Induction of quinone reductase by withanolides

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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...

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Detalles Bibliográficos
Autor principal: Misico, R.I
Otros Autores: 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
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-0036113528 
024 7 |2 cas  |a reduced nicotinamide adenine dinucleotide (phosphate) dehydrogenase (quinone), 9032-20-6; Quinone Reductases, 1.6.99.-; Steroids; Stilbenes 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a JNPRD 
100 1 |a Misico, R.I. 
245 1 0 |a Induction of quinone reductase by withanolides 
260 |c 2002 
270 1 0 |m Kinghorn, A.D.; Department of Medicinal Chemistry, College of Pharmacy, University of Illinois, Chicago, IL 60612, United States; email: kinghorn@uic.edu 
506 |2 openaire  |e Política editorial 
504 |a Talalay, P., De Long, M.J., Prochaska, H.J., (1988) Proc. Natl. Acad. Sci. U.S.A., 85, pp. 8261-8265 
504 |a 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 
504 |a Presetera, T., Zhang, Y., Spencer, S.R., Wilczak, C.A., Talalay, P., (1993) Adv. Enzyme Regul., 33, pp. 281-296 
504 |a Zhang, Y., Talalay, P., Cho, C.-G., Posner, G.H., (1992) Proc. Natl. Acad. Sci. U.S.A., 89, pp. 2399-2403 
504 |a 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 
504 |a 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 
504 |a Ray, A.B., Gupta, M., (1994) Prog. Chem. Org. Nat. Prod., 63, pp. 1-106 
504 |a Cirigliano, A.M., Veleiro, A.S., Oberti, J.C., Burton, G., (1995) Phytochemistry, 40, pp. 611-613 
504 |a Silva, G.L., Burton, G., Oberti, J.C., (1999) J. Nat. Prod., 62, pp. 949-953 
504 |a 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 
504 |a Bonetto, G.M., (1999) Studies of Steroidal Lactones in the Solanaceae Family, , Ph.D. Thesis, Universidad Nacional de Córdoba, Códoba, Argentina 
504 |a Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G., (1996) J. Nat. Prod., 59, pp. 717-721 
504 |a Tschesche, R., Schawng, H., Legler, G., (1966) Tetrahedron, 22, pp. 1121-1128 
504 |a Monteagudo, E.S., Burton, G., Gros, E.G., Gonzalez, C.M., Oberti, J.C., (1989) Phytochemistry, 28, pp. 2514-2515 
504 |a Monteagudo, E.S., Oberti, J.C., Gros, E.G., Burton, G., (1990) Phytochemistry, 29, pp. 933-935 
504 |a Cirigliano, A.M., Veleiro, A.S., Oberti, J.C., Burton, G., (2000) Molecules, 5, pp. 441-442 
504 |a Bonetto, G.M., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (1995) J. Nat. Prod., 58, pp. 705-711 
504 |a Glotter, E., Krinsky, P., Kirson, I., (1976) J. Chem. Soc. Perkin Trans. 1, pp. 669-672 
504 |a Veleiro, A.S., Oberti, J.C., Burton, G., (1992) Phytochemistry, 31, pp. 935-937 
504 |a Tettamanzi, M.C., Veleiro, A.S., Oberti, J.C., Burton, G., (1998) J. Nat. Prod., 61, pp. 338-342 
504 |a Misico, R.I., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (2000) J. Nat. Prod., 63, pp. 1329-1332 
504 |a Prochaska, H.J., Santamaria, A.B., (1988) Anal. Biochem., 169, pp. 328-336 
504 |a 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 
504 |a 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 
520 3 |a 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.  |l eng 
593 |a 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 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
593 |a Departamento de Química Orgánica (IMBIV-CONICET), Universidad Nacional de Córdoba, 5000 Córdoba, Argentina 
690 1 0 |a 18 HYDROXYWITHANOLIDE D 
690 1 0 |a ENZYME INDUCING AGENT 
690 1 0 |a JABOROSALACTONE 1 
690 1 0 |a JOBOROSALACTONE P 
690 1 0 |a REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE) 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a WITHANOLIDE DERIVATIVE 
690 1 0 |a WITHAPHYSALIN G 
690 1 0 |a WITHAPHYSALIN H 
690 1 0 |a WITHAPHYSALIN I 
690 1 0 |a WITHAPHYSALIN J 
690 1 0 |a ANIMAL CELL 
690 1 0 |a ANIMAL EXPERIMENT 
690 1 0 |a ANIMAL TISSUE 
690 1 0 |a ARTICLE 
690 1 0 |a BREAST 
690 1 0 |a COLON 
690 1 0 |a CONCENTRATION RESPONSE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG POTENCY 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a ENZYME INDUCTION 
690 1 0 |a HEPATOMA CELL 
690 1 0 |a LIVER 
690 1 0 |a LUNG 
690 1 0 |a MOUSE 
690 1 0 |a NONHUMAN 
690 1 0 |a PHYTOCHEMISTRY 
690 1 0 |a STOMACH 
690 1 0 |a ANIMALS 
690 1 0 |a BRASSICACEAE 
690 1 0 |a BREAST 
690 1 0 |a CARCINOMA, HEPATOCELLULAR 
690 1 0 |a COLON 
690 1 0 |a ENZYME INDUCTION 
690 1 0 |a INHIBITORY CONCENTRATION 50 
690 1 0 |a LIVER 
690 1 0 |a LUNG 
690 1 0 |a MICE 
690 1 0 |a MICE, INBRED BALB C 
690 1 0 |a MOLECULAR STRUCTURE 
690 1 0 |a NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR 
690 1 0 |a PLANTS, MEDICINAL 
690 1 0 |a QUINONE REDUCTASES 
690 1 0 |a SOLANACEAE 
690 1 0 |a STEREOISOMERISM 
690 1 0 |a STEROIDS 
690 1 0 |a STILBENES 
690 1 0 |a STOMACH 
690 1 0 |a TUMOR CELLS, CULTURED 
690 1 0 |a ANIMALIA 
690 1 0 |a MURINAE 
700 1 |a Song, L.L. 
700 1 |a Veleiro, A.S. 
700 1 |a Cirigliano, A.M. 
700 1 |a Tettamanzi, M.C. 
700 1 |a Burton, G. 
700 1 |a Bonetto, G.M. 
700 1 |a Nicotra, V.E. 
700 1 |a Silva, G.L. 
700 1 |a Gil, R.R. 
700 1 |a Oberti, J.C. 
700 1 |a Kinghorn, A.D. 
700 1 |a Pezzuto, J.M. 
773 0 |d 2002  |g v. 65  |h pp. 677-680  |k n. 5  |p J. Nat. Prod.  |x 01633864  |t Journal of Natural Products 
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856 4 0 |u https://doi.org/10.1021/np0106337  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_01633864_v65_n5_p677_Misico  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v65_n5_p677_Misico  |y Registro en la Biblioteca Digital 
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962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 66288 

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