• Title/Summary/Keyword: quinones

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Synthesis and Cation Binding Properties of Triester Calix[4]arenes and Calix[4]quinones

  • 남계천;강성옥;전종철
    • Bulletin of the Korean Chemical Society
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    • v.18 no.10
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    • pp.1050-1052
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    • 1997
  • The complexes M(CO)4-1,2-(PPh2)2-1,2-C2B10H10 (M=Cr 2a, Mo 2b, W 2c) have been prepared in good yields from readily available bis-diphenylphosphino-o-carboranyl ligand, closo-1,2-(PPh2)2-1,2-C2B10H10 (1), by direct reaction with Group Ⅵ metal carbonyls. The infrared spectra of the complexes indicate that there is an octahedral disposition of chelate bis-diphenylphosphino-o-carboranyl ligand around the metal atom. The crystal structure of 2a was determined by X-ray diffraction. Complex 2a crystallizes in the monoclinic space group P21/n with cell parameters a = 12.2360(7), b = 17.156(1), c = 16.2040(6) Å, V = 3354.1(3) Å3, and Z =4. Of the reflections measured a total of 2514 unique reflections with F2 > 3σ(F2) was used during subsequent structure refinement. Refinement converged to R1 = 0.066 and R2 = 0.071. Structural studies showed that the chromium atom had a slightly distorted pseudo-octahedral configuration about the metal center with two phosphine groups of o-carborane occupying the equatorial plane cis-orientation to each other. These metal carbonyl complexes are rapidly converted to the corresponding metal carbene complexes, [(CO)3M=C(OCH3)(CH3)]-1,2-(PPh2)2-1,2-C2B10H10 (M= Cr 3a, Mo 3b, W 3c), via alkylation with methyllithium followed by O-methylation with CF3SO3CH3.

Molecular Cloning and Characterization of an NADPH Quinone Oxidoreductase from Kluyveromyces marxianus

  • Kim, Wook-Hyun;Chung, Ji-Hyung;Back, Jung-Ho;Choi, Ju-Hyun;Cha, Joo-Hwan;Koh, Hun-Yeoung;Han, Ye-Sun
    • BMB Reports
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    • v.36 no.5
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    • pp.442-449
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    • 2003
  • NAD(P)H quinone oxidoreductase is a ubiquitous enzyme that is known to directly reduce quinone substrates to hydroquinones by a two-electron reaction. We report the identification of NADPH quinone oxidoreductase from Kluyveromyces marxianus (KmQOR), which reduces quinone substrates directly to hydroquinones. The KmQOR gene was sequenced, expressed in Escherichia coli, purified, and characterized. The open-reading frame of the KmQOR gene consists of 1143 nucleotides, encoding a 380 amino acid polypeptide. The nucleotide sequence of the KmQOR gene was assigned to EMBL under accession number AY040868. The $M_r$ that was determined by SDS-PAGE for the protein subunit was about 42 kDa, and the molecular mass of the native KmQOR was 84 kDa, as determined by column calibration, indicating that the native protein is a homodimer. The KmQOR protein efficiently reduced 1,4-benzoquinone, whereas no activities were found for menadiones and methoxyquinones. These observations, and the result of an extended sequence analysis of known NADPH quinone oxidoreductase, suggest that KmQOR possesses a different action mechanism.

The Role of Fungal Laccase in Biodegradation of Lignin

  • Andrzej Leonowicz;Jolanta Luterek;Maria W.Wasilewska;Anna Matuszewska;M.Hofrichter;D.Ziegenhagen;Jerzy Rogalski;Cho, Nam-Seok
    • Journal of Korea Technical Association of The Pulp and Paper Industry
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    • v.31 no.5
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    • pp.1-11
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    • 1999
  • Wood components, cellulose and lignin, are degraded simultaneously and the general outline for the complementary character of carbohydrates and lignin decomposition as well as the existence of enzymatic systems combining these processes is still valid. The degradatiion of free cellulose or hemicellulose into monosaccharides has long been known to be relatively simple, but the mechanism of lignin degradatiion wasn ot solved very clearly yet. Anyway the biodegradation of woold constituents is understood at present as an enzymatic process. Kigninolytic activity has been correlated with lignin and manganese peroxidases. At present the attention is paid to laccase. Laccase oxidizes lignin molecule to phenoxy radicals and quinones . This oxidation can lead to the cleavageo f C-C or C-O bonds in the lignin phenyl-propane subunits, resulting either in degradation of both side chains and aromatic rings, or in demethylation processes. The role of laccase lies in the "activation" of some low molecular weight mediators and radicals produced by fungal cultures. Such activated factors produced also in cooperation with other enzymes are probably exported to the wood environment where they work in degradation processes as the ' enzyme messengers." It is worth mentioning that only fungi possessing laccase show demethylating activity. Thus demethylation, the process important for ligninolysis, is probably caused exclusively by laccase. Under natural conditions laccase seems to work with other fungal enzymes , mediators and mediating radicals. It has shown the possibility of direct Bjrkman lignin depolymerization by cooperative activity of laccase and glucose oxidase.

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Effects of Natural Products on the Induction of NAD(P)H: Quinone Reductase in Hepa 1c1c7 Cells for the Development of Cancer Chemopreventive Agents

  • Kim, Young-Mi;Chang, Il-Moo;Mar, Woong-Chon
    • Natural Product Sciences
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    • v.3 no.2
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    • pp.81-88
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    • 1997
  • NAD(P)H:quinone reductase (QR) is one of the protective phase II enzymes against toxicity that accomplishes the capacity of detoxification by modulating the effects of mutagens and carcinogens. The detoxification mechanism is that quinone reductase promotes the 2-electron reduction of quinones to hydroquinones which are less reactive. This study is to search new inducers of quinone reductase from natural products, which can be used as cancer chemopreventive agents. Plant extracts were evaluated by using quinone reductase generating system With Hepa 1c1c7 murine hepatoma cell lines for enzyme inducing properties and crystal violet staining method for the measurement of cytotoxicity provoked. We have tested approximately 106 kinds of natural products after partition into n-hexane, ethyl acetate and aqueous layers from 100% methanol extracts of natural products. The ethyl acetate fractions of Vitex rotundifolia $(fruits,\;2FC:\;12.7\;{\mu}g/ml)$, Cnidium officinale $(aerial\;parts,\;2FC:\;10.5\;{\mu}g/ml)$, Chrysanthemum sinese $(flowers,\;2FC:\;17.4{\mu}g/ml)$ and the hexane fractions of Angelica gigas $(roots,\;2FC:\;13.2\;{\mu}g/ml)$, Smilax china $(roots,\;2FC:\;l1.9\;{\mu}g/ml)$, Sophora flavescens $(roots,\;2FC:\;16.3\;{\mu}g/ml)$ revealed the significant induction of quinone reductase in a murine hepatic Hepa 1c1c7 cell culture system.

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Effects of Caffeic Acid on the Rates of Maillard Reaction (마이얄반응속도에 미치는 카페인산의 영향)

  • Son, Jong-Youn;Ahn, Myung-Soo
    • Korean journal of food and cookery science
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    • v.10 no.2
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    • pp.161-165
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    • 1994
  • It was aimed to investigate the effects of caffeic acid on the rates of Maillard reaction. The rates of browning reaction increased as the browning temperature increased. The color intensity of the browning mixtures indicated to depend on the amino acid rather than reducing sugar. Also, the color intensity of the browning mixtures increased more rapidly in the presence of caffeic acid. The increase in color intensity seemed to depend mainly to the polymerization of o-quinones formed from caffeic acid. The caffeic acid, furthermore, appeared to enhance the color intensity of the browning mixtures through the interaction with amino acid, especially methionine and phenylalanine. The activation ener-gies of the browning reaction without caffeic acid were 108∼130 J/mol, and Q10 values were 2.6∼3.2. The activation energies and Q10 values of browning mixtures decreased in the presence of CA. The activation energies of the browning mixtures with caffeic acid were 90∼101J/mol, and Q$\_$10/ values were 2.0∼2.6.

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Induction of Quinone Reductase, an Anticarcinogenic Marker Enzyme, by Extract from Chrysanthemum zawadskii var. latilobum K.

  • Kim, Ju-Ryoung;Kim, Jung-Hyun;Lim, Hyun-Ae;Jang, Chan-Ho;Kim, Jang-Hoon;Kwon, Chong-Suk;Kim, Young-kyun;Kim, Jong-Sang
    • Preventive Nutrition and Food Science
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    • v.10 no.4
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    • pp.340-343
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    • 2005
  • Induction of NAD(P)H:(quinone-acceptor) oxidoreductase (QR) which promotes obligatory two electron reduction of quinones and prevents their participation in oxidative cycling and thereby the depletion of intracellular glutathione, has been used as a marker for chemopreventive agents. Induction of phase II enzyme is considered to be an important mechanism of cancer prevention. In our previous study, we assessed the quinone reductase QR-inducing activities of 216 kinds of medicinal herb extracts in cultured murine hepatoma cells, BPRc1 and hepalc1c7 cells. Among the 216 herbal extracts tested in that study, extracts from Chrysanthemum zawadskii showed significant induction of QR. In this study, we examined QR-inducing activity of solvent fractions of the herbal extract. The dichloromethane fraction of the herb showed the highest QR induction among the samples fractionated with four kinds of solvents with different polarity. The fraction also significantly induced the activity of glutathione S-transferase (GST), one of the major detoxifying enzymes, at $4{\mu}g/mL\;and\;2{\mu}g/mL$ in hepalc1c7 and BPRc1 cells, respectively. In conclusion, dichloromethane-soluble fraction of Chrysanthemum zawadskii which showed relatively strong induction of detoxifying enzymes merits further study to identify active components and evaluate their potential as cancer preventive agents.

A Study on the Characteristics of Humic Materials Extracted from Plant Residues (composts) -II. Oxygen-containing Functional Groups and Infrared (IR) Spectra of Fulvic Acid Fractions (식물성(植物性) 유기물질(有機物質)의 부숙과정중(腐熟過程中) 부식특성(腐植特性)에 관(關)한 연구(硏究) -II. Fulv 산중(酸中)에 함유(含有)되어 있는 효소함유작용기(酵素含有作用基)와 적외선(赤外線) spectrum)

  • Kim, Jeong-Je;Shin, Young-Oh
    • Korean Journal of Soil Science and Fertilizer
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    • v.20 no.4
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    • pp.341-349
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    • 1987
  • Fulvic acids extracted from seven plant materials were tested. The IR spectra and the data obtained from chemical analyses in terms of oxygen-containing functional groups complemented one another. Selected samples covered straws of grain crops (rice, barley, wheat and rye), hay of wild grass, and leaves of trees (deciduous and coniferous). 1. No significant variation in IR spectra of fulvic acids was observed among samples taken from different plant residues and at different stages of humification. 2. Oxygen-containing functional goups, such as carboxyls, phenolics, alcoholics, carbonyls, and quinones were identified on IR spectra and confirmed by chemical analyses. 3. The acidity of fulvic acids was directly related with the content of carboxyl groups. 4. Alcoholic hydroxyl groups predominated over phenolic hydroxyls. 5. The major part of fulvic acid structure appeared to be strongly aliphatic in many respects of chemical characteristics.

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Effects of Raw Materials and Bulking Agents on the Thermophilic Composting Process

  • Tang, Jing-Chun;Zhou, Qixing;Katayama, Arata
    • Journal of Microbiology and Biotechnology
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    • v.20 no.5
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    • pp.925-934
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    • 2010
  • Three typical biological solid wastes, namely, animal manure, garbage, and sewage sludge, were compared with regard to the composting process and the changes in microbial community structure. The effects of different bulking agents such as rice straw, vermiculite, sawdust, and waste paper were compared in manure compost. The differences in the microbial community were characterized by the quinone profile method. The highest mass reduction was found in garbage composting (56.8%), compared with manure and sludge (25% and 20.2%, respectively). A quinone content of $305.2\;{\mu}mol/kg$ was observed in the late stage of garbage composting, although the diversity index of the quinone profile was 9.7, lower than that in manure composting. The predominant quinone species was found to be MK-7, which corresponds to Gram-positive bacteria with a low G+C content, such as Bacillus. The predominance of MK-7 was especially found in the garbage and sludge composting process, and the increase in quinones with partially saturated long side-chains was shown in the late composting process of manure, which corresponded to the proliferation of Actinobacteria. The effects of different bulking agents on the composting process was much smaller than the effects of different raw materials. High organic matter content in the raw materials resulted in a higher microbial biomass and activity, which was connected to the high mass reduction rate.

Oxidation-Deficient Silkworm Hemolymph as a Medium Supplement for Insect Cell Culture

  • Kim, Eun-Jeong;Park, Ji-Young;Kim, Sam-Eun;Park, Tai-Hyun
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.3 no.2
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    • pp.87-90
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    • 1998
  • Hemolymph is oxidized and darkens visibly during the collection from silkworm due to the activity of tyrosinase in it. Toxic quinones are produced by the oxidation and consequently inhibit the cell growth. Heat treatment can be used to prevent the oxidation ; however, the oxidation may occur during the collection of hemolymph before it is heat-treated. It makes the hemolymph collection difficult especially on a large-scale preparation. Hemolymphs collected from 257 different strains of silkworms were examined to select the slowly oxidized hemolymphs. Hemolymphs collected from mutant strains such as Lemone, TBO, Cre, Y4, and wEb showed relatively slow color changes. Oxidation rates of the hemolymphs were measured by the absorbance change using a spectrophotometer. The hemolymph of wEb showed the slowest oxidation. The absorbance of this mutant hemolymph reached the saturation value at 20$^{\circ}C$ in 450 min, whereas the total oxidation time of the wild-type (Baekokjam) hemolymph at the same temperature was 120 min. We tested if this mutant hemolymph is useful as a medium supplement for insect cell culture. Cell growth rate and final cell concentration in the medium supplemented with the wEb hemolymph were almost same as those in the medium supplemented with the wild-type hemolymph. Hemolymph is collected on a small scale by clipping the abdominal leg; however, this method is not appropriate fro large scale preparation. Centrifugation after chopping the silkworm hemolymph by a blending mixer is a more appropriate procedure for large scale collection. Slowly oxidized wEb hemolymph resulted in higher cell concentration than the wild-type hemolymph when hemolymph was collected by the large scale preparation method.

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Induction of Anticarcinogenic Enzymes by Dichloromethane-soluble Fraction of Physalis alkekengi var. francheti Hort. in Mouse Hepatoma Cells

  • Seo, JiYeon;Kim, Hyo Jung;Kim, Jong-Sang
    • Current Research on Agriculture and Life Sciences
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    • v.32 no.3
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    • pp.119-124
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    • 2014
  • Physalis alkekengi var. francheti Hort. is known as an insecticide and traditional remedy for liver related diseases. Therefore, this study investigated the chemopreventive effects of extracts and several solvent fractions (n-hexane, dichloromethane, n-butanol, water) of Physalis alkekengi var. francheti Hort. First, their cytotoxicity and NQO1 activity were measured using an MTT assay, plus a quinone reductase [NAD(P)H dehydrogenase (quinone); NAD(P)H: (quinone acceptor) oxidoreductase, EC 1.6.99.2]-inducing activity assay was performed using cultured murine hepatoma cells (Hepa1c1c7) and its mutant cells(BpRc1). The reduction of electrophilic quinones by NQO1 is an important detoxification pathway and major mechanism of chemoprevention. When compared with the other solvent soluble fractions with different polarities, the dichloromethane fraction of Physalis alkekengi var. francheti Hort. showed a higher NQO1-inducing activity that was also dose-dependent. Moreover, the dichloromethane fraction of Physalis alkekengi var. francheti Hort. induced ARE-luciferase activities in HepG2-C8 cells that were generated by transfecting the ARE-luciferase gene construct, suggesting the Nrf2-ARE-mediated induction of anti-oxidative enzymes. In conclusion, the dichloromethane-soluble fraction of Physalis alkekengi var. francheti Hort. showed a relatively strong induction of detoxifying enzymes, thereby meriting further study to identify the active components and evaluate their potential as cancer preventive agents.