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 (20 S )‐20‐hydroxy‐6α‐(4‐ O ‐sulfo‐β‐ D ‐quinovopyranosyloxy)‐3β‐sulfooxy‐5α‐cholesta‐9(11),24‐diene ( 1 ), (20 S )‐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.