Artículo
Misico, R.I.; Song, L.L.; Veleiro, A.S.; Cirigliano, A.M.; Tettamanzi, M.C.; Burton, G.; Bonetto, G.M.; Nicotra, V.E.; Silva, G.L.; Gil, R.R.; Oberti, J.C.; Kinghorn, A.D.; Pezzuto, J.M. "Induction of quinone reductase by withanolides" (2002) Journal of Natural Products. 65(5):677-680
Estamos trabajando para incorporar este artículo al repositorio
Consulte la política de Acceso Abierto del editor
Abstract:
Thirty-seven naturally occurring withanolides (1-37), previously isolated in our laboratories, were evaluated for their potential to induce quinone reductase with cultured murine hepatoma cells (Hepa 1c1c7). Spiranoid (29, 32) and 18-functionalized withanolides (2-5, 7-9, 24) were found to be potent inducers of the enzyme, while 5α-substituted derivatives exhibited weak activity. Preliminary studies were performed with compound 29 to evaluate enzyme-inducing capacity in multiple organ sites of BALB/c mice. Significant induction was observed in liver and colon, but not in lung, stomach, or mammary gland.
Registro:
| Documento: | Artículo |
| Título: | Induction of quinone reductase by withanolides |
| Autor: | Misico, R.I.; Song, L.L.; Veleiro, A.S.; Cirigliano, A.M.; Tettamanzi, M.C.; Burton, G.; Bonetto, G.M.; Nicotra, V.E.; Silva, G.L.; Gil, R.R.; Oberti, J.C.; Kinghorn, A.D.; Pezzuto, J.M. |
| Filiación: | Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, United States Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina Departamento de Química Orgánica (IMBIV-CONICET), Universidad Nacional de Córdoba, 5000 Córdoba, Argentina |
| Palabras clave: | 18 hydroxywithanolide d; enzyme inducing agent; jaborosalactone 1; joborosalactone p; reduced nicotinamide adenine dinucleotide (phosphate) dehydrogenase (quinone); unclassified drug; withanolide derivative; withaphysalin g; withaphysalin h; withaphysalin i; withaphysalin j; animal cell; animal experiment; animal tissue; article; breast; colon; concentration response; controlled study; drug potency; drug structure; enzyme induction; hepatoma cell; liver; lung; mouse; nonhuman; phytochemistry; stomach; Animals; Brassicaceae; Breast; Carcinoma, Hepatocellular; Colon; Enzyme Induction; Inhibitory Concentration 50; Liver; Lung; Mice; Mice, Inbred BALB C; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal; Quinone Reductases; Solanaceae; Stereoisomerism; Steroids; Stilbenes; Stomach; Tumor Cells, Cultured; Animalia; Murinae |
| Año: | 2002 |
| Volumen: | 65 |
| Número: | 5 |
| Página de inicio: | 677 |
| Página de fin: | 680 |
| DOI: | http://dx.doi.org/10.1021/np0106337 |
| Título revista: | Journal of Natural Products |
| Título revista abreviado: | J. Nat. Prod. |
| ISSN: | 01633864 |
| CODEN: | JNPRD |
| CAS: | reduced nicotinamide adenine dinucleotide (phosphate) dehydrogenase (quinone), 9032-20-6; Quinone Reductases, 1.6.99.-; Steroids; Stilbenes |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v65_n5_p677_Misico |
Referencias:
- Talalay, P., De Long, M.J., Prochaska, H.J., (1988) Proc. Natl. Acad. Sci. U.S.A., 85, pp. 8261-8265
- Talalay, P., (1992) Cellular Molecular Targets of Chemoprevention, pp. 193-205. , Steele V.E. Stoner G.D. Boone C.W. Kelloff G.H. Eds. Crc Press: Boca Raton, FL
- Presetera, T., Zhang, Y., Spencer, S.R., Wilczak, C.A., Talalay, P., (1993) Adv. Enzyme Regul., 33, pp. 281-296
- Zhang, Y., Talalay, P., Cho, C.-G., Posner, G.H., (1992) Proc. Natl. Acad. Sci. U.S.A., 89, pp. 2399-2403
- Kennelly, E.J., Gerhäuser, C., Song, L.L., Graham, J.G., Beecher, C.W.W., Pezzuto, J.M., Kinghorn, A.D., (1997) J. Agric. Food Chem., 45, pp. 3771-3777
- Anjaneyulu, A.S.R., Rao, D.S., Le Quesne, P.W., (1998) Studies in Natural Products Chemistry, 20, pp. 135-261. , Structure and Chemistry (Part F); Attaur-Rahman Ed
- Ray, A.B., Gupta, M., (1994) Prog. Chem. Org. Nat. Prod., 63, pp. 1-106
- Cirigliano, A.M., Veleiro, A.S., Oberti, J.C., Burton, G., (1995) Phytochemistry, 40, pp. 611-613
- Silva, G.L., Burton, G., Oberti, J.C., (1999) J. Nat. Prod., 62, pp. 949-953
- Gil, R.R., Misico, R.I., Sotes, I.R., Oberti, J.C., Veleiro, A.S., Burton, G., (1997) J. Nat. Prod., 60, pp. 568-572
- Bonetto, G.M., (1999) Studies of Steroidal Lactones in the Solanaceae Family, , Ph.D. Thesis, Universidad Nacional de Córdoba, Códoba, Argentina
- Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G., (1996) J. Nat. Prod., 59, pp. 717-721
- Tschesche, R., Schawng, H., Legler, G., (1966) Tetrahedron, 22, pp. 1121-1128
- Monteagudo, E.S., Burton, G., Gros, E.G., Gonzalez, C.M., Oberti, J.C., (1989) Phytochemistry, 28, pp. 2514-2515
- Monteagudo, E.S., Oberti, J.C., Gros, E.G., Burton, G., (1990) Phytochemistry, 29, pp. 933-935
- Cirigliano, A.M., Veleiro, A.S., Oberti, J.C., Burton, G., (2000) Molecules, 5, pp. 441-442
- Bonetto, G.M., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (1995) J. Nat. Prod., 58, pp. 705-711
- Glotter, E., Krinsky, P., Kirson, I., (1976) J. Chem. Soc. Perkin Trans. 1, pp. 669-672
- Veleiro, A.S., Oberti, J.C., Burton, G., (1992) Phytochemistry, 31, pp. 935-937
- Tettamanzi, M.C., Veleiro, A.S., Oberti, J.C., Burton, G., (1998) J. Nat. Prod., 61, pp. 338-342
- Misico, R.I., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (2000) J. Nat. Prod., 63, pp. 1329-1332
- Prochaska, H.J., Santamaria, A.B., (1988) Anal. Biochem., 169, pp. 328-336
- Gerhäuser, C., You, M., Liu, J., Moriarty, R., Hawthorne, M., Metha, R.G., Moon, R.C., Pezzuto, J.M., (1997) Cancer Res., 57, pp. 272-278
- Song, L.L., Kosmeder J.W. II, Lee, S.K., Gerhäuser, C., Lantvit, D., Moon, R.C., Moriarty, R.M., Pezzuto, J.M., (1999) Cancer Res., 59, pp. 578-585
Citas:
---------- APA ----------
Misico, R.I., Song, L.L., Veleiro, A.S., Cirigliano, A.M., Tettamanzi, M.C., Burton, G., Bonetto, G.M.,..., Pezzuto, J.M. (2002) . Induction of quinone reductase by withanolides. Journal of Natural Products, 65(5), 677-680.http://dx.doi.org/10.1021/np0106337
---------- CHICAGO ----------
Misico, R.I., Song, L.L., Veleiro, A.S., Cirigliano, A.M., Tettamanzi, M.C., Burton, G., et al. "Induction of quinone reductase by withanolides" . Journal of Natural Products 65, no. 5 (2002) : 677-680.http://dx.doi.org/10.1021/np0106337
---------- MLA ----------
Misico, R.I., Song, L.L., Veleiro, A.S., Cirigliano, A.M., Tettamanzi, M.C., Burton, G., et al. "Induction of quinone reductase by withanolides" . Journal of Natural Products, vol. 65, no. 5, 2002, pp. 677-680.http://dx.doi.org/10.1021/np0106337
---------- VANCOUVER ----------
Misico, R.I., Song, L.L., Veleiro, A.S., Cirigliano, A.M., Tettamanzi, M.C., Burton, G., et al. Induction of quinone reductase by withanolides. J. Nat. Prod. 2002;65(5):677-680.http://dx.doi.org/10.1021/np0106337
