Two new 9,11-secosterols from the marine sponge Spongia officinalis. Synthesis of 9,11-seco-3 beta,6 alpha,11-trihydroxy-5 alpha-cholest-7-en-9-one.
Two new 9,11-secosterol, 9,11-seco-3 beta,6 alpha,11-trihydroxy-5 alpha-cholest-7-en-9-one (2) and 9,11-seco-3 beta,6 alpha,11-trihydroxy-24- methylene-5 alpha-cholest-7-en-9-one (3), have been isolated from the marine sponge Spongia officinalis and their structures elucidated by analysis of spectral data including 1H nuclear magnetic resonance correlation spectroscopy (COSY) experiments. Partial synthesis of 2 starting from 3 beta,6 alpha-dihydroxy-9-oxo-9,11-seco-5 alpha-cholest-7-en-11- al (1) confirmed the structure assignment.
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Dipartimento di Chimica Organica e Biologica, Università degli studi di Napoli, Italy.
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D000818:Animals; D002783:Cholestenones / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D012632:Secosteroids / Q000737:chemistry* / Q000302:isolation & purification
D002783:Cholestenones; D012632:Secosteroids; C077273:9,11-seco-3,6,11-trihydroxycholest-7-en-9-one; C077274:9,11-seco-3,6,11-trihydroxy-24-methylenecholest-7-en-9-one