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Nicotra, V.E.; Ramacciotti, N.S.; Gil, R.R.; Oberti, J.C.; Feresin, G.E.; Guerrero, C.A.; Baggio, R.F.; Garland, M.T.; Burton, G. "Phytotoxic withanolides from Jaborosa rotacea" (2006) Journal of Natural Products. 69(5):783-789
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Abstract:

Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid δ-lactone (1-5); one contained a 26,12-δ-lactone and a C-12-C-23 bond (6); five corresponded to trechonolide-type withanolides with configuration at C-23 opposite of those previously isolated (7, 8, 10-12); two of these have an additional oxido-bridge between C-21 and C-24; finally a withanolide with a hemiketal ring formed between a 21-hydroxyl and a 12-ketone (13) and the closely related jaborosalactone R were also isolated. New compounds were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS). The structures of the spiranoid withanolide and of the epimer of trechonolide A were confirmed by X-ray diffraction studies. Compounds 4, 5, 6, and 8 showed selective phytotoxicity toward monocotyledoneous and dicotyledoneous species. © 2006 American Chemical Society and American Society of Pharmacognosy.

Registro:

Documento: Artículo
Título:Phytotoxic withanolides from Jaborosa rotacea
Autor:Nicotra, V.E.; Ramacciotti, N.S.; Gil, R.R.; Oberti, J.C.; Feresin, G.E.; Guerrero, C.A.; Baggio, R.F.; Garland, M.T.; Burton, G.
Filiación:Departamento de Química Orgánica and IMBIV, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 5000 Córdoba, Argentina
Instituto de Biotecnología, Facultad de Ingeniería, Universidad Nacional de San Juan, San Juan, Argentina
Departamento de Física, CNEA, Buenos Aires, Argentina
Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile, Chile
Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA Buenos Aires, Argentina
Department of Chemistry, Carnegie Mellon University, 4400 Fifth Ave., Pittsburgh, PA 15213, United States
Palabras clave:herbicide; jaborosalactone 29 [(20s,22s) 6alpha chloro 12alpha,22 epoxy 5beta,12beta,17beta trihydroxy 1 oxo witha 2,24 dien 26,22 olide]; jaborosalactone 30 [(20s,22s) 12alpha 22 epoxy 6beta,12beta,17beta trihydroxy 1 oxo witha 2,4,24 (trien 26,22 olide]; jaborosalactone 31 [(20s,23r) 12beta,26 epoxy 5alpha,6beta,17beta trihydroxy 26 oxo 12alpha,23 cycloergosta 2,24 (dien 1,22 dione]; jaborosalactone 33 [(22s,23r) 12alpha,22 epoxy 5alpha,6beta,12beta,17beta tetrahydroxy 1 oxo witha 2,24 dien 26,23 olide]; unclassified drug; withanolide; angiosperm; article; Jaborosa rotacea; nuclear magnetic resonance; phytotoxicity; spectroscopy; X ray diffraction; Argentina; Crystallography, X-Ray; Ergosterol; Lettuce; Molecular Conformation; Molecular Structure; Phalaris; Seedling; Solanaceae; Jaborosa
Año:2006
Volumen:69
Número:5
Página de inicio:783
Página de fin:789
DOI: http://dx.doi.org/10.1021/np0600090
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:withanolide, 40326-62-3; Ergosterol, 57-87-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v69_n5_p783_Nicotra

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Citas:

---------- APA ----------
Nicotra, V.E., Ramacciotti, N.S., Gil, R.R., Oberti, J.C., Feresin, G.E., Guerrero, C.A., Baggio, R.F.,..., Burton, G. (2006) . Phytotoxic withanolides from Jaborosa rotacea. Journal of Natural Products, 69(5), 783-789.
http://dx.doi.org/10.1021/np0600090
---------- CHICAGO ----------
Nicotra, V.E., Ramacciotti, N.S., Gil, R.R., Oberti, J.C., Feresin, G.E., Guerrero, C.A., et al. "Phytotoxic withanolides from Jaborosa rotacea" . Journal of Natural Products 69, no. 5 (2006) : 783-789.
http://dx.doi.org/10.1021/np0600090
---------- MLA ----------
Nicotra, V.E., Ramacciotti, N.S., Gil, R.R., Oberti, J.C., Feresin, G.E., Guerrero, C.A., et al. "Phytotoxic withanolides from Jaborosa rotacea" . Journal of Natural Products, vol. 69, no. 5, 2006, pp. 783-789.
http://dx.doi.org/10.1021/np0600090
---------- VANCOUVER ----------
Nicotra, V.E., Ramacciotti, N.S., Gil, R.R., Oberti, J.C., Feresin, G.E., Guerrero, C.A., et al. Phytotoxic withanolides from Jaborosa rotacea. J. Nat. Prod. 2006;69(5):783-789.
http://dx.doi.org/10.1021/np0600090