Biologically active glycosides from asteroidea, 35: Isolation and structure of four new steroid glycoside di-O-sulfates from the starfish Asteropecten latespinosus

Four new steroid di-O-sulfates, latespinoside A (1), B (2), C (3), and D (4), were isolated from the crude glycoside fraction of the chloroform/methanol extract of the starfish Asteropecten latespinosus as minor components. Their structures were determined on the basis of spectral data as disodium salts of (20S)-20-hydroxy-6α-(4-O-sulfo-β-D-quinovopyranosyloxy)-3β- sulfooxy-5α-cholesta-9(11),24-diene (1), (20S)-20-hydroxy-6α-(4-O-sulfo-β-D-quinovopyranosyloxy)-3β- sulfooxy-5α-cholest-9(11)-ene (2), 6α-(4-O-sulfo-β-D-quinovopyranosyloxy)-3β-sulfooxy-5α- cholesta-9(11),17(20)Z,24-trien-23-one (3), and 6α-(4-O-sulfo-β-D-quinovopyranosyloxy)-3β-sulfooxy-5α- androst-9(11)-en-17-one (4). Compound 4 is, to the authors' knowledge, the first androstane derivative isolated from starfish. In addition, compounds 3 and 4 show weakly cytotoxic activity against murine lymphoma L1210 cells in vitro.