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Abstract:

Seven new withanolides (1-7) were isolated from the aerial parts of Jaborosa caulescens var. caulescens and Jaborosa caulescens var. bipinnatifida. Three of the new compounds are related to jaborosalactones R, S, and T with a δ5-lactone side chain and a hemiketal (or ketal) ring formed between a 21-hydroxyl and a 12-ketone (1-3). Compounds 4-7 are trechonolide-type withanolides with a γ-lactone side chain and a hemiketal (or ketal) ring formed between a 22-hydroxyl and a 12-ketone. Compounds 4 and 5 also contain a hydroxyl group at C-21. Compounds 1, 2, and 7 showed selective phytotoxicity toward monocotyledonous and dicotyledonous species. © 2007 American Chemical Society and American Society of Pharmacognosy.

Registro:

Documento: Artículo
Título:Withanolides with phytotoxic activity from Jaborosa caulescent var. caulescens and J. caulescens var. bipinnatifida
Autor:Nicotra, V.E.; Gil, R.R.; Oberti, J.C.; Burton, G.
Filiación:Departamento de Química Orgánica and IMBIV, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, 5000 Córdoba, Argentina
Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas Y Naturales, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Department of Chemistry, Carnegie Mellon University, 4400 Fifth Ave., Pittsburgh, PA 15213, United States
Palabras clave:12 o ethyljaborosalactone 42; 12 o methyljaborosalactone 38; acetal; hydroxyl group; Jaborosa caulescens extract; jaborosalactone 38; jaborosalactone 39; jaborosalactone 40; jaborosalactone 41; jaborosalactone 42; ketone; plant extract; unclassified drug; withanolide; article; chromatography; drug structure; Jaborosa caulescens; medicinal plant; nonhuman; nuclear magnetic resonance; phytotoxicity; Argentina; Avena sativa; Ergosterol; Germination; Herbicides; Lettuce; Molecular Structure; Plants, Medicinal; Seedling; Solanaceae; Jaborosa
Año:2007
Volumen:70
Número:5
Página de inicio:808
Página de fin:812
DOI: http://dx.doi.org/10.1021/np070030g
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:acetal, 105-57-7, 37217-19-9; withanolide, 40326-62-3; Ergosterol, 57-87-4; Herbicides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v70_n5_p808_Nicotra

Referencias:

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  • Compounds 4 and 5 slowly decomposed on standing, as evidenced by TLC, and required purification at the moment of carrying out the spectroscopic analyses. This did not allow obtaining the corresponding high-resolution mass spectra when samples were submitted for analysis; Herz, W., Hogenauer, G., (1961) J. Org. Chem, 26, pp. 5011-5013

Citas:

---------- APA ----------
Nicotra, V.E., Gil, R.R., Oberti, J.C. & Burton, G. (2007) . Withanolides with phytotoxic activity from Jaborosa caulescent var. caulescens and J. caulescens var. bipinnatifida. Journal of Natural Products, 70(5), 808-812.
http://dx.doi.org/10.1021/np070030g
---------- CHICAGO ----------
Nicotra, V.E., Gil, R.R., Oberti, J.C., Burton, G. "Withanolides with phytotoxic activity from Jaborosa caulescent var. caulescens and J. caulescens var. bipinnatifida" . Journal of Natural Products 70, no. 5 (2007) : 808-812.
http://dx.doi.org/10.1021/np070030g
---------- MLA ----------
Nicotra, V.E., Gil, R.R., Oberti, J.C., Burton, G. "Withanolides with phytotoxic activity from Jaborosa caulescent var. caulescens and J. caulescens var. bipinnatifida" . Journal of Natural Products, vol. 70, no. 5, 2007, pp. 808-812.
http://dx.doi.org/10.1021/np070030g
---------- VANCOUVER ----------
Nicotra, V.E., Gil, R.R., Oberti, J.C., Burton, G. Withanolides with phytotoxic activity from Jaborosa caulescent var. caulescens and J. caulescens var. bipinnatifida. J. Nat. Prod. 2007;70(5):808-812.
http://dx.doi.org/10.1021/np070030g