Novel sterols from the finger sponge Haliclonaoculata

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Abstract
From the finger sponge, Haliclona oculata (Linnaeus), six new polar sterols have been isolated and their structures determined by chemical and spectroscopic means. These are 3.beta.-hydroxy-cholesta-5,25-dien-24-one (2), 3.beta.-hydroxy-24-methylene-5-cholesten-7-one (6), 24-methylene-5-cholesten-3.beta.,7.beta.-diol (9), 24-methylcholesta-5,22-dien-3.beta.,7.beta.-diol (11), 24-methylene-5-cholesten-3.beta.,7.alpha.-diol (12), and 5.beta.,6-epoxy-24-methylene-cholestan-3.beta.-ol (16). Also shown to be present are the known monohydroxysterols (22E,24S)-24-methylcholesta-5,22-dien-3.beta.-ol (1), (22Z)-24-norcholesta-5,22-dien-3.beta.-ol, 24-methylene-5-cholesten-3.beta.-ol, 24-isoethylidene-5-cholesten-3.beta.-ol, (22E)-24-norcholesta-5,22-dien-3.beta.-ol and (23E)-cholesta-5,23-dien-3.beta.,25-diol. The structure 14 is tentatively proposed for a novel C24 sterol and 8 is suggested for the structure of a compound accompanying 6.