Structure and cytotoxicity of new polyhydroxylated sterols from the Caribbean gorgonian Plexaurella grisea.
The gorgonian Plexaurella grisea contains the new steroids 9-hydroxygorgosterol (1), 9,11 alpha,14-trihydroxygorgosterol (2), 5 beta,6 beta-epoxyergost-24(28)-ene-3 beta,7 beta-diol (3), ergost-24(28)-ene-3 beta,5 alpha,6 beta,7 beta-tetrol (4), an unseparable 1:1 mixture of the epimers (25R) and (25S)-26-acetoxy-3 beta,5 alpha-dihydroxyergost-24(28)-en-6-one (5/6), and seven related, known compounds (7-13). The structures of these new compounds were defined by spectroscopic analysis. All the compounds (1-13) isolated from P. grisea were tested against P 388, A 549, and HT 29 tumor cell lines. Compounds 3, 5/6, and 12 exhibited selective activity against the HT 29 cell line (ED(50) = 0.1 microg/ml).
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Dpto. de Química Orgánica, Facultad de Ciencias del Mar, Universidad de Cádiz, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
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Ortega
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Salvá
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D000818:Animals; D017691:Caribbean Region; D002851:Chromatography, High Pressure Liquid; D003063:Cnidaria / Q000737:chemistry*; D019073:HT29 Cells; D006801:Humans; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009904:Optical Rotation; D013261:Sterols / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D013379:Substrate Specificity; D014407:Tumor Cells, Cultured
D013261:Sterols