• Title/Summary/Keyword: NMR spectral analysis

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Structural Studies on Conjugated Oximes (II). Nuclear Magnetic Resonance spectral Analysis on the Configuration and Hydrogen Bond of cis-2-Butenedialdioxime in Solutions (Conjugated Oxime의 立體構造에 關한 硏究 (第2報). NMR에 依한 cis-2-Butenedialdioxime의 Configuration 및 水素結合에 對한 考察)

  • Hong Young-Suek;Lee Hak-Ki
    • Journal of the Korean Chemical Society
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    • v.19 no.4
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    • pp.233-239
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    • 1975
  • The configuration of two oxime groups in cis-2-butenedialdioxime, unsymmetrical compound conjugated by three double bonds, is determined by a NMR study on the effects of the solvent, temperature and concentration; it is certain that, in solutions of usual conditions, the configuration exists as only "syn-syn". And the relative strengths of the hydrogen bond between these oxime groups and several solvents are compared and somc effects of the temperature and concentration are also considered. The several models of hydrogen bond between oxime and solvents are proposed; especially it is to be noted here that the hydrogen bond in pyridine solvent is not resulted from the interaction between a lone electron pair on nitrogen atom of pyridine and the hydroxyl proton of oxime, but the result of $\pi$-complex formed between the $\pi$-orbital of pyridine and the hydroxyl proton of the solute.

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In vitro Anti-Cancer Effect of Wellness-Compound (Ochnaflavone) (In vitro 웰니스 화합물 (Ochnaflavone)에 의한 암세포 성장 저해)

  • Lee, Jae-Sook;Choi, Hwa-Jung;Kim, Myung-Ju;Park, Jang-Soon
    • Journal of Digital Convergence
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    • v.13 no.5
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    • pp.337-344
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    • 2015
  • Medicinal plants containing wellness-fusion-complex compound are increasingly being pursued as suitable alternative sources of various biological properties. In this study, inhibitory effect of Quintinia acutifolia, which is a New Zealand plant, on P388 murine lymphocytic leukemia cells using MTT [3-(4,5-dimethylthiazol-2-yl)- 2,5-diphenyl-tetrazolium bromide] assay. Based on $^1H-NMR$, $^{13}C-NMR$ spectral data and other spectral analysis, 2,3,2'',3''-tetrahydroochanaflavone (1) and 2'',3''-dihydroochana-flavone (3) inhibited the leukemia cells were purified from the plants. 2,3,2'',3''-tetrahydroochanaflavone (1) and 2'',3''-dihydroochana-flavone (3) are biflavonoids possessing two basic flavonoids and actively inhibited growth of P388 murine lymphocytic leukemia cells with a 50% inhibitory concentration ($IC_{50}$) of $8.2{\mu}g/mL$ and $3.1{\mu}g/mL$, respectively. Specially, 2'',3''-dihydroochana-flavone (3) possessed unconjugated flavonone system, which isn't consist of a pair with B ring of 2,3,2'',3''-tetrahydroochanaflavone (1). Therefore, the two compounds could be considered as a candidate for development of anticancer drugs and need to much studies in the future.

Polyacetylene Compounds from Panax ginseng C.A. Meyer (인삼의 Polyacetylene 화합물)

  • Shim Sang Chul;Chang Suk-Ku
    • Proceedings of the Ginseng society Conference
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    • 1988.08a
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    • pp.122-128
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    • 1988
  • Several major polyacetylene compounds were isolated from the petroleum-ether fraction of fresh Korean ginseng roots through solvent fractionation. partition and silica gel column chromatography. Further separation of acetylenic compounds was accomplished by bonded normal phase HPLC utilizing a moderately nonpolar microparticulate column. The preparative separation for the various spectral measurements was carried out by low pressure preparative liquid chromatography. The chemical structure of these polyacetylenes separated was determined by UV. IR/FTIR. $^{1}H$ NMR. mass spectral and elemental analysis. These are identified to be heptadeca-1-en-4.6-diyn-3.9.l0.-triol [1] heptadeca-1.9-dien-4.6-diyn-3-ol. heptadeca-1.8-dien-4.6-diyn-3.10-diol and the 4th was denatured polyacetylene. heptadeca-1.4-dien-6.8-diyn-3.10-diol. Two different p-substituted benzoates of panaxynol were synthesized for the determination of exciton chirality. The circular dichroism spectra in the UV region show that panaxynol p-bromobenzoate and p-dimethyl-aminobenzoate constitute negative exciton chirality [2]. Isolated major polyacetylene compounds were irradiated in aerated solution with 300 nm UV light to obtain the oxidized product at the allylic alcohol center to corresponding carbonyl compounds such as heptadeca-1-en-4.6-diyn-9.10-diol-3-one and heptadeca-1.9-dien-4.6-diyn-3-one. These photooxidation compounds have en-on-diyne chromophore and undergo nucleophilic addition reaction with methanol to yield ${\beta}-methoxy$ carbonyl compounds such as heptadeca-9-en-4.6-diyn-1-methoxy-3-one and heptadeca-4.6-diyn-1-methoxy-9.10-diol-3-one.

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Quantitative Analysis of Eupatilin and Jaceosidin in Artemisia herba (약쑥 함유 Eupatilin과 Jaceosidin 성분의 분석)

  • Ryu Su-Noh;Kang Sam Sik;Kim Ju Sun;Ku Bon Il
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.49 no.6
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    • pp.452-456
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    • 2004
  • Artemisia Herb is the dry aboveground part of Artemisia asiatica (Compositae). This is listed officially in the Korean Herbal Pharmacopoeia and used mainly in stopping all kinds of bleeding, regulating menses and curing menstrual disorders as well as in alleviating pain. Eupatilin and jaceosidin were isolated from Sazabalsuk and Sajuarisuk. and identified by means of spectral methods $(UV,\;^1H\;and\;^{13}C-NMR,\;MS) $ and quantitative analysis using HPLC. Regression equations for two flavonoid component standards obtained from Artemisia asiatica were $y=76069_x\;+\;107329\;(r=0.9999^{**})$ for eupatilin, $y=76651_x\;+\;77399\;(r=0.9996^{**})$ for jaceosidin. The eupatilin content of Sazabalsuk was 240mg, jaceosidin was 10mg in 100 g dry leaves. The Sajuarisuk were 330mg, 123mg in 100g dry leaves, respectively.

Quantitative analysis of anthraquinones in Polygonum multiflorum Thunberg (하수오(何首烏)의 안트라퀴논 함량분석)

  • Lee, Hye-Won;Park, So-Young;Choo, Byung-Kil;Chae, Sung-Wook;Lee, A-Yeong;Kim, Ho-Kyoung
    • Korean Journal of Oriental Medicine
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    • v.13 no.3
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    • pp.157-163
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    • 2007
  • Objective: Polygonum multiflorum Thunberg (Polygonaceae) has been traditionally used as a tonic and the purgative in China and Korea. The genus Polygonum is a source of a wide range of phenolic compound, flavanoids, anthraquinones, stilbenes and tannins. In this study, three anthraquinones were isolated and quantitative determination of anthraquinones from P multiflorum has been developed for quality standardization. Methods : Three anthraquinone derivatives were isolated from a methanol extract of the radix of P. multiflorum by the chromatographic separation. Their structures were identified as emodin, physcion and ${\omega}$-hydroxyemodin on the basis of spectral data (MS, lH-NMR, 13C-NMR) and chemical analysis. HPLC analysis was performed to determine the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin in P. multiflorum from different specimens were collected from twenty Korean markets. Results: According to the results, the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin were 0.145%, 0.434%, 0.016%, 0.026%, 0.030% by HPLC, respectively. Conclusions : In these results, we have determined the contents of emodin, physcion, chrysophanol, rhein and ${\omega}$-hydroxyemodin in P. multiflorum, respectively. We hope that this study will contribute to the standardization and quality control of herbal medicine.

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NMR Spectroscopy and Mass Spectrometry of 1, 2-Hexanediol Galactoside synthesized using Escherichia coli β-Galactosidase (대장균 베타-갈락토시데이즈를 이용하여 합성된 1, 2-Hexanediol Galactoside의 NMR Spectroscopy 및 Mass spectrometry)

  • Kim, Yi-Ok;Lee, Hyang-Yeol;Jung, Kyung-Hwan
    • Journal of the Korean Applied Science and Technology
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    • v.33 no.2
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    • pp.286-292
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    • 2016
  • 1, 2-Hexanediol galactoside (HD-gal) has been synthesized from 1, 2-hexanediol (HD), a cosmetic preservative, using recombinant Escherichia coli ${\beta}$-galactosidase (${\beta}$-gal) at the high lactose concentration (300 g/l). To confirm the molecular structure of synthesized HD-gal, NMR ($^1H$- and $^{13}C$-) spectroscopy and mass spectrometry of HD-gal were conducted. $^1H$ NMR spectrum of HD-gal showed multiple peaks corresponding to the galactocyl group, which is an evidence of galactocylation on HD. Downfield proton peaks at ${\delta}_H$ 4.44 ppm and multiple peaks from ${\delta}_H$3.96~3.58 ppm were indicative of galactocylation on HD. Up field proton peaks at ${\delta}_H$ 1.60~1.35 ppm and 0.92 ppm showed the presence of $CH_2$ and $CH_3$ protons of HD. $^{13}C$ NMR spectrum revealed the presence of 21 carbons suggestive of ${\alpha}$- and ${\beta}$-anomers of HD-gal. Among 12 carbon peaks from each anomers, the 3 peaks at dC 68.6, 60.9 and 13.2 ppm were assigned to be overlapped showing only 21 peaks out of total 24 peaks. The mass value (protonated HD-gal, m/z = 281.1601) from mass spectrometry analysis of HD-gal, and $^1H$ and $^{13}C$ NMR spectral data were in well agreement with the expecting structure of HD-gal. For further study, the minimum inhibitory concentrations (MICs) of HD-gal against bacteria will be investigated, and, in addition, cytotoxicity to human skin cells of HD-gal will be examined. It is expected that it will eventually be able to develop a new cosmetic preservative, which have low cytotoxicity against human skin cell and maintains antimicrobial effect.

Isolation and Structure Determination of Streptochlorin, an Antiproliferative Agent from a Marine-derived Streptomyces sp. 04DH110

  • Shin, Hee-Jae;Jeong, Hyun-Sun;Lee, Hyi-Seung;Park, Song-Kyu;Kim, Hwan-Mook;Kwon, Ho-Jeong
    • Journal of Microbiology and Biotechnology
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    • v.17 no.8
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    • pp.1403-1406
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    • 2007
  • An antiproliferative agent, streptochlorin, was isolated from the fermentation broth of a marine actinomycete isolated from marine sediment. Phylogenetic analysis of the 16S rRNA gene sequence indicated that the strain belongs to the genus Streptomyces. Bioactivity guided fractionation of the culture extract by solvent partitioning, ODS open flash chromatography, and reversed-phase HPLC gave a pure compound, streptochlorin. Its structure was elucidated by extensive 2D NMR and mass spectral analyses. Streptochlorin exhibited significant antiproliferative activity against human cultured cell lines.

Isolation and Structural Identification of Minor Constituents from Sasa borealis

  • Jeong, Yeon-Hee;Nam, Joo-Won;Lee, Na-Youn;Seo, Eun-Kyoung;Kwon, Young-Joo
    • Natural Product Sciences
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    • v.11 no.3
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    • pp.170-173
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    • 2005
  • Compounds of (+)-5,5'-dimethoxylariciresinol (1) and (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (2) were isolated from an EtOAc extract of the whole plant of Sasa borealis (Hack.) Makino (Gramineae) for the first time in the present investigation. The structures of compounds were identified by analysis of spectral data including 1D- and 2D-NMR spectra as well as by comparison of their data with the published values. These compounds have never been isolated previously from the family Gramineae.

Synthesis and Characterization of Derivatives of Dibutyl Sn(IV)-Ti(IV)-μ-Oxoisopropoxide with Schiff Bases

  • Kumar, Rajesh;Sharma, H.K.
    • Journal of the Korean Chemical Society
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    • v.56 no.1
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    • pp.54-57
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    • 2012
  • New Schiff base derivatives of organoheterobimetallic-${\mu}$-oxoisopropoxide $[Bu_2SnO_2Ti_2(OPr^i)_6]$ have been synthesized by the thermal condensation ${\mu}$-oxoisopropoxide compound with Schiff bases in different molar ratios (1:1-1:4) yielded the compounds of the type $[Bu_2SnO_2Ti_2(OPr^i)_{6-n}(SB)_n]$ (where n is 1-4 and SB=Schiff base anion) respectively. The ${\mu}$-oxoisopropoxide derivatives have been characterized by elemental, spectral analysis (IR, $^1H$, $^{13}C$, $^{119}Sn$ NMR) and molecular weight measurement The studies reveal that the derivative compounds show monomeric nature. Further these are found less susceptible to hydrolysis as compared to parent compound and may prove excellent precursors for the mixed metal oxides.

Synthesis and Biological Evaluation of Novel Isopropyl 2-thiazolopyrimidine-6-carboxylate Derivatives

  • Kotaiah, Y.;Krishna, N. Hari;Raju, K. Naga;Rao, C.V.;Jonnalagadda, S.B.;Maddila, Suresh
    • Journal of the Korean Chemical Society
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    • v.56 no.1
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    • pp.68-73
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    • 2012
  • In the present study, we have synthesized novel Isopropyl 2-(4-substitutedbenzylidene)-5-methyl-3-oxo-7-phenyl-3,7-dihydro-2H-thiazolo[3,2-a]-pyrimidine-6-carboxylate derivatives (6a-j). Elemental analysis, IR, $^1H$ NMR and mass spectral data elucidated structure of newly synthesized compounds. The newly synthesized compounds were screened for antiinflammatory and anti microbial studies. Their biological activity data of the 10 compounds indicates that two compounds posses potent anti-inflammatory and five have antimicrobial activities.