• Title/Summary/Keyword: flavone

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Antimicrobial Effects of Flavone Analogues and Their Structure-Activity Relationships

  • Young, Jung-Mo;Park, Young-Hee;Lee, Yong-Uk;Kim, Ho-Jung;Shim, Yhong-Hee;Ahn, Joong-Hoon;Lim, Yoong-Ho
    • Journal of Microbiology and Biotechnology
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    • v.17 no.3
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    • pp.530-533
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    • 2007
  • It has been well known that the use of Saccharomyces cerevisiae can cause fungemia in critically ill patients and flavone shows an antimicrobial effect on S. cerevisiae. Therefore, we have investigated the activities of thirteen flavone analogues on S. cerevisiae in our studies. Because flavonoids including flavones have antioxidative effects, we try to carry out the activity studies of flavone analogues in vitro and in vivo. In addition, the relationships between the structures of flavone analogues and their biological activities, such as antimicrobial and antioxidative effects, were elucidated using Comparative Molecular Field Analysis calculations. Of the flavone analogues tested here, 3,2'-dihydroxyflavone showed both good antimicrobial and antioxidative activities.

Enhanced extraction and Antioxidant activity analysis of Flavone C-glycosides from Black bamboo using Ultrasonic wave (초음파를 이용한 오죽으로부터 Flavone C-glycosioes의 추출 및 항산화활성분석 향상)

  • Choi, Sun-Do;Lee, Kwang-Jin
    • KSBB Journal
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    • v.23 no.4
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    • pp.297-302
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    • 2008
  • In this work, the amounts of Flavone C-glycosides homoorientin, orientin extracted from Black bamboo by various ultrasonic waves frequency (35, 72, 170 KHz, 300 Watt $\pm$1) time (15, 30, 60 min) and temperature ($25^{\circ}C$) were compared using 50% aqueous ethanol solution. And describesanalysis of the antioxidant potential of Black bamboo using an high-performance liquid chromatography (HPLC) on-line $ABTS^+$antioxidant screening method. In conjunction with the analysis of their 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid ($ABTS^+$) radical scavenging ability. The optimum operating conditions were experimentally determined to analyze the Flavone C-glycosides homoorientin, orientin in the pretreatment ultrasonic extracts. From the results, the effect on extraction yield of variations in frequency, solvent composition and extraction time was investigated. The highest yield of Black bamboo was obtained by ultrasonic waves with a frequency of 72 KHz and an extraction time of 60 min, The extraction frequency 35 KHz ($25^{\circ}C$), time 30 min was selected as an optimal antioxidant activity condition.

NMR Data of Flavone Derivatives and Their Anti-oxidative Activities

  • Park, Yeong-Hui;Lee, Yong-Uk;Kim, Ho-Jung;Lee, Young-Shim;Yoon, Young-Ah;Mun, Byeong-Ho;Jeong, Yu-Hun;An, Jung-Hun;Shim, Yhong-Hee;Lim, Yoong-Ho
    • Bulletin of the Korean Chemical Society
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    • v.27 no.10
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    • pp.1537-1541
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    • 2006
  • The $^1H$ and $^{13}C$ chemical shifts of eleven flavone derivatives were completely determined by basic 1D and 2D NMR experiments. Nineteen flavone derivatives including the above eleven derivatives were examined for anti-oxidative effects using the 1,1-diphenyl-2-picryl-hydrazyl assay and Caenorhabditis elegans. In order to understand the relationships between the structures of flavone derivatives and their anti-oxidative activities, a Comparative Molecular Field Analysis was performed.

Biotransformation of Flavone by CYP105P2 from Streptomyces peucetius

  • Niraula, Narayan Prasad;Bhattarai, Saurabh;Lee, Na-Rae;Sohng, Jae Kyung;Oh, Tae-Jin
    • Journal of Microbiology and Biotechnology
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    • v.22 no.8
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    • pp.1059-1065
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    • 2012
  • Biocatalytic transfer of oxygen in isolated cytochrome P450 or whole microbial cells is an elegant and efficient way to achieve selective hydroxylation. Cytochrome P450 CYP105P2 was isolated from Streptomyces peucetius that showed a high degree of amino acid identity with hydroxylases. Previously performed homology modeling, and subsequent docking of the model with flavone, displayed a reasonable docked structure. Therefore, in this study, in a pursuit to hydroxylate the flavone ring, CYP105P2 was co-expressed in a two-vector system with putidaredoxin reductase (camA) and putidaredoxin (camB) from Pseudomonas putida for efficient electron transport. HPLC analysis of the isolated product, together with LC-MS analysis, showed a monohydroxylated flavone, which was further established by subsequent ESI/MS-MS. A successful 10.35% yield was achieved with the whole-cell bioconversion reaction in Escherichia coli. We verified that CYP105P2 is a potential bacterial hydroxylase.

Characterization of flavone synthase I from rice

  • Lee, Yoon-Jung;Kim, Jeong-Ho;Kim, Bong-Gyu;Lim, Yoong-Ho;Ahn, Joong-Hoon
    • BMB Reports
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    • v.41 no.1
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    • pp.68-71
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    • 2008
  • Flavones are synthesized from flavanones through the action of flavone synthases (FNSs). There are two FNSs, FNS I and II. FNS I is a soluble dioxygenase present in members of the Apiaceae family and FNS II is a membrane bound cytochrome P450 enzyme that has been identified in numerous plant species. In this study, we cloned OsFNS I-1 from rice by RTPCR, expressed it in E. coli, and purified the recombinant protein. By NMR analysis, we found that OsFNS I-1 converted the flavanone (2S)-naringenin into the flavone, apigenin. Moreover, we found that the cofactors oxoglutarate, $FeSO_4$, ascorbate and catalase are required for this reaction. OsFNS I-1 encodes a flavone synthase I. This is the first type I FNS I found outside of the Apiaceae family.

Structural Characterization of a Flavonoid Compound Scavenging Superoxide Anion Radical Isolated from Capsella bursa-pastoris

  • Kweon, Mee-Hyang;Kwak, Jae-Hyock;Ra, Kyung-Soo;Sung, Ha-Chin;Yang, Han-Chul
    • BMB Reports
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    • v.29 no.5
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    • pp.423-428
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    • 1996
  • A superoxide anion radical scavenger isolated from Capsella bursa-pastoris was characterized by infrared (IR) spectroscopy, sugar analysis, ultraviolet (UV) spectroscopy, $^{1}H$ and $^{13}C$ nuclear magnetic resonance (NMR) spectroscopies, and fast atom bombardment (FAB) mass analysis. The compound was assumed to be a flavonoid-O-glycoside from IR spectrum and UV absorption maxima. When the sugar composition of the compound was examined by thin layer chromatography (TLC) and gas chromatography (GC) of the acid hydrolysate, only glucose was detected. According to the results of UV spectrotroscopy by using shift reagents, the compound was supposed to be luteolin (5,7,3',4'-tetrahydroxy flavone) or chrysoeriol (5,7,4'-trihydroxy-3'-methoxy flavone) with glucose. Based on $^{1}H$- and $^{13}C-NMR$ spectroscopies, the compound was deduced as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone. In FAB mass analysis the compound was finally characterized as 7,4'-dihydroxy-5,3'-dimethoxy-${\alpha}$-6-c-glucosyl-${\beta}$-2"-o-glucosyl flavone ($C_{29}H_{34}O_{16}$, M.W.=638).

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Isolation and Biological Activity of Flavone Glycosides from the Aerial Part of Cirsium japonicum var. ussuriense in Korea (엉겅퀴 지상부에서 분리한 후라본 배당체 및 생리활성)

  • 박종철;이종호;최종원
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.24 no.6
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    • pp.906-910
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    • 1995
  • Two flavone glycosides have been obtained from the aerial part of Cirsium japonicum var. ussuriense Kitamura(Co,positae) in Korea and identified by means of spectral analysis as linarin and cirsimarin. When 10-2mg/ml of cirsimas was added, lipid peroxide formation in the rat liver decreased by 12% compare to control.

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Synthesis of 2-Aroyloxyacetophenones as Intermediates for Flavone Synthesis (Flavone의 합성 중간체인 2-Aroyloxyacetophenone류의 새로운 합성법)

  • Song, Gyu-Yong;Ahn, Byung-Zun
    • YAKHAK HOEJI
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    • v.38 no.1
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    • pp.1-5
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    • 1994
  • We have synthesized some 2-(2-benzyloxybenzoyloxy)-and 2-(2,6-dibenzyloxybenzoyloxy)-acetophenones as intermediates for flavone synthesis. The reaction of polyoxygenated 2-hydroxyacetophenones with 2-benzyloxybenzoic acid or 2,6-dibenzyloxybenzoic acid in the presence of dicyclohexylcarbodiimide and p-dimethylaminopyridine resulted in a good yield$(70{\sim}89%)$ of 2-(2-benzyloxybenzoyloxy)-acetophenones or 2-(2,6-dibenzyloxybenzoyloxy) acetophenones under milder conditions and in shorter time than the previous methods. This new methods using benzoic acids instead of benzoyl chlorides saves one reaction step of acid chlorination in comparision of the previous methods.

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Synthesis of 2'-Hydroxydihydrochalcone from Flavone

  • Kim, Mi-Hyang;Shin, Bok-Kyu;Won, Dong-Ho;Han, Jae-Hong
    • Journal of Applied Biological Chemistry
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    • v.50 no.2
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    • pp.85-87
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    • 2007
  • To establish the synthetic method for dihydrochalcones as an important bioactive compounds, 2'-hydroxydihydrochalcone has been synthesized from the reduction of flavone in 20% yield. Flavone with five equivalents of ammonium formate in the presence of Pd/C in methanol under $N_2$ atmosphere produced the C-ring opened product. It was characterized by UV-VIS, ESI-MS and $^1H-NMR$ spectroscopy, and identified as 2'-hydroxydihydrochalcone.

The flavone glycosides of Sasa borealis (조릿대잎의 flavone 배당체 성분)

  • Yoon, Ki-Dong;Kim, Chul-Young;Huh, Hoon
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.224-227
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    • 2000
  • As part of study of the constituents of bamboo grasses, the leaves of Sasa borealis (Hackel) Makino (Gramineae) were examined. Friedelin, glutinol, isoorientin and isovitexin have been reported as constituents of bamboo grasses. In this study, tricin and two flavone glycosides, tricin $7-O-{\beta}-D-glucopyranoside$ and luteolin $6-C-{\alpha}-L-arabinopyranoside$ have been isolated from EtOAc extract of S. borealis, by consecutive silica gel, Sephadex LH-20 column chromatography and a repetitive HPLC. The structures of these compounds were determined by IR, $^1H-NMR,\;^{13}C-NMR,\;^{13}C-^1H\;COSY,\;^1H-^1H\;COSY,\;HMBC$ and Mass spectral data.

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