Minor and trace sterols in marine invertebrates. Part 35. Isolation and structure elucidation of seventy-four sterols from the sponge Axinella cannabina

Abstract

Seventy-four 3β-hydroxy-sterols, of which twenty-four are new, with seven different nuclei [Δ^5,7,9(11), Δ^5,7, Δ⁸, Δ⁷, Δ⁵, 5α-saturated; and 5α-methoxy-Δ^6,8(14)], and with eighteen different C₇–C₁₀-side chains, have been isolated by reverse-phase h.p.l.c. and argentic t.l.c. from the marine sponge Axinella cannabina. Characterization was accomplished by g.l.c.–m.s., high-resolution m.s., and 360-MHz ¹H n.m.r. and u.v. spectroscopy.