Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa
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 wh...
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2010
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| LEADER | 10368caa a22012377a 4500 | ||
|---|---|---|---|
| 001 | PAPER-7617 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203722.0 | ||
| 008 | 190411s2010 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-77956344209 | |
| 024 | 7 | |2 cas |a Alkaloids; Antineoplastic Agents, Phytogenic; Sesquiterpenes; Triterpenes | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a PYTCA | ||
| 100 | 1 | |a De Almeida, M.T.R. | |
| 245 | 1 | 0 | |a Antiproliferative terpenoids and alkaloids from the roots of Maytenus vitis-idaea and Maytenus spinosa |
| 260 | |c 2010 | ||
| 270 | 1 | 0 | |m Palermo, J. A.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina; email: palermo@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Alvarenga, N., Ferro, E.A., Bioactive triterpenes and related compounds from Celastraceae (2006) Stud. Nat. Prod. Chem., 33, pp. 239-307 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Gao, J.M., Wu, W.J., Zhang, J.W., Konishi, Y., The dihydro-β-agarofuran sesquiterpenoids (2007) Nat. Prod. Rep., 24, pp. 1153-1189 | ||
| 504 | |a González, A.G., Ferro, E.A., Ravelo, A.G., Horridine, a new isoeuonyminol skeleton alkaloid (1986) Heterocycles, 24, pp. 1295-1299 | ||
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| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Gunatilaka, A.A.L., Triterpenoid quinonemethides and related compounds (Celastroloids) (1996) Progress in the Chemistry of Organic Natural Products, 67. , Springer Wien New York | ||
| 504 | |a Gunatilaka, A.A.L., 1H and 13C NMR analysis of three quinone-methide triterpenoids (2005) Magn. Res. Chem., 27, pp. 803-807 | ||
| 504 | |a 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 | ||
| 504 | |a Harada, R., Kakisawa, K., Kobayashi, S., Musya, M., Nakanishi, K., Takahashi, Y., Structure of pristimerin, a quinoid triterpene (1962) Tetrahedron Lett., pp. 603-607 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Nakanishi, K., Kakisawa, H., Hirata, Y., Structure of pristimerin and celastrol (1955) J. Am. Chem. Soc., 77, pp. 3169-3171 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a Shirota, O., Morita, H., Takeya, K., Itokawa, H., Sesquiterpene pyridine alkaloids from Maytenus ilicifolia (1994) Heterocycles, 38, pp. 383-389 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 504 | |a 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 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior | ||
| 536 | |a Detalles de la financiación: Umweltbundesamt | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT, 14321 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PEI 6478 | ||
| 536 | |a Detalles de la financiación: We thank Prof. Juan Carlos Oberti and Dr. Viviana Nicotra (Universidad de Córdoba) for encouraging this work, collecting the plant material and providing the extracts, and Prof. Angel Gutiérrez Ravelo (IUBO, Universidad de La Laguna, Tenerife, Spain) for mass spectra, reference NMR spectra, and helpful suggestions. We also thank Mg. Laura Patiño Cano, Mr. José Gallardo and Lic. Gernot Eskuche (UMYMFOR–CONICET) for technical assistance. Research at the University of Buenos Aires was supported by grants from CONICET (PEI 6478), UBA (X 260 Programación 2004–2007), and ANPCyT (PICT (2003) 14321). Research at the University of La Laguna was co-financed by the EU FEDER: the Spanish MICIIN (CTQ2008-06806-C02-01/BQU) and MSC (RTICC RD06/0020/1046); the Canary Islands ACIISI (PI 2007/021) and FUNCIS (PI 01/06 and 35/06). J.M.P. thanks the Spanish MEC-FSE for a Ramón y Cajal contract. M.T.R. de A. thanks CAPES (Brazil) for a doctoral fellowship. Appendix A | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina | ||
| 593 | |a BioLab, Instituto Universitario de Bio-Orgánica Antonio González (IUBO-AG), Universidad de la Laguna, Spain | ||
| 593 | |a Departamento de Ciências Farmacêuticas, Universidade Federal de Santa Catarina, Campus Trindade, 88040-970 Florianópolis, SC, Brazil | ||
| 690 | 1 | 0 | |a Β-DIHYDROAGAROFURAN SESQUITERPENOID ALKALOIDS |
| 690 | 1 | 0 | |a CELASTRACEAE |
| 690 | 1 | 0 | |a CELASTROIDS |
| 690 | 1 | 0 | |a MAYTENUS SPINOSA |
| 690 | 1 | 0 | |a MAYTENUS VITIS-IDAEA |
| 690 | 1 | 0 | |a METHYLENEQUINONE |
| 690 | 1 | 0 | |a PENTACYCLIC TRITERPENOIDS |
| 690 | 1 | 0 | |a ALKALOID |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENT |
| 690 | 1 | 0 | |a SESQUITERPENE |
| 690 | 1 | 0 | |a TRITERPENE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DOSE RESPONSE |
| 690 | 1 | 0 | |a DRUG SCREENING |
| 690 | 1 | 0 | |a HELA CELL |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a ISOLATION AND PURIFICATION |
| 690 | 1 | 0 | |a MAYTENUS |
| 690 | 1 | 0 | |a MEDICINAL PLANT |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a PLANT ROOT |
| 690 | 1 | 0 | |a ALKALOIDS |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENTS, PHYTOGENIC |
| 690 | 1 | 0 | |a DOSE-RESPONSE RELATIONSHIP, DRUG |
| 690 | 1 | 0 | |a DRUG SCREENING ASSAYS, ANTITUMOR |
| 690 | 1 | 0 | |a HELA CELLS |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a MAYTENUS |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR |
| 690 | 1 | 0 | |a PLANT ROOTS |
| 690 | 1 | 0 | |a PLANTS, MEDICINAL |
| 690 | 1 | 0 | |a SESQUITERPENES |
| 690 | 1 | 0 | |a TRITERPENES |
| 690 | 1 | 0 | |a CELASTRACEAE |
| 690 | 1 | 0 | |a IDAEA |
| 690 | 1 | 0 | |a MAYTENUS |
| 690 | 1 | 0 | |a VITACEAE |
| 690 | 1 | 0 | |a VITIS |
| 651 | 4 | |a ARGENTINA | |
| 651 | 4 | |a ARGENTINA | |
| 700 | 1 | |a Ríos-Luci, C. | |
| 700 | 1 | |a Padrón, J.M. | |
| 700 | 1 | |a Palermo, J.A. | |
| 773 | 0 | |d 2010 |g v. 71 |h pp. 1741-1748 |k n. 14-15 |p Phytochemistry |x 00319422 |w (AR-BaUEN)CENRE-88 |t Phytochemistry | |
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