• Archives of Pharmacal Research
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• 제25권3호
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• pp.329-335
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• 2002

Previously, several prenylated flavonoids having a C-8 lavandulyl moiety were found to inhibit cyclooxygenase-1 (COX-1) as well as 5-lipoxygenase (5-LOX), and sophoraflavanone G was the most potent inhibitor against these eicosanoid generating enzymes among 19 prenylated flavonoids tested. In this investigation, effects of sophoraflavanone G on COX-2 induction from RAW 264.7 cells and in vivo inflammatory response were studied. Sophoraflavanone G inhibited prostaglandin $E_2{\;}(PGE_2)$ production from lipopolysaccharide (LPS)-treated RAW cells by COX-2 down-regulation at 1-50 uM. Other prenylated flavonoids including kuraridin and sanggenon D also down-regulated COX-2 induction at 10-25 uM, while kurarinone and echinoisoflavanone did not. In addition, sophoraflavanone G showed in vivo anti-inflammatory activity against mouse croton oil-induced ear edema and rat carrageenan paw edema via oral (2-250 mg/kg) or topical administration (10-250 ug/ear). Although the potencies of inhibition were far less than that of a reference drug, prednisolone, this compound showed higher anti-inflammatory activity when applied topically, suggesting a potential use for several eicosanoidrelated skin inflammation such as atopic dermatitis.

• Applied Biological Chemistry
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• 제47권2호
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• pp.270-273
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• 2004

꾸지뽕나무(Cudrania tricuspidata Bureau)의 클로로포름 추출물로부터 2종의 prenylated flavonoid 항균 물질을 분리하였다. 분리할 화합물에 대하여 항균활성을 실험 한 결과 화합물 1과 2는 $10\;{\mu}g/disk$의 농도에서 Gram 양성균인 Staphylococcus aureus, Bacillus subtilis 그리고 Bacillus cereus에 대하여 활성을 보였다. 이들의 구조를 $^lH\;NMR,\;^{13}C\;NMR$ 및 2D NMR을 포함한 분광학적인 방법을 통하여 분석한 결과, 화합물 1과 2는 euchrestaflavanone B와 euchrestaflavanone C로 각각 동정 되었다.

• Archives of Pharmacal Research
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• 제27권11호
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• pp.1132-1135
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• 2004

In order to find new tyrosinase inhibitors and the effects of prenyl residue on flavonoid molecules, eight prenylated and three synthetic vinylated flavonoids were examined on their inhibitory effect against tyrosinase activity. From the results, kuwanon C, papyriflavonol A, sanggenon D and sophoflavescenol were found to possess the considerable inhibitory activity. Especially, sanggenon D is revealed as a potent inhibitor ($IC_{50}$ =7.3$\mu$ M), compared to the reference compound, kojic acid ($IC_{50}$ =24.8 $\mu$M). However, the prenylation with isoprenyl group or the vinylation to flavonoid molecules did not enhance tyrosinase inhibitory activity.

• 생약학회지
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• 제49권3호
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• pp.189-202
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• 2018

Hop cones (Humuli Strobili) are the female inflorescences of hop plants (Humulus lupulus L.) belonging to the family Cannabaceae. They have been used as herbal remedies to treat mood and sleep disturbances, and mainly to add as a bittering ingredient in brewing process. Considerable interests on pharmacological and biological activities of hop cones have been focused on their major constituents, namely, phloroglucinols (humulone, lupulone), terpenes (myrcene, humulene), and prenylated flavonoids (xanthohumol, isoxanthohumol, 6-prenylnaringenin, and 8-prenylnaringenin). The present review describes and discusses biological activity profiles of these major compounds in the hop cones.

• 생약학회지
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• 제43권4호
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• pp.302-307
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• 2012

The herb of Artemisia capillaris in Chinese medicine is used to treat hepatic diseases. In this research, qualitative analysis was performed using a UPLC/Q-TOF-ESI-MS/MS method for rapid identification of phenolic substances from A. capillaris: three caffeoylquinic acids (chlorogenic acid, 3,5-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid), three flavonoids (hyperoside, isorhamnetin 3-O-robinobioside and quercetin) and three prenylated coumarins (6,8-diprenylumbelliferone, cedrelopsin and osthol) were identified. The three prenylated coumarins have not been reported from A. capillaris.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 2007년도 Proceedings of The Convention
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• pp.67-73
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• 2007

There have been various inflammatory skin disorders in humans including atopic dermatitis, eczema and psoriasis. Although some drugs have been used for these disorders, there is an urgent need for safer and more effective topical anti-inflammatory agents. Plant flavonoids possess anti-inflammatory activity and some of them have multiple pharmacological mechanisms, inhibition of eicosanoid metabolizing enzymes, histamine release and/or down-regulation of pro inflammatory gene expression. These properties of flavonoids may be suitable for treating chronic skin inflammatory disorders. Especially, wogonin, some prenylated flavonoids and biflavonoids have a strong potential as new anti-inflammatory agents by topical application.

• 생약학회지
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• 제33권2호통권129호
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• pp.110-115
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• 2002

Seven prenylated flavonoids and two pterocarpans together with a saponin were isolated from the roots of Echinosophora koreensis. They were identical with echinoisosophoranone, echinoisoflavanone, isosophoranone, sophoraisoflavanone A, kenusanone C, kenusanone A, sophoraflavanone D, 4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxy-pterocarpans, (-)-maackiain, and $3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}2)-{\beta}-D-galactopyranosyl(1{\rightarrow}2)-{\beta}-D-glucuronopyranosyl$ kuzusapogenol A. Among them, a pterocarpan, 4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxypterocarpan, and a saponin, $3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}2)-{\beta}- D-galactopyranosyl(l{\rightarrow}2)-{\beta}-D-glucuronopyranosyl$ kuzusapogenol A, were isolated for the first time from this plant.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 2001년도 추계학술대회 및 정기총회
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• pp.82-82
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• 2001

Previously, several prenylated flavonoids having a C-8 lavandulyl moiety were found to inhibit cyclooxygenase-1 (COX-1) as well as 5-lipoxygenase (5-LOX), and sophoraflavanone G was the most potent inhibitor against these eicosanoid generating enzymes among the prenylated flavonoids tested. In this investigation, effects of sophoraflavanone G on COX-2 induction from RAW 264.7 cells and in vivo inflammatory response were studied. Sophoraflavanone G inhibited prostaglandin E$_2$(PGE$_2$) production from lipopolysaccharide (LPS)-treated RAW cells by COX-2 down-regulation without significantly affecting COX-2 activity at 1 50 $\mu$M. Other prenylated flavonoids including kuraridin and sanggenon D also down-regulated COX-2 induction at 10-25 $\mu$M, lirhile kurarinone and echinoisoflavanone did not. In addition, sophoraflavanone G shelved in vivo anti-inflammatory activity against mouse croton oil-induced ear edema and rat carrageenan paw edema via oral (2-250mg/kg) or topical administration (10 - 250 $\mu\textrm{g}$/ear). Although the potencies of inhibition were far less than that of a reference drug, prednisolone, this compound showed higher anti-inflammato교 activity when applied topically, suggesting a potential use for several eicosanoid-related skin inflammation such as atopic dermatitis.

• Journal of Microbiology and Biotechnology
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• 제20권10호
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• pp.1397-1402
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• 2010

Papyriflavonol A (PapA), a prenylated flavonoid [5,7,3',4'-tetrahydroxy-6,5'-di-(${\gamma},{\gamma}$-dimethylallyl)-flavonol], was isolated from the root barks of Broussonetia papyrifera. Our previous study showed that PapA has a broad-spectrum antimicrobial activity against pathogenic bacteria and fungi. In this study, the mode of action of PapA against Candida albicans was investigated to evaluate PapA as an antifungal agent. The minimal inhibitory concentration (MIC) values were 10~25 ${\mu}g/ml$ for C. albicans and Saccharomyces cerevisiae, Gram-negative bacteria (Escherichia coli and Salmonella typhimurium), and Gram-positive bacteria (Staphylococcus epidermidis and Staphylococcus aureus). The kinetics of cell growth inhibition, scanning electron microscopy, and measurement of plasma membrane florescence anisotrophy revealed that the antifungal activity of PapA against C. albicans and S. cerevisiae is mediated by its ability to disrupt the cell membrane integrity. Compared with amphotericin B, a cell-membrane-disrupting polyene antibiotic, the hemolytic toxicity of PapA was negligible. At 10~25 ${\mu}g/ml$ of MIC levels for the tested strains, the hemolysis ratio of human erythrocytes was less than 5%. Our results suggest that PapA could be a therapeutic fungicidal agent having potential as a broad spectrum antimicrobial agent.

• Natural Product Sciences
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• 제25권3호
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• pp.268-274
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• 2019

Morus alba L., known as white mulberry, is a medicinal plant belongs to family Moraceae. It has long been used commonly in Ayurvedic for the treatment of lung-heat, cough, asthma, hematemesis, dropsy and hypertension. In the present study, seven prenylated flavonoids, along with four benzofuran compounds were isolated by means of repeated column chromatography. The structures of the known compounds were identified as kuwanon G (1), kuwanon E (2), kuwanon T (3), morusin (4), sanggenon A (5), sanggenon M (6), sanggenol A (7), moracin R (8), mulberofuran G (9), mulberofuran A (10) and mulberofuran B (11), by comparing their spectroscopic data with those reported in the literature. For these isolates, containing trace compounds, the inhibitory activity against IL-6 production in $TNF-{\alpha}$ stimulated MG-63 cells was examined. All isolated compounds (1 - 11) showed excellent inhibitory activity against IL-6 production in $TNF-{\alpha}$ stimulated MG-63 cells. Especially this study is first time to report that sanggenon A (5), sanggenon M (6), sanggenol A (7), mulberofuran G (9), mulberofuran A (10) and mulberofuran B (11) showed the inhibitory activity of IL-6 production. Our study suggested the possibility of anti-inflammatory regulation by compounds (1 - 11) isolated from M. alba.