• Title/Summary/Keyword: quinizarin

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Transient Protection of Intramolecular Hydrogen Bonding: A Simple but Elegant Approach for Functional Imaging

  • Kim, Jong-Man;Min, Sung-Jun;Park, Bum-Jun;Lee, Jae-Hyung;Ahn, Kwang-Duk
    • Macromolecular Research
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    • v.12 no.5
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    • pp.493-500
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    • 2004
  • We have developed a novel method for patterning functional images in thin polymer films. The key materials we utilized for the imaging were dihydroxyanthraquinones protected with acid-labile tert-butoxycarbonyl (t-Boc) blocking groups. Among the tested compounds, 1,4-dihydroxyanthraquinone (quinizarin; 1) underwent the most drastic change in terms of its color and fluorescence upon protection. We prepared the t-Boc-protected quinizarin and polymers bearing the protected quinizarins as pendent groups. To investigate the possibility of a single-component imaging system, we synthesized a styrenic monomer 14 incorporating protected quinizarin and a maleimide derivative 15 bearing a photoacid generating group and subjected them to polymerization. Selective removal of the protecting groups of the quinizarin moieties in the exposed area using photolithographic techniques allowed regeneration of quinizarin and patterned fluorescence images in the polymer films.

Inhibitory Effects of Quinizarin Isolated from Cassia tora Seeds Against Human Intestinal Bacteria and Aflatoxin $B_1$ Biotransformation

  • Lee, Hoi-Seon
    • Journal of Microbiology and Biotechnology
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    • v.13 no.4
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    • pp.529-536
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    • 2003
  • The growth-inhibitory activity of Cassia tora seed-derived materials against seven intestinal bacteria was examined in vitro, and compared with that of anthraquinone, anthraflavine, anthrarufin, and 1-hydroxyanthraquinone. The active constituent of C. tore seeds was characterized as quinizarin, using various spectroscopic analyses. The growth responses varied depending on the compound, dose, and bacterial strain tested. At 1 mg/disk, quinizarin exhibited a strong inhibition of Clostridium perfringens and moderate inhibition of Staphylococcus aureus without any adverse effects on the growth of Bifidobacterium adolescentis, B. bifidum, B. longum, and Lactobacillus casei. Furthermore, the isolate at 0.1 mg/disk showed moderate and no activity against C. perfringens and S. aureus. The structure-activity relationship revealed that anthrarufin, anthraflavine, and quinizarin moderately inhibited the growth of S. aureus. However. anthraquinone and 1-hydroxyanthraquinone did not inhibit the human intestinal bacteria tested. As for the morphological effect of 1 mg/disk quinizarin, most strains of C. perfringens were damaged and disappeared, indicating that the strong activity of quinizarin was morphologically exhibited against C. perfringens. The inhibitory effect on aflatoxin $B_1$ biotransformation by anthraquinones revealed that anthrarufin ($IC_50,\;11.49\mu\textrm{M}$) anthraflavine ($IC_50,\;26.94\mu\textrm{M}$), and quinizarin ($IC_50,\;4.12\mu\textrm{M}$), were potent inhibitors of aflatoxin ${B_1}-8,9-epoxide$ formation. However, anthraquinone and 1-hydroxyanthraquinone did not inhibit the mouse liver microsomal sample to convert aflatoxin $B_1$ to aflatoxin ${B_1}-8,9-epoxide$. These results indicate that the two hydroxyl groups on A ring of anthraquinones may be essential for inhibiting the formation of aflatoxin ${B_1}-8,9-epoxide$. Accordingly, as naturally occurring inhibitory agents, the C. tora seed-derived materials described could be useful as a preventive agent against diseases caused by harmful intestinal bacteria, such as clostridia, and as an inhibitory agent for the mouse liver microsomal conversion of aflatoxin $B_1$ to aflatoxin ${B_1}-8,9-epoxide$.

Biosynthesis of Rhamnosylated Anthraquinones in Escherichia coli

  • Nguyen, Trang Thi Huyen;Shin, Hee Jeong;Pandey, Ramesh Prasad;Jung, Hye Jin;Liou, Kwangkyoung;Sohng, Jae Kyung
    • Journal of Microbiology and Biotechnology
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    • v.30 no.3
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    • pp.398-403
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    • 2020
  • Rhamnose is a naturally occurring deoxysugar present as a glycogenic component of plant and microbial natural products. A recombinant mutant Escherichia coli strain was developed by overexpressing genes involved in the TDP-ʟ-rhamnose biosynthesis pathway of different bacterial strains and Saccharothrix espanaensis rhamnosyl transferase to conjugate intrinsic cytosolic TDP-ʟ-rhamnose with anthraquinones supplemented exogenously. Among the five anthraquinones (alizarin, emodin, chrysazin, anthrarufin, and quinizarin) tested, quinizarin was biotransformed into a rhamoside derivative with the highest conversion ratio by whole cells of engineered E. coli. The quinizarin glycoside was identified by various chromatographic and spectroscopic analyses. The anti-proliferative property of the newly synthesized rhamnoside, quinizarin-4-O-α-ʟ-rhamnoside, was assayed in various cancer cells.

Inorganic polymers of metal (Ⅱ) ions with Schiff's Base of quinizarin-ethylenediamine (Quinizarin-ethylenediamine의 Schiff's Base 와 금속 (Ⅱ) 이온이 만드는 Coordination polymer의 합성에 관하여)

  • Joon Suk Oh;Won Suk Kwak
    • Journal of the Korean Chemical Society
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    • v.13 no.1
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    • pp.29-36
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    • 1969
  • lnorganic polymers, which are composed of metal (Ⅱ) ions and Schiff's Base of quinizarin-ethylenediamine, have been prepared. In order to find out proper conditions for the reaction, some investigations have been carried out to test the effect of pH, kind of solvent and the state of reagent. As a result, the highest yield occurred near pH 7 and it was found that there were not great difference in the kind of solvent and the state of reagent we had used. Most of the polymers are seemed not to be those we have attempted to prepare. They are found to be coordination polymers which have rather low molecular weight.

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The First Synthesis of a Transition Metal-Catalyzed Homopolymer Having Pendent t-Boc-Protected Quinizarin for Patterned Fluorescence Images

  • Jimmy Yoo;Lee, Jae-Hyoung;Iwhan Cho;Ahn, Kwang-Duk;Kim, Jong-Man
    • Macromolecular Research
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    • v.11 no.1
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    • pp.69-72
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    • 2003
  • A homopolymer having pendent t-Boc-protected quinizarin moieties has been prepared for patterned fluorescence images. The homopolymer P(t-BQN (2-norbornenylmethyl di-tert-butoxycarbonylquinizarin)) 5 was prepared by palladium-catalyzed addition polymerization. The t-Boc-protecting groups of the polymer were efficiently removed during chemical amplification process and revealed original properties of quinizarin, allowing patterned fluorescence images in the polymer film.

Absorbance Elevation of Orimax Blue 2N, Orimax Green 151, Quinizarin, Topasol (P-250) and Lubricant (P-8) on the Spectrophotometric Analysis of Unimark 1494 DB (식별제(Unimark 1494DB) 정량시험에서 파란색 색소(Orimax Blue 2N, Orimax Green 151), Quinizarin, 토파졸(P-250) 및 윤활유 원료(P-8)의 흡광도상승 효과)

  • Lee, Ji-Yun;Kim, Chang-Jong
    • YAKHAK HOEJI
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    • v.50 no.5
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    • pp.313-321
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    • 2006
  • There are three kinds of liquid petroleum marker which is extracted by the basic or acidic, and both developer. Korean marker, Unimark 1494 DB (marker) have been spectrophotometrically analysed by the determination of absorbance at 582 nm after base extraction by Unimark 1494 DB Developer C-5 (developer). Some blue dyes which have same reactive radical of marker and can be changed deep blue color in base developer extraction (BDE), may be increased absorbance at 582 nm, but dyes or markers which can be increased the absorbance, were not unclear. In this experiment, effects of three dyes or marker such as Orimax Green 151 (the mixture of CI Solvent Yellow 16 and CI Solvent Blue 70), quinizarin and Orimax Blue 2N (CI Solvent Blue 35), and two solvent such as topasol (P-250) and lubricant (P-8) on the absorbance were studied by HITACHI Recording Spectrophotometer U-3300. It shows that all of them increased absorbance at 582 nm after BDE. Absorbance at 582 nm can be showed 0.0544 by Orimax Green 151 at the concentration of 3.96 mg/l, quinizarin at the concentration of 1.38 mg/l, and Orimax Blue 2N at the concentration of 2.73 mg/l in the artificial petroleum (normal diesel oil: topasol: lubricant=2 : 4: 4), respectively. Absorbance, 0.0544 indicates that concentration of marker is 1.64 mg/l in the reference curves, respectively. And also these results can be showed that the artificial petroleum have about 10% cheep fuel such as kerosene which have marker (16.0 mg/l). Absorbance of P-250 was 0.01361-0.22842 depending upon the purchasing date, and that of P-8 was 0.05644. pH of developer was 14.83, and so this result indicates that Unimark 1494 DB is a base extractable petroleum marker, phenylazophenol (US Patent No. 5,252,106). In the BDE, the slight color of Orimax Blue 2N, Orimax Green 151 and quinizarin in artificial petroleum changed to deep bright blue color, respectively. These result indicate that the absorbance at 582 nm by BDE may be increased not only by azo, diazo, amine and ketone (anthraquinone, coumarin) dyes or markers, but also the contaminants of P-250 and P-8 which have same as reactive radical of dyes or markers.

Photo-grafting Dyeing of Wool Fabrics with Dimethacrylated Quinizarin Dye (반응성 염료의 광그라프트에 의한 양모직물의 염색)

  • Dong, Yuanyuan;Jang, Jin-Ho
    • Proceedings of the Korean Society of Dyers and Finishers Conference
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    • 2012.03a
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    • pp.26-26
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    • 2012
  • The hydrophobic nature of the wool surface give rise to difficult penetration of dye molecules. Among all the methods of modification, graft polymerization is an attractive method to impart a variety of functional groups to a polymer. Grafting has been made by irradiating the light on the polymer in the presence of a solvent containing monomer. The energy source commonly used are high-energy electrons, X-rays, UV and visible light. UV irradiation is a relatively low-energy radiation in comparison with others since it has the least possibility to change bulk properties. In the present paper, a photo-reactive dye was synthesized from quinizarin by the reaction with methacryloyl chloride. The synthesized dye was continuously grafted onto wool fabric at room temperature by UV irradiation. Several key parameters including UV energy, dye concentration and pH have been examined to understand their influence on the photoreactive coloration.

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