• Title/Summary/Keyword: 3-methyl catechol

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Salsolinol, a catechol neurotoxin, induces oxidative modification of cytochrome c

  • Kang, Jung Hoon
    • BMB Reports
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    • v.46 no.2
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    • pp.119-123
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    • 2013
  • Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (salsolinol), an endogenous neurotoxin, is known to perform a role in the pathogenesis of Parkinson's disease (PD). In this study, we evaluated oxidative modification of cytochrome c occurring after incubation with salsolinol. When cytochrome c was incubated with salsolinol, protein aggregation increased in a dose-dependent manner. The formation of carbonyl compounds and the release of iron were obtained in salsolinol-treated cytochrome c. Salsolinol also led to the release of iron from cytochrome c. Reactive oxygen species (ROS) scavengers and iron specific chelator inhibited the salsolinol-mediated cytochrome c modification and carbonyl compound formation. It is suggested that oxidative damage of cytochrome c by salsolinol might induce the increase of iron content in cells, subsequently leading to the deleterious condition which was observed. This mechanism may, in part, provide an explanation for the deterioration of organs under neurodegenerative disorders such as PD.

Composition of the Adhesive Used for Fixing Glass Eyes of the Stone Standing Maitreya of Daejosa Temple, Buyeo (Treasure No. 217)

  • Park, Jongseo;Lee, Sunmyung
    • Journal of Conservation Science
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    • v.35 no.4
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    • pp.295-307
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    • 2019
  • In the process of the conservation treatment of the glass eyes of the stone standing Maitreya of Daejosa temple, Buyeo (Treasure No. 217), a blackish material, expected to be the adhesive for fixing the glass eyes, was collected and analyzed. Infrared spectroscopy and pyrolysis/gas chromatography/mass spectrometry (pyrolysis/GC/MS) were employed to identify the organic material in the sample. The IR analysis revealed the presence of materials such as apatite or bone black. The pyrogram of the sample was similar to that of Asian lacquer, among traditional adhesives. In particular, the pyrolysis/GC/MS analysis with online methylation detected 1,2-dimethoxy-3-pentadecylbenzene, methyl 7-(2,3- dimethoxyphenyl) heptanoate, and methyl 8-(2,3-dimethoxyphenyl)octanoate. These are known to be the pyrolysis products of catechol and its oxidation product, which indicated the presence of Asian lacquer in the sample. X-ray diffraction, X-ray fluorescence, and thermal gravimetry analysis showed that the sample contained ca. 60% inorganic substances, including apatite. Radiocarbon dating of the sample suggested that the blackish material was applied between the late 13th and early 15th century, revealing some discrepancy with the art-historical manufacturing time of the Maitreya. From the above analysis, it was concluded that Asian lacquer and bone ash were used to attach the glass eyes by forming a thick blackish lacquer layer.

PHENOLOXIDASE AND ANTIOXIDANT IN KOREAN GINSENG (고려인삼에 있어서의 페놀 산화효소의 항산화물질)

  • Park E.Y.;Luh B.S.;Branen A.L.
    • Proceedings of the Ginseng society Conference
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    • 1984.09a
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    • pp.257-275
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    • 1984
  • Enzymatic browning is considered desirable in tea and tobacco processing but undesirable in many fruits processing at the present time. It is necessary to understand the nature of the enzyme, phenoloxidase, in order to control browning reactions, and extend its effects to formation of browning products as antioxidants in ginseng. Ginseng exhibits antioxidant activity when incorporated with turkey dark meat patties. The activity in red ginseng showed about two times stronger than white ginseng. One of the phenolic antioxidants from fresh, white and reprocessed white ginseng was identified as phenol 2.6 Bis(1.1 dimethyl ethyl) 4-methyl among several unknown compounds by GC/mass spectrometer. In red ginseng, no phenol 2.6 Bis (1.1 dimethyl ethyl) 4-methyl was detected, the compound may be polymerized by phenoloxidase and form some higher molecular compounds which may possess high antioxidant activity. Phenoloxidase isozymes in fresh Korean ginseng (panax ginseng C.A. Meyer) were extracted with phosphate buffer at pH 7.3. The isozymes were purified through ammonium sulfate fractionation, dialysis and chromatography on a DEAE-cellulose column. Two groups of phenoloxidase were shown to be present, one in the floating agglomerated group and the other in the precipitate. group from the 0.85 saturation ammonium sulfate. The DEAE-cellulose column chromatography, the phenoloxidase isozyme present in the precipitate appears as the first peak (I), and that in the agglomerate in the second peak (II). Isozyme I showed higher activity with catechin and catechal, and isozyme II showed higher activity with p-cresol. The isozyme showed two optimum pH activity one at pH 4.5 and the other at 8.5 with catechin as substrate. Korean ginseng phenoloxidase has high heat stability. When heated at $75^{\circ}C$ for 2 hours, its activity remained $90\%\;and\;80\%$ on phenoloxidase I and II respectively. Phenoloxidase I was most active on (+) catechin followed by p-cresal, catechol and epicatechin. Phenoloxidase II was most active on p-cresal followed by (+) catechin, catechol, p-coumanic acid and epicatechin. Sodium bisulfite, sodium cyanide, ascorbic acid glutachion in the oxidized form, sodium diethyl dithiocarbomate and ethylendiamine tetra acetate (EDTA) acted as inhibitors. Red ginseng color development was initiated by phenoloxidase and finished by a followed sun drying process. The antiaging activity of ginseng may be initiated by the antioxidant in the ginseng.

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Study of The Relation between Smoke Component and Sensory Evaluation of Cigarettes with the Different Leaf Blending (엽배합 특성에 따른 담배 연기성분과 관능특성과의 상관관계 구명)

  • 황건중;이문수;나도영
    • Journal of the Korean Society of Tobacco Science
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    • v.25 no.2
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    • pp.144-153
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    • 2003
  • This study was carried out to determine the relationship between smoke components and sensory evaluation by changes tobacco leaf blending. Seven different cigarettes were made by adding different types of oriental, reconstituted and expanded tobacco leaves. 62 kinds of smoke components which were 6 of general components, 34 of semi-volatile and volatile components, 9 of acid components, and 13 of phenolic components were analyzed. Eight kinds of sensory item were evaluated and also electronic nose system data was collected. All smoke components and sensory characteristics of mainstream smoke were changed by the different blending. To determine the relationship between smoke components and sensory test, the correlation and regression analysis were carried out by using SPSS statistical program. Tar, pH, and CO showed a high correlation with sensory evaluation item. As tar related to hotness, CO have a high correlation with offensive aroma. Semi-volatile and volatile components of smoke related to sensory characteristics such as aroma, taste, irritation, hotness and smoothness. When propylene, l,3-butadiene, butane, isoprene, and 2-methylfuran showed a high correlation with aroma; methyl chloride, methanol, toluene, ethyl benzene showed a high correlation with irritation. Some acidic components and phenolic components of smoke also had a high relation to smoke volume. Especially the acidic components such as 2-furoic acid, 2-hydroxybutyric acid, phenylacetic acid and palmitic acid; the phenolic components such as 4-vinyl phenol, pyrocatechol, 3-methyl catechol, hydroquinone showed a high correlation with smoke volume. As using regression analysis, it was possible to estimate the results of sensory evaluation from the smoke analysis data. From the results of electronic nose system analysis, we can find the different pattern by adding expanded tobacco leaf.

Changes of Tobacco Smoke Components by Adding Oriental, Reconstituted, and Expanded tobacco leaves (오리엔트엽, 판상엽, 팽화엽 첨가에 따른 담배 연기성분 변화)

  • 황건중;이문수;나도영;이윤환
    • Journal of the Korean Society of Tobacco Science
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    • v.24 no.2
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    • pp.113-120
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    • 2002
  • This study was conducted to determine the smoke component changes by adding oriental, reconstituted, and expanded tobacco leaves. 7 different cigarette brands which were mixed with flue-cured, burley, oriental, reconstituted and expanded tobacco leaves were used for this study. 64 kinds of smoke components which were 6 of general components, 34 of semi-volatile and volatile components, 9 of acid components, and 15 of phenolic components were analyzed. All smoke components of mainstream smoke were changed by the different branding. As Tar, nicotine, ammonia, pH, all of acid compounds(except lacatic and glycolic acid) were decreased; HCN, levoglucosame, 4-vinyl phenol, 4-vinyl catechol, quinic acid-r-lactone, acetaldehyde, 2,3-butadiene, stylene were increased by adding oriental tobacco leaves. When the reconstituted tobaccos were added to 20%, the concentration of nicotine, all of acid compounds(except lactic. glycolic, palmitic acid) and all of phenol compounds were reduced; the concentration of ammonia, HNC, CO, aeconitrile, benzene, 2-butanone, moth-acrolene, butyronitrile, stylene, o-xylene were increased. As decreasing ammonia, pH, nicotine, all of acid compounds, all of phenol compounds, Isoprene, acetonitrile, 2-methyl-2-butene, 1,3-pentadiene, 2-nlethyl furane, ethylene cyclopentanone, ethyl bezene; increasing CO concentration were followed by adding expanded tobacco leaves.

The Isolation of the Inhibitory Constitutents on Melanin Polymer Formation from the Leaves of Cercis chinensis (박태기나무의 잎으로부터 피부멜라닌 색소생성 억제성분의 분리)

  • Kim, So-Young;Kim, Jin-Joon;Jang, Tae-Soo;Chung, See-Ryun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.30 no.4
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    • pp.397-403
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    • 1999
  • Tyrosinase plays an important role in the process of melanin polymer biosynthesis. Therefore, the enzyme inhibitors have been of great concern as cosmetics to have skin-whitening effects on the local hyperpigmentation. During the search for new inhibitory compounds on melanin polymer biosynthesis from natural sources, MeOH extracts of 589 higher plants were tested for the inhibitory effect on tyrosinase activity by the muschroom tyrosinase assay in vitro. Among plants tested, the leaves of Cercis chinensis exhibited potent inhibitory effect on mushroom tyrosinase activity. Subsequently seven active compounds were isolated from the ethyl acetate soluble part of acetone extract of the leaves of C. chinensis by the activity guided fractionation monitoring the inhibitory effect on tyrosinase activity. Their chemical structures were identified as $kaempferol-3-0-{\alpha}-L-rhamnoside$, quercitrin, $myricetin-3-0-{\alpha}-L-rhamnoside$, myricetin-3-0-(2'-O-galloyl)- ${\alpha}$ -L-rhamopyranoside (desmanthin), (-)-epicatechin-3-0-gallate, (-)-epigallocatechin-3-0-gallate, and methyl gallate on the basis of the speculation of spectral data and chemical reaction. Among the flavonol rhamnosides, myricetin-3-0-(2'-O-galloyl)- -L-rhamnoside(desmanthin) showed most potent inhibitory effect on tyrosinase activity and the structure of B-ring in flavonol moiety was related to the activity. (-)-Epigallocatechin-3-O-gallate having pyrogallol group in flavan-3-ol moiety exhibited more potent inhibitory effect than (-)-epicatechin-3-0-gallate having catechol group in flavan-3-ol moiety on mushroom tyrosinase activity.

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Biodegradation of Aromatic Compounds by Nocardioform Actinomycetes

  • CHA CHANG-JUN;CERNIGLIA CARL E.
    • Proceedings of the Microbiological Society of Korea Conference
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    • 2001.11a
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    • pp.157-163
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    • 2001
  • Mycolic acid-containing gram-positive bacteria, so called nocardioform actinomycetes, have become a great interest to environmental microbiologists due to their metabolic versatility, multidegradative capacity and potential for bioremediation of priority pollutants. For example, Rhodococcus rhodochrous N75 was able to metabolize 4-methy1catechol via a modified $\beta$-ketoadipate pathway whereby 4-methylmuconolactone methyl isomerase catalyzes the conversion of 4-methylmuconolactone to 3-methylmuconolactone in order to circumvent the accumulation of the 'dead-end' metabolite, 4-methylmuconolactone. R. rhodochrous N75 has also shown the ability to transform a range of alkyl-substituted catechols to the corresponding muconolactones. A novel 3-methylmuconolactone-CoAsynthetase was found to be involved in the degradation of 3-methylmuconolactone, which is not mediated in a manner analogous to the classical $\beta$-ketoadipate pathway but activated by the addition of CoA prior to hydrolysis of lactone ring, suggesting that the degradative pathway for methylaromatic compounds by gram-positive bacteria diverges from that of proteobacteria. Mycobacterium sp. Strain PYR-l isolated from oil-contaminated soil was capable of mineralizing various polyaromatic hydrocarbons (PAHs), such as naphthalene, phenanthrene, pyrene, fluoranthrene, 1-nitropyrene, and 6-nitrochrysene. The pathways for degradation of PAHs by this organism have been elucidated through the isolation and characterization of chemical intermediates. 2-D gel electrophoresis of PAH-induced proteins enabled the cloning of the dioxygenase system containing a dehydrogenase, the dioxygenase small ($\beta$)-subunit, and the dioxygenase large ($\alpha$)-subunit. Phylogenetic analysis showed that the large a subunit did not cluster with most of the known sequences except for three newly described a subunits of dioxygenases from Rhodococcus spp. and Nocardioides spp. 2-D gel analysis also showed that catalase-peroxidase, which was induced with pyrene, plays a role in the PAH metabolism. The survival and performance of these bacteria raised the possibility that they can be excellent candidates for bioremediation purposes.

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New Unsymmetric Dinuclear Copper(II) Complexes of Trans-disubstituted Cyclam Derivatives: Spectral, Electrochemical, Magnetic, Catalytic, Antimicrobial, DNA Binding and Cleavage Studies

  • Prabu, R.;Vijayaraj, A.;Suresh, R.;Jagadish, L.;Kaviyarasan, V.;Narayanan, V.
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1669-1678
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    • 2011
  • Six new binuclear copper(II) complexes have been prepared by template condensation of the dialdehydes 1,8-[bis(3-formyl-2-hydroxy-5-methyl)benzyl]-l,4,8,11-tetraazacyclotetradecane (PC-a) and 1,8-[bis(3-formyl-2-hydroxy-5-bromo)benzyl]-l,4,8,11-tetraazacyclotetradecane (PC-b) with appropriate aliphatic diamines, and copper(II) perchlorate. The structural features of the complexes have been confirmed by elemental analysis, IR, UV-vis and mass spectra etc. The electrochemical behavior of all the copper(II) complexes show two irreversible one electron reduction process. The room temperature magnetic moment studies depict the presence of an antiferromagnetic interaction in the binuclear complexes. The catechol oxidation and hydrolysis of 4-nitrophenylphosphate were carried out by using the complexes as catalyst. The antimicrobial screening data show good results. The binding of the complexes to calf thymus DNA (CT DNA) has been investigated with absorption and emission spectroscopy. The complex [$Cu_2L^{1a}$] displays significant cleavage property of circular plasmid pBR322 DNA in to linear form. Spectral, electrochemical, magnetic and catalytic studies support the distortion of the copper ion geometry that arises as the macrocyclic ring size increases.

Relationship Between Tyrosinase Inhibitory Action and Oxidation-Reduction Potential of Cosmetic Whitening Ingredients and Phenol Derivatives

  • Sakuma, Katsuya;Ogawa, Masayuki;Sugibayashi, Kenji;Yamada, Koh-ichi;Yamamoto, Katsumi
    • Archives of Pharmacal Research
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    • v.22 no.4
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    • pp.335-339
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    • 1999
  • The oxidation-reduction potentials of cosmetic raw materials, showing tyrosinase inhibitory action, and phenolic compounds structurally similar to L-tyrosine were determined by cylcic voltammetry. The voltammograms obtained could be classified ito 4 patterns (patterns 1-4). Patterns 1, characterized by oxidation and reduction peaks as a pair, was observed with catechol, hydroquinone or phenol, and pattern 2 exhibiting another oxidation peak in addition to oxidation and reduction peaks as a pair was found with arbutin, kojic acid, resorcinol, methyl p-hydroxybenzoate and L-tyrosine as the substrate of tyrosinase. Pattern 3 with an independent oxidation peak only was expressed by L-ascorbic acid, and pattern 4 with a reduction peak only at high potentials, by hinokitiol. The tyrosinase inhibitory activity of these compounds was also evaluated using the 50% inhibitory concentration ($IC_{50}$) and the inhibition constant (Ki) as parameters. Hinokitiol, classified as patterns 4, showed the highest inhibitory activity (lowest $IC_{50}$ and Ki). Hydroquinone showing the second highest activity belonged to pattern 1, which also included compounds exhibiting pattern 2 was relatively low with Ki values being in the order of 10-4 M. Although there was no consistent relationship between oxidation-reduction potentials and tyrosinase inhibitory action, the voltammetry data can be used as an additional index to establish the relationship between the structure and the tyrosine inhibitory activity.

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Physiological and Phylogenetic Analysis of Burkholderia sp. HY1 Capable of Aniline Degradation

  • Kahng, Hyung-Yeel;Jerome J. Kukor;Oh, Kye-Heon
    • Journal of Microbiology and Biotechnology
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    • v.10 no.5
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    • pp.643-650
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    • 2000
  • A new aniline-utilizing microorganism, strain HY1 obtained from an orchard soil, was characterized by using the BIOLOG system, an analysis of the total cellular fatty acids, and a 16S rDNA sequence. Strain HY1 was identified as a Burkholderia species, and was designated Burkholderia sp. HY1. GC and HPLC analyses revealed that Burkholderia sp. HY1 was able to degrade aniline to produce catechol, which was subsequently converted to cis,cis-muconic acid through an ortho-ring fission pathway under aerobic conditions. Strain HY1 exhibited a drastic reduction in the rate of aniline degradation when glucose was added to the aniline media. However, the addition of peptone or nitrate to the aniline media dramatically accelerated the rate of aniline degradation. A fatty acid analysis showed that strain HY1 was able to produce lipids 16:0 2OH, and 11 methyl 18:1 ${\omega}7c$ approximately 3.7-, 2.2-, and 6-fold more, respectively, when grown on aniline media than when grown on TSA. An analysison the alignment of a 1,435 bp fragment. A phylogenetic analysis of the 16S rDNA sequence based on a 1,420 bp multi-alignment sowed of the 16s rDNA sequence revealed that strain HY1 was very closely related to Burkholderia graminis with 95% similarity based that strain HY1 was placed among three major clonal types of $\beta$-Proteobacteria, including Burkholderia graminis, Burkholderia phenazinium, and Burkholderia glathei. The sequence GAT(C or G)${\b{G}}$, which is highly conserved in several locations in the 16S rDNA gene among the major clonal type strains of $\beta$-Proteobacteria, was frequently replaced with GAT(C or G)${\b{A}}$ in the 16S rDNA sequence from strain HY1.

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