and the polymer was reused for 3 cycles maintaining high metal recovery. The presence of chloride ions influences metal speciation and affinity for the polymer and "playing" with metal speciation allowed using the PEUF process for mercury separation from cadmium; at pH 11 the formation of hydroxo-complexes of Hg(II) limits it retention. Cake formation reveals the predominant controlling step for permeation flux.

Phenolic Glycosides Isolated from Safflower (Carthamus tinctorius L.) Seeds Increase the Alkaline Phosphatase (ALP) Activity of Human Osteoblast-like Cells

  • Kim, Dong-Hyun;Lee, Jin-Hee;Ahn, Eun-Mi;Lee, Youn-Hyung;Baek, Nam-In;Kim, In-Ho
    • Food Science and Biotechnology
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    • v.15 no.5
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    • pp.781-785
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    • 2006
  • The chemical compositions of the seeds of the safflower (Carthamus tinctorius L.) plant were evaluated to determine possible compound having proliferative effects on human osteoblast cells. Three-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) test and alkaline phosphatase (ALP) activity were used to assess the effects of the isolates on the human osteoblast-like line (Saos-2). Activity guided fractionation led to the isolation of ALP activating lignin and alkaloid glycosides through the extraction of the seeds, solvent partitioning and repeated silica gel and octadecyl silica (ODS) column chromatographic separations. The data from Nuclear Magnetic Resonance (NMR), Mass (MS), and Infrared (IR) analyses enabled the determination of the chemical structure and characterization of two compounds as a tracheloside and an N-(p-coumaroyl)-serotonin mono-${\beta}$-D-glucopyranoside. These two compounds showed respectively $149.2{\pm}4.2$ and $138.9{\pm}3.5%$ ALP activity compared to the control when evaluated at a concentration of $100\;{\mu}g/mL$.

Enzymatic Synthesis and Characterization of Galactosyl Trehalose Trisaccharides

  • Kim, Bong-Gwan;Lee, Kyung-Ju;Han, Nam-Soo;Park, Kwan-Hwa;Lee, Soo-Bok
    • Food Science and Biotechnology
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    • v.16 no.1
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    • pp.127-132
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    • 2007
  • [ ${\alpha},\;{\alpha}$ ]-Trehalose was efficiently modified by a transgalactosylation reaction of Escherichia coli ${\beta}-galactosidase$ using lactose as a donor to yield two galactosyl trehalose trisaccharides. The reaction products of trehalose by the enzyme were observed by thin layer chromatography (TLC) and high performance anion exchange chromatography (HPAEC) and were purified by BioGel P2 gel permeation chromatography and recycling preparative HPLC. Liquid chromatography-mass spectrometry (LC-MS) and ^{13}C$ nuclear magnetic resonance (NMR) analyses revealed that the structures of the main products were $6^2-{\beta}-D-galactosyl$ trehalose (1) and $4^2-{\beta}-D-galactosyl$ trehalose (2). A reaction of 30%(w/v) trehalose and 15%(w/v) lactose at pH 7.5 and $45^{\circ}C$ resulted in a total yield of approximately 27-30% based on the amount of trehalose used. The galactosyl trehalose products were not hydrolyzed by trehalose. In addition the mixture of transfer products (9:1 ratio of 1 to 2) showed higher thermal stability than glucose, lactose, and maltose, but less than trehalose, against heat treatment over $100^{\circ}C$ at pH 4 and 7. It also exhibited better thermal stability than sucrose at pH 4 alone.

Homology Modeling and Active Sites of PolyMG-specific Alginate Lyase from Stenotrophomonas maltophilia KJ-2 (Stenotrophomonas maltophilia KJ-2 균주로부터 얻은 PolyMG-specific 알긴산분해효소의 상동성 모델링 및 활성자리 연구)

  • Kim, Hee Sook
    • Journal of Life Science
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    • v.24 no.2
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    • pp.128-136
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    • 2014
  • Alginates are linear acidic polysaccharides composed with (1-4)-linked ${\alpha}$-L-guluronic acid and ${\beta}$-Dmannuronic acid. Alginate can be degraded by diverse alginate lyases, which cleave the alginate using a ${\beta}$-elimination reaction and produce unsaturated uronate oligomers. A gene for a polyMG-specific alginate lyase possessing a novel structure was previously identified and cloned from Stenotrophomonas maltophilia KJ-2. Homology modeling of KJ-2 polyMG-specific alginate lyase showed it belongs to the PL6 family, whereas three Azotobacter vinelandii polyMG lyases belong to the PL7 family of polysaccharide lyases. From $^1H$-NMR spectra data, KJ-2 polyMG lyase preferably degraded the M-${\beta}$(1-4)-G glycosidic bond than the G-${\alpha}$(1-4)-M glycosidic bond. Seventeen mutants were made by site-directed mutagenesis, and alginate lyase activity was analyzed. Lys220Ala, Arg241Ala, Arg241Lys, and Arg265Ala lost alginate lyase activity completely. Arg155Ala, Gly303Glu, and Tyr304Phe also lost the activity by 60.7-80.1%. These results show that Arg155, Lys220, Arg241, Arg265, Gly303, and Tyr304 are important residues for catalytic activity and substrate binding.

Syntheses and Properties of Copolymers of Tetramethyldisiloxane and 1,4-Bis(dimethylhydroxysilyl)benzene (Tetramethyldisiloxane-1,4-bis(dimethylhydroxysilyl)benzene 공중합체의 합성 및 특성)

  • Kim, Sun-ll;Yun, Young-Jae;Na, Jae-Woon
    • Applied Chemistry for Engineering
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    • v.7 no.3
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    • pp.490-495
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    • 1996
  • Low molecular weight linear chlorine terminated siloxanes (yields;71.2~86.5%) were prepared by reactions of cyclotri-, cyclotetra- and cyclopentasiloxane with dimethyldichlorosilane in the presence of pyridine N-oxide catalyst. The amine terminated siloxane oligomers were obtained in good yields(76.2~85.3%) by the reaction of linear chlorine terminated siloxanes with dimethylamine at $0^{\circ}C$. In this investigation, we have studied on the syntheses and properties of copolymers (yields;58.0~71.0%) obtained from the reaction of amine terminated siloxane oligomers with 1,4-bis(dimethylhydroxysilyl)benzene. The structures and properties of the copolymers were examined by FT-IR, $^1H$-NMR, TGA and DSC. Initial degradation temperatures($T_D{^i}$) of the polymer I and IV were confirmed as 476 and $485^{\circ}C$, respectively. The thermal stabilities of the polymers were found to be increased with increasing n of $(R_2SiO)_n$. The glass transition temperatures(Tg) of the polymers were increased with decreasing n of $(R_2SiO)_n$, and the lowest Tg revealed $-76^{\circ}C$ when n=5.

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Induction of Apoptotic Cell Death in Human Jurkat T Cells by a Chlorophyll Derivative (Cp-D) Isolated from Actinidia arguta Planchon

  • Park, Youn-Hee;Chun, En-Mi;Bae, Myung-Ae;Seu, Young-Bae;Song, Kyung-Sik;Kim, Young-Ho
    • Journal of Microbiology and Biotechnology
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    • v.10 no.1
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    • pp.27-34
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    • 2000
  • The chloroform and methanol (2;1, v/v) extract from an edible plant, Actinidia arguta Planchon, appeared to possess antitumor activity against human leukemias Jurkat T and U937 cells through inducing apoptosis. The substance in the solvent extract was purified by silica gel column chromatography, preparative TLC, and Sephadex LH-20 column chromatography. Characteristics of the substance analyzed by UV scanning analysis, $^1H$ and $^{13}C$ NMR spectra suggested that the substance belongs to the chlorophyll derivatives-like group. The $IC_{50}$ value of the chlorophyll derivative (Cp-D) determined by MTT assay was $15\mu\textrm{g}/ml$ for Jurkat, $10\mu\textrm{g}/ml$ for U937, and $11.4\mu\textrm{g}/ml$ for HL-60m and was more toxic to these leukemias than to solid tumors or normal fibroblast. In order to elucidate cellular mechanisms underlying the cytotoxicity, the effect of the Cp-D on Jurkat T cells was investigated. When cells were treated with the Cp-D at a concentration of $15\mu\textrm{g}/ml$, [3H]thymidine incorporation declined rapidly and wa undetectable in 1h. However, no significant changes were made in the cell cycle distribution of the cells by 24h. The sub-Gl peak representing apoptotic cells began to be detectable in 36h, at which time apoptotic DNA fragmentation was also detected on agarose gel electrophoresis, demonstrating that the cytotoxic effect of the Cp-D is attributable to the induced apoptosis. Under the same conditions, although the protein level of cyclin-dependent kinases such as cdc4, csk6, cdk2, and cdc2 was not significantly changed until 24h, the kinase activity of all c안 rapidly declined and reached a minimum level within 1-6h and then recovered to the initial level by 12h and sustained until 24h. These results suggest that inactivation of cdks at an inappropriate time during the cell cycle progression in jurkat T cells following a treatment with the Cp-D leads to induction of apoptotic cell death.

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Steroids from the Cold Water Starfish Ctenodiscus crispatus with Cytotoxic and Apoptotic Effects on Human Hepatocellular Carcinoma and Glioblastoma Cells

  • Quang, Tran Hong;Lee, Dong-Sung;Han, Se Jong;Kim, Il Chan;Yim, Joung Han;Kim, Youn-Chul;Oh, Hyuncheol
    • Bulletin of the Korean Chemical Society
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    • v.35 no.8
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    • pp.2335-2341
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    • 2014
  • Chemical investigation on the methanol extract of the starfish Ctenodiscus crispatus resulted in the isolation of five steroids, (22E,$24{\zeta}$)-26,27-bisnor-24-methyl-$5{\alpha}$-cholest-22-en-$3{\beta}$,5,$6{\beta}$,$15{\alpha}$,25-pentol 25-O-sulfate (1), (22E,24R,25R)-24-methyl-$5{\alpha}$-cholest-22-en-$3{\beta}$,5,$6{\beta}$,$15{\alpha}$,25,26-hexol 26-O-sulfate (2), (28R)-24-ethyl-$5{\alpha}$-cholesta-$3{\beta}$,5,$6{\beta}$,8,$15{\alpha}$,28,29-heptaol-24-sulfate (3), (25S)-$5{\alpha}$-cholestane-$3{\beta}$,5,$6{\beta}$,$15{\alpha}$,$16{\beta}$,26-hexaol (4), and ${\Delta}7$-sitosterol (5). Their structures were identified by extensive spectroscopic analyses, including 1D, 2D NMR and MS and chemical methods. Compound 4 showed cytotoxicity against human hepatoma HepG2 and glioblastoma U87MG cells via inhibition of cell growth and induction of apoptosis. Induction of apoptosis by 4 was demonstrated by cell death, DNA fragmentation, increased Bax/Bcl-2 protein ratio and the activation of caspase-3, caspase-9 and poly (ADP-ribose) polymerase (PARP).