Rutacridone

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A. A. Voerste - One of the best experts on this subject based on the ideXlab platform.

Walter Maier - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to Rutacridone by cell-free extracts of Ruta graveolens cell cultures
    Phytochemistry, 1993
    Co-Authors: Walter Maier, A. Baumert, Brigitte Schumann, Hiroshi Furukawa, Detlef Gröger
    Abstract:

    Abstract Acridone synthase was isolated from cell suspension cultures of Ruta graveolens which catalysed the formation of 1,3-dihydroxy-N- methylacridone from N-methylanthraniloyl-CoA and malonyl-CoA. No cofactors were required for this enzyme reaction. Potassium phosphate buffer was superior compared to Tris-HCl. Sodium ascorbate instead of mercaptoethanol as oxidation protectant showed an advantageous effect on acridone synthase activity. The enzyme was strongly inhibited by 1,3-dihydroxy-N-methylacridone and by the antibiotic cerulenin. Microsomal preparations from Ruta graveolens cell suspension cultures catalysed an NADPH- and oxygen-dependent condensation of 1,3-dihydroxy-N- methylacridone and isopentenyl pyrophosphate. The reaction product was identified as Rutacridone. Mg2+ or Mn2+ ions were necessary for optimal Rutacridone synthase activity. The enzyme was inhibited by a number of inhibitors of cytochrome P-450 enzymes. A prenylated acridone, viz. glycocitrine-II was identified as an essential intermediate. Under in vivo conditions glycocitrine-II is incorporated into Rutacridone, but a clear-cut conversion of glycocitrine-II by microsomal preparations (cyclase) was not observed. Microsomes converted Rutacridone into furofoline-I. A number of detergents was used for solubilization of membrane-bound proteins of Ruta microsomes. Highest specific glycocitrine -II synthase (prenyltransferase) activity was obtained after solubilization with dodecylmaltoside.

  • Increased Accumulation of Acridone Alkaloids by Cell Suspension Cultures of Ruta graveolens in Response to Elicitors
    Journal of Plant Physiology, 1991
    Co-Authors: A. Baumert, Walter Maier, Brigitte Schumann, D. Gröger
    Abstract:

    Summary Two dark-grown cell suspension cultures of Ruta graveolens L. were challenged with fungal elicitors. The treatment of cell line R-4 resulted in increased accumulation of hydroxy Rutacridone epoxide, Rutacridone epoxide and gravacridontriol. The latter alkaloid was not detectable in non-elicited cells. Another response was observed in cell line R-15. Besides Rutacridone epoxide, for the first time Rutacridone accumulation was stimulated either by a yeast, Phytophthora or Colletotrichum elicitor. Using cell line R-15, an elicitor-mediated induction of 5-adenosyl-L-methionine: anthranilic acid N-methyltransferase, N-methylanthranilic acid «activating» enzyme and Rutacridone synthase was recorded. Enzyme activities were influenced by incubation time and amount of elicitor.

István Zupkó - One of the best experts on this subject based on the ideXlab platform.

  • Antiproliferative effects of various furanoacridones isolated from ruta graveolens on human breast cancer cell lines
    Anticancer research, 2016
    Co-Authors: Zsuzsanna Schelz, Imre Ocsovszki, Noémi Bózsity, Judit Hohmann, István Zupkó
    Abstract:

    BACKGROUND/AIM Thanks to its biologically active constituents, Ruta graveolens L. (Rutaceae) is a widely used medicinal plant. In our study, six furanoacridone alkaloids isolated from Ruta graveolens were investigated for their antiproliferative and pro-apoptotic effects on human breast cancer cell lines (MCF-7, MDA-MB-361, MDA-MB-231 and T47D). MATERIALS AND METHODS The cell lines were pretreated with alkaloid components (Rutacridone, isogravacridone chlorine (IGC), gravacridonediol monomethyl ether, gravacridonediol, gravacridonetriol, a 1:1 mixture of gravacridonetriol and - diol monoglucosides) and their antiproliferative effects were determined by the MTT assay. RESULTS IGC had the most marked effect on cell proliferation of MDA-MB-231 (half maximal inhibitory concentration (IC50)=2.27 μM). Cell-cycle analysis was applied to quantify the effect of IGC on subpopulations of MDA-MB-231 and MCF-7 cells. It caused a cell-cycle disturbance by decreasing the G2/M and G0/G1 and increasing the S phase and the appearance of the subdiploid (sub-G1) population. Hoechst 33258-propidium iodide staining was used to evaluate the morphological changes in IGC-pretreated MDA-MB-231 and MCF-7 cells, revealing the appearance of apoptotic features. IGC was found to cause a modest activation of caspase-3 and -9, but not caspase-8, indicating the activation of an intrinsic apoptotic pathway in MDA-MB-231 cells. CONCLUSIONS These in vitro findings indicate that furanoacridones are suitable candidates for anticancer drug development.

  • Investigation of cytotoxic effects of various furanoacridones isolated from Ruta graveolens
    Planta Medica, 2015
    Co-Authors: Zsuzsanna Schelz, Imre Ocsovszki, Judit Hohmann, István Zupkó
    Abstract:

    Ruta graveolens L. (Rutaceae) is a widely used medicinal plant due to its constituents like furanocoumarins and rutoside. In our study, six furanoacridone alcaloids isolated from Ruta graveolens [1] were investigated on human breast cancer cell lines (MCF-7, MDA-MB-361, MDA-MB-231, T47D) for antiproliferative effects and further studies were employed in order to determine the effects on cell cycle and morphology. Breast cancer is by far the most frequent malignant disease among women and accountable for the most cancer-related deaths in the female population worldwide. These data support the urgent need for developing new antiproliferative agents with higher efficacy and better tolerability profile. The cancer cell lines had been pretreated with the alkaloid components (Rutacridone, isogravacridone chlorine (IGC), gravacridonediol monomethyl ether, gravacridonediol, gravacridonetriol, mixture of garvacridonetriol and diol monomethyl ether) and the antiproliferative effects were determined by MTT assay and IC50 values were calculated. IGC had the most marked effect on cell proliferation of MDA-MB-231 (IC50= 2.27 µM) and MCF-7 (IC50= 4.55 µM). Flow cytometric cell cycle analysis had been applied in order to quantify the effect of IGC on the subpopulations of MDA-MB-231 and MCF-7 during cell cycle. It caused cell cycle disturbance decreasing G2/M and G0/G1 and increasing S phase. Hoechst 33258-propidium iodide dual staining was used for the evaluation of morphological changes in MDA-MB-231 and MCF-7 cells pretreated with IGC, resulting in the appearance of nuclear condensation. Caspase-3 activation was additionally determined from IGC-treated MDA-MB-231 cell in order to prove its apoptotic potential. Based on these in vitro findings IGC could be considered for further in vitro and in vivo studies to characterize the mechanism of its antiproliferative action. References: [1] Rethy B et al. Planta Med 2007; 73: 41 – 48

Detlef Gröger - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to Rutacridone by cell-free extracts of Ruta graveolens cell cultures
    Phytochemistry, 1993
    Co-Authors: Walter Maier, A. Baumert, Brigitte Schumann, Hiroshi Furukawa, Detlef Gröger
    Abstract:

    Abstract Acridone synthase was isolated from cell suspension cultures of Ruta graveolens which catalysed the formation of 1,3-dihydroxy-N- methylacridone from N-methylanthraniloyl-CoA and malonyl-CoA. No cofactors were required for this enzyme reaction. Potassium phosphate buffer was superior compared to Tris-HCl. Sodium ascorbate instead of mercaptoethanol as oxidation protectant showed an advantageous effect on acridone synthase activity. The enzyme was strongly inhibited by 1,3-dihydroxy-N-methylacridone and by the antibiotic cerulenin. Microsomal preparations from Ruta graveolens cell suspension cultures catalysed an NADPH- and oxygen-dependent condensation of 1,3-dihydroxy-N- methylacridone and isopentenyl pyrophosphate. The reaction product was identified as Rutacridone. Mg2+ or Mn2+ ions were necessary for optimal Rutacridone synthase activity. The enzyme was inhibited by a number of inhibitors of cytochrome P-450 enzymes. A prenylated acridone, viz. glycocitrine-II was identified as an essential intermediate. Under in vivo conditions glycocitrine-II is incorporated into Rutacridone, but a clear-cut conversion of glycocitrine-II by microsomal preparations (cyclase) was not observed. Microsomes converted Rutacridone into furofoline-I. A number of detergents was used for solubilization of membrane-bound proteins of Ruta microsomes. Highest specific glycocitrine -II synthase (prenyltransferase) activity was obtained after solubilization with dodecylmaltoside.

A. Baumert - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of 1,3-dihydroxy-N-methylacridone and its conversion to Rutacridone by cell-free extracts of Ruta graveolens cell cultures
    Phytochemistry, 1993
    Co-Authors: Walter Maier, A. Baumert, Brigitte Schumann, Hiroshi Furukawa, Detlef Gröger
    Abstract:

    Abstract Acridone synthase was isolated from cell suspension cultures of Ruta graveolens which catalysed the formation of 1,3-dihydroxy-N- methylacridone from N-methylanthraniloyl-CoA and malonyl-CoA. No cofactors were required for this enzyme reaction. Potassium phosphate buffer was superior compared to Tris-HCl. Sodium ascorbate instead of mercaptoethanol as oxidation protectant showed an advantageous effect on acridone synthase activity. The enzyme was strongly inhibited by 1,3-dihydroxy-N-methylacridone and by the antibiotic cerulenin. Microsomal preparations from Ruta graveolens cell suspension cultures catalysed an NADPH- and oxygen-dependent condensation of 1,3-dihydroxy-N- methylacridone and isopentenyl pyrophosphate. The reaction product was identified as Rutacridone. Mg2+ or Mn2+ ions were necessary for optimal Rutacridone synthase activity. The enzyme was inhibited by a number of inhibitors of cytochrome P-450 enzymes. A prenylated acridone, viz. glycocitrine-II was identified as an essential intermediate. Under in vivo conditions glycocitrine-II is incorporated into Rutacridone, but a clear-cut conversion of glycocitrine-II by microsomal preparations (cyclase) was not observed. Microsomes converted Rutacridone into furofoline-I. A number of detergents was used for solubilization of membrane-bound proteins of Ruta microsomes. Highest specific glycocitrine -II synthase (prenyltransferase) activity was obtained after solubilization with dodecylmaltoside.

  • Increased Accumulation of Acridone Alkaloids by Cell Suspension Cultures of Ruta graveolens in Response to Elicitors
    Journal of Plant Physiology, 1991
    Co-Authors: A. Baumert, Walter Maier, Brigitte Schumann, D. Gröger
    Abstract:

    Summary Two dark-grown cell suspension cultures of Ruta graveolens L. were challenged with fungal elicitors. The treatment of cell line R-4 resulted in increased accumulation of hydroxy Rutacridone epoxide, Rutacridone epoxide and gravacridontriol. The latter alkaloid was not detectable in non-elicited cells. Another response was observed in cell line R-15. Besides Rutacridone epoxide, for the first time Rutacridone accumulation was stimulated either by a yeast, Phytophthora or Colletotrichum elicitor. Using cell line R-15, an elicitor-mediated induction of 5-adenosyl-L-methionine: anthranilic acid N-methyltransferase, N-methylanthranilic acid «activating» enzyme and Rutacridone synthase was recorded. Enzyme activities were influenced by incubation time and amount of elicitor.