Abstract:
Seven new withanolides, salpichrolides O-U (1-7), the known 2,3-dihydrosalpichrolide B (9), a substance not previously isolated from a natural source, and three known compounds, salpichrolide D (8), salpichrolide A (10), and salpichrolide C (11), were isolated and characterized from the aerial parts of Salpichroa origanifolia and S. tristis var. lehmannii. Compounds 1-4 and 8 have an oxygenated D ring, while compounds 5-7 and 9-11 possess a six-membered aromatic D ring. The structures of the isolated compounds were identified by analysis of their spectroscopic data including NMR and MS. Withanolides 1, 3, 8, 10, and 11 exhibited selective radicle growth inhibition toward Lactuca sativa (lettuce) at 150 and 400 ppm. © 2013 The American Chemical Society and American Society of Pharmacognosy.
Registro:
Documento: |
Artículo
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Título: | Withanolides with phytotoxic activity from two species of the genus salpichroa: S. origanifolia and s. tristis var. lehmannii |
Autor: | Nicotra, V.E.; Basso, A.V.; Ramacciotti, N.S.; Misico, R.I. |
Filiación: | Facultad de Ciencias Químicas, Instituto Multidisciplinario de Biología Vegetal (IMBIV-CONICET), Universidad Nacional de Córdoba, Casilla de Correo 495, 5000 Córdoba, Argentina Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Buenos Aires, Argentina
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Palabras clave: | 2,3 dihydrosalpichrolide b; salpichrolide a; salpichrolide c; salpichrolide o; salpichrolide p; salpichrolide q; salpichrolide r; salpichrolide s; salpichrolide t; salpichrolide u; unclassified drug; withanolide; article; lettuce; mass spectrometry; nuclear magnetic resonance spectroscopy; oat; phytotoxicity; plant; Salpichroa origanifolia; Salpichroa tristis var. lehmannii; Argentina; Ergosterol; Molecular Structure; Solanaceae; Withanolides |
Año: | 2013
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Volumen: | 76
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Número: | 12
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Página de inicio: | 2219
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Página de fin: | 2225
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DOI: |
http://dx.doi.org/10.1021/np400559p |
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
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v76_n12_p2219_Nicotra |
Referencias:
- Ray, A.B., Gupta, M., (1994) Prog. Chem. Org. Nat. Prod., 63, pp. 1-106
- Veleiro, A.S., Oberti, J.C., Burton, G., (2005) Studies in Natural Products Chemistry, Bioactive Natural Products (Part L), 32, pp. 1019-1052. , In; Atta-ur-Rahman, Elsevier Science Publishers: Amsterdam, Vol
- Chen, L., He, H., Qiu, F., (2011) Nat. Prod. Rep., 28, pp. 705-740
- Misico, R.I., Nicotra, V., Oberti, J.C., Barboza, G., Gil, R.R., Burton, G., (2011) Progress in the Chemistry of Organic Natural Products, 94, pp. 127-229. , In; Kinghorn, A. D. Falk, H. Kobayashi, J. Springer-Verlag: Vienna, Vol. Chapter 3
- Hunziker, A.T., (2001) The Genera of Solanaceae Illustrated: Arranged According to A New System, 16, p. 500. , A. R. G. Gantner Verlag K.-G. Ruggell, Germany, Vol
- Veleiro, A.S., Oberti, J.C., Burton, G., (1992) Phytochemistry, 31, pp. 935-937
- Veleiro, A.S., Burton, G., Bonetto, G.M., Gil, R.R., Oberti, J.C., (1994) J. Nat. Prod., 57, pp. 1741-1745
- Tettamanzi, M.C., Veleiro, A.S., Oberti, J.C., Burton, G., (1996) Phytochemistry, 43, pp. 461-463
- Tettamanzi, M.C., Veleiro, A.S., Oberti, J.C., Burton, G., (1998) J. Nat. Prod., 61, pp. 338-342
- Tettamanzi, M.C., Veleiro, A.S., De La Fuente, J.R., Burton, G., (2001) J. Nat. Prod., 64, pp. 783-786
- Mareggiani, G., Picollo, M.I., Zerba, E., Burton, G., Tettamanzi, M.C., Benedetti-Doctorovich, M.O.V., Veleiro, A.S., (2000) J. Nat. Prod., 63, pp. 1113-1116
- Mareggiani, G., Picollo, M.I., Veleiro, A.S., Tettamanzi, M.C., Benedetti-Doctorovich, M.O.V., Burton, G., Zerba, E., (2002) J. Agric. Food Chem., 50, pp. 104-107
- Bado, S., Mareggiani, G., Amiano, N., Burton, G., Veleiro, A.S., (2004) J. Agric. Food Chem., 52, pp. 2875-2878
- Misico, R.I., Song, L.L., Veleiro, A.S., Cirigliano, A.M., Tettamanzi, M.C., Burton, G., Bonetto, G.M., Pezzuto, J.M., (2002) J. Nat. Prod., 65, pp. 677-680
- Machin, R.P., Veleiro, A.S., Nicotra, V.E., Oberti, J.C., Padrón, J.M., (2010) J. Nat. Prod., 73, pp. 966-968
- Vaccarini, C.E., Bonetto, G.M., (2000) J. Chem. Ecol., 26, pp. 2187-2193
- Nicotra, V.E., Gil, R.R., Vaccarini, C.E., Oberti, J.C., Burton, G., (2003) J. Nat. Prod., 66, pp. 1471-1475
- Nicotra, V.E., Ramacciotti, N.S., Gil, R.R., Oberti, J.C., Feresin, G.E., Guerrero, C.A., Baggio, R.F., Burton, G., (2006) J. Nat. Prod., 69, pp. 783-789
- Nicotra, V.E., Ramacciotti, N.S., (2007) J. Nat. Prod., 70, pp. 1513-1515
- Nicotra, V.E., Gil, R.R., Oberti, J.C., Burton, G., (2007) J. Nat. Prod., 70, pp. 808-812
- Maldonado, E., Amador, S., Martinez, M., Pérez-Castorena, A., (2010) Steroids, 75, pp. 346-349
- Bonetto, G.M., Gil, R.R., Oberti, J.C., Veleiro, A.S., Burton, G., (1995) J. Nat. Prod., 58, pp. 705-711
- Shingu, K., Yahara, S., Nohara, T., (1994) Chem. Pharm. Bull., 42, pp. 318-321
- Gill, H.K., Smith, R.W., Whiting, D.A., (1990) J. Chem. Soc., Perkin Trans.1, pp. 2989-2993
- Bravo, J.A., Sauvain, M., Gimenez, A., Balanza, E., Serani, L., Laprévote, O., Massiot, G., Lavaud, C., (2001) J. Nat. Prod., 64, pp. 720-725
- Begley, M.J., Crombie, L., Ham, P.J., Whitting, D.A., (1972) J. Chem. Soc., Chem. Commun., pp. 1250-1251
- Bates, R.B., Eckert, D.J., (1972) J. Am. Chem. Soc., 94, pp. 8258-8260
Citas:
---------- APA ----------
Nicotra, V.E., Basso, A.V., Ramacciotti, N.S. & Misico, R.I.
(2013)
. Withanolides with phytotoxic activity from two species of the genus salpichroa: S. origanifolia and s. tristis var. lehmannii. Journal of Natural Products, 76(12), 2219-2225.
http://dx.doi.org/10.1021/np400559p---------- CHICAGO ----------
Nicotra, V.E., Basso, A.V., Ramacciotti, N.S., Misico, R.I.
"Withanolides with phytotoxic activity from two species of the genus salpichroa: S. origanifolia and s. tristis var. lehmannii"
. Journal of Natural Products 76, no. 12
(2013) : 2219-2225.
http://dx.doi.org/10.1021/np400559p---------- MLA ----------
Nicotra, V.E., Basso, A.V., Ramacciotti, N.S., Misico, R.I.
"Withanolides with phytotoxic activity from two species of the genus salpichroa: S. origanifolia and s. tristis var. lehmannii"
. Journal of Natural Products, vol. 76, no. 12, 2013, pp. 2219-2225.
http://dx.doi.org/10.1021/np400559p---------- VANCOUVER ----------
Nicotra, V.E., Basso, A.V., Ramacciotti, N.S., Misico, R.I. Withanolides with phytotoxic activity from two species of the genus salpichroa: S. origanifolia and s. tristis var. lehmannii. J. Nat. Prod. 2013;76(12):2219-2225.
http://dx.doi.org/10.1021/np400559p