• Title/Summary/Keyword: 1D $^1H-NMR$

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Isolation and Identification of Lipids from the Roots of Canna generalis (칸나(Canna generalis)의 뿌리로부터 지질화합물의 분리.동정)

  • Bang, Myun-Ho;Song, Myoung-Chong;Lee, Dae-Young;Yang, Hye-Jung;Han, Min-Woo;Baek, Nam-In;Lee, Youn-Hyung
    • Applied Biological Chemistry
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    • v.49 no.4
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    • pp.339-342
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    • 2006
  • Canna generalis was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. from the EtOAc and n-BuOH fractions, four compounds were isolated through the repeated silica gel and ODS column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as $\beta$-sitosterol(1), linoleic acid methyl ester(2),1-O-oleoyl-2-O-linoleoyl-3-O-$\beta$-D-galactopyranosyl-sn-glycerol(3), and daucosterol(4). They were the first to be isolated from Canna generalis.

Thelephoric acid and Kynapcin-9 in Mushroom Polyozellus multiflex Inhibit Prolyl Endopeptidase In Vitro

  • Kwak, Ju-Yeon;Rhee, In-Koo;Lee, Kyung-Bok;Hwang, Ji-Sook;Yoo, Ick-Dong;Song, Kyung-Sik
    • Journal of Microbiology and Biotechnology
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    • v.9 no.6
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    • pp.798-803
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    • 1999
  • Prolyl endopeptidase [PEP; EC 3.4.21.26], a serine protease which is known to cleave peptide bonds on the carboxy side of a proline residue, plays an important role in the degradation of proline-containing neuropeptides that have been suggested to participate in learning and memory processes. An abnormal increase in the level of PEP, which can lead to generation of $A{\beta}$, is also suggested to be involved in Alzheimer's type senile dementia. In the course of screening PEP inhibitors from Basidiomycetes, the mushroom Polyozellus multiplex exhibited a high inhibitory activity against PEP. Two active compounds were isolated from the ethyl acetate soluble fraction by consecutive purification, using silica gel, Sephadex LH-20, and Lobar RP-18 chromatography. The chemical structures of these compounds were identified as thelephoric acid and 12-acety1-2,3,7,8-tetrahydroxy-[12H]-12-hydroxymethylbenzobis[I.2b,3.4b'] benzofuran-11-one (kynapcin-9) by spectral data including UV, IR, MS, HR-MS, $^1H-,{\;}^{13}C-$, and 2D-NMR. The $IC_{50}$ values of the thelephoric acid and kynapcin-9 were 0.157 ppm (446nM) and 0.087 ppm (212nM) and their inhibitor constants ($K_i$) were 0.73ppm ($2.09{\;}\mu\textrm{m}$) and 0.060 ppm (146 nM), respectively. Furthermore, they were non-competitive with a substrate in Dixon plots.

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Isolation of an Anticariogenic Compound from Magnoliae Bark (후박피(Magnoliae bark)로부터 항충치활성을 갖는 물질의 분리)

  • Lee, Youn-Soo;Park, Hun-Joo;You, Jae-Sun;Park, Hyung-Hwan;Kwon, Ik-Boo;Lee, Hyeon-Yong
    • Korean Journal of Food Science and Technology
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    • v.30 no.1
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    • pp.230-236
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    • 1998
  • We have screened total 32 herbal drugs to find the highest activity against human cariogenic enzyme, glucosyltransferase (GTase) from the extracts of Magnoliae bark. The extracts were separated into three phases, i. e. water, n-butanol and ethylacetate according to their solvent polarity. Among them, ethylacetate fraction had approximately more than 70% of total activities, and the active principle was further isolated by prep. HPLC following silicagel column chromatography to yield single compound as white powder. The chemical structure of the compound was finally elucidated to be 4,4'-dihydroxy-3,3'-dimethoxylignan from the spectral data of FAB-MS. $^1H-\;and\;^{13}C-NMR$ spectrometries. The compound was also shown to have relatively strong antibacterial activity against ten types of cariogenic oral bacteria and one kind of Actinomyces sp.

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Evaluation of Hydration Effect on Human Skin by $^1H$ MRS at 14.1T

  • Choi Chi-Bong;Hong Sung-Tak;Choe Bo-Young;Woo Dong-Chul;Yoon Seong-Ik;Cho Ji-Hyun;Lee Chul-Hyun;Cheong Chae-Joon;Park Sang-Yong;Oh Chil-Hwan
    • Journal of the Korean Magnetic Resonance Society
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    • v.10 no.1
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    • pp.105-114
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    • 2006
  • Purpose: We achieved high resolution MR imaging and spectra of human skin in vitro with using a 14.1 T MRI/MRS system, and evaluated the hydration effect of various cosmetic products by measuring the skin's. moisture concentration. Materials and Methods: We used the Bruker 14.1 T MRI/MRS system with a vertical standard bore that was equipped with a DMX spectrometer gradient system (200 G/cm at a maximum 40 A), RF resonators (2, 5 and 10 mm) and Para Vision software. Spin echo and fast spin echo pulse sequences were employed for obtaining the high resolution MR images. The 3D-localized point resolved spectroscopy (PRESS) method was used to acquire the MR spectra. Results: The high resolution MR images and spectra of human skin in vitro were successfully obtained on a 14.1 T system. The water concentration of human skin after applying a moisturizer was higher than that before applying a moisturizer. Conclusions: The present study demonstrated that the high-resolution MR images and spectra of human skin from a high field NMR instrument could be applicable to evaluating the hydration state of the stratum corneum.

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Beryllium(II) Recognition by Allosteric Effects in 1,2-Ethylenedioxybenzene Based Ditopic Receptors

  • Kim, Dong-Wan;Kim, Jung-Hwan;Hwang, Jae-Young;Choi, Myong-Yong;Kim, Jae-Sang
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2643-2647
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    • 2011
  • Efficient ditopic receptor, uranyl(II) N,N'-(ethylenedioxy)benzenebis(salicylideneimine) (3) for beryllium ion has been obtained upon functionalization of 1,2-ethylenedioxybenzene (1) with a uranyl-salphen (salphen = N,N'-phenylenebis(salicylideneimine)) unit. Binding affinities of the receptor, 3 in AN-DMSO (v/v 95:5) solution have been measured for alkali and alkaline earth metal ions by conductometry comparing 1. The results showed that both monotopic 1 and ditopic receptor 3 were selective for $Be^{2+}$ ions over other cations, while especially 3 that can complex both with cations (coordinated to basic oxygen of ethylenedioxybenzene) and anions (coordinated to the Lewis acidic uranyl center) results in an increase of the stability constants by a factor of $10^{2.42}$ with respect to 1. Furthermore, the $Be^{2+}$-3 interactions are demonstrated by $^1H$ NMR experiments in highly polar solvent medium, DMSO-$d_6$. Higher selectivities were also observed for $Be^{2+}$ when the ditopic receptor, 3 was incorporated into PVC membranes and tested as ion selective electrodes at neutral pH.

Alkaloids from the Tuber of Aconitum chiisanense (지리바꽃 괴경의 알카로이드)

  • Lee, Moo-Taek;Sung, Hwan-Kil;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • YAKHAK HOEJI
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    • v.41 no.2
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    • pp.161-173
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    • 1997
  • Tuber of Aconitum chiisanense(Ranunculaceae) a specific medicinal plant in Korea, which is known to have the activity to recover reduced metabolism of feeble patients and has been used to symptoms such as pain, paralysis, atonia and coldness of extremities, etc. were studied. The powdered tubers of the plant were extracted with 10% EtOH 3 times and the combined extract was dissolved in 1N HCl solution and washed with ethyl acetate. The aqueous layer was basified with solid $Na_2CO_3$ and extracted with $CHCl_3$ to obtain an alkaloidal fraction. The alkaloidal fraction was subjected to column chromatography using silica gel, alumina and Sephdex LH 20, etc. From the alkaloidal fraction, five diterpene alkaloids, mesaconitine, aconitine, hypaconitine, 8-O-ethyl 14-benzoylmesaconine and talatizamine, were isolated and identified on the basis of their physico-chemical properties and spectroscopic evidences($^1H$-, $^{13}C$-NMR, EI-MS, IR, 2D-NMR) respectively. Especially the Compound IV, 8-O-ethyl 14-benzoylmesaconine, was assumed to be an artifact resulting from mesaconitine during extraction procedures. The contents of mesaconitine, aconitine and hypaconitine in the mother tuber of this plant were 0.300%, 0.024%, and 0.068%. And that of the attached tuber(new one) of this plant were 0.336%, 0.034% and 0.240% respectively.

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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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The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

  • Yoon, Hoe-Jin;Jung, Hein;Ahn, Yun-Soo;Nandhakumar, Raju;Kim, Jun-Soo;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1715-1718
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    • 2012
  • 2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

Sesquiterpene Glycosides from the whole Plant Extract of Youngia japonica (뽀리뱅이 전초로부터 분리한 Sesquiterpene 배당체)

  • Kim, Mi-Ri;Cha, Mi-Ran;Choi, Yeon-Hee;Choi, Chun-Whan;Choi, Sang-Un;Kim, Young-Sup;Kim, Young-Kyoon;Kim, Young-Ho;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.41 no.2
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    • pp.103-107
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    • 2010
  • Extensive phytochemical investigation of the methanol extract from the whole plant of Youngia japonica (Asteraceae) led us to the isolation of a new guaiane-type sesquiterpene (1), together with three related guaianolides, youngiajaponicoside A (2), crepiside H (3) and crepeside E (4). The chemical structure of 1 was elucidated by the aid of spectroscopic analyses including 2D-NMR experiments (COSY, HMBC, HMQC and ROESY). The isolated components (1-4) were evaluated for the inhibitory effect on the proliferation of four cultured human tumor cell lines such as A549, SK-OV-3, SK-MEL-2 and HCT-15, in vitro.

A Bisdesmosidic Cholestane Glycoside from the Rhizomes of Polygonatum sibiricum

  • Ahn, Mi-Jeong;Cho, Hee-Yeong;Lee, Mi-Kyeong;Bae, Ji-Yeong;Choi, Jang-Gyoo;Kim, Chul-Young;Kim, Jin-Woong
    • Natural Product Sciences
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    • v.17 no.3
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    • pp.183-188
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    • 2011
  • A bisdesmosidic cholestane glycoside was isolated from the rhizomes of Polygonatum sibiricum and the structure was elucidated by spectroscopic methods and acid hydrolysis as (22S)-cholest-5-ene-$1{\beta}$,$3{\beta}$,$16{\beta}$,22-tetrol 1-O-${\alpha}$-L-rhamnopyranosyl 16-O-${\beta}$-D-glucopyranoside. This compound exhibited weak cytotoxic activity with the $IC_{50}$ value, $63.6\;{\mu}M$ in human MCF-7 breast cancer line, whereas it failed to show agonistic activity at $100{\mu}M$ in TGR5 assay with Chinese hamster ovary (CHO) cells. This is the first report of a bisdesmosidic cholestane glycoside from Polygonatum species and the full assignments of $^1H$, $^{13}C$ NMR by HMBC, TOCSY and NOESY experiments were provided.