• Title/Summary/Keyword: $^{17}O$ NMR

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Chemical Constituents of Abies koreana Leaves with Inhibitory Activity against Nitric Oxide Production in BV2 Microglia Cells

  • Baek, Sa-Wang;Kim, E. Ray;Kim, Jin-Woong;Kim, Young-Choong
    • Natural Product Sciences
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    • v.17 no.3
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    • pp.175-180
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    • 2011
  • Eleven compounds were isolated from fresh leaves of Abies koreana (Pinaceae), and structures of these compounds were determined to be 3-hydroxy-2-methyl-4-pyrone (1), maltol-3-O-${\beta}$-D-glucoside (2), (-)-epicatechin (3), naringenin 7-O-${\beta}$-D-glucopyranoside (4), naringenin-7-O-rhamnoglucoside (5), kaempferol 3-O-${\beta}$-D-glucopyranoside (6), (+)-isolariciresinol (7), secoisolariciresinol (8), rhododendrol (9), ferulic acid (10) and 4-(4-hydroxyphenyl)butan-2-one (rheosmin) (11) by comparing $^1H$-, $^{13}C$-NMR and MS spectroscopic data with reference values. Compounds 3, 5, 7, 8, 9, 10, 11 were isolated for the first time from A. koreana. Among eleven isolates, compounds 1, 7 and 11 showed inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia in a concentration dependent manner.

A Novel Benzoyl Glucoside and Phenolic Compounds from the Leaves of Camellia japonica

  • Cho, Jeong-Yong;Ji, Soo-Hyun;Moon, Jae-Hak;Lee, Kye-Han;Jung, Kyung-Hee;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.17 no.5
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    • pp.1060-1065
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    • 2008
  • A novel benzoyl glucoside (4) and 13 known phenolic compounds were isolated from the leaves of Camellia japonica by a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The structure of 4 was determined to be 4-hydroxy-2-methoxyphenol 1-O-$\beta$-D-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (camelliadiphenoside). The 13 known compounds were identified as (E)-coniferyl alcohol (1), (-)-epicatechin (2), 4-hydroxyphenol 1-O-$\beta$-D-(6-O-p-hydroxybenzoyl) glucopyranoside (3), naringenin 7-O-$\beta$-D-glucopyranoside (5), quercetin 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (6), kaempferol 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (7), (+)-catechin (8), 1,6-di-O-p-hydroxybenzoyl-$\beta$-D-glucopyranoside (9), phloretin 2'-O-$\beta$-D-glucopyranoside (10), quercetin 3-O-$\beta$-D-glucopyranoside (11), quercetin 3-O-$\beta$-D-galactopyranoside (12), kaempferol 3-O-$\beta$-D-galactopyranoside (13), and kaempferol 3-O-$\beta$-D-glucopyranoside (14). Their chemical structures were determined by the spectroscopic data of fast atom bondardment mass spectrometry (FABMS) and nuclear magnetic resonance (NMR). Flavonoids having the catechol moiety showed significantly higher DPPH radical scavenging activity than other isolated compounds having monohydroxy phenyl group.

Evidence for a Common Molecular Basis for Sequence Recognition of N3-Guanine and N3-Adenine DNA Adducts Involving the Covalent Bonding Reaction of (+)-CC-1065

  • Park, Hyun-Ju
    • Archives of Pharmacal Research
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    • v.25 no.1
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    • pp.11-24
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    • 2002
  • The antitumor antibiotic (+)-CC-1065 can alkylate N3 of guanine in certain sequences. A previous high-field $^1H$ NMR study on the$(+)-CC-1065d[GCGCAATTG*CGC]_2$ adduct ($^*$ indicates the drug alkylation site) showed that drag modification on N3 of guanine results in protonation of the cross-strand cytosine [Park, H-J.; Hurley, L. H. J. Am. Chem. Soc.1997, 119,629]. In this contribution we describe a further analysis of the NMR data sets together with restrained molecular dynamics. This study provides not only a solution structure of the (+)-CC-1065(N3- guanine) DNA duplex adduct but also new insight into the molecular basis for the sequence- specific interaction between (+)-CC-1065 and N3-guanine in the DNA duplex. On the basis of NOESY data, we propose that the narrow minor groove at the 7T8T step and conformational kinks at the junctions of 16C17A and 18A19T are both related to DNA bending in the drugDNA adduct. Analysis of the one-dimensional $^1H$ NMR (in $H_2O$) data and rMD trajectories strongly suggests that hydrogen bonding linkages between the 8-OH group of the (+)-CC-1065 A-sub-unit and the 9G10C phosphate via a water molecule are present. All the phenomena observed here in the (+)-CC-1065(N3-guanine) adduct at 5'$-AATTG^*$are reminiscent of those obtained from the studies on the (+)-CC-1065(N3-adenine) adduct at $5'-AGTTA^*$, suggesting that (+)-CC-1065 takes advantage of the conformational flexibility of the 5'-TPu step to entrap the bent structure required for the covalent bonding reaction. This study reveals a common molecular basis for (+)-CC-1065 alkylation at both $5'-TTG^*$ and $5'-TTA^*$, which involves a trapping out of sequence-dependent DNA conformational flexibility as well as sequence-dependent general acid and general base catalysis by duplex DNA.

The Structures of Alditol Acetates (Alditol Acetates의 분자구조)

  • Park, Yeong Ja;Park, Myeong Hui;Sin, Jeong Mi
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.517-526
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    • 1990
  • The crystal structures of two alditol acetates, D-glucitol hexaacetate and xylitol pentaacetate, have been determined by diffraction methods with Mo-K$\alpha$radiation, using direct methods for phase determinations. The crystal data are: for D-glucitol hexaacetate, P2$_1$, with a = 10.275 (2), b = 8.363 (1), c = 12.560 (5) $\AA;\beta$ = 95.97 $(2)^{\circ}$, Z = 2; for xylitol pentaacetate, P2$_1$/C with a = 18.126 (1), b = 11.422 (2), c = 8.649 (1) $\AA$, $\beta = 95.03 (1)^{\circ}$, Z = 4. Both molecules have extended zigzag carbon chain conformations which differ from previous studies of the structures of D-glucitol and xylitol and also differ from NMR studies on alditol acetates. The bond lengths and angles are normal, with mean values over both structures of C($sp^3)-C(sp^3): 1.514 (10),\; C(sp^3)-O: 1.444 (6),\; C(sp^2)-O: 1.347 (9),\; C(sp^2)=O: 1.197 (6),\; C(sp^2)-C(sp^3): 1.479(9){\AA},\; C(sp^3)-C(sp^3)-C(sp^3): 114.6 (17),\; O-C(sp^3)-C(sp^3): 109.4 (23),\; C(sp^2)-O-C(sp^3): 117.4 (6),\; O=C(sp^2)-O: 122.6 (6),\; C(sp^3)-C(sp^2)-O: 111.8 (7),\; C(sp^3)-C(sp^2)=O: 125.5 (4)^{\circ}$. The atoms of acetate groups are in coplanar. There are no particularly short intermolecular contacts and the molecules are held together by van der Waals force only.

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The Environmental Control of $Er^{3+}$ ions in $R-SiO_2/ZrO_2$ Sol-Gel Matrix ($R-SiO_2/ZrO_2$ 졸-겔 재료내 $Er^{3+}$이온의 결합 환경 제어)

  • 김주현;권정오;석상일;안복엽
    • Proceedings of the Materials Research Society of Korea Conference
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    • 2003.03a
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    • pp.224-224
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    • 2003
  • 광통신을 위한 구성 요소는 빛을 발생시키는 발광소자, 빛을 검출하는 수광소자 그리고 광신호를 처리하는 광신호처리 소자로 구성된다. 이때 각 소자간 광전송과 광소자에 의한 광 신호 처리 과정에서 광전송 손실이 심각하게 일어나 광정보를 상실하게 되므로 각 요소별로 광신호 증폭이 반드시 필요하다. 뿐만 아니라 완전 광화에 의한 초고속/대용량 광통신망의 구축에는 저가이며, 광집적화가 가능한 광도파로형 광증폭기가 요구되고 있다. 짧은 거리에 높은 증폭 효율을 얻기 위한 광도파로형 광증폭기를 구현하기 위해서는 광통신 파장대인 1.55$\mu\textrm{m}$ 대역의 증폭이 가능한 Er 이온을 고농도로 도핑 할 필요가 있다. 그러나 Er 이온을 단순히 고농도로 첨가하면 Er-Er 간 뭉침 현상에 의해 더 이상의 증폭이 어렵게 된다. 본 연구에서는 이러한 문제를 해결하면서 스핀 코팅이 가능하여 저가 공정이 가능한 유/무기 졸-겔 재료 내에 Er 이온을 제어된 방법으로 첨가하고 그 결합 환경을 FT-IR 및 $^{17}$ O-NMR로 분석하였다. 유/무기 졸겔 재료 제조를 위하여 먼저 MPTS(MethAcryoxyPropylTrimethoxySilane)를 부분 가수분해한 후 ZrOCl$_2$.8$_2$O (Zirconyl Chloride Octahydrate) 와 ErCl$_3$. 6$H_2O$ (Erbium(III) Chloride Hexahydrate)를 순차적으로 결합시키고, Zr/MPTS 및 Zr/Er의 첨가비에 따른 발광 특성을 PL(photoluminescence) 스팩트럼으로 분석하여 Er 이온의 주위 결합 환경이 PL에 미치는 영향을 조사하였다. 또한 Si 기판에 코팅한 Er이 도핑된 유/무기 하이브리드 졸-겔 코팅막의 굴절율 등 광도파로 재료로서의 특성도 프리즘 커플러 등을 이용하여 조사하였다.

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Iridoid Glycoside (IV) -Studies on the Iridoid Glucoside of Melampyrum roseum Max- (Iridoid 배당체(配糖體) (IV) -꽃며느리밥풀의 Iridoid 배당체(配糖體)에 관(關)한 연구(硏究)-)

  • Chung, Bo-Sup;Kim, Young-Ho
    • Korean Journal of Pharmacognosy
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    • v.13 no.3
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    • pp.106-111
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    • 1982
  • Melampyrum roseum Max. is an annual herb in Scrophulariaceae plants. The materials were collected in Kyeongi-Do in 1980. The BuOH extract was evaporated under reduced pressure. The residue was column chromatographed over silica gel with benzene-MeOH (8 : 1) as an eluent and it gave the amorphus powder. Compound I has a molecular formula $C_{17}H_{26}O_{10}$ and it was identified as mussaenoside by chemical data, UV, IR, NMR spectra and compared with the authentic sample of mussaenoside tetraacetate.

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$^{13}C-Nuclear$ Magnetic Resonance of the Phenolic Compounds (I) -A Systematic Evaluation of the Chemical Shifts of the Phenolic Compounds- (Phenol성(性) 화합물(化合物)의 $^{13}C$-핵자기(核磁氣) 공명(共鳴)(I) -Phenol성(性) 화합물(化合物)의 Chemical Shift에 관(關)한 연구(硏究)-)

  • Ahn, Byung-Zun
    • Korean Journal of Pharmacognosy
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    • v.8 no.1
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    • pp.17-21
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    • 1977
  • $^{13}C-NMR$ behaviors of phenolic compounds such as phenol, catechol, pyrogallol, resorcine, phoroglucine and hydroquinone were studied. From the study on the effects of OH-substitution on benzene and its dervatives it was found that the additivity rule can be applied to the ortho-and para-effect but not to the meta-effect for the OH-function. The empirically calculated chemical shifts regarding the o-and p-effects coincide very well with the results of measurement. The chemical shifts of the phenolic compounds can be classified into three types. 1) Catechol-type C-1 and C-2 145 ppm C-3 and C-6 116-107 ppm 2) Pyrogallol-type C-1 132ppm C-2 and C-6 146ppm C-3 and C-5 106ppm 3) Resorcin-type C-1 and C-3 159ppm C-2 103-95ppm C-4 and C-6 107ppm

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Lignans from the Roots of Berberis amurensis

  • Park, Hyun-Bong;Lee, Kyu-Ha;Kim, Ki-Hyun;Lee, Il-Kyun;Noh, Hyung-Jun;Choi, Sang-Un;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.15 no.1
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    • pp.17-21
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    • 2009
  • Column chromatographic separation of the alcoholic extract from the roots of Berberis amurensis yielded eight phenolic constituents including six lignans, hanultarin (1), (-)-secoisolariciresinol (3), (+)-lyoniresinol (5), (+)-syringaresinol (6), (+)-syringaresinol-O-$\beta$-D-glucopyranoside (7), liriodendrin (8), and two phenylpropanoids, 4-glucosyloxy-3-methoxyphenyl trans-propenoic ethyl ester (2), trans-ferulic acid (4). The structures were determined on the basis of NMR spectroscopic data. All isolated compounds(1-8) were reported for the first time from this source. Compound 1 exhibited moderate cytotoxicity against four human cancer cell lines in vitro using sulforhodamin B bioassay.

Development of Artificial Skin from Chitosan Derivatives

  • Yong-Don Won;Chang-Kook Lee;Beung-Ho Ryu
    • Journal of Life Science
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    • v.9 no.1
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    • pp.17-21
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    • 1999
  • Chitosan derivitives, a sulfated N-acetylchitosan was synthesized, and artificial skin of sulfated N-acetylchitosan and N-carboxyl butyl chitosan were investigated. Sulfated derivatives of chitosan were analyzed by {TEX}${13}^C${/TEX}-NMR and the structure on N-acetyl chitosan 3,6-O-disulfate were confirmed. Rabbits underwent a midline laparotomy followed either by a bilateral peritoneal sidewall abraison(3.0×1.5cm). The injured surface was then covered with 0.2mm thick sulfated N-acetyl chitosan membrane. Sulfated N-acetyl chitosan membrane was found to reduce postsurgical bleeding after abraison of peritoneal surface treated with sulfated N-acetyl chitosan membrane. Sulfated N-acetyl chitosan implanted rabbit showed quick wound healing than N-carboxybutyl chitosan. With a sterilization procedure of chemical sterilization, sulfated N-acetyl chitosan seem to be better substitutes than N-carboxybutyl chitosan.

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Synthesis and characterization of polyimides for FPC applications

  • Yeon, J.H.;Bae, Y.U.;Yoon, T.H.
    • Proceedings of the Polymer Society of Korea Conference
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    • 2006.10a
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    • pp.227-227
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    • 2006
  • It was attempted to synthesize polyimides from PPMDA and 3FPPMDA with mDAPPO/pPDA in order to afford CTE of 17ppm and adhesion property of 80g/mm, besides high Tg (>$300^{\circ}C$), good thermal stability (>$500^{\circ}C$), low water absorption and good solubility. The polyimides were prepared via a conventional two-step process; preparation of poly(amic-acid), followed by solution imidization by refluxing in NMP with o-DCB and the molar ratio of mDAPPO/pPDA was varied. The polyimides were characterized by FT-IR, NMR, DSC and TGA. In addition, intrinsic viscosity, solubility and coefficient of thermal expansion (CTE) were also measured.

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