• Title/Summary/Keyword: 1D $^1H-NMR$

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Isolation and Determination of Phenolic Compounds in Peony (Paeonia lactiflora Pall.)Root

  • Choung, Myoung-Gun;Kang, Kwang-Hee;An, Young-Nam
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.45 no.2
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    • pp.83-87
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    • 2000
  • The five phenolic compounds of peony root were isolated by Sephadex LH-20 column chromatography. Their chemical structures were identified by spectroscopic methods (UV, FT-IR, FAB-MS and $^1H$ .&^13C$-NMR). The complete structures of these compounds were elucidated to be (+)-taxifolin-3-0-$\beta$-D-glucopyranoside, benzoic acid, gallic acid, (-)-epicatechin and (+)-catechin. The concentrations of five phenolic compounds in the peony root of three Korean cultivars (Youngchonjakyak, Euisungjakyak and Jomjakyak) were determined by reverse-phase HPLC. The constituents concentration in Youngchonjakyak were generally higher than in Euisungjakyak and Jomjakyak. The concentrations of (+)-taxifolin-3-O-$\beta$-D-glucopyranoside, benzoic acid, gallic acid, (-)-epicatechin and (+)-catechin in three different cultivars were ranged 0.23-0.52%, 0.20-0.30%, 0.26-0.28%, 0.09-0.12% and 0.34-0.63%, respectively.

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Enhanced Antimicrobial Activities and Physicochemical Characteristics of Isoliquiritigenin Encapsulated in Hydroxypropyl-β-Cyclodextrin (아이소리퀴리티게닌을 담지한 2-하이드록시프로필-베타사이클로덱스트린의 물리화학적 특성 및 항균활성 연구)

  • Kim, Hae Soo;Im, Na Ri;Park, Soo Nam
    • Applied Chemistry for Engineering
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    • v.26 no.6
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    • pp.719-724
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    • 2015
  • Isoliquiritigenin (ILG) is a hydrophobic component in licorice and has a variety of pharmaceutical and biological activities. In this study, we prepared an isoliquiritigenin-hydroxypropyl-${\beta}$-cyclodextrin (ILG/HP-${\beta}$-CD) complex by freeze-drying method to enhance its water solubility. The complex was characterized by phase solubility studies, DSC, SEM, and 1H NMR. Antimicrobial activities against Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli) were evaluated by broth dilution method. The results showed that the stoichiometry of ILG/HP-${\beta}$-CD complex was 1 : 1. The antimicrobial activity of ILG/HP-${\beta}$-CD complex was higher than that of using free ILG against S. aureus and E. coli. Therefore, we suggest that ILG/HP-${\beta}$-CD complex may be used as a natural antiseptic and could potentially replace synthetic preservatives in cosmetic and food industries.

New Butyrylcholinesterase Inhibitory Triterpenes from Salvia santolinifolia

  • Mehmood Sajid;Riaz Naheed;Nawaz Sarfraz Ahmed;Afza Nighat;Malik Abdul;Choudhary Muhammad Iqbal
    • Archives of Pharmacal Research
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    • v.29 no.3
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    • pp.195-198
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    • 2006
  • Slavins A (1) and B (2), the new amyrin type triterpenes, have been isolated from the chloroform soluble fraction of Salvia santolinifolia and assigned structures on the basis of spectral studies including 2D NMR. Both the compounds displayed inhibitory potential against the enzyme butyrylcholinesterase.

Ellagitannins from Bark of Juglans mandshurica

  • 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.480-485
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    • 2009
  • Juglans mandshurica bark was collected and extracted with 70% aqueous acetone. 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 $H_2O$ fraction was chromatographed on a Sephadex LH-20 column using aqueous methanol to isolate (S)-2,3-HHDP-D-glucopyranoside (1). Some of EtOAc fraction was also treated on a Sephadex LH-20 column using aqueous methanol and EtOH-hexane mixture to purify pedunculagin (2). The structures of these two epimeric ellagitannins were elucidated by spectroscopic tools, NMR and MS.

Isolation and Identification of a Photosensitizer from Pueraria thunbergiana Leaves that Induces Apoptosis in SK-HEP-1 Cells (P. thunbergiana 잎으로부터 SK-HEP-1세포에 대한 apoptosis를 유도하는 광과민성물질의 분리 및 구조동정)

  • Lee, Jun Young;Kim, Mi Kyeong;Ha, Jun Young;Kim, Yong Gyun;Hong, Chang Oh;Kim, So Young;Kim, Chung-Hwan;Kim, Keun Ki
    • Journal of Life Science
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    • v.24 no.3
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    • pp.242-251
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    • 2014
  • The objective of this study was to isolate a photosensitizer from Pueraria thunbergiana leaves that induces apoptosis in SK-HEP-1 cells. Column chromatography and thin layer chromatography were used to isolate active compounds from extracts of P. thunbergiana leaves. The structures of the isolated compounds were determined by 1D-NMR, 2D-NMR, and FAB-mass spectroscopy. A substance, named M4-3, was purified from the leaves of P. thunbergiana using various chromatography methods, and the absorbance of the substance was measured. The absorbance was highest at 410 nm, suggesting that the M4-3 substance was a different compound from chlorophyll a and b, which absorb at 410, 502, 533, and 607 nm. Further analyses revealed that the M4-3 compound was a $13^2$-hydoxy pheophorbide, a methyl ester with a molecular weight of 662. M4-3 was identified as a derivative compound of pheophorbide, with a structure that magnesium comes away from the porphyrin ring. The results of the analysis of the cytotoxicity of the M4-3 substance against the SK-HEP-1 cells revealed that it inhibited rates of cell growth by 40% and 80% at a concentration of 0.04 ${\mu}M$ and 0.08 ${\mu}M$, respectively. The M4-3 compound was found to be a photosensitizer for cytotoxicity because it was appeared only in light condition as examining activity in different irradiation conditions (light condition and nonlight condition) under the same concentration. Analysis of morphological changes in the cells following cell death induced by exposure to the M4-3 substance reveled representative phenomena of apoptosis (nuclear condensation, vesicle formation, and fragmentation of DNA). The induction of apoptosis was attributed to the compound's photodynamic activity.

Synthesis and Physicochemical Properties of Schiff Base Macrocyclic Ligands and Their Transition Metal Chelates

  • Rafat, Fouzia;Siddiqi, K.S.
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.912-918
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    • 2011
  • Tetraaza Schiff base macrocyclic ligands, $L^1$,$L^2$ and their transition metal chelates have been synthesized and characterized by elemental analyses, IR, electronic, EPR and $^1H$ NMR spectra, TGA and magnetic measurements. The molar conductance of one milli-molar solution of the complexes measured in DMF indicates that the divalent metal complexes are nonelectrolyte while those of trivalent metal ion, are 1:1 electrolytic in the same solvent. The reduction of Racah parameter from the free ion value confirms the presence of considerable covalence of metal ligand sigma bond in the Co(II) and Mn(II) complexes. The EPR spectra of Cu(II) complexes at room temperature shows axial symmetry indicating a $d_x{^2}_{-y}{^2}$ ground state with significant covalent character. The thermal analysis suggests that the complexes do not contain water molecules because only the metal is left as residue.

A Calix[4]pyrrole Bearing a Quaternary Ammonium Group: A Fluoride-Selective Anion Receptor

  • Oh, Ju Hyun;Lee, Joon Hwa;Kim, Sung Kuk
    • Journal of the Korean Magnetic Resonance Society
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    • v.25 no.4
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    • pp.45-50
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    • 2021
  • A calix[4]pyrrole (1) bearing a quaternary ammonium pendant via its meso phenoxy linker has been synthesized as the bromide salt form. It was revealed by 1H NMR spectroscopic analyses performed in DMSO-d6 that receptor 1 binds F- with high affinity and selectivity over other halide anions. The binding of receptor 1•Br- with F- and Cltakes place by anion metathesis with the anions including F- and Cl-.

Synthesis and Properties of Anionic Tetrakis(pentafluorophenyl)indium(Ⅲ) Complexes (Tetrakis(pentafluorophenyl)indium(Ⅲ) 음이온 착물의 합성과 특성)

  • Choi, Zel Ho
    • Journal of the Korean Chemical Society
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    • v.43 no.1
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    • pp.52-57
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    • 1999
  • The anionic complexes, [ln($C_6F_5)_4$]-, which are thermal and moisture sensitive, have been prepared by the reaction of In($C_6F_5)_3{\cdot}D(D=CH_3CN$, O($C_2H_5)_2$) with the system ($CH_3)_3SiC_6F_5$/CsF, $C_6F_5$MgBr or Cd($C_6F_5)_2$. The stable anionic indium(III) complexes are obtained through cation exchange with PNPCI ([PNP]= bis(triphenylphosphino)ammonium). The pure substance is obtained by column chromatography. These new anionic complexes are unambiguously identifed by NMR-spectroscopy, IR spectroscopy, molecular weight, DTA/TG and elemental analysis.

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Cytotoxicity of the Components of Albizzia julibrissin (합환피 (Albizzia julibrissin)의 성분이 종양세포에 미치는 영향)

  • Choi, Boung-Don;Ryeom, Kon
    • Biomolecules & Therapeutics
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    • v.7 no.4
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    • pp.371-376
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    • 1999
  • By cytotoxicity screening of the 65 Korean medicinal plants against leukemia L1210 and P388D$_{1}$ cell line using the MTT assay in vitro, Albizzia julibrissin was studied. This plant was extracted with MeOH and MeOH extract was solvent-fractionated with CHCl$_{3}$, EtOAc and n-BuOH in sequence. Each fraction by various solvents system was purified by column chromatography and preparative TLC, and four compounds were isolated. The structure of each compound was deduced from UV, IR, $^{1}$H-HMR, $^{13}$ C-NMR and CI-MS spectral data. The cytotoxic activity ($IC_{50}$/_ of the compounds, quercetin-3-rhamnoside, 4',5,7-trihydroxyfla-van-3-glucoside, spinasterol-3-glucoside and acacic acid lactone, were evaluated as 5 $\mu\textrm{g}$/ml, 2$\mu\textrm{g}$/ml, 1 $\mu\textrm{g}$/ml against L1210 and as 9$\mu\textrm{g}$/ml, 10$\mu\textrm{g}$/ml, 1.5 $\mu\textrm{g}$/ml, 1.5 $\mu\textrm{g}$/ml and 0.9 $\mu\textrm{g}$/ml against P388D$_{1}$, respectively.

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Synthesis and Characterization of Novel Fullerene($C_{60}$) Derivative with Photoresponsive Azobenzene Group (광감응형 아조벤젠기를 갖는 신규 플러렌 유도체의 합성과 물성분석)

  • Han, Ki-Jong
    • Journal of the Korean Applied Science and Technology
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    • v.31 no.1
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    • pp.50-58
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    • 2014
  • A novel fullerene derivative with photoresponsive azobenzene group was designed and synthesized, and its photoresponsive properties were reported. Starting from 4-nitrophenol, compound 1, which is containing fullerene moiety connected to azobenzene group through covalent linkage was synthesized by 5 steps. All the intermediates and the final compound were characterized by $^1H$, $^{13}C$-NMR, FAB-Mass or elemental analysis. Compound 1 exhibited the expected photoresponsive behavior. Chloroform solution($10^{-5}M$) of it served to maximize the absorption at 351 nm corresponding to the trans-azobenzene chromophore. Irradiation of this solution with 365 nm light resulted in photoisomerization to cis-azobenzene, as evidenced by decrease in the absorbance at 351 nm and an increase in absorbance at 450nm. A photostationary state was reached within about 150 s. Thermal reversion to the original spectrum was observed over the course of about 6 h at room temperature in the dark. However, exposure to bright sun light for about 5 s also effect almost complete reversion to the trans-isomer. This indicates that there is no strong steric influence on the trans-cis reversible isomerization of compound 1.