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Abstract:

Two new sulfated steroidal hexaglycosides, anasterosides A (2) and B (3), along with the known versicoside A (1) have been isolated from the Patagonian starfish Anasterias minuta. Their structures have been elucidated by spectroscopic analysis (NMR and FABMS) and chemical transformations. Compounds 1 and 2 and the synthetic pentaglycoside 1b derived from versicoside A showed antifungal activity against the plant pathogenic fungus Cladosporium cucumerinum. Desulfation of hexaglycoside 1 rendered a totally inactive saponin.

Registro:

Documento: Artículo
Título:Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations
Autor:Chludil, H.D.; Seldes, A.M.; Maier, M.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, 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
Palabras clave:anasteroside a; anasteroside b; antifungal agent; glycoside; thornasteroside; unclassified drug; versicoside a; anasterias minuta; antifungal activity; article; Asterias; chemical modification; Cladosporium cucumerinum; correlation analysis; drug isolation; nonhuman; nuclear magnetic resonance spectroscopy; plant fungus interaction; structure activity relation; structure analysis; sulfation and desulfurization; Animals; Antifungal Agents; Argentina; Cholestenones; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Cladosporium; Dose-Response Relationship, Drug; Glycosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pregnenes; Starfish; Structure-Activity Relationship; Asterias; Asteroidea; Cladosporium; Cladosporium cucumerinum; Fungi
Año:2002
Volumen:65
Número:2
Página de inicio:153
Página de fin:157
DOI: http://dx.doi.org/10.1021/np010332x
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:Antifungal Agents; Cholestenones; Glycosides; Pregnenes; anasteroside A; anasteroside B; versicoside A
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v65_n2_p153_Chludil

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Citas:

---------- APA ----------
Chludil, H.D., Seldes, A.M. & Maier, M.S. (2002) . Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations. Journal of Natural Products, 65(2), 153-157.
http://dx.doi.org/10.1021/np010332x
---------- CHICAGO ----------
Chludil, H.D., Seldes, A.M., Maier, M.S. "Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations" . Journal of Natural Products 65, no. 2 (2002) : 153-157.
http://dx.doi.org/10.1021/np010332x
---------- MLA ----------
Chludil, H.D., Seldes, A.M., Maier, M.S. "Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations" . Journal of Natural Products, vol. 65, no. 2, 2002, pp. 153-157.
http://dx.doi.org/10.1021/np010332x
---------- VANCOUVER ----------
Chludil, H.D., Seldes, A.M., Maier, M.S. Antifungal steroidal glycosides from the Patagonian starfish Anasterias minuta: Structure - Activity correlations. J. Nat. Prod. 2002;65(2):153-157.
http://dx.doi.org/10.1021/np010332x