• Title/Summary/Keyword: 1,4-Hydroquinone

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Molecular Docking and Kinetic Studies of the A226N Mutant of Deinococcus geothermalis Amylosucrase with Enhanced Transglucosylation Activity

  • Hong, Seungpyo;Siziya, Inonge Noni;Seo, Myung-Ji;Park, Cheon-Seok;Seo, Dong-Ho
    • Journal of Microbiology and Biotechnology
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    • v.30 no.9
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    • pp.1436-1442
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    • 2020
  • Amylosucrase (ASase, E.C. 2.4.1.4) is capable of efficient glucose transfer from sucrose, acting as the sole donor molecule, to various functional acceptor compounds, such as polyphenols and flavonoids. An ASase variant from Deinococcus geothermalis, in which the 226th alanine is replaced with asparagine (DgAS-A226N), shows increased polymerization activity due to changes in the flexibility of the loop near the active site. In this study, we further investigated how the mutation modulates the enzymatic activity of DgAS using molecular dynamics and docking simulations to evaluate interactions between the enzyme and phenolic compounds. The computational analysis revealed that the A226N mutation could induce and stabilize structural changes near the substrate-binding site to increase glucose transfer efficiency to phenolic compounds. Kinetic parameters of DgAS-A226N and WT DgAS were determined with sucrose and 4-methylumbelliferone (MU) as donor and acceptor molecules, respectively. The kcat/Km value of DgAS-A226N with MU (6.352 mM-1min-1) was significantly higher than that of DgAS (5.296 mM-1min-1). The enzymatic activity was tested with a small phenolic compound, hydroquinone, and there was a 1.4-fold increase in α-arbutin production. From the results of the study, it was concluded that DgAS-A226N has improved acceptor specificity toward small phenolic compounds by way of stabilizing the active conformation of these compounds.

Study on the Catalytic Properties of Copper Oxide Nanoparticles Synthesized by Levitational Gas Condensation (LGC) Method (부양가스증발응축법에 의해 제조된 구리산화물 나노분말의 촉매 특성 연구)

  • Uhm, Y.-R.;Kim, W.-W.;Oh, J.-S.;Rhee, C.-K.
    • Journal of Powder Materials
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    • v.12 no.1
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    • pp.64-69
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    • 2005
  • The copper oxide nano powders were synthesized by levitational gas condensation(LGC) method, and their high heterogeneous catalytic effects of oxidation of 2,3,5-trimethyl-1,4- hydroquinone (TMHQ) and catalase activity were studied. The observation of transmission electron microscopy (TEM) shows that most of these nano powders are uniform in size, with the average particle size of 35 nm. The nano powder consists of mainly $Cu_2O$, but it is aged to CuO phase. The catalytic effect which was clarified by oxidation of TMHQ and catalase depends on the amount of cuprite phase and the particle size.

Antimicrobial Activities of 1,4-Benzoquinones and Wheat Germ Extract

  • Kim, Myung-Hee;Jo, Sung-Hoon;Ha, Kyoung-Soo;Song, Ji-Hye;Jang, Hae-Dong;Kwon, Young-In
    • Journal of Microbiology and Biotechnology
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    • v.20 no.8
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    • pp.1204-1209
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    • 2010
  • We evaluated the antibacterial activities of selected edible Korean plant seeds against the food-borne pathogens Staphylococcus aureus KCTC1927, Escherichia coli KCTC2593, Salmonella typhimurium KCTC2054, and Bacillus cereus KCTC1014. While screening for antibacterial agents, we discovered that wheat germ extract contains 2,6-dimethoxy-1,4-benzoquinone (DMBQ) and is highly inhibitory to S. aureus and B. cereus. This is the first report of the antibacterial activity of wheat germ extract. We also investigated the antibacterial activities of the 1,4-benzoquinone standards 1,4-benzoquinone (BQ), hydroquinone (HQ), methoxybenzoquinone (MBQ), and 2,6-dimethoxy-1,4-benzoquinone (DMBQ). DMBQ and BQ were the most highly inhibitory to S. aureus and S. typhimurium, followed by MBQ and HQ. MICs for DMBQ and BQ ranged between 8 and 64 ${\mu}g/ml$ against the four foodborne pathogens tested. DMBQ and BQ showed significant antibacterial activity; the most sensitive organism was S. aureus with an MIC of 8 ${\mu}g/ml$. BQ exhibited good activity against S. typhimurium (32 ${\mu}g/ml$) and B. cereus (32 ${\mu}g/ml$). The results suggest that wheat germ extract has potential for the development of natural antimicrobials and food preservatives for controlling foodborne pathogens.

An Effects of Enzymatic Browning Reaction Products of Potato on the Antimutagenesis

  • Ham, Seung-Shi;Park, Kun-Pyo;Park, Book-Kil;Deoghwan Oh
    • Preventive Nutrition and Food Science
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    • v.2 no.3
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    • pp.232-235
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    • 1997
  • This study was investigated to determine antimutagenic effects of enzymatic browning reaction products (PEBRPs) obtained by reaction of polyphenol compouns with oxidase extracted from potato. Catechol (Ca) PEBRPs showed the strongeest inhibitor effects with 90% inhibition on benzo-($\alpha$)-pyrene(B($\alpha$)P) induced mutagenesis in Salmonella typhimurium TA98, but he least with40% inhibition on the 2-aminofluorene (2-AF) induced mutagenesis in TA98. The strong antimutagenic activities with 80% inhibition were observed in the presence of 100$\mu\textrm{g}$/plate of hydroquinone(HQ)-PEBRP on the B($\alpha$)P or 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole(Trp-P-1) induced mutagenesis in TA98, whereas HQ-PEBRP showed the least antimutagenic effect on 2-AF-induced mutagenesis. The addition of 100$\mu\textrm{g}$ hydroxyhydroquinone(HHQ)-PEBRP to the plate led to approximately 82% inhibitory effects on 2-AF or Trp-P-1 induced mutagenesis in TA98, whereas the least antimutagenicity was obsrved in the4-nitroquinoline-1-oxide(4-NQO) induced mutagenesis in the presence of 100$\mu\textrm{g}$/plate of HHQ-PEBRP. More than 80% inhibiton were observed in the presence of 200$\mu\textrm{g}$/plate of Pyrogalol(Py)-PEBRP on the B($\alpha$)P or Trp-P-1 induced mutagenesis in TA98, but the least with 38% inhibition on 4-NQO induced mutagenesis in TA98. The results indicate that enzymatic browing reaction products of potato have a strong modulatory effect on mutagen induced mutagenesis in TA98.

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Synthesis and Characterization of New Main Chain Liquid Crystalline Coumarin Compound with Ester Moiety (Ester기를 갖는 새로운 주쇄형 액정 coumarin 화합물의 합성 및 특성분석)

  • Lee, Jong-Back;Kang, Byung-Chul;Lee, Gang-Choon;Lee, Dong-Jin;Hideyuki, Kihara
    • Elastomers and Composites
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    • v.44 no.4
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    • pp.416-422
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    • 2009
  • 4-(6-bromohexyloxy)benzoic acid was synthesized from benzyl 4-Hydroxybenzoate and 1,6-dibromohexane. It was reacted with hydroquinone to obtain a new mesogenic ester having an bromine group. One kind of new photoresponsive coumarin compound was prepared by the reaction of mesogenic ester with coumarin sensitive to the ultraviolet. Structures of the compound were identified by FT-IR and $^1H$-NMR spectroscopies. Their phase transition temperatures and thermal stability were also investigated by differential scanning calorimetry (DSC), polarized optical microscopy (POM) and x-ray diffraction analysis. From optical polarizing microscopy, the prepared compound was found to show enantiotropic liquid crystallinity with smectic and nematic textures.

Effects of Operating Parameters on Phenol Degradation by Pulsed Corona Discharges in Aqueous Solutions (펄스 코로나 방전에 의한 페놀 분해에 미치는 운전변수의 영향)

  • Chung, Jae-Woo;Moon, Ji-Hoon;Park, Eun-Ok
    • Journal of Korean Society of Environmental Engineers
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    • v.32 no.1
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    • pp.79-86
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    • 2010
  • Effects of operating parameters such as applied voltage, solution conductivity, ferrous ion concentration, electrode material on phenol degradation by pulsed corona discharges were investigated in laboratory scale experiments. The increase of applied voltage enhanced the phenol degradation by generating more energetic electrons. The solution conductivity inversely affected phenol removal rate in the tested ranges because the increase of conductivity decreased the electric field strength through the liquid phase. The addition of ferrous sulfate promoted the phenol degradation through the OH radical production by the Fentonlike reactions between ferrous ion and hydrogen peroxide generated by pulsed corona discharges. Catechol and hydroquinone were detected as primary intermediates of phenol degradation and the decrease of pH and the increase of conductivity were observed probably due to the generation of organic acids. Almost all of the initial phenol was disappeared and 29% of total organic corbon (TOC) was removed in the condition of 0.5 mM of ferrous sulfate after approximately 230 kJ of discharge energy transferred to the reactor.

Purification and Characterization of an Intracellular NADH: Quinone Reductase from Trametes versicolor

  • Lee, Sang-Soo;Moon, Dong-Soo;Choi, Hyoung-T.;Song, Hong-Gyu
    • Journal of Microbiology
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    • v.45 no.4
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    • pp.333-338
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    • 2007
  • Intracellular NADH:quinone reductase involved in degradation of aromatic compounds including lignin was purified and characterized from white rot fungus Trametes versicolor. The activity of quinone reductase was maximal after 3 days of incubation in fungal culture, and the enzyme was purified to homogeneity using ion-exchange, hydrophobic interaction, and gel filtration chromatographies. The purified enzyme has a molecular mass of 41kDa as determined by SDS-PAGE, and exhibits a broad temperature optimum between $20-40^{\circ}C$, with a pH optimum of 6.0. The enzyme preferred FAD as a cofactor and NADH rather than NADPH as an electron donor. Among quinone compounds tested as substrate, menadione showed the highest enzyme activity followed by 1,4-benzoquinone. The enzyme activity was inhibited by $CuSO_4,\;HgCl_2,\;MgSO_4,\;MnSO_4,\;AgNO_3$, dicumarol, KCN, $NaN_3$, and EDTA. Its $K_m\;and\;V_{max}$ with NADH as an electron donor were $23{\mu}M\;and\;101mM/mg$ per min, respectively, and showed a high substrate affinity. Purified quinone reductase could reduce 1,4-benzoquinone to hydroquinone, and induction of this enzyme was higher by 1,4-benzoquinone than those of other quinone compounds.

Ionic Conductivities of the LiCF$_3$SO$_3$Complexes with Liquid Crystalline Aromatic Polyesters Having Oligo(oxyethylene) Pendants

  • Lee, Jun-Woo;Joo, Sung-Hoon;Jin, Jung-Il
    • Macromolecular Research
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    • v.12 no.2
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    • pp.195-205
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    • 2004
  • We have synthesized new aromatic polyesters (DiPEG-HQ and DiPEG-BP) by condensation polymerization of a terephthalic acid derivative bearing a pendant oligo(oxyethylene) (DP = 7, MW = 350), which has a methoxy terminal group, and two different aromatic diols, hydroquinone and 4,4'-biphenoI. The synthesized polymers were characterized by differential scanning calorimetry (DSC), polarizing microscopy, and X-ray diffractometry for their liquid crystallinity (LC), thermal transitions, and structural morphologies in mesophases. The morphology of the LC phases depends strongly on the length of the rigid backbone repeating unit. The DiPEG-BP polymer having a longer repeating unit exhibits both layered and nematic structures before isotropization, whereas the DiPEG-HQ polymer having a shorter repeating unit shows only the layered structure in the mesophase. We found that the layer spacing for DiPEG-HQ is larger than that for DiPEG-BP. Both polymers easily form complexes with LiCF$_3$SO$_3$; we studied this complex formation by FT-IR spectroscopy. The layer spacing of the polymer-electrolyte composites increases upon increasing the amount of the lithium salt. The polymer/salt electrolyte mixtures we investigated at molar ratios of EO:salt in the range of 5-20 exhibit electrical conductivity values at 40$^{\circ}C$ of 2.4${\times}$10$\^$5/ and 1.1${\times}$10$\^$-5/ S/cm for DiPEG-HQ/LiCF$_3$SO$_3$ and DiPEG-BP/LiCF$_3$SO$_3$, respectively. At 80 $^{\circ}C$, these values are higher: 4.6${\times}$10$\^$-3/ and 1.1${\times}$10$\^$-4/ S/cm, respectively. The activation energy of conductivity depends strongly on the salt concentration.

Synthesis and Properties of Semi-flexible Liquid Crystalline Polyesters with Rigid Lateral Group (강직한 측쇄기를 갖는 반 유연성 액정폴리에스터의 합성 및 성질)

  • Park, Jong-Ryul;Lee, Eung-Jae;Yoon, Doo-Soo;Bang, Moon-Soo;Choi, Jae-Kon
    • Elastomers and Composites
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    • v.48 no.4
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    • pp.306-311
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    • 2013
  • A series of liquid crystalline polyesters containing the 4-chloro benzoate group on the hydroquinone unit of rigid group were synthesized through solution polymerization of 2,5-di(4-chlorobenzoate)hydroquinones and 4,4'-dicarboxy-${\alpha},{\omega}$-diphenoxy alkane. The structure and properties for synthesized polymers were investigated by $^1H$-NMR, FT-IR, DSC, TGA, and POM. As result of investigations, The presence of the methylene group and bulky lateral groups in polymer chain have a great influence on the properties of polymers such as solubilities and thermal transitions. The optical textures of polymers revealed a weak birefringence in the melt and indicated that they form nematic mesophase. All polymers have very narrow mesophase temperature ranges.

Purificaton and Some Properties of Polyphenol Oxidase from Ginko biloba Leaves (은행잎에서 분리한 Polyphenol Oxidase의 정제 및 특성)

  • Seol, Ji-Yeon;Park, Soo-Sun;Kim, An-Keun
    • Korean Journal of Pharmacognosy
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    • v.30 no.3
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    • pp.306-313
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    • 1999
  • Polyphenol Oxidase(PPO) was purified from an extract of Ginkgo biloba leaves by ammonium sulfate fractionation followed by sephadex G-150 column chromatography, which resulted in a 18-fold increase in specific activity. The enzyme was most active at pH 8.5 and the temperature optimum for the PPO catechol oxidation reaction was $45^{\circ}C$. Heat inactivation studies showed that heating for 7, 9 and 48 min, at 80, 70 and $60^{\circ}C$ respectively caused a 50% loss in enzymatic activity and that the enzyme was completely inactivated after heat treatment at $90^{\circ}C$ for 60 min. Km values of the PPO for catechol, hydroquinone and 4-methylcatechol derived from Lineweaver-Burk plots were $6.06\;{\times}\;10^{-4}M,\;1.02\;{\times}\;10^{-3}M,\;1.41\;{\times}\;10^{-3}M$ respectively. Of the substrates tested, 4-methylcatechol was oxidized most readily and the enzyme did not oxidize monophenols. The enzyme datalyzed browning reaction was completely inhibited in the presence of reducing reagents, namely ascorbic acid, cysteine, glutathione, 2-mercaptoethanol, potassium metabisulfite at 0.5 mM level. Sodium chloride showed very little inhibition effect on Ginkgo biloba leaves PPO. Lineweaver-Burk analysis of inhibition data revealed that the inhibition by cysteine, 2-mercaptoethanol, potassium cyanide was competitive with ki values of $1.1\;{\times}\;10^{-5}M,\;2.4\;{\times}\;10^{-5}M,\;8\;{\times}\;10^{-5}M$, respectively. Among the divalent cations, $Cu^{2+}ion$ was a strong activator on PPO and $Mn^{2+}ion$ was little or no effect on PPO activity $Ni^{2+}ion$ was an inhibitor on PPO.

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