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Cirigliano, A.M.; Veleiro, A.S.; Bonetto, G.M.; Oberti, J.C.; Burton, G. "Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana" (1996) Journal of Natural Products. 59(8):717-721
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Abstract:

From the aerial parts of Jaborosa runcinata six new withanolides were isolated and named jaborosalactones 1-6 (1-6). All contain a side chain with a carbon-carbon bond between C-12 of the intact steroid nucleus and C-23 and a spiranoid γ-lactone at the latter position. The additional ring thus formed has a 17(20)-ene-22-keto system. Jaborosalactones 4-6 (4-6) also contain a hydroxyl group at C-21. From the aerial parts of Jaborosa araucana were isolated the known withanolides trechonolide A (8), its 5α,6β- dihydroxy analogue jaborosotetrol (9), and the spiranoid withanolide jaborosalactone 2 (2), also isolated from J. runcinata. The stereochemistry of the spiranoid center at C-23 was determined as 23R based on NOESY NMR spectra and molecular modeling using the AM1 semiempirical method.

Registro:

Documento: Artículo
Título:Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana
Autor:Cirigliano, A.M.; Veleiro, A.S.; Bonetto, G.M.; Oberti, J.C.; Burton, G.
Filiación:Depto. de Quim. Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Depto. de Quim. Organ. and IMBIV, Facultad de Ciencias Químicas, Univ. Nacional de Córdoba, Casilla 61, 5016 Córdoba, Argentina
Palabras clave:jaborosalactone 1; jaborosalactone 2; jaborosalactone 3; jaborosalactone 4; jaborosalactone 5; jaborosalactone 6; unclassified drug; withanolide; article; biogenesis; cell transformation; drug isolation; molecular model; nonhuman; spectroscopy; structure analysis; Jaborosa araucana; Jaborosa runcinata
Año:1996
Volumen:59
Número:8
Página de inicio:717
Página de fin:721
DOI: http://dx.doi.org/10.1021/np960210i
Título revista:Journal of Natural Products
Título revista abreviado:J. NAT. PROD.
ISSN:01633864
CODEN:JNPRD
CAS:withanolide, 40326-62-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v59_n8_p717_Cirigliano

Referencias:

  • Glotter, E., (1991) Nat. Prod. Rep., 8, pp. 415-440
  • Baumann, T.W., Meier, C.M., (1993) Phytochemistry, 33, pp. 317-321
  • Hunziker, A.T., (1979) Linn. Soc. Symp. Ser., 7, p. 60
  • Bonetto, G.M., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (1995) J. Nat. Prod., 58, pp. 705-711. , and references cited therein
  • Misico, R.I., Oberti, J.C., Veleiro, A.S., Burton, G., (1996) J. Nat. Prod., 59, pp. 66-68. , and references cited therein
  • Monteagudo, E.S., Oberti, J.C., Gros, E.G., Burton, G., (1990) Phytochemistry, 29, pp. 933-935
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  • Fajardo, V., Podesta, F., Shamma, M., Freyer, A.J., (1991) J. Nat. Prod., 54, pp. 554-563
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  • Besalle, R., Lavie, D., (1992) Phytochemistry, 31, pp. 3648-3651
  • Veleiro, A.S., Oberti, J.C., Burton, G., (1992) Phytochemistry, 31, pp. 935-937
  • 13C-NMR assignments may be interchanged

Citas:

---------- APA ----------
Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C. & Burton, G. (1996) . Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana. Journal of Natural Products, 59(8), 717-721.
http://dx.doi.org/10.1021/np960210i
---------- CHICAGO ----------
Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G. "Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana" . Journal of Natural Products 59, no. 8 (1996) : 717-721.
http://dx.doi.org/10.1021/np960210i
---------- MLA ----------
Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G. "Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana" . Journal of Natural Products, vol. 59, no. 8, 1996, pp. 717-721.
http://dx.doi.org/10.1021/np960210i
---------- VANCOUVER ----------
Cirigliano, A.M., Veleiro, A.S., Bonetto, G.M., Oberti, J.C., Burton, G. Spiranoid withanolides from Jaborosa runcinata and Jaborosa araucana. J. NAT. PROD. 1996;59(8):717-721.
http://dx.doi.org/10.1021/np960210i