Artículo

La versión final de este artículo es de uso interno de la institución.
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The present study focused on the effect of a series of extracts and two 5,6,7-trioxygenated coumarins isolated from Pterocaulon polystachyum on the proliferation and differentiation of human promonocytic U-937 cells. The petroleum ether extract was the only extract that significantly reduced cell proliferation and induced cell differentiation. Treatment with pure 5-methoxy-6,7-methylenedioxycoumarin (C1) and 5-(3-methyl-2-butenyloxy)-6,7- methylenedioxycoumarin (C2), present in the petroleum ether extract, showed a time and concentration-dependent inhibition on cell proliferation. In addition, the coumarin derivatives were also able to induce CD88 functionality and NBT reduction, markers of monocytic cell differentiation. These results suggest that C1 and C2 might have a potential therapeutic role in the management of leukemia. © 2004 Elsevier Ireland Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum
Autor:Riveiro, M.E.; Shayo, C.; Monczor, F.; Fernández, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C.
Filiación:Laboratorio de Radioisótopos, Fac. de Farmacia Y Bioquímica, Universidad de Buenos Aires, Junín 956 PB, 1113, Capital Federal, Buenos Aires, Argentina
Inst. de Biol. Y Med. Experimental, Buenos Aires, Argentina
Depto. Fisiol., Biol. Molec. Y Cel., Fac. de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Department of Organic Chemistry, Fac. of Agric. and Appl. Biol. Sci., Ghent University, Ghent, Belgium
Cátedra de Farmacognosia, Facultad de Ciencias Exactas, Universidad Nacional de la Plata, Argentina
Palabras clave:5-oxygenated-6,7-methylenedioxycoumarins; ATRA, all trans retinoic acid; CD88; Cell differentiation; dbcAMP, dibutyryl cAMP; Leukemia; NBT, nitrobluetetrazolium; PMA, phorbol 12-myristate 13-acetate; Pterocaulon polystachyum; 5 (3 methyl 2 butenyloxy) 6,7 methylenedioxycoumarin; 5 methoxy 6,7 methylenedioxycoumarin; antineoplastic agent; complement component C5a receptor; coumarin derivative; plant extract; unclassified drug; article; cell differentiation; concentration response; controlled study; human; human cell; inhibition kinetics; leukemia; leukemia cell; medicinal plant; nitroblue tetrazolium test; priority journal; Pterocaulon polystachyum; Asteraceae; Cell Differentiation; Coumarins; Humans; Leukemia, Promyelocytic, Acute; Monocytes; Plant Extracts; Tumor Cells, Cultured; Pterocaulon
Año:2004
Volumen:210
Número:2
Página de inicio:179
Página de fin:188
DOI: http://dx.doi.org/10.1016/j.canlet.2004.03.015
Título revista:Cancer Letters
Título revista abreviado:Cancer Lett.
ISSN:03043835
CODEN:CALED
CAS:Coumarins; Plant Extracts
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03043835_v210_n2_p179_Riveiro

Referencias:

  • Leszczyniecka, M., Roberts, T., Dent, P., Grant, S., Fisher, P.B., Differentiation therapy of human cancer: Basic science and clinical applications (2001) Pharmacol. Ther., 90, pp. 105-156
  • Domen, J., Weissman, I.L., Self-renewal, differentiation or death: Regulation and manipulation of hematopoietic stem cell fate (1999) Mol. Med. Today, 5, pp. 201-208
  • Drach, J., McQueen, T., Engel, H., Andreeff, M., Robertson, K., Collins, S.J., Malavasi, F., Mehta, K., Retinoic acid-induced expression of CD38 antigen in myeloid cells is mediated through retinoic acid receptor-alpha (1994) Cancer Res., 54, pp. 1746-1752
  • Lawrence, R.N., Rediscovering natural product biodiversity (1999) Drug Discov. Today, 4, pp. 449-451
  • Fujioka, T., Furumi, K., Fujii, H., Okabe, H., Mihashi, K., Nakano, Y., Matsunaga, H., Mori, M., Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica (1999) Chem. Pharm. Bull., 47, pp. 96-100
  • Kofinas, C., Chinou, L., Loukis, A., Harvala, C., Roussakis, C., Maillard, M., Hostettmann, K., Cytotoxic coumarins from the aerial parts of Tordylium apulum and their effects on a non-small-cell bronchial carcinoma cell line (1998) Planta Med., 64, pp. 174-176
  • Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M., Yoshizawa, Y., The antiproliferative effect of coumarins on several cancer cell lines (2001) Anticancer Res., 21, pp. 917-923
  • Murray, R.D.H., Méndez, J., Brown, R.A., (1982) The Natural Coumarins: Occurrence, Chemistry and Biochemistry, , New York, NY: Wiley
  • Murray, R.D., Coumarins (1991) Progress in the Chemistry of Organic Natural Products, pp. 83-316. , W. Herz, G.W. Kirby, W. Steglich, & C. Tamm. New York, NY: Springer
  • Murray, R.D., Coumarins (1997) Progress in the Chemistry of Organic Natural Products, pp. 2-119. , W. Herz, G.W. Kirby, W. Steglich, & C. Tamm. New York, NY: Springer
  • Murray, R.D.H., Coumarins (1989) Nat. Prod. Rep., 8, pp. 591-624
  • Hoult, J., Paya, M., Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential (1996) Gen. Pharmacol., 27, pp. 713-722
  • Egan, D., O'Kennedy, R., Moran, E., Thornes, R.D., The pharmacology, metabolism, analysis and applications of coumarin and coumarin related compounds (1990) Drug Metab. Rev., 22, pp. 503-529
  • Laurin, P., Klich, M., Dupis-Hamelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A., Musicki, B., Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B (1999) Bioorg. Med. Chem. Lett., 9, pp. 2079-2084
  • Pillai, S., Menon, S., Mitscher, L., Pillai, C., Shankel, D., Umbelliferone analogues and their potential to inhibit benzo(a)pyrene and hydrogen peroxide induced mutations (1999) J. Nat. Prod., 62, pp. 1358-1362
  • Lin, W.L., Wang, C.J., Tsai, Y.Y., Liu, C.L., Hwang, J.M., Tseng, T.H., Inhibitory effect of esculetin on oxidative damage induced by t-butyl hydroperoxide in rat liver (2000) Arch. Toxicol., 74, pp. 467-472
  • Roma, G., Braccio, M.D., Carrieri, A., Grossi, G., Leoncini, G., Grazia Signorello, M., Coumarin, chromone, and 4(3H)-pyrimidinone novel bicyclic and tricyclic derivatives as antiplatelet agents: Synthesis, biological evaluation, and comparative molecular field analysis (2003) Bioorg. Med. Chem., 11, pp. 123-138
  • Kirkiacharian, S., Thuy, D.T., Sicsic, S., Bakhchinian, R., Kurkjian, R., Tonnaire, T., Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors (2002) Farmaco, 57, pp. 703-708
  • Seliger, B., (1997) The Effects of Coumarin and Its Metabolites on Cell Growth and Development, pp. 93-102. , R. O'Kennedy, & R.D. Thornes
  • Zlabinger, G.J., (1997) Coumarin As An Immunomodulator, pp. 103-124. , R. O'Kennedy, & R.D. Thornes
  • Noguchi, M., Earashi, M., Minami, M., Miyazaki, I., Tanaka, M., Sasaki, T., Effects of piroxicam and esculetin on the MDA-MB-231 human (1995) Prostaglandins Leukot. Essent. Fatty Acids, 53, pp. 325-329
  • Chimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D., Dall'Acqua, F., New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents (2002) Tetrahedron Lett., 43, pp. 7473-7476
  • Jimenez-Orozco, F.A., Molina-Guarneros, J.A., Mendoza-Patino, N., Leon-Cedeno, F., Flores-Perez, B., Santos-Santos, E., Cytostatic activity of coumarin metabolites and derivatives in the B16-F10 murine melanoma cell line (1999) Melanoma Res., 9, pp. 243-247
  • Hofmanova, J., Kozubik, A., Kusek, L., Pachemik, J., Inhibitors of lipoxygenase metabolism exert synergistic effects with retinoic acid on differentiation of human leukemia HL-60 cells (1998) Eur. J. Pharmacol., 350, pp. 273-284
  • Palacios, R.S., Rojo, A.A., Coussio, J.D., De Kimpe, N., Debenedetti, S.L., 6,7-Dioxygenated and 5,6,7-trioxygenated coumarins from Pterocaulon polystachyum (1999) Planta Med., 65, pp. 294-295
  • Mongelli, E., Pampuro, S., Coussio, J.D., Salomon, H., Ciccia, G., Cytotoxic and DNA interaction activities of extracts from medicinal plants used in Argentina (2000) J. Ethnopharmacol., 71, pp. 145-151
  • Sundstrom, C., Nilsson, K., Establishment and characterization of a human histiocytic lymphoma cell line (U-937) (1976) Int. J. Cancer, 17, pp. 565-577
  • Harris, P., Ralph, P., Human leukemic models of myelomonocytic development: A review of the HL-60 and U937 cell lines (1985) J. Leukoc. Biol., 37, pp. 407-422
  • Gavison, R., Matzner, Y., Fibach, E., Differential induction of monocytic functions by dibutyryl cyclic AMP and retinoic acid in a human monoblast cell line U937 (1988) Isr. J. Med. Sci., 24, pp. 697-701
  • Shayo, C., Davio, C., Brodsky, A., Mladovan, A.G., Legnazzi, B.L., Rivera, E., Histamine modulates the expression of c-fos through cyclic AMP production via the H2 receptor in the human promonocytic cell line U937 (1997) Mol. Pharmacol., 51, pp. 983-990
  • Grynkiewicz, G., Poenie, M., Tsien, R.Y., A new generation of Ca2+ indicators with greatly improved fluorescence properties (1985) J. Biol. Chem., 260, pp. 3440-3450
  • Burg, M., Martin, U., Rheinheimer, C., Kohl, J., Bautsch, W., Bottger, E.C., Klos, A., IFN-gamma up-regulates the human C5a receptor (CD88) in myeloblastic U937 cells and related cell lines (1995) J. Immunol., 155, pp. 4419-4426
  • Snyderman, R., Goetzl, E., Molecular and cellular mechanism of leucocyte chemotaxis (1981) Science, 213, pp. 830-837
  • Fernandez, N., Monczor, F., Lemos, B., Notcovich, C., Baldi, A., Davio, C., Reduction of G protein-coupled receptor kinase 2 expression in U-937 cells attenuates H2 histamine receptor desensitization and induces cell maturation (2002) Mol. Pharmacol., 62, pp. 1506-1514
  • Hong, W.K., Sporn, M.B., Recent advances in chemoprevention of cancer (1997) Science, 278, pp. 1073-1077
  • Suh, N., Luyengi, L., Fong, H.H., Kinghorn, A.D., Pezzuto, J.M., Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model (1995) Anticancer Res., 15, pp. 233-239
  • Rubin, J., Biskobing, D., Titus, L., Thornton, D.L., Catherwood, B.D., Nanes, M.S., 1,25(OH)2D3 and cAMP synergistically induce complement 5a receptor messenger RNA (1996) Am. J. Med. Sci., 311, pp. 73-79
  • Debenedetti, S.L., Palacios, P.S., Wilson, E.G., Coussio, J.D., Polyphenols of Pterocaulon polystachyum (1994) Fitoterapia, 65, pp. 188-189
  • Finn, G.J., Creaven, B., Egan, D., Study of the in vitro potential of natural and synthetic coumarin derivatives, using human normal and neoplastic skin cell lines (2001) Melanoma Res., 11, pp. 461-467
  • Finn, G.J., Kenealy, E., Creaven, B.S., Egan, D.A., In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines (2002) Cancer Lett., 183, pp. 61-68
  • Wu, S., Lo, Y.K., Chen, C.C., Li, H.F., Chiang, H.T., Inhibitory effect of the plant-extract osthole on L-type calcium current in NG108-15 neuronal cells (2002) Biochem. Pharmacol., 63, pp. 199-206
  • Thastrup, O., Knudsen, J.B., Lemmich, J., Winther, K., Inhibition of human platelet aggregation by dihydropyrano-and dihydrofuranocoumarins, a new class of cAMP-phosphodiesterase inhibitors (1985) Biochem. Pharmacol., 34, pp. 2137-2140
  • Yang, E.B., Zhao, Y.N., Zhang, K., MacK, P., Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor (1999) Biochem. Biophys. Res. Commun., 260, pp. 682-685
  • Chu, Y., Tsai, Y.Y., Wang, C.J., Lin, W., Tseng, T.H., Induction of apoptosis by esculetin in human leukemia cells (2001) Eur. J. Pharmacol., 416, pp. 25-32
  • Jimenez-Orozco, F.A., Lopez-Gonzalez, J.S., Nieto-Rodriguez, A., Velasco-Velazquez, M.A., Molina-Guarneros, J.A., Mendoza-Patino, N., Decrease of cyclin D1 in the human lung adenocarcinoma cell line A-427 by 7-hydroxycoumarin (2001) Lung Cancer, 34, pp. 185-194

Citas:

---------- APA ----------
Riveiro, M.E., Shayo, C., Monczor, F., Fernández, N., Baldi, A., De Kimpe, N., Rossi, J.,..., Davio, C. (2004) . Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum. Cancer Letters, 210(2), 179-188.
http://dx.doi.org/10.1016/j.canlet.2004.03.015
---------- CHICAGO ----------
Riveiro, M.E., Shayo, C., Monczor, F., Fernández, N., Baldi, A., De Kimpe, N., et al. "Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum" . Cancer Letters 210, no. 2 (2004) : 179-188.
http://dx.doi.org/10.1016/j.canlet.2004.03.015
---------- MLA ----------
Riveiro, M.E., Shayo, C., Monczor, F., Fernández, N., Baldi, A., De Kimpe, N., et al. "Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum" . Cancer Letters, vol. 210, no. 2, 2004, pp. 179-188.
http://dx.doi.org/10.1016/j.canlet.2004.03.015
---------- VANCOUVER ----------
Riveiro, M.E., Shayo, C., Monczor, F., Fernández, N., Baldi, A., De Kimpe, N., et al. Induction of cell differentiation in human leukemia U-937 cells by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon polystachyum. Cancer Lett. 2004;210(2):179-188.
http://dx.doi.org/10.1016/j.canlet.2004.03.015