Steroids from sponges

The sponges Stelleta clarella Tethya aurantia, Lissodendoryx noxiosa, Haliclona permollis and Haliclona sp. were examined for steroids. All sponges contained C27-C29, Δ5, mono and diunsaturated sterols. In addition, the sponge Tethya aurantia contained Z - 24 - propylidene - cholest - 5- en -3β-ol (19) and the 5α,8α-peroxides of cholesta - 5,7 - dien - 3β - ol, ergosterol, ergosta - 5,7,24(28) - trien - 3β - ol and 24ξ - ethyl - cholesta - 5,7 - dien - 3β - ol (29, 30, 31 and 32). The sponge Stelleta clarella also contained 24 - nor - cholesta - 4,22 - dien - 3 - one (21), cholesta - 4,22 - dien - 3 - one (22), 24ξ - methyl - cholesta - 4,22 - dien - 3 - one (24), ergosta - 4,24(28) - dien - 3 - one (25), (E) - stigmasta - 4,24(28) - dien - 3 - one (28), 5α - cholestanol (5), 5α - ergostanol (7) and 5α - poriferastanol (9) The possible biosynthetic significance of these hitherto undescribed peroxides and enones from marine sources is discussed. A synthesis of 19 is also described.