• Title/Summary/Keyword: $^2H$ NMR

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Isolation and Identification of Phenolic Compounds from the Root Bark of Morus alba L. (상백피(Morus alba root barks)로부터 페놀화합물의 분리 및 동정)

  • Jung, Jae-Woo;Park, Ji-Hae;Seo, Kyeong-Hwa;Baek, Yoon-Su;Oh, Eun-Ji;Lee, Dae-Young;Lim, Dong-Wook;Han, Daeseok;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.2
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    • pp.153-155
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    • 2015
  • The root barks of Morus alba L. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH, and $H_2O$ fractions. The repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies of the EtOAc and n-BuOH fractions led to isolation of four phenolic compounds. The chemical structures of the compounds were determined as norartocarpanone (1), 2',4',7-trihydroxy-(2S)-flavanone (2), methyl ${\beta}$-resorcylate (3), and (Z)-oxyresveratrol-4-O-${\beta}$-$\small{D}$-glucopyranoside (4). Compound 4 was isolated for the first time from the root barks of M. alba L.

Biological Activities and Bioactive Compounds in the Extract of Acer tegmentosum Maxim. Stem (산겨릅나무 줄기추출물의 생리활성 및 유효성분 분리)

  • Hong, Bo-Kyong;Eom, Seok-Hyun;Lee, Chan-Ok;Lee, Ji-Won;Jeong, Jong-Hyun;Kim, Jae-Kwang;Cho, Dong-Ha;Yu, Chang-Yeon;Kwon, Yong-Soo;Kim, Myong-Jo
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.4
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    • pp.296-303
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    • 2007
  • Acer tegmentosum (Acereaceae) has been used a source of traditional medicines for the treatment of hepatic disorders in Korea. This research was conducted to determine biofunctional activities of A. tegmentosum stem extract and to identify its bioactive components. Methanolic extract from A. tegmentosum stem was partitioned by using organic solvents, including n-hexane, ethyl acetate, n-butanol, and water. Two compounds were isolated by using an ODS column chromatography from ethyl acetate soluble fraction shown to the strongest antioxidant activity ($RC_{50}=3.15\;{\mu}g/m{\ell}$) among the fractions. The isolated compounds were analyzed by $^1H$ and $^{13}C$ NMR, IR, UV/VIS, MS spectrum data and identified as catechin, ${\rho}-Hydroxyphenethyl$ alcohol $1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$. The compounds have shown strong antioxidant activity, with similar activity to BHA ($RC_{50}=2\;{\mu}g/m{\ell}$). Especially, ${\rho}-Hydroxyphenethyl$ alcohol 1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$ was shown strong anti-lipid peroxidative activity. However, the compounds were not shown antimicrobial activities. In antimicrobial activity assays, ethyl acetate soluble fraction was effective to bacterial inhibition, such as Escherichia coli and Klebsiella pneumonia, with minimum inhibitory concentrations in $125\;{\mu}g/m{\ell}$. Otherwise, antifungal activity against Candida albicans was shown in n-hexane soluble fraction exhibiting $63\;{\mu}g/m{\ell}$ of minimum inhibitory concentration. In anticomplementary activity assays, water soluble fraction was the most effective exhibiting 24% inhibitory activity.

Kinetic Studies on Homopolymerization of $\alpha$-Methylstyrene and Sequential Block Copolymerization of Isobutylene with $\alpha$-Methylstyrene by Living/Controlled Cationic Polymerization (리빙/조절 양이온중합에 의한 알파메틸스티렌 호모중합 및 이소부틸렌과의 블록공중합에 대한 반응속도론 연구)

  • Wu, Yibo;Guo, Wenli;Li, Shuxin;Gong, Huiqing
    • Polymer(Korea)
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    • v.32 no.4
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    • pp.366-371
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    • 2008
  • The controlled/living cationic polymerization of $\alpha$-methylstyrene (${\alpha}MeSt$) and sequential block copolymerization of isobutylene (IB) with ${\alpha}MeSt$ were achieved using 2-chloro-2,4,4-trimethylpentane (TMPCl)/titanium tetrachloride ($TiCl_4$)/titanium isopropoxide ($Ti(OiPr)_4$)/2,6-ditert-butylpyridine (DtBP) initiating system in $CH_3Cl$/hexane(50/50 v/v) solvent mixture at $-80^{\circ}C$. The polymerization rate decreased with increasing $[Ti(OiPr)_4]/[TiCl_4]$ ratio in the homopolymerization of ${\alpha}MeSt$. The effects of $[Ti(OiPr)_4]/[TiCl_4]$ ratios and $PIB^+$ molecular weight on the polymerization rate and blocking efficiency were also investigated. Well-defined poly(isobutylene-b-$\alpha$-methylstyrene)s were demonstrated by $^1H$-NMR and triple detection SEC; refractive index (RI), multiangle laser light scattering (MALLS) and ultraviolet (UV) detectors. Blocking efficiencies for the poly(isobutylene-b-$\alpha$-methylstyrene)s of almost 100% were obtained when ${\alpha}MeSt$ was induced by PIB's of $M_n\;{\geq}\;41000$ at $[Ti(OiPr)_4]/[TiCl_4]=1$. Differential scanning calorimetry (DSC) of the block copolymers showed two glass transition temperatures, thereby demonstrating microphase separation.

Liquid Crystalline Properties of Dimers Having o-, m- and p- Positional Molecular Structures

  • Park, Joo-Hoon;Choi, Ok-Byung;Lee, Hwan-Myung;Lee, Jin-Young;Kim, Sung-Jo;Cha, Eun-Hee;Kim, Dong-Hyun;Ramaraj, B.;So, Bong-Keun;Kim, Kyung-Hwan;Lee, Soo-Min;Yoon, Kuk-Ro
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1647-1652
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    • 2012
  • With the objective to design and synthesis of Schiff's base symmetrical liquid crystal dimmers and to study the effect of molecular structure variation ($o-ortho$, $m-meta$, $p-para$) and change in alkoxy terminal chain length on mesomorphic properties of liquid crystals, We have synthesized Schiff base dimers from dialdehyde derivative containing 2-hydroxy-1,3-dioxypropylene as short spacer with aniline derivatives having different lengths of terminal alkoxy chains ($n$ = 5, 7, 9). The chemical structure of the final products was characterized by proton nuclear magnetic resonance ($^1H$ NMR) spectroscopy and fourier transform infrared (FT-IR) spectroscopy. The mesomorphic properties and optical textures of the resultant dimers were characterized by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). The existence of smectic A phase transition was confirmed by the observation of batonnets and fan shaped textures in optical microscopy when compound were heated from crystalline phase. All of the dimers of this series, with the exception of $\mathbf{2S_5}$ -ortho, -meta, -para, were thermotropic liquid crystal. The compound $\mathbf{2S_9}$ -meta was monotropic, while the rest were enantiotropic. It was found that the change in terminal alkoxy chain length has pronounced effect on the mesomorphic properties. The temperature range of smectic A phase window widens with increasing alkoxy chain length.

Isolation of Natural Antioxidants from the Root of Zingiber officinale R. (생강(Zingiber officinale R.)근경으로부터 항산화 활성물질의 분리)

  • Bang, Myun-Ho;Song, Jung-Choon;Kim, Sun-Lim;Hur, Han-Sun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.44 no.3
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    • pp.202-205
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    • 2001
  • The root of Zingiber officinale R. was extracted with 80% aqueous MeOH, and the concentrated extract was fractionated with EtOAc, n-BuOH and water phases. The EtOAc fraction exhibited most potent antioxidant activity among them, and two active compounds were isolated by activity-guided separation using repetitive silica gel column chromatography. On the bases of spectral data and the chemical characteristics, the structure of the compounds were determined as 6-shogaol and 12-shogaol, respectively. The $EC_{50}$ values of them were evaluated as 26.4 ${\mu}M$ and 22.5 ${\mu}M$, respectively, where these values were higher than the commercial antioxidants, such as, BHA, BHT and ${\alpha}-tocopherol$.

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Poly(Ethylene Glycol)-branched Polyethylenimine-poly(L-phenylalanine) Block Copolymer Synthesized by Multi-initiation Method for Formation of More Stable Polyelectrolyte Complex with Biotherapeutic Drugs

  • Park, Woo-Ram;Na, Kun
    • Journal of Pharmaceutical Investigation
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    • v.41 no.2
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    • pp.95-102
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    • 2011
  • An amphiphilic cationic branched methoxy poly (ethylene glycol)-branched polyethylenimine - poly(L-phenylalanine) (mPEG-bPEI-pPhe) block copolymer was successfully synthesized by ring-opening polymerization (ROP) of N-carboxyanhydride of L-phenylalanine (Phe-NCA) with mPEG-bPEI for the preparation of more stable polyelectrolyte complex (PEC) included a hydrophobic interaction. mPEG-bPEI was firstly prepared by the coupling of mPEG and bPEI using hexamethylene diisocyanate (HMDI). The structural properties of mPEG-bPEI-pPhe copolymers were confirmed by $^1H$ NMR. The copolymers exhibited a self-assemble behavior in water above critical aggregate concentration (CAC) in the range of 0.01-0.14 g/L. The CAC of copolymers obviously depended on the hydrophobic block content in the copolymers (the value decreased with the increase of the pPhe block content). The cationic copolymers have the ability to form multi-interaction complex (MIC) with bovine serum albumin (BSA) and plasmid DNA through multi-interaction (electrostatic and hydrophobic interaction). The physicochemical characterization of the complex was carried out by the measurement of zeta potential and particle size. Their zeta-potentials were positive (approximately +10 mV) and their sizes decreased with increasing pPhe contents in the copolymers (PPF/BSA wt% ratio = 2). The complex showed good stability at high ionic strength. Therefore, mPEG-bPEI-pPhe block copolymer was considered as a potential material to enhance the stability of complex including biotherapuetic drugs.

Screening System for Chitin Synthase II Inhibitors from Natural Resources and its Inhibitor Prodigiosin

  • Hwang, Eui-Il;Kim, Young-Kook;Lee, Hyang-Bok;Kim, Hong-Gi;Kim, Sung-Uk
    • Journal of Microbiology and Biotechnology
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    • v.10 no.2
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    • pp.251-257
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    • 2000
  • Chitin synthases are identified as key enzymes of chitin biosynthesis in most of the fungi. Among them, chitin synthase II has been reported to be and essential enzyme in chitin biosynthesis, and exists as a membrane-bound form. To search and screen new antifungal agents from natural resources to inhibit chitin synthase II, the assay conditions were established using the enzyme isolated from Saccharomyces cerevisiae ECY38-38A(pAS6) that overproduces only chitin synthase II. This enzyme was activated only by partial proteolysis with trypsin. Its actibity reached the maximum at $80{\;}\mu\textrm{g}/ml$ of trypsin and was strongly stimulated by 2.0 mM $Co^{2+}$, 1.0 nM UDP-[$^{14}C$]-GicNAc, and 32 mM free-GlcNAc. Under these assay conditions, the highest chitin synthase II activity was observed by incubation at $30^{\circ}C$ for 90 min. However, and extremely narrow range of organic solvents up to as much as 25% of DMSO and 25% of MeOH was useful for determining optimal assay conditions. After a search or potent inhibitors of chitin synthase II from natural resources, prodigiosin was isolated from Serratia marcescens and purified by solvent extration and silica gel column chromatographies. The structure of prodigiosin was determined by UV, IR, Mass spectral, and NMR spectral analyses. Its molecular weight and formula were found to be 323 and $C_{20}H_{25}N_{3}O$, respectively. Prodigiosin ingibited chitin synthase II by 50% at the concentration of $115{\;}\mu\textrm{g}/ml$.

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${\alpha},{\omega}$-Bis[4-(4'(S)-(+)-2-methylbutylbiphenyl-4-carboxy)phenoxy]alkanes-Synthesis and Liquid Crystalline Properties of New Dimesogenic Compounds (${\alpha},{\omega}$-비스[4-(4'-(S)-(+)-2-메틸부틸비페닐-4-카르복시)페녹시]알칸 -새로운 디메소겐 화합물의 합성 및 액정성)

  • Kim, Jae Hoon;Lee, Soo Min;Jin, Jung Il
    • Journal of the Korean Chemical Society
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    • v.42 no.6
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    • pp.679-695
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    • 1998
  • A series of ${\alpha}{\omega}-bis[4-(4'-(S)-(+)-2-methylbutylbiphenyl-4-carboxy)phenoxy]alkanes$, were synthesized, and their thermal and liquid crystalline properties were studied. The chain length of the central polymethylene spacers, x, of the chiral twin compounds was varied from 3 to 12. These compounds were characterized by elemental analysis, IR and NMR spectroscopy, differential thermal analysis (DSC), and crosspolarized microscopy. All compounds were found to be enantiotropic liquid crystalline, and the values of melting $(T_m)$ and isotropization temperature $(T_i)$ as well as ${\delta}H_I$ and ${\delta}S_I$ decreased in a zig-zag fashion, revealing the so called odd-even effect as x increased. Their mesomorphic properties fell into four categories depending upon x; (a) compounds with x=3, 4 and 5 formed only a cholesteric phase on heating, while on cooling they went through two transitions of isotropic (I)-to-cholesteric (Ch) and Ch-to-smectic $A\;(S_A)$ phases before crystallization. (b) compounds with x=6, 8 and 10 exhibited only a cholesteric phase both on heating and on cooling. (c) compounds with x=7 and 9 went through three transitions of crystal $(C)-to-S_A,\;S_A-to-Ch,$ and Ch-to-I phases on heating while on cooling they went through four transitions of I-to-Ch, $Ch-to-S_A,\;S_A-to-Smectic\;C\;(S_C),\;and\;S_c-to-C$ phases in that order, and (d) compounds with x=11 and 12 went reversibly through four transitions of $C-to-S_C,\;S_C-to-S_A,\;S_A-to-Ch,$ and Ch-to-I phases.

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Effects of PEO Additions on the Mechanical and Thermal Proprieties of PLA/PBAT Blends (폴리에틸렌옥사이드가 PLA/PBAT 블렌드 물성에 미치는 영향)

  • Jang, Hyunho;Kwon, Sangwoo;Eom, Yoojun;Yoo, Seungwoo;Park, Su-il
    • KOREAN JOURNAL OF PACKAGING SCIENCE & TECHNOLOGY
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    • v.26 no.2
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    • pp.93-98
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    • 2020
  • The blends of Poly(lactic acid) (PLA) and Poly(butylene adipate-co-terephthalate) (PBAT) have been recognized as a replacement for commodity plastic films and bags in biodegradable packaging industries. The purpose of this study is to identify changes in the thermal and mechanical properties of PLA/PBAT blends with the addition of poly(ethylene oxide)(PEO). PLA (80%) and PBAT (20%) were melt mixed with 0 to 10 phr of PEO and processed using a hot press. The addition of PEO into PLA/PBAT increased the elongation at break and improved thermal stability. With PEO addition, two melting temperature (Tm) peaks of PLA/PBAT merged into one peak showing improved miscibility. The result of this study showed that the addition of PEO increased the ductility and thermal stability of PLA/PBAT blends.

Development of Antitoxic Agents from Sophora flavescens Ait. (고삼 추출물을 이용한 해독물질의 개발)

  • 양희태;정승일;이영철;윤경아;백승화
    • The Korean Journal of Food And Nutrition
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    • v.15 no.1
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    • pp.36-41
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    • 2002
  • The aim of this study was to assess the antitoxic compounds, flavanones(Leachianone A=LA and Sophoraflavanone G=SFG), from Sophora flavescens(S. flavescens). We investigated the possibility of antitoxicity of LA and SFG against NIH 3T3 fibroblasts cell lines using calorimetric MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl -2H-tetra-azolium bromide] assay. The results were as follows : After cadmium was treated against NIH 3T3 cell lines, we determined IC$\_$50/. Accordingly we have examined the detoxification effects of S. flavescens, LA and SFG under cadmium IC$\_$50/=12.5$\mu$M and was carried out to observe morphological changes by the light microscopic study In NIH 3T3 cells, Sophora flavescens, LA, SFG and LA + SFG showed inhibitory effects on the cytotoxicity of cadmium and these detoxication effects increased in proportion to the concentration of these drugs. These results suggest that LA and SFG from S. flavescens retain a potential antitoxic activity.