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Biologically Active Glycosides from Asteroidea, 35. Isolation and Structure of Four New Steroid Glycoside Di-O-sulfates from the Starfish Asteropecten latespinosus

✍ Scribed by Higuchi, Ryuichi ;Fujita, Masanori ;Matsumoto, Shuji ;Yamada, Koji ;Miyamoto, Tomofumi ;Sasaki, Takuma

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 389 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960530

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✦ Synopsis

Abstract

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.

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