New polyoxygenated steroids from the Antarctic octocoral Dasystenella acanthina.
The chemical study of the Antarctic octocoral Dasystenella acanthina has led to the isolation of the new polyoxygenated steroids (24R,22E)-24-hydroxycholest-4,22-dien-3-one (1), 23-acetoxy-24,25-epoxycholest-4-en-3-one (2), 12beta-acetoxycholest-4-en-3,24-dione (3), 12beta-acetoxy-24,25-epoxycholest-4-en-3-one (4), (22E)-25-hydroxy-24-norcholest-4,22-dien-3-one (5), 3alpha-acetoxy-25-hydroxycholest-4-en-6-one (6), and 3alpha,11alpha-diacetoxy-25-hydroxycholest-4-en-6-one (7), whose structures have been established by spectroscopic analysis. The absolute stereochemistry at C-24 in compound 1 has been determined through the 1H NMR study of the corresponding (R)- and (S)-MPA esters. All the new compounds showed significant activities as growth inhibitors of several human tumor cell lines. In addition, cytostatic and cytotoxic effects were also observed on selected tumor cell lines.
Mellado
Gonzalo G
GG
Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Apdo. 40, 11510-Puerto Real, Cádiz, Spain.
Zubía
Eva
E
Ortega
María J
MJ
López-González
Pablo J
PJ
D000818:Animals; D000864:Antarctic Regions; D037421:Anthozoa / Q000737:chemistry*; D045744:Cell Line, Tumor; D004847:Epithelial Cells / Q000187:drug effects; D005260:Female; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D019906:Nuclear Magnetic Resonance, Biomolecular; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*
D013256:Steroids