Abstract:
In addition to the known compounds withanolide A (4), withanone (5), and NIC-3 (6), three 16-hydroxylated withanolides were isolated from Exodeconus maritimus. The new withanolides were identified as 6α,7α-epoxy-5α,16β- dihydroxy-1-oxowitha-2,17(20),24-trienolide (exodeconolide A, 1), 6α,7α- epoxy-5α,16α-dihydroxy-l-oxowitha-2,17(20),24-trienolide (exodeconolide B, 2), and 6α7α-epoxy-5α,16α,17α-trihydroxy-1-oxowitha-2, 24-dienolide (exodeconolide C, 3), by a combination of spectroscopic (1D and 2D NMR, MS) and chemical methods with the aid of molecular modeling.
Registro:
Documento: |
Artículo
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Título: | 16-hydroxylated withanolides from Exodeconus maritimus |
Autor: | Gil, R.R.; Misico, R.I.; Sotes, I.R.; Oberti, J.C.; Veleiro, A.S.; Burton, G. |
Filiación: | Depto. de Quim. Organ. and IMBIV, Facultad de Ciencias Químicas, Univ. Nacional de Córdoba, Agenda Postal 4-CC 61, 5000 Córdoba, Argentina Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
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Palabras clave: | exodeconolide a; exodeconolide b; exodeconolide c; nic 3; unclassified drug; withanolide; withanolide a; withanone; antiinflammatory activity; antimicrobial activity; antineoplastic activity; article; defense mechanism; drug isolation; drug structure; immunomodulation; mass spectrometry; nuclear magnetic resonance; phytochemistry; species differentiation; structure activity relation; taxonomy; Exodeconus maritimus |
Año: | 1997
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Volumen: | 60
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Número: | 6
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Página de inicio: | 568
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Página de fin: | 572
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DOI: |
http://dx.doi.org/10.1021/np970048z |
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_v60_n6_p568_Gil |
Referencias:
- Axelius, B., (1994) Plants System. Evol., 193, pp. 153-172
- Subramanian, S.S., Sethi, P.D., Glottler, E., Kirson, I., Lavie, D., (1971) Phytochemistry, 10, pp. 685-688
- Kirson, I., Glotter, E., Lavie, D., (1971) J. Chem. Soc. (C), pp. 2032-2044
- Begley, M.J., Crombie, L., Ham, P.J., Whiting, D.A., (1976) J. Chem. Soc., Perkin Trans. I, pp. 296-303
- Ray, A.B., Gupta, M., (1994) Prog. Chem. Org. Nat. Prod., 63, pp. 1-106
- Dinan, L., Whiting, P., Alfonso, D., Kapetanidis, I., (1996) Entomol. Exp. Appl., 80, pp. 415-420
- Kirson, I., Glotter, E., Lavie, D., Abraham, A., (1971) J. Chem. Soc. (C), pp. 2032-2044
- Haasnoot, C.A.G., De Leeuw, A.A.M., Altona, C.A., (1980) Tetrahedron, 36, pp. 2783-2792
- Habtemariam, S., Gray, A.I., Waterman, P.G., (1993) Phytochemistry, 34, pp. 807-811
- See, for example, Kirson et. al. in reference 7; Pelletier, S.W., Chokshi, H.P., Desai, H.K., (1986) J. Nat. Prod., 49, pp. 892-900
Citas:
---------- APA ----------
Gil, R.R., Misico, R.I., Sotes, I.R., Oberti, J.C., Veleiro, A.S. & Burton, G.
(1997)
. 16-hydroxylated withanolides from Exodeconus maritimus. Journal of Natural Products, 60(6), 568-572.
http://dx.doi.org/10.1021/np970048z---------- CHICAGO ----------
Gil, R.R., Misico, R.I., Sotes, I.R., Oberti, J.C., Veleiro, A.S., Burton, G.
"16-hydroxylated withanolides from Exodeconus maritimus"
. Journal of Natural Products 60, no. 6
(1997) : 568-572.
http://dx.doi.org/10.1021/np970048z---------- MLA ----------
Gil, R.R., Misico, R.I., Sotes, I.R., Oberti, J.C., Veleiro, A.S., Burton, G.
"16-hydroxylated withanolides from Exodeconus maritimus"
. Journal of Natural Products, vol. 60, no. 6, 1997, pp. 568-572.
http://dx.doi.org/10.1021/np970048z---------- VANCOUVER ----------
Gil, R.R., Misico, R.I., Sotes, I.R., Oberti, J.C., Veleiro, A.S., Burton, G. 16-hydroxylated withanolides from Exodeconus maritimus. J. NAT. PROD. 1997;60(6):568-572.
http://dx.doi.org/10.1021/np970048z