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Abstract:

Two new sulfated triterpene glycosides, hemoiedemosides A (1) and B (2), have been isolated from the Patagonian sea cucumber Hemoiedema spectabilis. Their structures have been established by a combination of spectroscopic analysis (NMR and FABMS) and chemical transformations. Both glycosides present the same aglycon and differ in the degree of sulfation of the tetrasaccharide chain. Hemoiedemoside B (2) is a new example of a small number of trisulfated triterpene glycosides from sea cucumbers belonging to the family Cucumariidae. Glycosides 1 and 2 exhibit considerable antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum, while the semisynthetic desulfated derivative 1a is less active.

Registro:

Documento: Artículo
Título:Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis
Autor:Chludil, H.D.; Muniain, C.C.; Seldes, A.M.; Maier, M.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Departamento de Química, Facultad de Ciencias Naturales, Universidad Nacional de la Patagonia San Juan Bosco, Km 4, 9000 Comodoro Rivadavia, Chubut, Argentina
Museo Argentino de Ciencias Naturales Bernardino Rivadavia, Av. A. Gallardo 470, 1405 Buenos Aires, Argentina
Palabras clave:glycoside; hemoiedemoside A; hemoiedemoside B; triterpene derivative; unclassified drug; antifungal activity; article; chemical modification; Cladosporium cucumerinum; cytotoxicity; drug structure; echinoderm; Hemoiedema spectabilis; nonhuman; nuclear magnetic resonance; sulfation; Animals; Antifungal Agents; Argentina; Artemia; Cladosporium; Dose-Response Relationship, Drug; Glycosides; Hydrolysis; Inhibitory Concentration 50; Larva; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Sea Cucumbers; Triterpenes; Cladosporium; Cladosporium cucumerinum; Cucumariidae; Cucumis sativus; Echinodermata; Fungi; Holothuroidea
Año:2002
Volumen:65
Número:6
Página de inicio:860
Página de fin:865
DOI: http://dx.doi.org/10.1021/np0106236
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:Antifungal Agents; Glycosides; Triterpenes; hemoiedemoside A; hemoiedemoside B
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v65_n6_p860_Chludil

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., Anisimov, M.M., Prokofieva, N.G., Avilov, S.A., Afiyatullov, Sh.Sh., Stonik, V.A., Biological activities and biological role of triterpene glycosides from holothuroids (Echinodermata) (1996) Echinoderm Studies, 5, pp. 139-181. , Jangoux, M., Lawrence, J.M., Eds.; A.A. Balkema: Rotterdam
  • Maier, M.S., Roccatagliata, A.J., Kuriss, A., Chludil, H., Seldes, A.M., Pujol, C.A., Damonte, E.B., (2001) J. Nat. Prod., 64, pp. 732-736
  • Maier, M.S., Kuriss, A., Seldes, A.M., (1998) Lipids, 33, pp. 825-827
  • Comin, M.J., Maier, M.S., Roccatagliata, A.J., Pujol, C.A., Damonte, E.B., (1999) Steroids, 64, pp. 335-340
  • Murray, A.P., Muniain, C., Seldes, A.M., Maier, M.S., (2001) Tetrahedron, 57, pp. 9563-9568
  • Kitagawa, I., Yamanaka, H., Kobayashi, M., Nishino, T., Yosioka, I., Sugawara, T., (1978) Chem. Pharm. Bull., 26, pp. 3722-3731
  • Garneau, F.-X., Simard, J.-L., Harvey, O., ApSimon, J.W., Girard, M., (1983) Can. J. Chem., 61, pp. 1465-1471
  • Miyamoto, T., Togawa, K., Higuchi, R., Komori, T., Sasaki, T., (1992) J. Nat. Prod., 55, pp. 940-946
  • Zurita, M.B., Ahond, A., Poupat, C., Potier, P., (1986) J. Nat. Prod., 49, pp. 809-813
  • Stonik, V.A., Kalinin, V.I., Avilov, S.A., (1999) J. Nat. Toxins, 8, pp. 235-248
  • Breitmaier, E., Voelter, W., (1987) Carbon-13 NMR Spectroscopy, , VCH: Weinheim, Germany
  • Björndal, H., Lindberg, B., Svensson, S., (1967) Carbohydr. Res., 5, pp. 433-440
  • Miyamoto, T., Togawa, K., Higuchi, R., Komori, T., Sasaki, T., (1990) Liebigs Ann. Chem., pp. 453-460
  • 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
  • Drozdova, O.A., Avilov, S.A., Kalinin, V.I., Kalinovsky, A.I., Stonik, V.A., Riguera, R., Jiménez, C., (1997) Liebigs Ann./Recl., pp. 2351-2356
  • Avilov, S.A., Drozdova, O.A., Kalinin, V.I., Kalinovsky, A.I., Stonik, V.A., Gudimova, E.N., Riguera, R., Jiménez, C., (1998) Can. J. Chem., 76, pp. 137-141
  • Homans, A.L., Fuchs, A., (1970) J. Chromatogr., 51, pp. 327-329
  • Meyer, B.N., Ferrigni, N.R., Putnam, J.E., Jacobsen, L.B., Nichols, D.E., McLaughlin, J.L., (1982) Planta Med., 45, pp. 31-34

Citas:

---------- APA ----------
Chludil, H.D., Muniain, C.C., Seldes, A.M. & Maier, M.S. (2002) . Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis. Journal of Natural Products, 65(6), 860-865.
http://dx.doi.org/10.1021/np0106236
---------- CHICAGO ----------
Chludil, H.D., Muniain, C.C., Seldes, A.M., Maier, M.S. "Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis" . Journal of Natural Products 65, no. 6 (2002) : 860-865.
http://dx.doi.org/10.1021/np0106236
---------- MLA ----------
Chludil, H.D., Muniain, C.C., Seldes, A.M., Maier, M.S. "Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis" . Journal of Natural Products, vol. 65, no. 6, 2002, pp. 860-865.
http://dx.doi.org/10.1021/np0106236
---------- VANCOUVER ----------
Chludil, H.D., Muniain, C.C., Seldes, A.M., Maier, M.S. Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis. J. Nat. Prod. 2002;65(6):860-865.
http://dx.doi.org/10.1021/np0106236