Abstract:
Two new trisulfated triterpene glycosides, liouvillosides A (1) and B (2), have been isolated from the Antarctic sea cucumber Staurocucumis liouvillei. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Liouvillosides A (1) and B (2) are two new examples of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Both glycosides were found to be virucidal against herpes simplex virus type 1 (HSV-1) at concentrations below 10 μg/mL.
Registro:
Documento: |
Artículo
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Título: | Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber Staurocucumis liouvillei |
Autor: | Maier, M.S.; Roccatagliata, A.J.; Kuriss, A.; Chludil, H.; Seldes, A.M.; Pujol, C.A.; Damonte, E.B. |
Filiación: | Departamento de Química Orgánica, Facultad Ciencias Exactas Naturales, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina Departamento de Química Biológica, Facultad Ciencias Exactas Naturales, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | antivirus agent; liouvilloside A; liouvilloside B; triterpene derivative; unclassified drug; antiviral activity; article; cytostasis; cytotoxicity; drug isolation; echinoderm; Herpes simplex virus 1; immunomodulation; structure analysis; sulfation; Animals; Antineoplastic Agents; Antiviral Agents; Carbohydrate Conformation; Cercopithecus aethiops; Drug Screening Assays, Antitumor; Herpesvirus 1, Human; Hydrolysis; Magnetic Resonance Spectroscopy; Methylation; Microbial Sensitivity Tests; Oligosaccharides; Sea Cucumbers; Spectrometry, Mass, Fast Atom Bombardment; Triterpenes; Vero Cells |
Año: | 2001
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Volumen: | 64
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Número: | 6
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Página de inicio: | 732
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Página de fin: | 736
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DOI: |
http://dx.doi.org/10.1021/np000584i |
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: | Antineoplastic Agents; Antiviral Agents; Oligosaccharides; Triterpenes; liouvilloside A; liouvilloside B
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v64_n6_p732_Maier |
Referencias:
- Stonik, V.A., Elyakov, G.B., Secondary Metabolites from Echinoderms as Chemotaxonomic Markers (1988) Bioorganic Marine Chemistry, 2, pp. 43-86. , Scheuer P. J., Ed.; Springer: Berlin
- Kalinin, V.I., Volkova, O.V., Likhatskaya, G.N., Prokofieva, N.G., Agafonova, I.G., Anisimov, M.M., Kalinovsky, A.I., Stonik, V.A., (1992) J. Nat. Toxins, 1, pp. 31-37
- Kalinin, V.I., Anisimov, M.M., Prokofieva, N.G., Avilov, S.A., Afiyatullov, Sh.Sh., Stonik, V.A., Biological activities and biological role of triterpene glycosides from holothuroidea (Echinodermata) (1996) Echinoderm Studies, 5, pp. 139-181. , Jangoux, M., Lawrence, J. M., Eds.; A. A. Balkema: Rotterdam
- McKee, T.C., Cardellina, J.H., Riccio, R., D'Auria, M.V., Iorizzi, M., Minale, L., Moran, R.A., Boyd, M.R., (1994) J. Med. Chem., 37, pp. 793-797
- Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Pujol, C.A., Damonte, E.B., (1996) J. Nat. Prod., 59, pp. 887-889
- Comin, M.J., Maier, M.S., Roccatagliata, A.J., Pujol, C.A., Damonte, E.B., (1999) Steroids, 64, pp. 335-340
- Maier, M.S., Kuriss, A., Seldes, A.M., (1998) Lipids, 33, pp. 825-827
- Roccatagliata, A.J., Maier, M.S., Seldes, A.M., (1998) J. Nat. Prod., 61, pp. 370-374
- Avilov, S.A., Kalinovsky, A.I., Stonik, V.A., (1990) Khim. Prirod. Soedin, 1, pp. 53-57
- Girard, M., Bélanger, J., ApSimon, J.W., Garneau, F.-X., Harvey, C., Brisson, J.-R., (1990) Can. J. Chem., 68, pp. 11-18
- Breitmaier, E., Voelter, W., (1987) Carbon-13 NMR Spectroscopy, , VCH: Weinheim, Germany
- Miyamoto, T., Togawa, K., Higuchi, R., Komori, T., Sasaki, T., (1990) Liebigs Ann. Chem., pp. 453-460
- Cases, M.R., Cerezo, A.S., Stortz, C.A., (1995) Carbohydr. Res., 269, pp. 333-341
- Drozdova, O.A., Avilov, S.A., Kalinovsky, A.I., Stonik, V.A., Milgrom, Y.M., Rashkes, Y.V., (1993) Khim. Prirod. Soedin, pp. 369-374
- Avilov, S.A., Kalinovsky, A.I., Kalinin, V.I., Stonik, V.A., Riguera, R., Giménez, C., (1997) J. Nat. Prod., 60, pp. 808-810
- Sietnick, A.J., De Bruyne, T., Apers, S., Pieters, L.A., (1998) Planta Med., 64, pp. 97-109
- Simoes, C.M.O., Amoros, M., Schenkel, E.P., Shin-Kim, J.S., Rucker, G., Girre, L., (1990) Planta Med., 56, pp. 652-653
- Simoes, C.M.O., Amoros, M., Girre, L., (1999) Phytother. Res., 13, pp. 323-328
- Dargan, D.J., Subak-Sharpe, J.H., (1985) J. Gen. Virol., 66, pp. 1771-1784
Citas:
---------- APA ----------
Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A. & Damonte, E.B.
(2001)
. Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber Staurocucumis liouvillei. Journal of Natural Products, 64(6), 732-736.
http://dx.doi.org/10.1021/np000584i---------- CHICAGO ----------
Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., et al.
"Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber Staurocucumis liouvillei"
. Journal of Natural Products 64, no. 6
(2001) : 732-736.
http://dx.doi.org/10.1021/np000584i---------- MLA ----------
Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., et al.
"Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber Staurocucumis liouvillei"
. Journal of Natural Products, vol. 64, no. 6, 2001, pp. 732-736.
http://dx.doi.org/10.1021/np000584i---------- VANCOUVER ----------
Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., et al. Two new cytotoxic and virucidal trisulfated triterpene glycosides from the antarctic sea cucumber Staurocucumis liouvillei. J. Nat. Prod. 2001;64(6):732-736.
http://dx.doi.org/10.1021/np000584i