• Title/Summary/Keyword: 2-D NMR

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Synthesis and characterization of sulfonated poly(arylene biphenylsulfone ether) copolymers containing hydroquinone moiety for polymer electrolyte membrane (고분자 전해질 멤브레인용 하이드로퀴논 부분이 포함된 설폰화된 폴리(아릴렌 비페닐설폰 에테르) 공중합체의 합성과 특성평가)

  • Yoo, Dong-Jin
    • Journal of Energy Engineering
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    • v.19 no.2
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    • pp.121-127
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    • 2010
  • In present work, sulfonated poly(arylene biphenyklsulfone ether) copolymers containing hydroquinone moiety were successfully synthesized using 4,4'-bis[(4-chlorophenyl)sulfonyl]-1,1'-biphenyl(BCPSBP), hydroquinone sulfonic acid potassium salt(sHQ), 4,4'-sulfonyldiphenol and evaluated their characteristics. Three kinds of polymer electrolyte membranes, PBPSEH-HQ00, PBPSEH-HQ10 and PBPSEH-HQ30 were prepared by using mole fraction of sulfonated hydroquinone(sHQ). The structure of the fabricated polymers was analyzed using NMR, IR and GPC. The Mw(weight-average molecular weights) of the polymers were in the range of 62,000-213,000 g $mol^{-1}$, and the molecular weight distribution (Mw/Mn) varied from 1.66-4.04. The thermal analysis of the copolymers was carried out by TGA and DSC. The temperature of Td5% and Td10% was decreased with the mole fraction of sHQ but Tg was increased with the mole fraction. The water uptake, IEC and ion conductivity were increased with increasing the ionic cluster of the polymers. The proton conductivity equal to 9.4 mS $cm^{-1}$ was measured for the PBPSEH-HQ30 membrane at $90^{\circ}C$ and 100% relative humidity. From the observed results it is clear that the prepared hydrocarbon membrane can be considered as suitable polymer electrolyte membrane for the application of PEMFC.

Synthesis and Anti-corrosion Properties of Succinic Acid Alkyl Half-amide Derivatives (숙신산 알킬 하프-아마이드 유도체의 합성 및 해수에 대한 방청성능)

  • Baek, Seung-Yeob;Kim, Young-Wun;Chung, Keun-Wo;Yoo, Seung-Hyun;Kim, Nam-Kyun
    • Clean Technology
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    • v.17 no.4
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    • pp.314-324
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    • 2011
  • Several amide derivatives have been used as additives for base oil of metal working fluids and pressure working oils. In this paper, a series of succinic acid alkyl half-amide derivatives were synthesized as over 97% yields by ring-opening reaction of succinic anhydride and several amines and were soluble in 100 N base oil within 1 wt% concentration. The structures of the synthesized amides were confirmed by $^1H$-NMR, FT-IR spectrum and GC analysis. Anti-corrosion properties of the amides in sea water were evaluated through ASTM D665 method and weight loss method. As the results of anti-corrosion properties, the properties of the amides with shorter alkyl chain and high concentration showed better performance than those with longer alkyl chain and low concentration. Also, the dialkyl amides showed better anti-corrosion properties than those of the monoalkyl amides. Inhibition efficiency% (IE%) was over 93% in the concentration of 40 ppm and corrosion rate (CR) was below 0.5 mm/year in the same concentration.

Preparation and Characteristics of Polymer Additives for Functional Instant Adhesives (기능성 순간접착제용 중합체 첨가제의 제조 및 특성)

  • Ihm, H.J.;Ahn, K.D.;Kim, S.B.;Kim, E.Y.;Han, D.K.
    • Journal of Adhesion and Interface
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    • v.2 no.3
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    • pp.25-32
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    • 2001
  • Ethyl cyanoacrylate (ECA) is used as an instant adhesive, and it can be readily polymerized by moisture in air without any initiator and applied for industrial products and ohome use. However, pure ECA monomer is low-viscosity liquid at room temperature that flows into substrate surface. To thicken the instant adhesive, poly(methyl methacylate)(PMMA) is often added in it commercially. Another disadvantage of instant adhesive polymer is its brittleness In this study, functional polymers including PMMA for an additive of ECA were prepared to increase viscosity of the monomer and flexibility of the adhesive atthe same time The additives, P(MMA-VAc-EVE), were synthesized by radical copolymerization of MMA with VAc and EVE having low glass transition temperature (Tg). The additives were added to ECA to get functional instant adhesives. The chemical structures of the additives and ECA polymers were confirmed by $^1H$ NMR and FTIR, and their physical and mechanical properites were also evaluated. The Tg of the obtained additives decreased with increasing the content of VAc or VAc-EVE, indicating more improved flexibility. In addition, functional instant adhesive containing the additives showed higher bonding strength than that of the existing one.

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Identification of 5-Hydroxy-3,6,7,8,3',4'-Hexamethoxyflavone from Hizikia fusiforme Involved in the Induction of the Apoptosis Mediators in Human AGS Carcinoma Cells

  • Kim, Min Jeong;Lee, Hye Hyeon;Seo, Min Jeong;Kang, Byoung Won;Park, Jeong Uck;Kim, Kyoung-Sook;Kim, Gi-Young;Joo, Woo Hong;Choi, Yung Hyun;Cho, Young-Su;Jeong, Yong Kee
    • Journal of Microbiology and Biotechnology
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    • v.22 no.12
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    • pp.1665-1672
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    • 2012
  • An 80% ethanol extract of Hizikia fusiforme was obtained and followed by successive fractionation using the organic solvents n-hexane, ethyl acetate, and n-butanol to identify the antioxidative substance. The aqueous part of the nbutanol fractionation step, showing high antioxidative activity, was subjected to reverse-phase liquid chromatography. As a result, a substance purified from a BB-2 fraction showed high antioxidative activity. The m/z 419 [M+H] molecular ion peak in the fraction was observed by the analysis of the ESI-LC/MS spectrum. By the analysis of 1H NMR (500 MHz, DMSO-$d_6$) and $^{13}C$ NMR (125 MHz, DMSO-$d_6$) spectra, a unique compound of the fraction was biochemically identified as a 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone (5HHMF). We also investigated the effect of 5HHMF on human gastric AGS carcinoma cells. Western blot analysis suggested that the flavone substantially increased the levels of the death receptor-associated apoptosis mediators Fas, Fas L, FADD, TRADD, and DR4 in a concentration-dependent manner. The levels of Fas, Fas L, TRADD, and DR4 in the cells treated with 5HHMF ($5{\mu}g/ml$) were approximately 26.4-, 12.8-, 6.7-, and 9.8-times higher than those of non-treated cells, respectively. Of note, the level of FADD protein in the cells exposed to 5HHMF ($1{\mu}g/ml$) increased approximately 9.6-times. In addition, the cleavage of caspase-3, -8, and -9 in cultured AGS cells treated with 5HHMF was significantly confirmed. Therefore, our results suggest that 5HHMF from H. fusiforme is involved in the induction of death receptor-associated apoptosis mediators in human gastric AGS carcinoma cells.

Production of a New Biosurfactant by a New Yeast Species Isolated from Prunus mume Sieb. et Zucc.

  • Jeong-Seon Kim;Miran Lee;Dae-Won Ki;Soon-Wo Kwon;Young-Joon Ko;Jong-Shik Kim;Bong-Sik Yun;Soo-Jin Kim
    • Journal of Microbiology and Biotechnology
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    • v.33 no.8
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    • pp.1023-1029
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    • 2023
  • Biosurfactants reduce surface and interfacial tension due to their amphiphilic properties and are an eco-friendly alternative for chemical surfactants. In this study, a new yeast strain JAF-11 that produces a biosurfactant was selected using drop collapse method, and the properties of the extracts were investigated. The nucleotide sequences of the strain were compared with closely related strains and identified based on the D1/D2 domain of the large subunit ribosomal DNA (LSU) and internal transcribed spacer (ITS) regions. Neodothiora populina CPC 39399T, the closest species with strain JAF-11, showed a sequence similarity of 97.75% for LSU and 94.27% for ITS, respectively. The result suggests that the strain JAF-11 represents a distinct species that cannot be assigned to any existing genus or species in the family Dothideaceae. Strain JAF-11 produced a biosurfactant reducing the surface tension of water from 72 mN/m to 34.5 mN/m on the sixth day of culture and the result of measuring the critical micelle concentration (CMC) by extracting the crude biosurfactant was found to be 24 mg/l. The molecular weight 502 of the purified biosurfactant was confirmed by measuring the fast atom bombardment mass spectrum. The chemical structure was analyzed by measuring 1H nuclear magnetic resonance (NMR), 13C NMR, and two-dimensional NMRs of the compound. The molecular formula was C26H46O9, and it was composed of one octanoyl group and two hexanoyl groups to myo-inositol moiety. The new biosurfactant is the first report of a compound produced by a new yeast strain, JAF-11.

Proliferative Effects of Flavan-3-ols and Propelargonidins from Rhizomes of Drynaria fortunei on MCF-7 and Osteoblastic Cells

  • Chang, Eun-Ju;Lee, Won-Jung;Cho, Sung-Hee;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • v.26 no.8
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    • pp.620-630
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    • 2003
  • The proliferative effects of thirty Oriental medicinal herbs on MCF-7 (estrogen-sensitive breast cancer cell line) and ROS 17/2.8 osteoblast-like cells were determined using the MTT assay. Methanol extracts from several herbs was found to show proliferative activity on the above two cell lines in the range of 5 to 100 $\mu$g/mL. Among these active herbs, the methanol extract from the rhizomes of Drynaria fortunei showed the most potent proliferative activity, and the cell proliferations were significantly increase by 136 and 158% in the MCF-7 and ROS 17/2.8 cells, respectively, when treated with 100 $\mu$ g/mL. Through a bioassay-guided separation, eight flavonoids, including four new flavan-3-ols and two propelargonidins, together with the known (-)-epiafzelechin and naringin, were isolated. Their chemical structures were characterized as (-)-epiafzelechin (1), (-)-epiafzelechin-3-O-$\beta$-D-allopyranoside (2), (-)-epiafzelechin-3-O-(6"-O-acetyl)-$\beta$-D-allopyranoside (3), 4$\beta$-carboxymethyl-(-)-epiafzelechin methyl ester (4), 4$\beta$-car-boxymethyl-(-)-epiafzelechin sodium salt (5), naringin (6), (-)-epiafzelechin-(4$\beta$\rightarrow8)-4$\beta$-car-boxymethylepiafzelechin methyl ester (7) and (-)-epiafzelechin-($4\beta\rightarrow8, 2\beta\rightarrowΟ\rightarrow7)-epiafzelechin-(4\beta\righarrow8)-epiafzelechin (8) by extensive 1D and 2D NMR spectroscopy. Most of these flavonoids, in the range of $10^{-15}∼10^{-6}$ M, accelerated the proliferation of MCF-7 cell, with compounds 7 and 8, in the range of $10^{-15}∼10^{-12}$ M, showing especially potent proliferation effects. Meanwhile, seven flavonoids, with the exception of compound 4, stimulated the proliferation of ROS 17/2.8 cells in the range of $10^{-15}∼10^{-6}$ M, with compounds 5-8 especially accelerating the proliferation, in dose-dependent manners ($10^{-15}∼10^{-9}$ M), and their proliferative effect was much stronger than that of $E_2$ and genistein. These results suggest that propelargonidin dimers and trimers isolated from the rhizomes of Drynaria fortunei may be useful as potential phytoestrogens, which play important physiological roles in the prevention of postmenopausal osteoporosis.

Steroids from the Aerial Parts of Artemisia princeps Pampanini

  • Yoo, Jong-Su;Ahn, Eun-Mi;Bang, Myun-Ho;Song, Myoung-Chong;Yang, Hye-Joung;Kim, Dong-Hyun;Lee, Dae-Young;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.273-277
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    • 2006
  • Three stigmastane-type sterols and one ergostane-type sterol were isolated from the ethyl acetate soluble fraction of the aerial parts of Artemisia princeps Pampanini (Sajuarissuk). From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as $stigmasta-5,22-dien-3,{\beta}-ol (stigmasterol, 1),stigmast-5-en-3{\beta}-ol({\beta}-sitosterol,2), 5{\beta},8{\beta}-epidioxy-5{\beta},8{\beta}-ergosta-6,22-dien-3{\beta}-ol(ergosterol peroxide, 3),\;and\;{\beta}-sitosterol\;3-O-{\beta}D-glucopyranoside(daucosterol,4)$.

Anti-cancer Activity of Flavonoids from Aceriphyllum rossii (돌단풍(Aceriphyllum rossii)에서 분리한 플라보노이드의 항암활성)

  • Ahn, Eun-Mi;Han, Jae-Taek;Kwon, Byoung-Mog;Kim, Sung-Hoon;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.309-315
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    • 2008
  • The methanol extract from the aerial parts of Aceriphyllum rossii was fractionated into ethyl acetate, n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded five flavonol glycosides. They were identified as astragalin (1), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (2), rutin (3), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl 1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (4), and quercetin 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (5) on the basis of spectroscopic data. All of them showed an inhibition in farnesyl protein tranferase (FPTase) activity, and rutin (3) inhibited the growth of rat H-ras cell and the cell migration of human umbilical vein endothelial cells (HUVECs).

Surface Modification of Microcrystalline Cellulose (MCC) Filler for CO2 Capture (CO2 흡착 충전제 제조를 위한 microcrystalline cellulose (MCC) 입자 표면개질연구)

  • Yang, Yeokyung;Park, Seonghwan;Kim, Hanna;Hwang, Ki-Seob;Ha, KiRyong
    • Korean Chemical Engineering Research
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    • v.55 no.1
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    • pp.60-67
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    • 2017
  • In this study, we performed surface modification of biodegradable microcrystalline cellulose (MCC) to use as a filler in polyethylene (PE) composite in food packaging application. We modified MCC surface with (3-trimethoxysilylpropyl)diethylenetriamine (TPDT) silane coupling agent, which has one primary amino group and two secondary amino groups per molecule, to introduce amino groups with a carbon dioxide adsorption capability in MCC. Effects of each of the reaction conditions such as amount of TPDT introduced, swelling time, reaction temperature, and reaction time on surface modification degree of MCC were investigated by changing a variety of above reaction conditions. The amount of TPDT grafted on MCC surface and formation of chemical bonds were confirmed by Fourier transform infrared spectroscopy (FT-IR), elemental analysis (EA), X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TGA) and solid state $^{29}Si$ nuclear magnetic resonance (NMR) spectroscopy. We confirmed increase of grafted amount of TPDT on MCC with increasing reaction time, reaction temperature, and amount of introduced TPDT.

Study on Inhibition of Platelet Aggregation of Bioactive constituents from Paeonia lactiflora (작약의 혈소판 응집억제작용에 관한 연구)

  • 서범석;박관혁;손동주;박영현;장성근
    • Proceedings of the KAIS Fall Conference
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    • 2003.06a
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    • pp.320-321
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    • 2003
  • 최근 천연물을 중심으로 한 학문이 발전하면서 천연물이 가지는 생리활성 물질에 대한 관심이 중대되고 있다. 또한 인공합성품의 일부가 안정성의 문제가 제기되면서 천연물의 이용분야는 더욱 확대되고 있다. 급속한 경제발전과 생활수준의 향상으로 식생활을 포함한 생활방식의 다양화로 인하여 과거 감염 위주의 질병이 감소하고 선진국형의 만성퇴행성 질환이 증가하는 추세이다. 혈소판은 혈전증(thrombosis)과 지혈증(haemstasis)에서 중요한 역할을 담당하고 있는 인자로서 현관 내 병적 이상으로 인한 과도한 혈전의 생성은 뇌 -심혈관계 질환의 중요한 유발인자로 작용하므로 뇌ㆍ심혈관계 질환이나 항고지혈증을 연구하는데 유용하게 이용되고 있다. 본 연구에서는 토끼 혈액에서 분리한 세정 혈소판 부유액을 이용하여 작약 MeOH 추출물에서 분리한 천연생리활성물질들을 대상으로 혈소판 응집억제활성에 대하여 연구하였다. 작약 MeOH 추출물의 혈소판 응집억제활성 측정에서 강한 혈소판 응집억제활성 작용을 보였다. 따라서 작약 MeOH 추출물을 크로마토그라피법을 이용하여 분리하였고, NMR을 이용한 분광학적 방법으로 지금까지의 분리한 자료와 비교ㆍ분석하였다. Monoterpene glycoside 계열의 성분들인 15개의 compound와 다수의 fraction들을 HPLC를 이용하여 분리하였으며, collagen으로 유도된 혈소판 응집억제활성측정 방법에서 뛰어난 응집억제활성을 보였다. 표준물질을 이용한 HPLC 분석과 ¹H-NMR 관련 자료의 검색을 통하여 최종적으로 compound 1b가 benzoyloxy-paeoniflorin(2.6%). compound 1d가 paeond(1.3%), compound 2c가 albiflorin(3.2%), compound 2e가 paeoniflorin(33.6%)임을 확인할 수 있었다. Compound 3a의 분석결과 benzoyloxypaeoniflorin과 구조적 유사성은 있으나 동일한 구조식으로 확인할 수 없었다. 그러나 collagen에서 응집억제활성이 90% 이상으로 뛰어난 활성을 나타내므로 benzoyloxypaeoniflorin과 유사한 구조에서 benzoyl group이 다른 작용기로 치환되었거나 R₁ group이 다른 작용기로 치환된 형태로 추측하였다. Benzoyloxypaeoniflorin은 collagen>thrombin>U46616>A.A(arachidonic acid)>PAF의 순으로 활성을 보였다. 이는 paeoniflorin의 glycoside 5-carbon위치에 위치한 OH기 대신에 benzoyl기로 치환된 benzoyl 기가 혈소판 억제 산물로 작용한 것으로 추측했다. Paeoniflorin.은 U46619>thrombin>collagen>A.A>PAF순으로 억제를 보였다. Paeoniflorin이 collagen보다 thrombin에서 강한 억제를 보이는 것으로 Ca/sup 2+/ chelate를 형성함으로 인해 calciu 대사를 저해하는 것으로 추축했다. Compound 3a는 U46619>collagen>A.A>thrombin>PAF순으로 억제율을 보이므로 이 화합물은 paeoniflorin의 benzoyl기에 OH기가 다른 치환기로 바뀌거나 paeoniflorin의 glycoside 5-carbon 위치의 OH기 대신에 다른 작용기로 치환된 것으로 추정하였다. 이러한 결과로 작약의 주성분인 paeoniflorin과 유사한 구조를 가진 다른 monoterpene glycoside 계열의 화합물들과 비교 분석하고 구조를 화인하고 이들 성분이 어떻게 혈소판 응집억제활성에 작용하는지를 연구하였다.

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