• Title/Summary/Keyword: 1D $^1H-NMR$

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Antimicrobial Properties and Cytotoxicity of Sulfated (1,3)-β-D-Glucan from the Mycelium of the Mushroom Ganoderma lucidum

  • Wan-Mohtar, Wan Abd Al Qadr Imad;Young, Louise;Abbott, Grainne M.;Clements, Carol;Harvey, Linda M.;McNeil, Brian
    • Journal of Microbiology and Biotechnology
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    • v.26 no.6
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    • pp.999-1010
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    • 2016
  • Ganoderma lucidum BCCM 31549 has a long established role for its therapeutic activities. In this context, much interest has focused on the possible functions of the (1,3)-β-D-glucan (G) produced by these cultures in a stirred-tank bioreactor and extracted from their underutilized mycelium. In the existing study, we report on the systematic production of G, and its sulfated derivative (GS). The aim of this study was to investigate G and its GS from G. lucidum in terms of their antibacterial properties and cytotoxicity spectrum against human prostate cells (PN2TA) and human caucasian histiocytic lymphoma cells (U937). 1H NMR for both G and GS compounds showed β-glycosidic linkages and structural similarities when compared with two standards (laminarin and fucoidan). The existence of characteristic absorptions at 1,170 and 867 cm-1 in the FTIR (Fourier Transform Infrared Spectroscopy) for GS demonstrated the successful sulfation of G. Only GS exhibited antimicrobial activity against a varied range of test bacteria of relevance to foodstuffs and human health. Moreover, both G and GS did not show any cytotoxic effects on PN2TA cells, thus helping demonstrate the safety of these polymers. Moreover, GS showed 40% antiproliferation against cancerous U937 cells at the low concentration (60 μg/ ml) applied in this study compared with G (10%). Together, this demonstrates that sulfation clearly improved the solubility and therapeutic activities of G. The water-soluble GS demonstrates the potential multifunctional effects of these materials in foodstuffs.

Synthesis and Characterization of Polybenzimidazoles Containing Perfluorocyclobutane Groups for High-temperature Fuel Cell Applications

  • Chang, Bong-Jun;Kim, Dong-Jin;Kim, Jeong-Hoon;Lee, Soo-Bok;Joo, Hyeok-Jong
    • Korean Membrane Journal
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    • v.9 no.1
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    • pp.43-51
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    • 2007
  • This paper describes the preparation and characterization of two kinds of fluorinated polybenzimidazole (PBI)s which can be potentially used for phosphoric acid-doped, high-temperature polymer electrolyte membrane fuel cells. Two kinds of perfluorocyclobutane (PFCB)-containing monomers were prepared via following synthetic steps; after fluoroalkylation of methyl 3-(hydroxy) benzoate and methyl 4-(hydroxy) benzoate with 1,2-dibromotetrafluoroethane and subsequent Zn-mediated dehalogenation, these compounds were cyclodimerized at $200^{\circ}C$ affording the ester-terminated monomers containing PFCB ether groups. The synthesized intermediates and monomers were characterized using FT-IR, $^1H-NMR,\;^{19}F-NMR$, and mass spectroscopy. The fluorinated PBIs were then successfully prepared through the solution polycondensation of the monomers and 3,3'-diaminobenzidine in polyphosphoric acid. Compared with traditional PBI, the glass transition temperatures of the fluorinated PBIs were obtained at $262^{\circ}C\;and\;269^{\circ}C$ which are lower than that of PBI and their initial degradation temperatures were still high over $400^{\circ}C$ under nitrogen. The fluorinated PBIs showed higher d-spacing values and improved solubility in several organic solvents as well as phosphoric acid, which confirmed they could be good candidates for the high temperature fuel cell membranes.

Structure Determination of Antifungal KRF-001 Produced by Bacillus subtilis subsp. krictiensis (Bacillus subtilis subsp. krictiensis가 생산하는 항진균 물질 KRF-001의 구조 결정)

  • 김성기;이남경;정태숙;김영국;최진자;복성해
    • Microbiology and Biotechnology Letters
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    • v.19 no.6
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    • pp.598-603
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    • 1991
  • An antifungal mixture of six members (component A to F), KRF-001 produced by Bacillzts subtilis subsp. krictiensis was isolated from the fermentation broth. Molecular weight of component A to F was determined by FAB-MS to be 1042, 1056, 1056, 1070, 1070 and 1084 respectively. Various instrumental analyses (amino acid analysis, GC-MS, $^1H-NMR, ^1HH$ COSY NMR) revealed that the mixture was a homologous cyclic peptide composed of each one mole of glutamine, proline, tyrosine, serine, unusual $\beta$-amino acid and three moles of asparagine. The structural differences of component A to F were found in carbon number and terminal structure of the unusual $\beta$-amino acid. After determination of the sequence and stereochemistry of those amino acids, the tentative structure of KRF-001 was determined.

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Isolation and Identification of Antioxidant Compound from the Lythrum Salicaria L. Roots (털부처꽃(Lythrum Salicaria L.) 뿌리로부터 항산화 물질의 분리 및 구조동정)

  • Lee, Kyeong-Hee;Lee, Dae-Young;Lee, Seung-Eun;Noh, Hyung-Jun;Lee, Jeong-Hoon;Choi, Jehun;Park, Chun-Geun;Kim, Seung-Yu;Lee, Jun-Su;Kim, Geum-Soog
    • Journal of Applied Biological Chemistry
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    • v.57 no.4
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    • pp.359-363
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    • 2014
  • The roots of Lythrum salicaria L. were extracted in 80% aqueous MeOH and the concentrated extract was fractionated with EtOAc, n-BuOH, and $H_2O$, successively. The repeated silicagel and octadecyl $SiO_2$ column chromatographies of the EtOAc fractions led to isolation of an antioxidant compound and two major compounds. From the results of spectral data and the chemical characteristics including nuclear magnetic resonance, MS, and IR, the structures of compounds were determind as myricetin-3-O-${\beta}$-D-glucopyranoside (1), oleanolic acid (2), betulinic acid (3). This is the first reported isolation of compounds (1, 2) from L. salicaria. Compound 1 as well as EtOAc, n-BuOH, and $H_2O$ solvent fractions were evaluated for 2,2-dipicryl-1-phenylhydrazyl radical scavenging activity.

Influence of Hormones and Selection of Stable Cell Lines of Plumbago rosea for Accumulation of Plumbagin

  • Komaraiah P.;Jogeswar G.;Naga Amrutha R.;Sri Laxmi P.;Lavanya B.;Rama Krishna S.V.;Kavi Kishor P.B.
    • Journal of Plant Biotechnology
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    • v.5 no.3
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    • pp.181-185
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    • 2003
  • Callus and suspension cultures derived from leaf explants of Plumbago rosea were established on Murashige and Skoog's medium containing 1 mg/L IAA, 0.5 mg/L NAA and 0.3 mg/L BAP. Callus cultures were tested for their growth and accumulation of plumbagin, a naphthoquinone and was identified by $^1H$ NMR and electron ionization mass spectroscopy. While auxins (not 2,4-D) influenced growth and plumbagin accumulation, cytokinins did not influence them much. Increasing concentrations of IAA in presence of NAA and BAP increased plumbagin in suspensions only up to 1 mg/L. Growth of callus was optimum (8.3 g DCW/I) at a hormonal combination of 1.5 mg/L IAA, 0.5 mg/L NAA and 0.3 mg/L BAP, but high plumbagin accumulation (4.9 mg/g DCW) was recorded at 1.0 mg/L IAA plus 0.3 mg/L BAP. Since instability in growth and secondary metabolite accumulation was noticed, several cell lines/clumps of callus were screened for plumbagin accumulation by visual and analytical methods. Biomass and accumulation of plumbagin showed a negative correlation in several cell lines. But one cell line showed stability both in terms of biomass and plumbagin accumulation over a period of 6 months.

Isolation of 1',3'-Dilinolenoyl-2'-Linoleoylglycerol with Tyrosinase Inhibitory Activity from Flammulina velutipes

  • Jang, Se-Gul;Jeon, Kyung-Su;Lee, Eun-Hee;Kong, Won-Sik;Cho, Jae-Yong
    • Journal of Microbiology and Biotechnology
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    • v.19 no.7
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    • pp.681-684
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    • 2009
  • This study was carried out to evaluate the inhibitory effect of Flammulina velutipes extracts on tyrosinase activity and to identify its biologically active component. The ethyl acetate and n-butanol extracts showed potent tyrosinase inhibitory activities. Subsequently, fractions of the n-butanol extract showed only a partial tyrosinase inhibitory activity. The most active compound of tyrosinase inhibitory activity was identified from the ethyl acetate extract as 1',3'-dilinolenoyl-2'-linoleoylglycerol (LnLLn) by comparing its mass, $^1H-$, and $^{13}C-NMR$spectral data with those previously reported in the literature. LnLLn showed tyrosinase inhibitory activity with an $IC_{50}$value of 16.1 ${\mu}g/ml$. These results suggest that the ethyl acetate extract of F. velutipes could be applicable for the development of a new whitening agent.

Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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Free-Radical Copolymerization of Glycidyl Methacrylate with Phthalimidoethyl Acrylate : Synthesis and Determination of Monomer Reactivity Ratios (GMA와 프탈이미드아크릴레이트의 공중합체 합성과 반응성비)

  • Oh, Seung-Min;Oh, Dae-Hee
    • Journal of the Korean Applied Science and Technology
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    • v.30 no.2
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    • pp.297-304
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    • 2013
  • Free-radical copolymerization of glycidyl methacrylate(GMA) and N-phthalimidoethyl acrylate(NPEA) were carried out at $60^{\circ}C$ in dimethylformamide(DMF) solution in the presence of benzoylperoxide(BPO) at low conversion. The polymers were characterized by IR and $^1H$-NMR. The compositions of the copolymer was analyzed by ultra violet(UV/Vis) spectrophotometry. The reactivity ratios of the monomer was determined by the application of Fineman-Ross(FR) and Kelen-T$\ddot{u}$d$\ddot{o}$s(KT) methods. The monomer reactivity ratios of the system and Alfrey-Price's resonance effect(Q) and polar effect(e) value for NIEA were determined as follow. The reactivity ratios of the monomer obtained from FR and KT are found to be $r_1$=0.87, $r_2$=0.98 and $r_1$=0.88, $r_2$=0.99 respectively. The Q and e values of poly(GMA-co-NPEM) calculated from $r_1$ and $r_2$ was Q= 1.31, e=0.75 respectively.

Diels-Alder Type Adducts from Hairy Root Cultures of Morus macroura

  • Happyana, Nizar;Hakim, Euis H.;Syah, Yana M.;Kayser, Oliver;Juliawaty, Lia D.;Mujahidin, Didin;Ermayanti, Tri M.;Achmad, Sjamsul A.
    • Natural Product Sciences
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    • v.25 no.3
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    • pp.233-237
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    • 2019
  • Three Diels-Alder type adducts, guangsangon E (1), chalcomoracin (2) and sorocein I (3) were isolated from hairy root cultures of Morus macroura. The structures of the isolated compounds (1-3) were determined by spectroscopic method (NMR and MS), and spectral comparison to literature. Cytotoxic activities of the isolated compounds (1 - 3) were investigated against P-388 murine leukemia cell line. Guangsangon E (1) showed the most potent cytotoxicity against P-388 murine leukemia cell line with $IC_{50}$ value of $2.75{\pm}0.32{\mu}g/mL$. To the best of our knowledge, guangsangon E (1) and sorocein I (3) were reported for the first time from the tissue cultures of M. macroura.

Homology Modeling and Active Sites of PolyMG-specific Alginate Lyase from Stenotrophomonas maltophilia KJ-2 (Stenotrophomonas maltophilia KJ-2 균주로부터 얻은 PolyMG-specific 알긴산분해효소의 상동성 모델링 및 활성자리 연구)

  • Kim, Hee Sook
    • Journal of Life Science
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    • v.24 no.2
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    • pp.128-136
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    • 2014
  • Alginates are linear acidic polysaccharides composed with (1-4)-linked ${\alpha}$-L-guluronic acid and ${\beta}$-Dmannuronic acid. Alginate can be degraded by diverse alginate lyases, which cleave the alginate using a ${\beta}$-elimination reaction and produce unsaturated uronate oligomers. A gene for a polyMG-specific alginate lyase possessing a novel structure was previously identified and cloned from Stenotrophomonas maltophilia KJ-2. Homology modeling of KJ-2 polyMG-specific alginate lyase showed it belongs to the PL6 family, whereas three Azotobacter vinelandii polyMG lyases belong to the PL7 family of polysaccharide lyases. From $^1H$-NMR spectra data, KJ-2 polyMG lyase preferably degraded the M-${\beta}$(1-4)-G glycosidic bond than the G-${\alpha}$(1-4)-M glycosidic bond. Seventeen mutants were made by site-directed mutagenesis, and alginate lyase activity was analyzed. Lys220Ala, Arg241Ala, Arg241Lys, and Arg265Ala lost alginate lyase activity completely. Arg155Ala, Gly303Glu, and Tyr304Phe also lost the activity by 60.7-80.1%. These results show that Arg155, Lys220, Arg241, Arg265, Gly303, and Tyr304 are important residues for catalytic activity and substrate binding.