Antifungal steroidal glycosides from the patagonian starfish anasteriasminuta: structure-activity correlations.
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.
Chludil
Hugo D
HD
Departamento de Química, Facultad de Ciencias Naturales, Universidad Nacional de la Patagonia, San Juan Bosco, Chubut, Argentina.
Seldes
Alicia M
AM
Maier
Marta S
MS
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001118:Argentina; D002783:Cholestenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D002963:Cladosporium / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011283:Pregnenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013215:Starfish / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D002783:Cholestenones; D006027:Glycosides; D011283:Pregnenes; C451137:anasteroside A; C451139:anasteroside B; C451138:versicoside A