• Title/Summary/Keyword: 1D $^1H-NMR$

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The flavone glycosides of Sasa borealis (조릿대잎의 flavone 배당체 성분)

  • Yoon, Ki-Dong;Kim, Chul-Young;Huh, Hoon
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.224-227
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    • 2000
  • As part of study of the constituents of bamboo grasses, the leaves of Sasa borealis (Hackel) Makino (Gramineae) were examined. Friedelin, glutinol, isoorientin and isovitexin have been reported as constituents of bamboo grasses. In this study, tricin and two flavone glycosides, tricin $7-O-{\beta}-D-glucopyranoside$ and luteolin $6-C-{\alpha}-L-arabinopyranoside$ have been isolated from EtOAc extract of S. borealis, by consecutive silica gel, Sephadex LH-20 column chromatography and a repetitive HPLC. The structures of these compounds were determined by IR, $^1H-NMR,\;^{13}C-NMR,\;^{13}C-^1H\;COSY,\;^1H-^1H\;COSY,\;HMBC$ and Mass spectral data.

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Micelle Formation of Surfactant Solution(3) -Self-Diffusion and 1H Relaxation for Mixed Micelle of Nonionic and Ionic Surfactants- (계면활성제 수용액에서 미셀형성(제3보) -비이온성과 이온성계면활성제의 혼합 미셀에 있어 자기확산 및 프로톤 이완-)

  • Choi, Seung-Ok;Kwack, Kwang-Soo;Park, Heung-Jo;Nam, Ki-Dae
    • Applied Chemistry for Engineering
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    • v.10 no.6
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    • pp.876-880
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    • 1999
  • The surfactant self-diffusion coefficients of mixed micellar solutions of ionic and nonionic surfactants have been measured by the NMR pulsed field gradient spin echo(FT-PGSE) method. In addition, the line widths of $^1H$ NMR signal have been monitored. The system investgated are $C_{12}EO_5/SDS/D_2O$, $C_{12}EO_5/DTAC/D_2O$, and $C_{12}EO_8/SDS/D_2O$. In the sample series, the molar ratios of $D_2O$ to surfactant(ionic+nonionic) were kept constant while the surfactant mixing ratio was varied. For the $C_{12}EO_5$ system, the surfactant self-diffusion coefficient indicates minimum when the surfactant mixing ratio is about 20% ionic surfactant. The observed decrease in self-diffusion coefficients as nonionic surfactant was replaced by ionic surfactant is interpreted to mainly be due to an increased micelle-micelle repulsion. The increase in self-diffusion coefficients occurring at higher fraction of ionic surfactant is shown to be due to a decrease in micelle size. For the $C_{12}EO_8$ system, the effect of the surfactant mixing ratio is much weaker which can be understood by considering the molecular geometry and large headgroup area. The proton NMR line widths correlate well with the self-diffusion coefficients and broadening of the alkyl chain methylene signals is found when the self-diffusion coefficients is low.

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Isolation and Structure Identification of Antibacterial Substances from the Rhizome of Zingiber mioga Roscoe (양하의 근경에서 항균성 물질 분리 및 구조동정)

  • Kim, Seong-Cheol;Song, Eun-Young;Kim, Kong-Ho;Kwon, Hyeog-Mo;Kang, Sang-Heon;Park, Ki-Hun;Jung, Yong-Hwan;Jang, Ki-Chang
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.246-250
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    • 2003
  • In order to isolate antibacterial substances from the rhizome of Zingiber mioga Roscoe, the ethanol extracts was fractionated according to the activity against Bacillus subtilis, B. cereus and Staphylococcus aureus. Three antibacterial substances were isolated and purified by column chromatography and recrystallization. Compounds I and III showed activity against all the tested bacterias and compound II exhibited the activity against B. subtilis and B. cereus S. aureus. Compound I was examined antimicrobial activity against B. subtilis, B. cereus and S. aureus by optical density using Bioscreen C. Compound I showed strong growth inhibition at 10 ppm on B. subtilis and B. cereus for 72 hrs, and at 25 ppm on S. aureus. On the basis of spectrometric studies including $1^H-NMR$, ${13}^C-NMR$, DEPT, IH-lH COSY, HMQC, HMBC and IR, compounds I, II and III were identified as $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial\;(C_{20}H_{30}O_3,\;MW=318)$, galanolactone $(C_{20}H_{30}O_3\;MW=318)$ and galanal A $(C_{20}H_{30}O_3,\;MW=318)$, respectively. These results are the first reports on the isolation of $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial, galanolactone and galanal A from the rhizome of Zingiber mioga.

Isolation of Antibacterial Prenylated Flavonoids from Cudrania tricuspidata (꾸지뽕나무로부터 항균성 Prenylated Flavonoids의 분리)

  • Lee, Byong-Won;Kang, Nam-Suk;Park, Ki-Hun
    • Applied Biological Chemistry
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    • v.47 no.2
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    • pp.270-273
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    • 2004
  • Two prenylated flavonoids were isolated from a chloroform extract of the root bark of Cudrania tricuspidata. Both compounds (1, 2) showed antibacterial activity against Gram positive bacteria, Staphylococcus aureus, Bacillus subtilis and Bacillus cereus. Their structures were determined as euchrestaflavanone B (1) and euchrestaflavanone C (2) on the basis of $^1H\;NMR,\;^{13}C\;NMR$ and long-range coupling NMR techniques.

The Synthesis and Characterization of Some Novel Thioethers: Thio-Subsituted [3]Cumulenes, -1-Buten-3-ynes and Buta-1,3-dienes

  • Ibis, Cemil;Sahin, Aysecik
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2255-2260
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    • 2010
  • In this study, some novel thiosubstituted butenyne (3a-d, 7b, 15b), butadiene (4a-b, 4d, 5a, 5c, 6b, 8e, 9c, 10b, 16b, 18e) and [3]cumulene (11a-b with isomer 3a-b, 12a with isomer 13a, 14b, 17e) compounds were synthesized from the reaction of 2H-pentachloro-1,3-butadiene with thiols. The new compounds were characterized by elemental analysis, mass spectrometry, UV-vis, IR, 1H NMR, NMR ($^{13}C$ or APT) spectroscopy.

The constituents of taraxacum hallaisanensis roots

  • Yang, Deuk-Suk;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.507-513
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    • 1996
  • Three sesquiterpene lactone compounds, two novel(1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H -eudesm-12, 6-olide-1-O-.betha.-D-glucopyranoside, 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H-eudes m-12,6-olide-1-O-.betha.-D-glucopyranoside) and 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha., 7.alpha.H-eudesm-12,6-olide were isolated from the aqueous fraction of MeOH extract of the roots from Taraxacum hallaisanensis (Compositae) employing Amberlite XAD-2, ODS-gel, silica gel and Sephadex LH-20 column chromatographics. Another known compound, (-)-epicatechin, was isolated from the aqueous fraction of the MeOH extract. The total MeOH extract also contained phytosterol and a mixture of .betha.-amyrin acetate, .alpha.-amyrin acetate and lupeol acetate. Structures of isolated compounds were elucidated by spectroscopic parameters of IR, Mass, /sup 13/C-NMR, /sup 1/H-NMR, /sup 1/H-/sup 1/H COSY, /sup 13/C-/sup 1/H COSY and HMBC.

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Identification of Novel Saringosteryl Glucoside in Phaseolus vulgaris Seed (강낭콩 미숙종자내 신규 Saringosteryl Glucoside의 동정)

  • 김성기
    • Journal of Plant Biology
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    • v.37 no.4
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    • pp.441-444
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    • 1994
  • From immature seed of Phaseolus vulgaris L., a novel phytosteryl glucoside was isolated. Strong ion peaks at m/z 613 $[M+Na}^{+},\;696\;[M+Matrix]^{+}$ in positive F AB- MS and at m/z 589 $[M-1]^{-}$ in negative F AB- MS indicated the molecular weight of the compound is 590. Four hundred MHz $^IH-NMR$ analysis revealed that the compound canys a 24-hydroxy-24-vinyl-cholesterol (saringosterol) as an aglycone and a ${\beta}-D-glucopyranose$. Four hundred MHz $^IH-NMR$ analysis of the acetate derivate of the compound revealed that hydroxyls at C-1' in glucose moeity and at C-3 in aglycone have been condensed. Therefore, the phytosteryl glucoside was characterized to be $3-0-{\beta}-D-glucopyranosyl-24-hydroxy-24-vinyl-cholesterol$ (saringosteryl glucoside). This is the first demonstration for the presence of saringosterol in higher plants. Also this is the first identification of saringosteryl glucoside in natural materials.erials.

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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.

Partial Assignment of Heme Groups of Cytochrome $c_3$ of Desulfovibrio vulgaris Miyazaki F by $^{1}H$-NMR

  • Jang-Su Park;Shin Won Kang
    • Bulletin of the Korean Chemical Society
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    • v.14 no.5
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    • pp.588-592
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    • 1993
  • The $^1H-NMR$ signals of the heme methyl, propionate and related chemical groups of cytochrome $c_3$ from Desulfovibrio vulgaris Miyazaki F (D.v. MF) were site-specifically assigned by means of 1D-NOE, 2D-DQFCOSY and 2D-TOCSY spectra. They were consistent with the site-specific assignments of the hemes with the highest and second-lowest redox potentials reported by Fan et al. (Biochemistry, 29, 2257-2263 1990). The site-specific heme assignments were also supported by NOE between the methyl groups of these hemes and the side chain of Val-18.

Analysis of Beauvericin and Unusual Enniatins Co-Produced by Fusarium oxysporum FB1501 (KFCC 11363P)

  • Song Hyuk-Hwan;Ahn Joong-Hoon;Lim Yoong-Ho;Lee Chan
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1111-1119
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    • 2006
  • Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.