• Title/Summary/Keyword: 1D $^1H-NMR$

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A New Stilbene Dimer and Other Chemical Constituents from Monanthotaxis littoralis with Their Antimicrobial Activities

  • Dongmo, Arnaud Joseph Nguetse;Ekom, Steve Endeguele;Tamokou, Jean-de-Dieu;Tagousop, Cyrille Ngoufack;Harakat, Dominique;Voutquenne-Nazabadioko, Laurence;Ngnokam, David
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.317-325
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    • 2020
  • A new dimer stilbene [Monalittorin (1)] and ten known compounds [engeletin (2), aurantiamide acetate (3), lupeol (4), friedelin (5), quercetin (6), tiliroside (7), rutoside (8), astragalin (9), isoquercitrin (10) and quercimeritroside (11)] have been isolated from the leaves of Monanthotaxis littoralis (Annonaceae). The structures of these compounds were established by interpretation of their data, mainly, HR-TOFESIMS, 1-D NMR (1H and 13C) and 2-D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and by comparison with the literature. The evaluation of their antimicrobial activities against three bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli S2 (1) and Pseudomonas aeruginosa PA01) and three fungal strains (Candida albicans ATCC10231, Candida tropicalis PK233 and Cryptococcus neoformans H99) using broth micro dilution method, showed the largest antimicrobial activities of EtOAc fraction and compounds 1, 5, 6, 8 and 11 (MIC = 8 - 64 ㎍/mL). In addition, EtOAc fraction presented synergistic effect with Vancomycin and fluconazole against the tested microorganisms.

Secondary Metabolites from the Mycelial Culture Broth of Phellinus linteus (상황(Phellinus linteus) 배양 균사체의 2차 대사산물에 대한 화학적 연구)

  • Song, K.S.;Cho, S.M.;Ko, K.S.;Han, M.W.;Yoo, I.D.
    • Applied Biological Chemistry
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    • v.37 no.2
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    • pp.100-104
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    • 1994
  • From the 48 hour-cultured mycelial broth of Phellinus linteus, six compounds were isolated by means of ethyl acetate extraction, silica gel column chromatography and preparative thin layer chromatography, consecutively. Compound 1 was identified as a succinic acid by the comparison of its spectral data with authentic sample. Compounds 2 and 3 were identified as p-hydroxyphenyl acetic acid methyl ester and p-hydroxybenzaldehyde by spectroscopic studies, respectively. NMR and MS studies of compound 6 revealed that it was 2,5-dihydroxymethyl furan. Compound 4, which showed similar NMR absorptions and MS fragmentation pattern with those of compound 6 was identified as 2-hydroxymethyl-5-methoxymethylfuran. These structures were verified by the spectral data of the acetate derivatives of the compounds. Compound 5 was supposed to be a N-acetyltyramine from its $^1H-NMR$ and EI-MS data, and its structure was confirmed by a synthesis starting from tyramine.

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Production of Inulin Fructotransferase (Depolymerizing) from Enterobacter sp. S45 (Enterobacter sp. S45에 의한 Inulin fructotransferase의 생산)

  • 강수일;김수일
    • Microbiology and Biotechnology Letters
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    • v.21 no.1
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    • pp.36-40
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    • 1993
  • A bacterial strain, producing extracellular inulin fructotransferase which converts inulin into di-D-fructofuranose dianhydride (DFA) was isolated from soil and presumed as Enterobacter sp. The DFA isolated on Bio-gel P2 column was identified as DFA III by high performance liquid chromatography and $^13C-nmr$ spectroscopy. The enzyme production was induced by inulin and markedly enhanced by the addition of corn steep liquor and $NH_4H_2P0_4$ for nitrogen source. Under optimum condition, the enzyme activity in the culture broth reached at maximum, 0.22 unit/ml after cultivation for 72 hour.

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Synthesis, Docking Study and In-vitro Evaluation of Anti-Tuberculosis Activity of Tri Substituted Imidazoles Containing Quinoline Moiety

  • Sahana, S.;Vijayakumar, G.R.;Sivakumar, R.;Sriram, D.;Saiprasad, D.V.
    • Journal of the Korean Chemical Society
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    • v.66 no.3
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    • pp.194-201
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    • 2022
  • A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.

해양 유래 Pseudomonas aeruginosa BYK-2(KCTC 18012P)가 생산하는 Biosurfactant의 구조분석

  • Lee, Gyeong-Mi;Kim, Hak-Ju;Ha, Sun-Deuk;Gang, Yang-Sun;Gong, Jae-Yeol
    • 한국생물공학회:학술대회논문집
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    • 2000.11a
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    • pp.626-629
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    • 2000
  • The Pseudomonas aeruginosa BYK-2(KCTC 18012p) produced three kinds of glycolipids on olive oil as a substrate and purified two types of major glycolipids(Rf=0.48, BS-1; Rf=0.65, BS-2) using silica gel chromatography, TLC, HPLC, etc. From the analysis of the chemical structure, the glycolipid of BS-1 was estimated as rhamnolipid($2-O-{\alpha}-L-rhamnopyranosyl- {\alpha}-L-rhamnopyranosyl-{\beta}-hydroxyldecanoyl-{\beta}-hydroxydecanoic$ acid; M.W. 650) and BS-2 was detected as rhamnolipid methyl ester($2-O-{\alpha}-L-rhamnopyranosyl-{\alpha}-L-rhamnopyranosyl-{\beta}-hydroxyldecanoyl-{\beta}-hydroxydecanoic$ acid methyl ester; M.W. 664) by FT-IR, FAB Mass spectrometry, $^1H-NMR$, $^{13}C$ FT-NMR, DEPT, 2D-NMR (TOCSY, RELAY, NOESY, HSQC, HMBC). In particular, It was found that a marine bacterium Pseudomonas aeruginosa BYK-2(KCTC 18012P) remarkably produced rhamnolipid and rhamnolipid methyl ester simultaneously.

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Quantitative Analysis of Platycodin D from Platycodon grandiflorum by HPLC-ELSD (HPLC-ELSD법에 의한 길경의 platycodin D 정량분석)

  • Kim, Geum-Soog;Kim, Hyun-Tae;Seong, Jae-Duck;Park, Hee-Saeng;Kim, Soo-Dong
    • Korean Journal of Medicinal Crop Science
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    • v.10 no.3
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    • pp.200-205
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    • 2002
  • Platycodin D was isolated from n-butanol extract of Platycodi radix(Platycodon grandiflorum and identified by the spectroscopic analysis using $^1H$ and $^{13}C$ NMR techniques. A new method of analysis of platycodin D by high performance liquid chromatography(HPLC) was established using a reversed phase system with YMC-Pack ODS-AM( 250 X 4.6 mm) column and 30% acetonitrile as a mobile phase. Evaporative light scattering detector was used as detector. The kinds of extraction solvents and methods were examined to determine the efficient extraction condition and HPLC analysis was carried out to establish the optimum drying condition for the root of Platycodon grandiflorum. The contents of Platycodin D was highest as 0.083% when platycodon roots were dried at $60^{\circ}C$ using dry oven.

Isolation of Flavonoids from Carthami Flos and their Antioxidative Activity (홍화의 플라보노이드 성분 분리 및 항산화 활성)

  • Chung, Sung-Hee;Moon, Ye-Ji;Kim, Sung-Gun;Kim, Kyoung-Young;Lee, Kyoung-Tae;Kim, Ho-Kyoung;Whang, Wan-Kyunn
    • YAKHAK HOEJI
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    • v.52 no.4
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    • pp.241-251
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    • 2008
  • In this study, isolation of antioxidative compounds was performed for development of anti-oxidizing agent. $CHCl_{3}$, $H_{2}O$, 30%, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method, TBARS assay, and SOD like activity. It was revealed that 30%, 60% MeOH fractions had significant antioxidative activity. From 30%, 60% MeOH fraction, nine compounds were isolated and elucidated kaempferol $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), quercetin $7-O-{\beta}-D-glucopyranoside$ (II), quercetin $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)$ ${\beta}-D-glucopyranoside(rutin)$ (III), 6-hydroxykaempferol $3-O-{\beta}-D-glucopyranoside$ (lV), kaempferol $3-O-{\beta}-D-glucopyranosyl$ $(1{\rightarrow}2)$ ${\beta}-D-glucopyranoside$ (V), kaempferol $3-O-{\beta}-D-glucopyranoside$ (VI), luteolin (VII), quercetin $3-O-{\beta}-D-glucopyranoside$ (VIII), apigenin $7-O-{\beta}-D-glucuronopyranoside$ (IX) through physicochemical data and spectroscopic methods (Negative FAB-MS, $^1H-NMR$, $^{13}C-NMR$). Entirely, all compounds had similar antioxidative activity, but more OH group had more antioxidative activity.

NMR Data of Flavone Derivatives and Their Anti-oxidative Activities

  • Park, Yeong-Hui;Lee, Yong-Uk;Kim, Ho-Jung;Lee, Young-Shim;Yoon, Young-Ah;Mun, Byeong-Ho;Jeong, Yu-Hun;An, Jung-Hun;Shim, Yhong-Hee;Lim, Yoong-Ho
    • Bulletin of the Korean Chemical Society
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    • v.27 no.10
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    • pp.1537-1541
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    • 2006
  • The $^1H$ and $^{13}C$ chemical shifts of eleven flavone derivatives were completely determined by basic 1D and 2D NMR experiments. Nineteen flavone derivatives including the above eleven derivatives were examined for anti-oxidative effects using the 1,1-diphenyl-2-picryl-hydrazyl assay and Caenorhabditis elegans. In order to understand the relationships between the structures of flavone derivatives and their anti-oxidative activities, a Comparative Molecular Field Analysis was performed.

1H, 15N and 13C resonance assignment and secondary structure prediction of ss-DNA binding protein 12RNP2 precursor, HP0827 from Helicobacter pylori

  • Jang, Sun-Bok;Ma, Chao;Chandan, Pathak Chinar;Kim, Do-Hee;Lee, Bong-Jin
    • Journal of the Korean Magnetic Resonance Society
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    • v.15 no.1
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    • pp.69-79
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    • 2011
  • HP0827 has two RNP motif which is a very common protein domain involved in recognition of a wide range of ssRNA/DNA.We acquired 3D NMR spectra of HP0827 which shows well dispersed and homogeneous signals which allows us to assign 98% of all $^1H_N$, $^{15}N$, $^{13}C_{\alpha}$, $^{13}C_{\beta}$ and $^{13}C$=O resonances and 90% of all sidechain resonances. The sequence-specific backbone resonance assignment of HP0827 can be used to gain deeper insights into the nucleic acids binding specificity of HP0827 in the future study. Here, we report secondary structure prediction of HP0827 derived from NMR data. Additionally, ssRNA/DNA binding assay studies was also conducted. This study might provide a clue for exact function of HP0827 based on structure and sequence.

Synthesis of Novel Kojic Acid Derivative and Its Anti-pigmentation Effect

  • Kim, K. H.;Kim, K. S.;Kim, J. G.;Park, S. H.;E. K. Yang;Park, S. N.
    • Proceedings of the SCSK Conference
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    • 2003.09a
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    • pp.719-732
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    • 2003
  • A kojic acid derivative, kojic acid 7-O-$\beta$-D-tetraacetylglucopyranoside(KTG) was synthesized. Regio-and stereo-selective glycosylation at 7-postion in kojic acid with $\beta$-D-pentaacetylglucose was achieved with high yield(80%) by the use of Lewis acid and organic base in nonpolar solvent. KTG was hydrolyzed in methanol by the aid of sodium methoxide to give kojic acid 7-O-$\beta$-D-glucopyranoside(KGP). KGP is freely soluble in water and soluble in methanol and ethanol. Its structure was comfirmed by $^1$H-NMR and $^{13}$ C-NMR. Tyrosinase activity inhibition of KGP was measured with mushroom tyrosinase compared with ascorbic acid, kojic acid and arbutin. KGP showed higher tyrosinase inhibition activity($IC_{50}$/=33.3 $\mu\textrm{g}$/ml) than ascorbic acid(63.2 $\mu\textrm{g}$/ml) and arbutin(91.8 $\mu\textrm{g}$/ml) but lower inhibition activity than kojic acid(8.3 $\mu\textrm{g}$/ml). To test free-radical scavenging activity, we used 1, 1-diphenyl-2-picrylhydrazyl(DPPH) as a free-radical source. Free-radical scavenging activity of KGP was very low($SC_{50}$/>1000 $\mu\textrm{g}$/ml) compared with ascorbic acid($SC_{50}$/=2.68 $\mu\textrm{g}$/ml) and arbutin($SC_{50}$/=180$\mu\textrm{g}$/ml). Melanin formation inhibition of KGP was measured in B16 melanoma, compared with kojic acid, arbutin and Vitamin C. Inhibition activity of KGP for melanin formation was not found within test concentrations.

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