Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Investigation of the organic extracts of the roots of Maytenus vitis-idaea and Maytenus spinosa, collected in the province of Salta, Argentina, led to isolation of eighteen compounds belonging to several classes. From M. vitis-idaea, eight methylenequinone celastroids (1-8) were isolated, four of which (4-7) were hitherto unknown. Additionally, from M. spinosa, two known celastroids, a known celastroid dimer (9), three pentacyclic triterpenoids (10-12) and six β-dihydroagarofuran sesquiterpenoid alkaloids (13-18) were identified. Compounds 4-7 were active against six solid tumor cell lines at micromolar concentrations. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa
Autor:De Almeida, M.T.R.; Ríos-Luci, C.; Padrón, J.M.; Palermo, J.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
BioLab, Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Universidad de la Laguna, Spain
Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Campus Trindade, 88040-970 Florianópolis, SC, Brazil
Palabras clave:β-Dihydroagarofuran sesquiterpenoid alkaloids; Celastraceae; Celastroids; Maytenus spinosa; Maytenus vitis-idaea; Methylenequinone; Pentacyclic triterpenoids; alkaloid; antineoplastic agent; sesquiterpene; triterpene; Argentina; article; chemical structure; chemistry; dose response; drug screening; HeLa cell; human; isolation and purification; Maytenus; medicinal plant; nuclear magnetic resonance; plant root; Alkaloids; Antineoplastic Agents, Phytogenic; Argentina; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Hela Cells; Humans; Maytenus; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Roots; Plants, Medicinal; Sesquiterpenes; Triterpenes; Celastraceae; Idaea; Maytenus; Vitaceae; Vitis
Año:2010
Volumen:71
Número:14-15
Página de inicio:1741
Página de fin:1748
DOI: http://dx.doi.org/10.1016/j.phytochem.2010.06.023
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:Alkaloids; Antineoplastic Agents, Phytogenic; Sesquiterpenes; Triterpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v71_n14-15_p1741_DeAlmeida

Referencias:

  • Alvarenga, N., Ferro, E.A., Bioactive triterpenes and related compounds from Celastraceae (2006) Stud. Nat. Prod. Chem., 33, pp. 239-307
  • Alvarenga, N., Velásquez, C.A., Alvarenga, N.C., Actividad biológica de compuestos aislados de corteza de raíz de Maytenus vitis-idaea (Celastraceae) (2001) Revista de Ciencia y Tecnología - UNA, 1, pp. 51-55
  • De Souza E Silva, S.R., De Fátima Silva, G.D., De Almeida Barbosa, L.C., Duarte, L.P., Vieira Filho, S.A., Lupane pentacyclic triterpenes isolated from stems and branches of Maytenus imbricata (Celastraceae) (2005) Helv. Chim. Acta, 88, pp. 1102-1109
  • Delle Monache, F., Marini-Bettolo, G., Gonalves De Lima, O., D'Albuquerque, I., Barros Coelho, J., The structure of tingenone, a quinonoid triterpene related to pristimerin (1973) J. Chem. Soc. Perkin Trans., 1, pp. 2725-2728
  • Gao, J.M., Wu, W.J., Zhang, J.W., Konishi, Y., The dihydro-β-agarofuran sesquiterpenoids (2007) Nat. Prod. Rep., 24, pp. 1153-1189
  • González, A.G., Ferro, E.A., Ravelo, A.G., Horridine, a new isoeuonyminol skeleton alkaloid (1986) Heterocycles, 24, pp. 1295-1299
  • González, A.G., Alvarenga, N.L., Ravelo, A.G., Bazzocchi, I.L., Ferro, E.A., Navarro, A.G., Moujir, L., Scutione, a new bioactive norquinonemethide triterpene from Maytenus scutioides (Celastraceae) (1996) Bioorg. Med. Chem., 4, pp. 815-820
  • González, A.G., Alvarenga, N.L., Bazzocchi, I.L., Ravelo, A.G., Moujir, L., Triterpene trimers from Maytenus scutioides: Cycloaddition compounds? (1999) J. Nat. Prod., 62, pp. 1185-1187
  • González, A.G., Bazzocchi, I.L., Moujir, L.M., Jiménez, I.A., Ethnobotanical uses of the Celastraceae (2000) Bioactive Metabolites, Studies in Natural Products Chemistry, 23, pp. 649-738
  • Gunatilaka, A.A.L., Triterpenoid quinonemethides and related compounds (Celastroloids) (1996) Progress in the Chemistry of Organic Natural Products, 67. , Springer Wien New York
  • Gunatilaka, A.A.L., 1H and 13C NMR analysis of three quinone-methide triterpenoids (2005) Magn. Res. Chem., 27, pp. 803-807
  • Han, H.B., Park, M.K., Ryu, J.H., Park, J.H., Naoki, H., Sesquiterpene alkaloids from Euonymus japonica (1990) Phytochemistry, 29, pp. 2303-2307
  • Harada, R., Kakisawa, K., Kobayashi, S., Musya, M., Nakanishi, K., Takahashi, Y., Structure of pristimerin, a quinoid triterpene (1962) Tetrahedron Lett., pp. 603-607
  • Miranda, P.O., Padrón, J.M., Padrón, J.I., Villar, J., Martín, V.S., Prins-type synthesis and SAR study of cytotoxic alkyl chloro dihydropyrans (2006) ChemMedChem, 1, pp. 323-329
  • Monks, A., Scudiero, D.A., Skehan, P., Shoemaker, R.H., Paull, K.D., Vistica, D.T., Hose, C., Mayo, M.R., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines (1991) J. Natl. Cancer Inst., 83, pp. 757-766
  • Muñoz, O., Penaloza, A., Gonzalez, A.G., Ravelo, A.G., Bazzocchi, I.L., Alvarenga, N.L., The Celastraceae from Latin America, chemistry and biological activity (1995) Stud. Nat. Prod. Chem., 18, pp. 739-783
  • Nakanishi, K., Kakisawa, H., Hirata, Y., Structure of pristimerin and celastrol (1955) J. Am. Chem. Soc., 77, pp. 3169-3171
  • Ngassapa, O., Soejarto, D., Pezzuto, J., Farnsworth, N., Quinone methide triterpenes and salaspermic acid from Kokoona ochracea (1994) J. Nat. Prod., 57, pp. 1-8
  • Ravelo, A.G., Estévez-Braun, A., Chávez-Orellana, H., Pérez-Sacau, E., Mesa-Siverio, D., Recent studies on natural products as anticancer agents (2004) Curr. Top. Med. Chem., 4, pp. 241-265
  • Shirota, O., Morita, H., Takeya, K., Itokawa, H., Sesquiterpene pyridine alkaloids from Maytenus ilicifolia (1994) Heterocycles, 38, pp. 383-389
  • Shirota, O., Morita, H., Takeya, K., Itokawa, H., New geometric and stereoisomeric triterpene dimers from Maytenus chuchuhuasca (1998) Chem. Pharm. Bull., 46, pp. 102-106
  • Simmons, M.P., Cappa, J., Archer, R., Ford, A.J., Eichstedt, D., Clevinger, C., Phylogeny of the Celastreae (Celastraceae) and the relationships of Catha edulis (qat) inferred from morphological characters and nuclear and plastid genes (2008) Mol. Phylogenet. Evol., 48, pp. 745-757
  • Sugiura, K., Yamada, K., Hirata, Y., The structures of evonimine and euonine, two minor alkaloids obtained from Euonymus sieboldiana Blume (1973) Tetrahedron Lett., pp. 113-116

Citas:

---------- APA ----------
De Almeida, M.T.R., Ríos-Luci, C., Padrón, J.M. & Palermo, J.A. (2010) . Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa. Phytochemistry, 71(14-15), 1741-1748.
http://dx.doi.org/10.1016/j.phytochem.2010.06.023
---------- CHICAGO ----------
De Almeida, M.T.R., Ríos-Luci, C., Padrón, J.M., Palermo, J.A. "Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa" . Phytochemistry 71, no. 14-15 (2010) : 1741-1748.
http://dx.doi.org/10.1016/j.phytochem.2010.06.023
---------- MLA ----------
De Almeida, M.T.R., Ríos-Luci, C., Padrón, J.M., Palermo, J.A. "Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa" . Phytochemistry, vol. 71, no. 14-15, 2010, pp. 1741-1748.
http://dx.doi.org/10.1016/j.phytochem.2010.06.023
---------- VANCOUVER ----------
De Almeida, M.T.R., Ríos-Luci, C., Padrón, J.M., Palermo, J.A. Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa. Phytochemistry. 2010;71(14-15):1741-1748.
http://dx.doi.org/10.1016/j.phytochem.2010.06.023