• Title/Summary/Keyword: flavone

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Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

Molecular mechanisms of luteolin-7-O-glucoside-induced growth inhibition on human liver cancer cells: G2/M cell cycle arrest and caspase-independent apoptotic signaling pathways

  • Hwang, Yu-Jin;Lee, Eun-Ju;Kim, Haeng-Ran;Hwang, Kyung-A
    • BMB Reports
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    • v.46 no.12
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    • pp.611-616
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    • 2013
  • Luteolin-7-O-glucoside (LUT7G), a flavone subclass of flavonoids, has been found to increase anti-oxidant and anti-inflammatory activity, as well as cytotoxic effects. However, the mechanism of how LUT7G induces apoptosis and regulates cell cycles remains poorly understood. In this study, we examined the effects of LUT7G on the growth inhibition of tumors, cell cycle arrest, induction of ROS generation, and the involved signaling pathway in human hepatocarcinoma HepG2 cells. The proliferation of HepG2 cells was decreased by LUT7G in a dose-dependent manner. The growth inhibition was due primarily to the G2/M phase arrest and ROS generation. Moreover, the phosphorylation of JNK was increased by LUT7G. These results suggest that the anti-proliferative effect of LUT7G on HepG2 is associated with G2/M phase cell cycle arrest by JNK activation.

Immunosuppressive Activity of Wogonin from Scutellaria Radix on DNFB-induced Delayed Type Hypersensitivity in Mice (마우스에서 황금 유래 Wogonin의 Th1과 Th2 사이토가인 조절 효과)

  • Kim Young Jun;Lee Jeong Chi;Kim Hong Yong;Xie Guanghua;Yun Yong Gab;Jang Seon Il
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.4
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    • pp.1027-1031
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    • 2005
  • In the present study, wogonin, a major flavone isolated from Scutellaria Radix were examined for its imunosuppressive activity on the 2,4-dinitro-fluorobenzene (DNFB)-induced delayed type hypersensitivity (DTH) in C3H/HeN mice. This compound inhibited selectively $TNF-\alpha$ and IL-4, but not IL-6, IL-10 and $IFN-\gamma$ on DNFB-induced Th1 and Th2 cytokines in a concentration-dependent manner. Interestingly, this compound increased the expression of heme oxygenase-1 (HO-1) in a concentration-dependent manner The above results reveal that wogonin possesses anti-inflammatory, humoral and cellular immunomodulatory, and stress reducing activities on the DNFB-induced DTH in mice and these properties may contribute to the anti-atopic dermatitis activity of Scutellaria Radix.

Antioxidative Effects of Flavonoids toward Modification of Human Low Density Lipoprotein (플라보노이드에 의한 사람 Low Density Lipoprotein 변형에 대한 항산화 효과)

  • 류병호
    • The Korean Journal of Food And Nutrition
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    • v.12 no.3
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    • pp.320-327
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    • 1999
  • The flavonoids are one of the most numberous and widespread groups of natural consituents. The low molecular weight of benzo-${\gamma}$-pyrone derivative are ubiquitous in plants and are vegetables nuts, seeds, leaves, flowers, and bark. The flavonoids constitute of a large class of compounds ubiquitous in plants containing a number of phenolic hydroxyl groups attached to ring structures conferring the antioxidant activity. Epidemiologic studies suggest that the dietary intake of antioxidants constitutes a risk factor for vasclar disease indicating that oxidation may be important in the pathogenesis of human athero-sclerosis. Elevated plasma low density lipoprotein (LDL) cholesterol concentration are associated with accelerated atherosclerosis, LDL is oxidized by smooth muscle cells resulting in several chemicals and physical changes of LDL. Oxidized LDL is responsible for cholesterol loading of macrophages foam cells formation and atherogenesis. There have been insulficient tests of the protective effects of flavonoids against LDL oxidation to make definitive statements about their structure activity relationships. How-ever hydroxylation of the flavone uncleas can appears to be advantageous because polyhydroxylated aglycone flavonoids are potent inhibitor of LDL modification. This identification may lead to new and more effective antioxidant strategies for abrogating the atherosclerotic process the leading cause of death and disability in industrialized societies.

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Antimutagenic Effect of Plant Flavonoids in the Salmonella Assay System

  • Choi, Jae-Sue;Park, Kun-Young;Moon, Suk-Hee;Rhee, Sook-Hee;Young, Han-Suk
    • Archives of Pharmacal Research
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    • v.17 no.2
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    • pp.71-75
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    • 1994
  • The antimutagenic effects of 27 kinds of plant flavonoids on the mutagenicity of aflatoxin $B_1(AFB_1)$ and N-methyl-N'-nitro-N-nitrosoguanidine(MANG) in Salmonella typhimurium TA 100 were investigated. In the mixed applications of $AFB_1\;(1\;\mu{g/plate)}$ with the flavonoids $(300\;\mu{g/plate)}$ in the presence of a mammalian metabolic activation system (S9 mix), chrysin, apigenin, luteolin and its glucoside, kaempferol, fisetin, morin, naringenin, hesperetin, persicogenin, (+)-catechin and (-)epicatechin showed the antimutagenic effect against $AFB_1$ with more than 70% inhibition rate. A little or no antimutagenicities except flavone against MNNG $(0.5\;\mu{g/plate)}$ were observed. For the antimutagencity of the flavonoids on $AFB_1$, the flavonoid structure that contains the free 5, 7-hydroxyl gorup seemed to be essential. However, saturation of the 2, 3-double bond of elimination of the 4-keto group did not affect the activity.

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Aqueous Solubility Enhancement of Some Flavones by Complexation with Cyclodextrins

  • Kim, Hyun-Myung;Kim, Hyun-Won;Jung, Seun-Ho
    • Bulletin of the Korean Chemical Society
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    • v.29 no.3
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    • pp.590-594
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    • 2008
  • The inclusion complexes of cyclodextrins (CDs) with flavones in aqueous solution were investigated by phase solubility measurements. The effect of b -cyclodextrin (b -CD), heptakis (2,6-di-O-methyl) b -cyclodextrin (DM-b -CD) and 2-hydroxypropyl-b -cyclodextrin (HP-b -CD) on the aqueous solubility of three flavones, namely, chrysin, apigenin and luteolin was investigated, respectively. Solubility enhancements of all flavones obtained with three CDs followed the rank order: HP-b -CD > DM-b -CD > b -CD, and besides, CDs show higher stability constant on luteolin than that on others flavones. 1H-nuclear magnetic resonance (NMR) spectroscopy and molecular modeling was used to help establish the model of interaction of the CDs with luteolin. NMR spectroscopic analysis suggested that A-C ring, and part of the B ring of luteolin display favorable interaction with the CDs, which was also confirmed by docking studies based on the molecular simulation. The observed augmentation of solubility of luteolin by three CDs was explained by the difference of electrostatic interaction of each complex, especially hydrogen bonding.

Identification for Flavones in Different Parts of Cirsium japonicum

  • Kim, Su-Jeong;Kim, Gun-Hee
    • 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.

Norisoprenoids and Hepatoprotective Flavone Glycosides from the Aerial Parts of Beta vulgaris var. cicla

  • Kim, In-Kyum;Chin, Young-Won;Lim, Song-Won;Kim, Young-Choong;Kim, Jin-Woong
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.600-603
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    • 2004
  • (+)-Dehydrovomifoliol (1). 3-hydroxy-5$\alpha$,6$\alpha$-epoxy-$\beta$-ionone (2), vitexin 7 -O-$\beta$-D-glucopyrano-side (3), and vitexin 2'-O-$\beta$-D-glucopyranoside (4) were isolated as new constituents from the aerial parts of Beta vulgaris var. cicla. Compounds 3 and 4 demonstrated hepatoprotective activity with values of 65.8 and 56.1%, respectively, in primary cultured rat hepatocytes with $CCl_4$-induced cell toxicity, compared to controls. This was comparable to that of silibinin (69.8%) which was used as a positive control.trol.

위령선의 성분연구 제2보 Clematis brachyura Maxim의 flavone에 대하야

  • heo, Geom;Park, Su-Seon
    • YAKHAK HOEJI
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    • v.2 no.1_2
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    • pp.11-15
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    • 1953
  • Two flavons, which are a new flavon (the Authors are going to call it "CLEMATISIN") and a yellow crystalline flavon, are isolated from leaves of Clematis brachura Maxim. Clamatisin : A colorless needle crystal which has a Slightly sweet taste, mp 225 .deg.C (decomp). It is positive (Cherry red) for the Mg-HCl(Hg) reaction and is positive (purple) for the $FeCL_{3}$ reagent. It is soluble easily in methanol, ether, acetone, prydine, ethylacetate, hot water and alkali-solutions. It is soluble slightly in cold water and is insoluble in chloroform, benzene and toluence. According to the results of elementry analysis and molecular weight determination the formula of clematisin agrees with $C_{18}H_{18}O_{7}$ when dried at $80^{\circ}C$, crystalline clematisin (from water) contains one molecule of crystalline water. The following derivatives are prepared ; Clematisin-oxim; a colorless needle crystal, mp 215-216 .deg.C, Clematisin methylate; prepared by diazomethan. mp 191-$192^{\circ}C$ a colorless needle crystal. Acethylmethylate; a colorless powder, It is not sharp in melting point and melts at approximately $215^{\circ}C$, Yellow Crystalline Flavon; mp 285-$286^{\circ}C$ (dexo-mp.), yellow needle crystal. It has a slightly sweet teste and shows positive reaction Acetate; a colorless needle crystal, mp $168^{\circ}C$.

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Dyeing and Antibacterial Properties of N-Containing Fibers Dyed with Henna (질소성분 함유 섬유에 대한 헤나 염색성 및 항균성에 관한 연구)

  • Oh, Kyung-Wha;Park, Jeong-Eun;Park, Myung-Ja
    • Journal of the Korean Society of Clothing and Textiles
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    • v.29 no.11
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    • pp.1520-1526
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    • 2005
  • Henna is a natural colorant and has been used to dye hair, skin and leather since civilization began. It has reddish brown to orange shade. The major color components of Henna are Lawsone(2-hydroxy-1,4-naphthaquinone) and Luteolin (3',4',5,7-tetrahydroxy-flavone). In this study, various fibers containing the nitrogen component, especially used fur underwear, were dyed with Henna under various dyeing conditions, then dyeing characteristics, color fastness, and anti-bacterial properties were evaluated. from the results, Henna has good affinity to the chlorinated wool>wool>Pu/nylon>nylon>soybean>silk in decreasing order. The color fastness of the wool fabric dyed with Henna to washing, dry-cleaning, and perspiration showed 4-5 grade. The color fastness to light was 3rd grade. These results are relatively good comparing with other natural dyes. Moreover dyed fabric with Henna showed excellent antibacterial activity.