• Title/Summary/Keyword: 4',7-Dimethoxyisoflavone

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Structure and Biological Activity of K(H2O)L (L = 5,7-Dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate)

  • Guo, Ya-Ning;Zhang, Xue-Ling;Zhang, Zun-Ting
    • Bulletin of the Korean Chemical Society
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    • v.27 no.9
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    • pp.1289-1292
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    • 2006
  • Potassium(I) with 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate (L) assembles to K($H_2O$)L (L = 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate). It was characterized by single-crystal X-ray diffraction, element analysis, IR and $^1H$ NMR spectroscopy. It crystallizes in the monoclinic space group $P2_1$/n and reveals a seven-coordinate complex. Polyhedra potassium chains, C-H${\cdot}{\cdot}{\cdot}\pi$ and C-H${\cdot}{\cdot}{\cdot}$O and O-H${\cdot}{\cdot}{\cdot}$O hydrogen bonds lead K($H_2O$)L to a three-dimensional network structure. The biological activity of resistance to hypoxia was tested, and the results showed that the biological activity of resistance to hypoxia of K($H_2O$)L is as good as that of its precursor, irisolidone.

Antifungal Activity of 4',7-Dimethoxyisoflavone Against Some Fungi

  • Pandey, M.K.;Pandey, R.;Singh, V.P.;Pandey, V.B.;Singh, U.P.
    • Mycobiology
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    • v.30 no.1
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    • pp.55-56
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    • 2002
  • The 4',7-dimethoxyisoflavone was isolated from the leaves of Albizzia lebbeck for the first time. This flavonoid showed antifungal activity against some plant pathogenic fungi tested in vitro, e.g., Alternaria melongenae, A. brassicicola, A. brassicae, Curvularia maculans, C. pallescens, C. lunata, Curvularia species, Colletotrichum species, Helminthosporium penniseti and H. speciferum. The sensitivity of different fungi to this chemical varied considerably. A. brassicae was most sensitive as complete inhibition of germination was observed in all the concentrations(100 to 1000 ppm) of the chemical. Similar effect on H. speciferum and Curvularia species was also recorded at 500 ppm, whereas H. penniseti did not germinate at 250 ppm. A. melongenae and A. brassicicola also did not germinate at 1000 ppm while 750 ppm was inhibitory to C. lunata and C. maculans. Germination in almost all fungi was significantly inhibited at each concentration in comparison to control except Curvularia sp. and H. speciferum. Use of 4',7-dimethoxyisoflavone to control some plant diseases under field conditions has been suggested.

Prolyl Endopeptidase-inhibiting Isoflavonoids from Puerariae Flos and Some Revision of their $^{13}C-NMR$ Assignment (갈화의 Prolyl Endopeptidase 저해 활성 Isoflavonoid 및 이들의 $^{13}C-NMR$ Assignment)

  • Kim, Kyung-Bum;Kim, Sang-In;Kim, Jong-Sik;Song, Kyung-Sik
    • Applied Biological Chemistry
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    • v.42 no.4
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    • pp.351-355
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    • 1999
  • In order to find anti-dementia drugs from natural products, prolyl endopeptidase inhibitors were purified from Puerariae Flos by consecutive solvent partition, followed by silica gel, Sephadex LH-20, and HPLC. Four isoflavonoid inhibitors were isolated and identified as tectorigenin, genistein, 5,7-dihydroxy-4',6-dimethoxyisoflavone, and 5-hydroxy-6,7,4'-trimethoxyisoflavone by means of instrumental analyses including $^{1}H-$, $^{13}C-$, $^{2}D-NMR$ and MS and $IC_{50}$ values against PEP were 5.30 ppm$(17.7\;{\mu}M)$, 10.39 ppm$(38.5\;{\mu}M)$, 13.92 ppm$(44.3\;{\mu}M)$, and 20.61 ppm$(62.8\;{\mu}M)$, respectively. Some previous mistakes in $^{13}C-NMR$ assignment were revised by careful investigation of HMBC and HMQC data.

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Studies on Biological Activity of Wood Extractives(VII) - Antifungal activity of Isoflavonoids from Sophora japonica - (수목추출물의 생리활성에 관한 연구(VII) - 회화나무 Isoflavonoid의 항균활성 -)

  • Park, Young-Ki;Lee, Hak-Ju;Lee, Sung-Suk;Choi, Don-Ha;Yeo, Woon-Hong;Oh, Jung-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.4
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    • pp.89-96
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    • 2001
  • Three isoflavones and one isoflavanone were isolated from the wood of Sophora japonica (Leguminosae) which has been selected due to its high antifungal activity among the tested species, Four compounds were identified as 5,7-dihydroxy-4',6-dimethoxyisoflavone (irisolidone), 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), 7-hydroxy-4'-methoxyisoflavone (formononetin) and 7-hydroxy-4'-methoxy-isoflavanone by Mass and NMR spectroscopic analysis. The antifungal activity of the isoflavonoids was tested by medium dilution method and showed low antifungal activity indicating that the other compounds may contribute to high activity of the wood extractives of S. japonica.

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Immuno-Regulatory Activities of an Isoflavone Glycoside, 4', $6-Dimethoxylsoflavone-7-O-{\beta}-D-Glucopyranoside$ and the Crude Extract Isolated from Amorpha fruticosa LINNE

  • Kim, Jung-Hwa;Kim, Cheol-Hee;Kwon, Min-Cheol;Kim, Hyou-Sung;Lee, Kang-Yoon;Lee, Hyun-Jung;Kang, Ha-Young;Lee, Hak-Ju;Lee, Hyeon-Yong
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.2
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    • pp.63-69
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    • 2006
  • The methanolic (MeOH) extract of A. fruticosa bark, which showed immune-regulatory activities, was separated to purify an active compared by means of a multi-stage column chromatography. This resulted in the isolation and characterization of an isoflavone glycoside named 4', $6-Dimethoxyisoflavone-7-O-{\beta}-D-glucopyranoside$. Immuno-regulatory activities of the crude extract of Amorpha fruticosa LINNE bark were compared with that of an isoflavone glycoside (4', $6-dimethoxyisoflavone-7-O-{\beta}-D-glucopyranoside$). The crude methanolic extract of A. fruticosa and purified single compound showed 16% of relatively low cytotoxicity at a maximum concentration of 1.0 g/L in cultivated normal human lung cell line (HEL299). Cell growth of human T cells was increased up to 15%, 0.5 g/L of the crude extract added group. This was higher than a single compound added one. On the other hand, specific production rates of IL-6 and $TNF-{\alpha}$ from T cell were higher in the purified compound treat group ($0.82{\times}10^{-4}\;pg/cell$ and $1.08{\times}10^{-4}\;pg/cell$, respectively), compared to 0.5 g/L of the crude extract added group ($0.65{\times}10^{-4}\;pg/cell$ and $0.84{\times}10^{-4}\;pg/cell$, respectively). In addition, the growth of NK-92MI cells incubated with the crude extract was higher up to 56% over the cells grown with a single compound (0.5 g/L). In overall, the crude extract showed relatively higher immuno-regulatory activities compared with a single compound, probably due to the synergic effect given by other substances existed in the crude extract. Even though the siolated compound stimulated higher secretion of cytokines from human T cells.

Isoflavone Compounds of the Heartwood of Maackia fauriei (솔비나무(Maackia fauriei)의 이소플라본 화합물)

  • Hwang, Myoung-Hui;Kwon, Yong-Soo;Kim, Chang-Min
    • YAKHAK HOEJI
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    • v.41 no.4
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    • pp.444-449
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    • 1997
  • Five flavonoids were isolated from the heartwoods of Maackia fauriei. On the basis of spectroscopic evidences, the structure of these compounds were established as (-)maa ckiain(3-hydroxy-8,9-methylenedioxypterocarpan), ononin(4'-methoxyisoflavone- 7-O-${\beta}$-D-glucoside), wistin(4',6-dimethoxyisoflavone-7-O-${\beta}$-D-glucoside), daidzin(4'-hydroxyisoflavone-7-O-${\beta}$-D-glucoside) and 2'-methoxy-4'- hydroxyisoflavone-6-O-${\beta}$-D-glucoside. In these compounds, 2'-methoxy-4'-hydroxyisoflavone-6-O-${\beta}$-D-glucoside was for the first time isolated from the plant source.

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Studies on Biological Activity of Wood Extractives (X VIII) -Isolation and Antioxidant Activity of Chemical Constituents from Maackia amurensis- (수목추출물의 생리활성에 관한 연구(X VIII) -다릅나무(Maackia amurensis) 수피의 추출성분의 분리 및 항산화 활성-)

  • Kim, Woo-Jin;Lee, Hak-Ju;Lee, Sang-Keug;Kang, Ha-Young;Choi, Don-Ha;Choi, Tae-Ho
    • Journal of the Korean Wood Science and Technology
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    • v.35 no.6
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    • pp.135-144
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    • 2007
  • The dried barks of Maackia amurensis were ground, extracted with 95% EtOH, concentrated, and fractionated with a series of light petroleum ether, dichloromethane, ethyl acetate and water on a separatory funnel. Each fraction was concentrated, then a portion of dichloromethane and ethyl acetate soluble was chromatographed on a Sephadex LH-20 and silica gel 60 column using a various solvent system as eluents. The isolated compounds were identified by cellulose TLC, $^1H-$, $^{13}C-NMR$, COSY, NOESY, HMQC, HMBC, FAB and EI-MS. The structures were determined as: 7-O-$\beta$-D-glucopyranosyl-4'-methoxyisoflavone, 7-O-$\beta$-glucopyranosyl(1'''->6'')-$\beta$-D-glucopyranosyl-4'-methoxyisoflavone, 7-O-$\beta$-D-glucopyranosyl(1''''->6''')-$\beta$-D-glucopyranosyl(1'''->6'')-$\beta$-D-glucopyransoyl-4'-methoxyisoflavone, 7-O-$\beta$-D-glucopyranosyl-4', 6-dimethoxyisoflavone. The Free radical scavenging activity using DPPH of the isolated compounds were similar with that of BHT but lower than of $\alpha$-tocopherol.

Inhibitory Activities of Three Compounds from Mucuna birdwoodiana on $3{\alpha}-Hydroxysteroid\;dehydrogenase$ (계혈등(Mucuna birdwoodiana)의 $3{\alpha}-Hydroxysteroid\;dehydrogenase$억제 성분)

  • Kwon, Yong-Soo;Lee, Jin-Hun;Kim, Chang-Min
    • Korean Journal of Pharmacognosy
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    • v.30 no.2
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    • pp.216-221
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    • 1999
  • The NAD(P)-linked $3{\alpha}-Hydroxysteroid$ $dehydrogenase(3{\alpha}-HSD)$ of rat liver cytosol is powerfully inhibited by the non-steroidal anti-inflammatory drugs in rank-order of their therapeutic potency, and this observation has now been developed into a rapid screen for predicting the potency of products that show anti-inflammatory effect. Five-plants were screened by using this method. Among them, BuOH-fraction of Mucuna birdwoodiana showed strong inhibitory effect on $3{\alpha}-HSD$, and three isoflavone compounds were isolated. Inhibitory activates of isolated compounds were compared.

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