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
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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
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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
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Volumen: | 69
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Número: | 5
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Página de inicio: | 783
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Página de fin: | 789
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DOI: |
http://dx.doi.org/10.1021/np0600090 |
Título revista: | Journal of Natural Products
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Título revista abreviado: | J. Nat. Prod.
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ISSN: | 01633864
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CODEN: | JNPRD
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CAS: | withanolide, 40326-62-3; Ergosterol, 57-87-4
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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