Novel cytotoxic oxygenated C29 sterols from the Colombian marine sponge Polymastia tenax.
Three new sterols, 5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol (1), 5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol (2), and 3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one (3), have been isolated from the marine sponge Polymastia tenax, collected in the Colombian Caribbean, and their structures established on the basis of extensive NMR and MS studies. Compounds 1 and 2 showed antiproliferative activity toward A-549, HT-29, H-116, MS-1, and PC-3 tumor cells in the range 0.5-10 microg/mL.
Santafé
Gilmar
G
Departamento de Química Fundamental, Facultade de Ciencias, Universidade de A Coruña, 15071 A Coruña, Spain.
Paz
Vanessa
V
Rodríguez
Jaime
J
Jiménez
Carlos
C
D000818:Animals; D017691:Caribbean Region; D002851:Chromatography, High Pressure Liquid; D003105:Colombia; D003110:Colonic Neoplasms; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008175:Lung Neoplasms; D008297:Male; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011471:Prostatic Neoplasms; D013237:Stereoisomerism; D013261:Sterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism
C466363:3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one; C466362:5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol; C466364:5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol; D013261:Sterols