• Title/Summary/Keyword: quercetin derivatives

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Effects of quercetin derivatives from mulberry leaves: Improved gene expression related hepatic lipid and glucose metabolism in short-term high-fat fed mice

  • Sun, Xufeng;Yamasaki, Masayuki;Katsube, Takuya;Shiwaku, Kuninori
    • Nutrition Research and Practice
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    • v.9 no.2
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    • pp.137-143
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    • 2015
  • BACKGROUND/OBJECTIVES: Mulberry leaves contain quercetin derivatives, which have the effects of reducing obesity and improving lipid and glucose metabolism in mice with obesity. It is not clear whether or not mulberry leaves can directly affect metabolic disorders, in the presence of obesity, because of the interaction between obesity and metabolic disorders. The aim of the current study was to assess the direct action of quercetin derivatives on metabolic disorders in non-obese conditions in short-term high-fat diet fed mice. MATERIALS/METHODS: C57BL/6N mice were fed a high-fat diet, supplemented with either 0% (control), 1%, or 3% mulberry leaf powder (Mul) or 1% catechin powder for five days. Anthropometric parameters and blood biochemistry were determined, and hepatic gene expression associated with lipid and glucose metabolism was analyzed. RESULTS: Body and white fat weights did not differ among the four groups. Plasma triglycerides, total cholesterol, and free fatty acids in the 1%, 3% Mul and catechin groups did not differ significantly from those of the controls, however, plasma glucose and 8-isoprostane levels were significantly reduced. Liver gene expression of gp91phox, a main component of NADPH oxidase, was significantly down-regulated, and PPAR-${\alpha}$, related to ${\beta}$-oxidation, was significantly up-regulated. FAS and GPAT, involved in lipid metabolism, were significantly down-regulated, and Ehhadh was significantly up-regulated. Glucose-metabolism related genes, L-PK and G6Pase, were significantly down-regulated, while GK was significantly up-regulated in the two Mul groups compared to the control group. CONCLUSIONS: Our results suggest that the Mul quercetin derivatives can directly improve lipid and glucose metabolism by reducing oxidative stress and enhancing ${\beta}$-oxidation. The 1% Mul and 1% catechin groups had similar levels of polyphenol compound intake ($0.4{\times}10^{-5}$ vs $0.4{\times}10^{-5}$ mole/5 days) and exhibited similar effects, but neither showed dose-dependent effects on lipid and glucose metabolism or oxidative stress.

Excavation of Lead Compounds that Inhibit Mast Cell Degranulation by Combinatorial Chemistry and Activity-Guided

  • Hahn, Hoh-Gyu;Oh, Heong-Sub;Cheon, Seung-Hoon;Oak, Min-Ho;Kim, Young-Ran;Kim, Kyeong-Man
    • Archives of Pharmacal Research
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    • v.27 no.5
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    • pp.518-523
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    • 2004
  • An allergic reaction ensues after antigen binds to mast cell or basophil high affinity IgE receptor, Fc$\varepsilon$RI, resulting in degranulation of various inflammatory mediators that produce various allergic symptoms. In this study, i) we isolated the active component for the inhibition of mast cell degranulation from the extract of leaves of Castanea crenata and identified it as quercetin; ii) we established the total synthesis procedure of quercetin; iii) using quercetin as positive control, we excavated some lead compounds that possess inhibitory activities for mast cell degranulation by screening the chemical libraries of 1,3-oxazolidine derivatives prepared by solid phase combinatorial chemistry. Some of 1,3-oxazolidine compounds possessing acetyl and 3',4'-dichlorophenyl group displayed strong inhibitory activities on Fc$\varepsilon$RI-mediated mast cell degranulation, suggesting that they can be used as lead compounds for the development of anti-allergic agents.

Antiinflammatory Activity of Naturally Occurring Flavone and Flavonol Glycosides

  • Lee, Song-Jin;Son, Kun-Ho;Chang, Hyeun-Wook;Do, Jae-Chul;Jung, Keun-Young;Kang, Sam-Sik;Kim, Hyun-Pyo
    • Archives of Pharmacal Research
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    • v.16 no.1
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    • pp.25-28
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    • 1993
  • Our previous report demonstrated that certain flavonoid aglycones such as apigenin (flavone), quercetin, morin (flavonols), and biochanin A (isoflavone) showed in vivo antiinflammatory activity via topical and oral routes of adminstation. As a continual study, the various flavonoid glycosides have been evaluated in mouse ear edema assay using archidonic acid or croton-oil as a inflammagen. Flavonoids were orally administered (2 mg/mouse) and ear edema inhibition was measured. Significant antiinflammatory activities were found esepcially in flavone and flavonol glycosides (15-29% inhibition) although the flavonoid derivatives tested showed less antiinflammatory activity than hydrocortisone or indomethacin. Chalcone and flavanone derivatives were not significantly active. And in general, flavonol glycosides of kaempferol-type were found to have a higher oral antiinflammatory activity than that of flavonol glycosides of quercetin-type in mice.

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Flavonoid chemistry of Fallopia sect. Reynoutria (Polygonaceae) in Korea (한국산 닭의덩굴속 호장근절(마디풀과)의 화학분류학적 연구)

  • Park, Jin Hee;Moon, Hye-Kyoung;Park, Chong-Wook
    • Korean Journal of Plant Taxonomy
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    • v.41 no.1
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    • pp.10-15
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    • 2011
  • Fifteen populations comprising three taxa and a putative hybrid of Fallopia sect. Reynoutria in Korea were examined for their leaf flavonoid constituents. Nineteen flavonoid compounds were isolated and identified; they were glycosylated derivatives of the flavonols quercetin and kaempferol, and of the flavones apigenin and luteolin. Among them, quercetin 3-O-galactoside and quercetin 3-O-glucoside were major flavonoid constituents, and present in all taxa. The flavonoid data appear to be very useful for taxon delimitation, and all taxa examined are readily distinguished by their flavonoid profiles. In addition, the flavonoid data suggest that the Nonsan population may be of hybrid origin involving F. japonica var. japonica, F. forbesii, and F. sachalinensis. In F. japonica var. japonica, there is no apparent correlation between their levels of polyploidy and flavonoid chemistry, but geographical variation of the flavonoid profiles among some populations was detected.

Antiinflammatory Activity of Flavonoids:Mouse Ear Edema Inhibition

  • Kim, Hee-Kee;Namgoong, Soon-Young;Kim, Hyun-Pyo
    • Archives of Pharmacal Research
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    • v.16 no.1
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    • pp.18-24
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    • 1993
  • In this inverstigation, the various flavonoid aglycones were evaluated for their inhibitory activities against croton-oil or arachidonic acid induced mouse ear edema by oral or topical administration. The compounds tested were thirteen derivatives of flavan-3-ol(catechin and epicatechin), flavanone (flavanone and naringenin), flavone (flavone, chrysin and apigenin), flavonol(favonol, galangin, quercetin and morin) and isoflavone (biochanin A and 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone), along with hydrocortisone, indomethacin, 4-bormophenacyl bromide, nordihydroguaiaretic acid and phenidone as positive controls. A(isoflavone) were found to show broad inhibitoty activities (14-52%) against croton-oil or arachidonic acid induced ear edema by oral or topical application at the dose of 2 mg/mouse, although they showed less activity than hydrocortisone (26-88%) or indomethacin (36-80%). Flavonoid agtlycones tested showed higher activity when aplied topically than by the oral administration. It was also found that they inhibited arachidonic acid induced edema more profoundly than croton-oil induced edema by topical application. In arachidonic acid induced edema when applied topically, flavone derivatives such as flavone, chrysin and apigenin were revealed to be the good inhibitory agents in addition to flavonols and isoflavones. When quercetin and biochanin. A were selected for evaluating in carrageenan induced rat pleurisy and biochanin both flavonoids showed antiinflammatory activity at the dose of 70 mg/kg by the oral adminis-tration. All of these results revealed that flavonoid aglycones, especially 5,7-dihydroxy-flavonols having hydroxyl group(s) in B-ring and biochanin A (isoflavone) possessed in vivo antiinflammatory activity.

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Hybridization of Quercus aliena Blume and Q. serrata Murray in Korea - Analyses of Morphological variation and Flavonoid chemistry -

  • Park, Jin Hee;Park, Chong-Wook
    • Korean Journal of Environment and Ecology
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    • v.29 no.2
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    • pp.145-161
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    • 2015
  • This research was conducted in order to understand the hybridization between Quercus aliena Blume and Q. serrata Murray in Korea which show wide range of morphological variations within species and interspecific variations of diverse overlapping characteristics caused by hybridization. Morphological analysis (principal components analysis; PCA) of 116 individuals representing two species and their intermediates were performed. As a result, two species were clearly distinguished in terms of morphology, and intermediate morpho-types assumed to be hybrids between the two species were mostly located in the middle of each parent species in the plot of the principal components analysis. There was a clear distinction between two species in trichome distribution pattern which is an important diagnostic character in taxonomy of genus Quercus, whereas intermediate morpho-types showed intermediate state between two species' trichome distributions. Forty-two individuals representing two species and their intermediates were examined for leaf flavonoid constituents. Twenty-three flavonoid compounds were isolated and identified: They were glycosylated derivatives of flavonols, kaempferol, quercetin, isorhamnetin and myricetin. The flavonoid constituents of Q. aliena were five glycosylated derivatives: kaempferol 3-O-galactoside, kaempferol 3-O-glucoside, quercetin 3-O-galactoside, quercetin 3-O-glucoside, and Isorhamnetin 3-O-glucoside. The flavonoid constituents of Q. serrata had 20 diverse flavonol compounds including five flavonoid compounds found in Q. aliena. It was found that there is a clear difference in flavonoid constituents of Q. aliena and Q. serrata. Flavonoid chemistry is very useful in recognizing each species and putative hybrids. The flavonoid constituents of intermediates were a mixture of the two species' constituents and they generally showed similar characteristics to morpho-types. The hybrids between Q. aliena and Q. serrata showed morphologically and chemically diverse characteristics and it is assumed that there are frequent interspecific hybridization and introgression.

Determination of Several Phenolic Compounds in Cultivars of Grape in Korea (국내산 포도 품종의 주요 페놀계 화합물 함량 비교분석)

  • Chang, Seog-Won;Kim, Hyun-Ju;Song, Jeong-Hee;Lee, Ki-Yeol;Kim, Ik-Hwan;Rho, Yong-Taek
    • Food Science and Preservation
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    • v.18 no.3
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    • pp.328-334
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    • 2011
  • Natural polyphenolic compounds such as catechin, epicatechin derivatives, quercetin, and resveratrol, have been reported to have a wide range of biological activities against carcinogen and reactive oxygen species. The compounds can act together in synergy or can independently affect the activity. Contents of four compounds in different grape cultivar groups with different skin color were determined through HPLC. There were not significant differences in content of four phenolic compounds among the different skin color groups of the same grape cultivar groups, but were among different grape cultivars within the same skin color groups. Totally, contents of catechin, epicatechin derivatives were much higher than those of quercetin and resveratrol. In each skin color group, Campbell Early in Black, Seneka in Green, and Benigard in Red group showed highest contents, respectively. Nothing or a very small amount of four phenolic compounds was detected in some cultivars. This information would be useful for grape breeders and manufactures.

Antioxidant activity of ethanol extract and methanol fractions via column chromatography from Psidium guajava Leaf (구아바 잎 추출물 및 컬럼크로마토그래피를 이용한 메탄올 분획물의 항산화 활성)

  • Byeoung-Kyu Choi
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.266-271
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    • 2023
  • The antioxidant capacity of the Psidium guajava leaf extracted with EtOH and their MeOH fractions using column chromatography were evaluated by 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical scavenging assays, total phenolic and flavonoid content, and Superoxide dismutase (SOD) assay. To determine its utility as a functional material, the crude extract was fractionated by flash column chromatography on ODS using a stepwise elution with combinations of MeOH/H2O and then all the fractions were also investigated. In the results of antioxidant activities, the 40% and 60% MeOH fractions show the meaningful values, and then the two fractions were selected to examine the isolation and identification of the major constituents via HPLC and nuclear magnetic resonance. Further purification led to isolation of two quercetin derivatives; quercitrin (1) and isoquercetin (2). Through SOD assay, some methanol fractions via column chromatography and isolated compounds showed improved antioxidant activities compared to the extract.

Structural Determination of Oxidation Products of Flavonoids in Alcoholic Aqueous Solution with Reactive Oxygen Species

  • Hirose, Yuko;Kakita, Mitsuko;Washizu, Toshiyuki;Matsugo, Seiichi
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.424-426
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    • 2002
  • Recently, much attention has been paid to the physiological functions of flavonoids associated with their antioxidant properties. However, there was a lack of information on the molecular mechanism at which flavonoids play the antioxidative role. We have already studied on the oxidation of quercetin with hydrogen peroxide and sodium hypochlorite in alcoholic aqueous solution and determined the oxidation products. Through the structural analysis of the oxidation products, it was clarified that the hydroxyl group at C-3 in the C ring plays the important role in the antioxidative action of quercetin. Successively, rutin and (+)-catechin were oxidized with sodium hypochlorite and their mono- and di-chlorinated derivatives were obtained. These facts indicate that these flavonoids can directly scavenge hypochlorous acid and the active site in this scavenging reaction is not the hydroxyl group at C-3.

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Antioxidant Activity of Flavonoids and Their Glucosides from Sonchus oleraceus L.

  • Yin, Jie;Si, Chuan-Ling;Wang, Myeong-Hyeon
    • Journal of Applied Biological Chemistry
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    • v.51 no.2
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    • pp.57-60
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    • 2008
  • Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.