SULFATED STEROIDS FROM PACIFIC BRITTLE STARS OPHIOPHOLIS-ACULEATA, OPHIURA-SARSI, AND STEGOPHIURA-BRACHIACTIS

Five new and three known sulfated steroidal polyols have been identified from the ophiuroid Ophiopholis aculeata. All of the new steroids possess the C-5, C-6 double bond and sulfoxy groups attached to C-3 alpha and C-21. The structures of these new steroids were established from spectral data and chemical correlations with other steroids as (20R)-cholesta-5,25-diene-3 alpha,4 beta,21-triol 3,21-disulfate [1], (20R)-cholesta-5,22E-diene-3 alpha,4 beta,21-triol 3,21-disulfate [2], (20R)-24-nor-cholesta-5,22E-diene-2 beta,3 alpha,21-triol 3,21-disulfate [3], (20R,24R)-cholesta-5,25-diene-2 beta,3 alpha,21,24-tetrol 3,21-disulfate [4], and (20R,24S)-cholesta-5,25-diene-2 beta,3 alpha,21,24-tetrol 3,21-disulfate [5]. The previously known compounds were identified as the 3,21-disulfates of (20R)-5 alpha-cholestane-3 alpha,21-diol [6], (20R)-cholest-5-ene-3 alpha,21-diol [7], and (20R)-cholest-5-ene-3 alpha,4 beta,21-triol [8]. Compounds 6 and 7 were also isolated from both Ophiura sarsi and Stegophiura brachiactis.