• Journal of the Korean Wood Science and Technology
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• v.13 no.4
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• pp.58-66
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• 1985

In order to elucidate chemical structure of the wood extractives, softwood (Pinus koraiensis Sieb. et Zucc.) meal was extracted with 95% ethanol at room temperature for 72 hours. The extract was fractionated with organic solvents such as n-hexane, ether, ethylacetate, and acetone. From the n-hexane and ether soluble fraction of the wood extractives, four flavonoid compounds were isolated and identified as 5-hydroxy-7-methoxyflavone (I), 5-methoxy-7-hydroxyflavone (II), 5-hydroxy-7-methoxyflavanone (III), and 5-methoxy-7-hydroxyflavanone (IV) by UV, IR, $^1$H-NMR spectroscopy and MS spectrometry.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.286.1-286.1
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• 2003

Chrysin, a natural flavone compound contained in plants. has anti-inflammatory activity. Its anti-inflammatory effect has been previously explained in part by the suppression of promoter activities of inducible pro-inflammatory enzymes (cyclooxygenase-2 (COX-2) and inducible nitrogen synthase (iNOS)). Nitrate production triggered by the activation of lipopolysaccharides (LPS) was most highly suppressed by the treatment of chrysin, follwed by 5-hydroxy-7-methoxyflavone (Ch-2), 5,7-diacetylflavone (Ch-4) in cultured Raw 264.7 cells. (omitted)

• Archives of Pharmacal Research
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• v.27 no.5
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• pp.507-511
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• 2004

From the flowers of Chromolaena odorata (Eupatorium odoratum) four flavanones, isosakuranetin (5,7-dihydroxy-4'-methoxyflavanone) (1), persicogenin (5,3'-dihydroxy-7,4'-dimethoxyflavanone) (2), 5,6,7,4'-tetramethoxyflavanone (3) and 4'-hydroxy-5,6,7-trimethoxyfla-vanone (4), two chalcones, 2'-hydroxy-4,4',5',6'-tetramethoxychalcone (5) and 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (6), and two flavones, acacetin (5,7-dihydroxy-4'-methoxyflavone) (7) and luteolin (5,7,3',4'-tetrahydroxyflavone) (8) were isolated and identified. Compound 1 exhibited moderate antimycobacterial activity against Mycobacterium tuberculosis with the MIC value of 174.8 $\mu$M, whereas compounds 4,7, and 8 exhibited weak activity with the MIC values of 606.0, 704.2 and 699.3 $\mu$M respectively. Compound 7 showed moderate cytotoxicity against human small cell lung cancer (NCI-H187) cells with the MIC value of 24.6 $\mu$M, whereas compound 8 exhibited moderate toxicity against NCI-H187 cells and week toxicity against human breast cancer (BC) cells with the MIC values of 19.2 and 38.4 $\mu$M respectively.

• Biomolecules & Therapeutics
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• v.13 no.3
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• pp.133-137
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• 2005

Wogonin(5,7-dihydroxy-8-methoxyflavone), an anti-inflammatory plant flavonoid, was previously demonstrated to modulate the several parameters of animal skin inflammation. This compound inhibited edematic response as well as proinflammatory gene expression. In this investigation, the histopathological changes of the lesions from different types of experimental skin inflammation were compared and the potential therapeutic effect of topically applied wogonin was evaluated. From the results, it was found that multiple TPA treatment drastically increased ear edema accompanied with epidermal hyperplasia and inflammatory cell infiltration, while phenol treatment provoked only edematic response in the dermal area. Wogonin somewhat differently inhibited these animal models of skin inflammation.

• Biomolecules & Therapeutics
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• v.14 no.1
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• pp.36-39
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• 2006

Some flavones/flavonols were previously found to inhibit collagenase. To establish a therapeutic potential for skin inflammation, twenty-three synthetic flavone derivatives were examined for their inhibitory potential against collagenase from Clostridium histolyticum. From the results, it was found that most of them having various hydroxyl, methoxyl, methylsulfuryl and/or chloro substitution(s) on A- and B-rings were not efficient collagenase inhibitors. Among the synthetic flavones tested, only two synthetic derivatives, 3',4'-dihydroxyflavone and 5-hydroxy-4'-methoxyflavone, weakly inhibited bacterial collagenase (13-29% inhibition at 50-100 ${\mu}M$).

• YAKHAK HOEJI
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• v.53 no.6
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• pp.377-381
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• 2009

Isowogonin, 5,8-dihydroxy-7-methoxyflavone, is a flavonoid isolated from the root of Scutellaria baicalensis Georgi, a medicinal plant traditionally used since the ancient time. It was thought to possess a variety of biological activities, such as antioxidation, anti-inflammation and hepatoprotective effect. But a quantity of isowogonin obtained from Scutellaria baicalensis Georgi is not that enough for in vivo test. There have been no appropriate approaches available for a facile synthesis of isowogonin. So we describe a concise and efficient scheme for synthesis of isowogonin from a commercial available 2,4,6-trimethoxyphenol, which includes the Fries rearrangement and selective demethylation as key steps.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.155.3-156
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• 2003

Flavonoids from plant origin show anti-inflammatory activity in vitro and in vivo. In addition to inhibition of inflammation-associated enzymes such as cyclooxygenases and lipoxygenases, they have been found to regulate the expression of inflammation-associated proteins from in vitro experiments. In order to prove in vivo behavior and the potential for beneficial use against inflammatory skin disorders, the effect of wogonin (5,7-dihydroxy-8-methoxyflavone) on in vivo expression of several inflammation-associated genes was examined in the intact as well as in the inflamed mouse skin by reverse transcriptase-polymerase chain reaction analysis. (omitted)

• Preventive Nutrition and Food Science
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• v.8 no.4
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• pp.330-335
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• 2003

Cirsium japonicum is a herbaceous perennial plant grown worldwide, which has been used as a folklore medicine due to its anti-inflammatory properties. A few studies have reported its functional properties, but analytical methods that more confidently and reproductively analyze the flavonoids are required. To establish analytical methods for the detection of flavones in Cirsium japonicum, the potential of HPLC and LC/MS were investigated. For this, the plants were separated into 4 parts; the root, stem, leaves, and flowers. The flavones in each part of the dried materials were analyzed by HPLC. Identification of flavones was performed by LC/MS. The leaves and flowers of Cirsium japonicum gave the optimum peaks, which were not detected by HPLC in the other parts of plants. Using LC/MS, three kinds of flavones were tentatively identified from the leaves, which were thought to be luteolin (5,7,3',4'-tetrahydroxy-flavone), apigenin (4',5,7-trihy-droxyflavone), and hispidulin (4',5,7-trihydroxy-6-methoxyflavone). Two flavones were detected from the flowers, which were been assumed to be apigenin and luteolin.

• Archives of Pharmacal Research
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• v.28 no.2
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• pp.216-219
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• 2005

Wogonin (5,7-dihydroxy-8-methoxyflavone) has been reported to exhibit a variety of biological properties including anti-inflammatory and neuroprotective functions. In this study, biological activities of diverse synthetic wogonin derivatives have been evaluated in two experimental cell culture models. Inhibitory activities of wogonin derivatives on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglial cells and on hydrogen peroxide ($H_{2}O_2$)-induced neuronal cell death in SH-SY5Y human neuroblastoma were examined. Wogonin derivatives such as WS2 and WS3 showed more potent suppressive activities on LPS-induced NO production and $H_{2}O_2$-induced cytotoxicity than wogonin itself. In addition, thiol substitution played a minor role in enhancing the activities of the derivatives. These findings may contribute to the development of novel anti-inflammatory and neuroprotective agents derived from wogonin.

• Archives of Pharmacal Research
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• v.27 no.4
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• pp.442-448
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• 2004

Wogonin (5,7-dihydroxy-8-methoxyflavone) is a down-regulator of cyclooxygenase-2 and inducible nitric oxide synthase expression, contributing to anti-inflammatory activity in vivo. For further characterization of modulatory activity on ploinflammatory gene expression in vivo, the effect of wogonin was examined in this experiment using animal models of skin inflammation. By topical application, wogonin inhibited an edematic response as well as ploinflammatory gene expression against contact dermatitis In mice. Wogonin inhibited ear edema ($19.4-22.6\%$) at doses of $50-200\;{\mu}g$/ear and down-regulated interleukin-$1{\beta}$ induction ($23.1\%$) at $200{\mu}g$/ear in phenol-induced simple irritation. Wogonin ($2{\times}50-2{\times}200{\mu}g$/ear) also inhibited edematic response ($51.2-43.9\%$) and down-regulated ploinflammatory gene expression of cyclooxygenase-2, interleukin-$1{\beta}$, interferon-$\gamma$, intercellular adhesion molecule-1 and inducible nitric oxide synthase with some different sensitivity against picryl chloride-induced delayed hypersensitivity reaction. All these results clearly demonstrate that wogonin is a down-regulator of ploinflammatory gene expression in animal models of skin inflammation. Therefore, wogonin may have potential for a new anti-inflammatory agent against skin inflammation.