Abstract:
The investigation of the ethanol extract of Acanthospermum australe, collected in the province of Misiones, Argentina, yielded eight melampolides (1-8) of the acanthospermal type. Two of them, 8β-hydroxy-9α-(2-methylbutyryloxy)-14-oxo-acanthospermolide (3) and 9α-hydroxy-8β-(2-methylbutyryloxy)-14-oxo-acanthospermolide (7) are new compounds. Two other compounds (4 and 8) have been previously reported, and the NMR data of 4 are corrected. Compounds 1, 2, 5 and 6 have not been previously reported, but are probably artifacts formed during extraction. Compounds 3, 6 and 7 showed slight antibiotic activity against Gram-positive bacteria. © 2009 Phytochemical Society of Europe.
Registro:
Documento: |
Artículo
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Título: | Melampolides from Argentinean Acanthospermum australe |
Autor: | Sánchez, M.; Kramer, F.; Bargardi, S.; Palermo, J.A. |
Filiación: | UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon 2, 1428 Buenos Aires, Argentina Departamentos de Farmacia y Microbiología, Facultad de Ciencias Exactas, Químicas y Naturales, Univ. Nacional de Misiones, Av. Mariano Moreno 1375, 3300 Posadas, Misiones, Argentina
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Palabras clave: | Acanthospermolides; Acanthospermum australe; Melampolides; Sesquiterpene lactones; 8beta hydroxy 9alpha (2 methylbutyryloxy) 14 oxo acanthospermolide; 9alpha hydroxy 8beta (2 methylbutyryloxy) 14 oxo acanthospermolide; acanthospermum australe extract; melampolide; plant extract; unclassified drug; Acanthospermum australe; antimicrobial activity; Argentina; article; artifact; drug isolation; drug structure; Gram positive bacterium; nuclear magnetic resonance; priority journal; shrub; Acanthospermum australe; Posibacteria |
Año: | 2009
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Volumen: | 2
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Número: | 3
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Página de inicio: | 93
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Página de fin: | 95
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DOI: |
http://dx.doi.org/10.1016/j.phytol.2008.12.007 |
Título revista: | Phytochemistry Letters
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Título revista abreviado: | Phytochem. Lett.
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ISSN: | 18743900
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18743900_v2_n3_p93_Sanchez |
Referencias:
- Bohlmann, F., Jakupovic, J., Zdero, C., King, R.M., Robinson, H., Neue Melampolide und cis,cis-Germacranolide aus Vertretern der Subtribus Melampodiinae (1979) Phytochemistry, 18, pp. 625-630
- Bohlmann, F., Jakupovic, J., Dhar, A.K., King, R.M., Robinson, H., Two sesquiterpene and three diterpene lactones from Acanthospermum australe (1981) Phytochemistry, 20, pp. 1081-1083
- Bohlmann, F., Schmeda-Hirschmann, G., Jakupovic, J., New melampolides from Acanthospermum australe (1984) Planta Med., 50, pp. 37-39
- Debenedetti, S., Martino, V., Palacios, P., Coussio, J.D., 6-Methoxyflavonoids from Acanthospermum Australe (1987) J. Nat. Prod., 50, pp. 325-1325
- Herz, W., Kalyanaraman, P.S., Acanthospermal A and Acanthospermal B, two new melampolides from Acanthospermum species (1975) J. Org. Chem., 40, pp. 3486-3491
- Matsunaga, K., Sayito, M., Ohizumi, Y., Acanthostral, a novel antineoplastic cis-cis-cis-germacranolide from Acanthospermum australe (1996) Tetrahedron Lett., 37, pp. 1455-1456
- Saleh, A.A., Cordell, G.A., Farnsworth, N.R., Potential anticancer agents. Part 13. Cytotoxic constituents of Acanthospermum glabratum (Asteraceae) (1980) J. Chem. Soc. Perkin Trans., 1 (5), pp. 1090-1097
- Seaman, F.C., Fischer, N.H., Stuessy, T.F., Systematic implications of sesquiterpene lactones in the subtribe melampodiinae (1980) Biochem. Syst. Ecol., 8, pp. 263-271
- Xiang, Y., Fan, C.Q., Yue, J.M., Novel sesquiterpenoids from Siegesbeckia orientalis (2005) Helv. Chim. Acta, 88, pp. 160-170
Citas:
---------- APA ----------
Sánchez, M., Kramer, F., Bargardi, S. & Palermo, J.A.
(2009)
. Melampolides from Argentinean Acanthospermum australe. Phytochemistry Letters, 2(3), 93-95.
http://dx.doi.org/10.1016/j.phytol.2008.12.007---------- CHICAGO ----------
Sánchez, M., Kramer, F., Bargardi, S., Palermo, J.A.
"Melampolides from Argentinean Acanthospermum australe"
. Phytochemistry Letters 2, no. 3
(2009) : 93-95.
http://dx.doi.org/10.1016/j.phytol.2008.12.007---------- MLA ----------
Sánchez, M., Kramer, F., Bargardi, S., Palermo, J.A.
"Melampolides from Argentinean Acanthospermum australe"
. Phytochemistry Letters, vol. 2, no. 3, 2009, pp. 93-95.
http://dx.doi.org/10.1016/j.phytol.2008.12.007---------- VANCOUVER ----------
Sánchez, M., Kramer, F., Bargardi, S., Palermo, J.A. Melampolides from Argentinean Acanthospermum australe. Phytochem. Lett. 2009;2(3):93-95.
http://dx.doi.org/10.1016/j.phytol.2008.12.007