• 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)

• 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.

• Journal of Microbiology and Biotechnology
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• v.15 no.6
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• pp.1280-1285
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• 2005

Using the nodY::lacZ fusion system in Bradyrhizobium japonicum USDA 110, 22 flavonoids, which have structurally different features, were tested to define the role of the substituted functional groups as an inducer or inhibitor for the nod gene expression. A functional ,group of 4'-OH on the B-ring and the double bond between 2-C and 3-C on the C ring were required to induce the nod gene expression in B. japonicum USDA 110. In the case of isoflavones, the 4'-methoxyl group, which blocks the open 4'-OH functional group, did not significantly lower inducing activity, as compared with isoflavones with 4'-OH. However, all flavonols tested, which have a 3-OH functional group on the C-ring, did not induce, but inhibited the nod gene expression. Flavone, 7-hydroxyflavone, and kaempferol (5,7,4'-trihydroxyflavonol) at $1\;{\mu}M$ concentration significantly inhibited the nod gene expression induced by 7,4'-dihydroxyflavone. However, 7-hydroxy-4'-methoxyflavone at $1\;{\mu}M$ concentration showed a synergistic effect with genistein and 7,4'-dihydroxyflavone on the induction activity.

• Archives of Pharmacal Research
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• v.27 no.9
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• pp.930-936
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• 2004

Wogonin (5,7-dihydroxy-8-methoxyflavone), an active component originated from the root of Scutellaria baicalensis Georgi, has been reported to possess antioxidant and anti-inflamma-tory properties. In this study, we investigated the neuroprotective effect of wogonin in a focal cerebral ischemia rat model. Wogonin markedly reduced the infarct volume after 2 h middle cerebral artery occlusion followed by 22 h reperfusion. Wogonin decreased the production of nitric oxide and inflammatory cytokines such as TNF-$\alpha$ and IL-6 in lipopolisaccharide-stimu-lated microglial cells. While wogonin reduced the activity of NF-$textsc{k}$B, it did not change the activ-ity of mitogen-activated protein kinases family members, p38, ERK and JNK. The lipopolisaccharide-stimulated production of NO and cytokines was significantly blocked by vari-ous kinds of NF-$textsc{k}$B inhibitors such as N-acetyl cysteine, pyrrolidinedithiocarbamate and MG-132. The data may indicate that wogonin has neuroprotective effect by preventing the over-activation of microglial cells, possibly by inactivating NF-$textsc{k}$B signaling pathway

• Proceedings of the Korean Society of Applied Pharmacology
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• 2003.11a
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• pp.96-96
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• 2003

Previously, wogonin (5,7-dihydroxy-8-methoxyflavone) was found to suppress proinflammatory enzyme expression including cyclooxygenase-2 (COX-2), contributing to in vivo anti-inflammatory activity against skin inflammation. However, the detailed effect on each skin cell type has not been understood. Therefore, present investigation was carried out to find the effect of wogonin on inflammation-associated gene expression from skin fibroblasts in culture using reverse transcriptase-polymerase chain reaction. As a result, it was found that wogonin (10 - 100 ${\mu}$M) clearly down-regulated COX -2 expression from NIH/3T3 cells treated with 12-O-tetradecanoylphorbol 13-acetate, interleukin-1${\beta}$ or tumor necrosis factor-a. But, the expression levels of COX-1, interleukin-1${\beta}$ and fibronectin were not significantly affected. This finding was well correlated with significant reduction of prostaglandin E$_2$(PGE$_2$) production by wogonin. As a comparison, NS-398 (selective cyclooxygenase-2 inhibitor) did not suppress COX -2 expression and other gene levels, while PGE$_2$production was potently reduced at 0.1 - 10 ${\mu}$M. All these results suggest that COX -2 down-regulation of skin fibroblasts may be, at least in part, one of anti-inflammatory mechanisms of wogonin against skin inflammation.

• 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.

• 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.

• Journal of Applied Biological Chemistry
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• v.61 no.3
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• pp.227-232
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• 2018

Simultaneous determination of three methoxyflavones, namely, cirsimarin (1), hispidulin (2), and cirsimaritin (3) in selected Korean thistles was performed via reversed-phase high performance liquid chromatography system. Compound 1 was present in all the thistle species examined, whereas 2 and 3 were only detected in Cirsium japonicum and C. japonicum var. maackii (CJM). The concentration of compounds 1-3 in CJM varied according to the time of harvest. Plants collected in the spring (CJMS) and fall (CJMF) had the highest contents of 3 and 1, respectively. A lower content of 2 was observed in CJMF than in CJMS. This indicates that seasonal variation affects the flavonoid content of CJM. The results of this study show that CJM is an excellent source of compounds 1-3 and it can potentially be cultivated for industrial and pharmaceutical applications involving these compounds.

• 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.

• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1459-1462
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• 2009

Two new flavone glycosides, giraldiin A and B, together with three known compounds, annulatin, myricetin 3-O-$\alpha$- L-rhamnopyranoside and gallic acid, were isolated from the ethanol extract of the root of Pteroxygonum giraldii Damm. et Diels. The structures of giraldiin A and B are designated as 3'-($\alpha$-L-arabinopyranosyloxy)-4',5,5',7- tetrahydroxy-3-methoxyflavone and 4'-($\beta$-D-glucopyranosyloxy)-5,5',7-trihydroxy-2',3-dimethoxyflavone, respectively, on the basis of detailed spectroscopic analyses. The free radical scavenging activity of giraldiin A was evaluated by decolouring spectrophotometry of pentamethine cyanine dye (Cy5) with $Fe^{2+}-H_2O_2$ Fenton radical generating system. The results indicated the hydroxyl free radical scavenging activity of giraldiin A (E$D_{50}$ = 23.7 nmol/mL) is higher than that of some known antioxidants such as rutin, puerarin, daidzein and 2,6-di-tertbutyl-4-methylphenol.