Artículo

Sánchez, M.; Mazzuca, M.; Veloso, M.J.; Fernández, L.R.; Siless, G.; Puricelli, L.; Palermo, J.A. "Cytotoxic terpenoids from Nardophyllum bryoides" (2010) Phytochemistry. 71(11-12):1395-1399
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Abstract:

The investigation of the ethanol extract of fresh aerial parts of the Patagonian shrub Nardophyllum bryoides collected in the province of Chubut, Argentina, yielded eleven terpenoids. These include: three seco-ent-halimane diterpenoids (1-3), two ent-halimanes (4-5) and six pentacyclic oleanane and ursane triterpenoids (6-11). Four of these compounds (2, 6, 8 and 11) are hitherto unknown, while two others (1 and 4) have been previously reported but only as synthetic products. Several of these compounds showed moderate cytotoxicity against a human pancreatic adenocarcinoma cell line while compounds 4 and 5 were active at micromolar concentrations. The main component, seco-chiliolidic acid (1), could be isolated from this extract in large amounts, turning N. bryoides into a sustainable source of this bioactive compound. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Cytotoxic terpenoids from Nardophyllum bryoides
Autor:Sánchez, M.; Mazzuca, M.; Veloso, M.J.; Fernández, L.R.; Siless, G.; Puricelli, L.; Palermo, J.A.
Filiación:Departamento de Química Orgánica, UMYMFOR, Universidad de Buenos Aires, Pabellón 2, (1428), Buenos Aires, Argentina
Dpto. Química, Facultad de Ciencias Naturales, Universidad Nacional de la Patagonia San Juan Bosco, Km 4 (9000) Comodoro Rivadavia, Chubut, Argentina
Research Area, Angel H. Roffo Institute of Oncology, University of Buenos Aires, Av. San Martín 5481 (C1417DTB), Buenos Aires, Argentina
Palabras clave:Astereae; Nardophyllum bryoides; Seco-chiliolidic acid; Seco-ent-halimane; Terpenoid; antineoplastic agent; diterpene; drug derivative; oleanolic acid; terpene; antineoplastic agent; terpene; Argentina; article; Asteraceae; chemical structure; chemistry; drug screening; human; isolation and purification; nuclear magnetic resonance; analogs and derivatives; Asteraceae; isolation and purification; Antineoplastic Agents, Phytogenic; Argentina; Asteraceae; Diterpenes; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Terpenes; Astereae; Nardophyllum bryoides; Antineoplastic Agents, Phytogenic; Argentina; Asteraceae; Diterpenes; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid; Terpenes
Año:2010
Volumen:71
Número:11-12
Página de inicio:1395
Página de fin:1399
DOI: http://dx.doi.org/10.1016/j.phytochem.2010.04.019
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:oleanolic acid, 508-02-1; Antineoplastic Agents, Phytogenic; Diterpenes; Oleanolic Acid, 508-02-1; Terpenes; Antineoplastic Agents, Phytogenic; Diterpenes; Oleanolic Acid; Terpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v71_n11-12_p1395_Sanchez

Referencias:

  • Bonifacino, J., Nardophyllum cabrerae (Asteraceae: Astereae), a new species from Argentina and new taxonomic changes involving Nardophyllum Hook (2005) Et. Arn. Taxon., 54, pp. 688-692
  • Harde, C., Bohlmann, F., Synthesis of 3α-hydroxy-5β, 10β-epoxychiliolide, an isolabdane derivative from Chiliotrichium rosmarinifolium (1988) Tetrahedron, 44, pp. 81-90
  • Jakupovic, J., Banerjee, S., Bohlmann, F., King, R.M., Robinson, H.E., New diterpenes from Chiliotrichium rosmarinifolium and Nardophyllum lanatum (1986) Tetrahedron, 42, pp. 1305-1313
  • Quijano, L., Rios, T., Fronczek, F.R., Fischer, N.H., The molecular structure of maniladiol from Baccharis salicina (1998) Phytochemistry, 49, pp. 2065-2068
  • Siddiqui, S., Hafeez, F., Begum, S., Siddiqui, B.S., Kaneric acid, a new triterpene from the leaves of Nerium oleander (1986) J. Nat. Prod., 49, pp. 1086-1090
  • Tori, K., Yoshimura, Y., Seo, S., Sakurawi, K., Tomita, Y., Lshii, H., Carbon-13 NMR spectra of saikogenins. Stereochemical dependence in hydroxylation effects upon Carbon-13 chemical shifts of oleanene-type triterpenoids (1976) Tetrahedron Lett., 46, pp. 4163-4166
  • Urtreger, A.J., Ladeda, V.E., Puricelli, L.I., Rivelli, A., Vidal, M.C., Lustig, E.S., Bal De Kier Joffé, E., Modulation of fibronectin expression and proteolytic activity associated with the invasive and metastatic phenotype in two murine mammary tumor cell lines (1997) Int. J. Oncol., 11, pp. 489-496
  • Zdero, C., Bohlmann, F., Niemeyer, H.M., Diterpenes from Nardophyllum lanatum (1990) Phytochemistry, 29, pp. 1227-1230

Citas:

---------- APA ----------
Sánchez, M., Mazzuca, M., Veloso, M.J., Fernández, L.R., Siless, G., Puricelli, L. & Palermo, J.A. (2010) . Cytotoxic terpenoids from Nardophyllum bryoides. Phytochemistry, 71(11-12), 1395-1399.
http://dx.doi.org/10.1016/j.phytochem.2010.04.019
---------- CHICAGO ----------
Sánchez, M., Mazzuca, M., Veloso, M.J., Fernández, L.R., Siless, G., Puricelli, L., et al. "Cytotoxic terpenoids from Nardophyllum bryoides" . Phytochemistry 71, no. 11-12 (2010) : 1395-1399.
http://dx.doi.org/10.1016/j.phytochem.2010.04.019
---------- MLA ----------
Sánchez, M., Mazzuca, M., Veloso, M.J., Fernández, L.R., Siless, G., Puricelli, L., et al. "Cytotoxic terpenoids from Nardophyllum bryoides" . Phytochemistry, vol. 71, no. 11-12, 2010, pp. 1395-1399.
http://dx.doi.org/10.1016/j.phytochem.2010.04.019
---------- VANCOUVER ----------
Sánchez, M., Mazzuca, M., Veloso, M.J., Fernández, L.R., Siless, G., Puricelli, L., et al. Cytotoxic terpenoids from Nardophyllum bryoides. Phytochemistry. 2010;71(11-12):1395-1399.
http://dx.doi.org/10.1016/j.phytochem.2010.04.019