A&mm.-The steroidal composition of the sponge Stelodwyx chlwopbylla was examined, and twenty-two components were identified. The sponge contains "conventional" C2,-Cn, A'-mono and diunsaturated sterols, sterols with oxygenated side chains, e.g., ( 2 2 0 3 8 -hydroxycholesta-5,22dien-24-one f57, and sterols with short oxygenated side chains, e.g., 38-hydroxy-178-pregn-5-en-20-one 167 and (22E)-3P-hydroxy-26,27-bisnorcholesta-5,22-dien-24-one [;?. In addition, the extracts of the sponge contain the epimeric steroidal A'38-7-diols and the steroidal 3P-hydroxy-5-en-7-ones, well recognized autoxidation products of A'-sterols.The origin of the oxidized side chains is discussed.As a part of our investigation into marine organisms collected in New Caledonia we report the Occurrence of sterols with oxidized side chains from the deep-water sponge Stelodoryx chlwophylla Uvi sp. nov. (family Myxillidae, order Poecilosclerida). In addition to the "conventional" As-mono and diunsaturated sterols, this animal has been found to contain (22E)-3 P-hydroxycholesta-5,22-dien-24-one [57, 3P-hydroxy-17P-pregn-5-en-zO-one 161, and (22E)-3P-hydroxy-26,27-bisnorcholesta-5 ,22-dien-24-one 17. Extracts of this sponge also contain the epimeric steroidal As-3P-7-diols and the steroidal 3P-hydroxyAs-7-ones, well recognized as autoxidation products of As-sterols (1,2). The sponge was collected south of New Caledonia at a depth of 600-540 m in February 1986, and the freeze-dried material, dispatched to our laboratory in Naples inSeptember 1990, was extracted with n-hexane in a Soxhlet apparatus. The extract was chromatographed by mplc on Si gel in n-hexanelEtOAc followed by reversed-phase hplc on a Whatman Partisil 10 ODs-2 column to give the sterols 1-22 (Table 1). The common As marine sterols 1 4 were identified by comparison of mass spectra with those of standard sterols and confirmed by 'Hnmr spectra. The sterols with side chain oxygenation ( 5 6 , and 7, identified by ms, n m r and comparison with published data ( 3 4 , have been previously isolated from a sponge of the genus Hyrtios (3).The short side chain steroidal ketones 6 and 7 have also been found in the sponge Damiriana hawaiiana (4), whereas the pregnane-derived ketone 6 and its corresponding 20a-and 20P-hydroxy derivatives have also been reported from the sponge Haliclona rubms ( 5 ) and in trace amounts from Psammplysillapurpurea (6). Before that, the only C,, steroid isolated from a marine source was the 3P,6a-dihydroxy-5a-pregn-9( 1 l)-en-20-one, the most widely reported steroid obtained by acid hydrolysis of asterosaponins (7-9) and possibly an artifact generated by retro-aldol cleavage of the genuine
