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.