Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis.
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.
Chludil
Hugo D
HD
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina.
Muniain
Claudia C
CC
Seldes
Alicia M
AM
Maier
Marta S
MS
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001118:Argentina; D001156:Artemia / Q000187:drug effects; D002963:Cladosporium / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006868:Hydrolysis; D020128:Inhibitory Concentration 50; D007814:Larva / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012616:Sea Cucumbers / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000935:Antifungal Agents; D006027:Glycosides; D014315:Triterpenes; C464742:hemoiedemoside A; C464743:hemoiedemoside B