• Bulletin of the Korean Chemical Society
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• v.24 no.11
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• pp.1675-1679
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• 2003

The photodynamics of excited-state intramolecular proton transfer reaction of 1-hydroxyanthraquinone (1-HAQ) and 1-deuterioanthraquinone was investigated in toluene with time-resolved emission and femtosecond transient transmittance techniques at room temperature. The temporal profiles of transient transmittance of 1-HAQ could be well described with multi-decaying time constants. The ultrafast time constant within ca. 260 fs reflects the dynamics of proton transfer. The decay component of 2 ps is assigned to an additional proton translocation process induced by the intramolecular vibrational relaxation, whereas the decay component of 18 ps is assigned to the vibrational cooling process, while the long component (200 ps) can be explained in terms of the relaxation from excited-state keto-tautomer to its ground state. Time-resolved anisotropy decay dynamics and isotope effects on the photodynamics reveals that the ESIPT from enol-tautomer to keto-one of 1-HAQ is barrierless reaction and coupled to a vibrational relaxation process.

• 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 ${B_1}-8,9-epoxide$.

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.141-147
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• 1993

A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.

• Natural Product Sciences
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• v.8 no.2
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• pp.48-51
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• 2002

Antioxidative properties of fifteen anthraquinone derivatives, including eleven atural anthraquinones isolated from the roots of Morinda elliptica and four from synthetic origin were evaluated using thin layer chromatography (TLC), ferric thiocyanate (FTC) and thiobarbituric acid (TBA) methods. Five of the compounds, nordamnacanthal, damnacanthal, 2-formyl-1-hydroxyanthraquinone, morindone and alizarin showed higher antioxidative activity than standard natural antioxidant, ${\alpha}-tocopherol$, on the FTC assay. Morindone and alizarin showed the strongest antioxidant activity. The results from the bioassay using TBA method correlated well with the results of the FTC method.

• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.465-469
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• 2013

Proton transfer reaction is one of the most fundamental processes in chemistry and life science. Excited state intramolecular proton transfer (ESIPT) has been studied as a model system of the proton transfer, since it can be conveniently initiated by light. We report ESIPT reaction dynamic of 1-hydroxy-anthraquione (1-HAQ) in solution by highly time-resolved fluorescence. ESIPT time of 1-HAQ is determined to be $45{\pm}10$ fs directly from decay of the reactant fluorescence and rise of the product fluorescence. High time resolution allows observation of the coherent vibrational wave packet motion in the excited state of the reaction product tautomer. The coherently excited vibrational mode involves large displacement of the atoms, which shortens the distance between the proton donor and the acceptor. With the theoretical analysis, we propose that the ESIPT of 1-HAQ proceeds barrierlessly with assistance of the skeletal vibration, which in turn becomes excited coherently by the ESIPT reaction.

• Journal of Food Hygiene and Safety
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• v.28 no.4
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• pp.330-336
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• 2013

Rheum tanguticum has long been used in oriental medicine as antipyretics, analgesics, anti-inflammation, aperient, hypertension medicine and medicine for skin disease. This study has investigated the effectiveness of defense for gastritis making use of Rheum tanguticum and its similar plants, Rumex cripus, Rheum officinale, Rhem palmatum and Rheum undulatum. Chysophanol, chrysophanol-8-O-glc, Desoxyrhaponticin desoxyrhaponti-genin, emodin, isorhaponticin, 2-methoxy-4-hydroxyanthraquinone-5-O-glc, physcion, pirace-tannol-3'-O-glc, resveratrol, rhaponticin and rhapontigenin are used as the components of Rheum tanguticum. In HCl ethanol-induced gastritis in rat, the most effective extract was 70 percent ethanol which is of Rheum tanguticum, showing the inhibition of 91.8 percent to the gastric lesions. 70% ethanol extract of Rhem palmatum and Rumex cripus shown inhibition of 75.6 percent and 73.2 percent, respectively. This effectiveness is considered as acid-neutralizing capacity, anti-H.pylori and anti-oxidant activity. 70% ethanol extract of Rheum tanguticum and its component, piracetannol-3'-O-glc exhibited higher free radical scavenging activity than others. These results suggest that Rheum species extracts and their active components could be utilized for the treatment of gastritis. Furthermore, these results are expected to contribute the standardization with objectivity and reliability for Rheum species, medicinal herbs. In addition, it can contribute to the prevention of indiscriminate distribution of imitation, and the rising rate of dependence on imports of medicinal herbs, and mixing prevention of low-quality goods.