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Four New Asterosaponins, Hippasteriosides A – D, from the Far Eastern Starfish Hippasteria kurilensis
Author(s) -
Kicha Alla A.,
Kalinovsky Anatoly I.,
Ivanchitalia V.,
Malyarenko Timofey V.,
Dmitrenok Pavel S.,
Ermakova Svetlana P.,
Stonik Valentin A.
Publication year - 2011
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200900402
Subject(s) - starfish , chemistry , moiety , stereochemistry , glycoside , sulfation , clonogenic assay , two dimensional nuclear magnetic resonance spectroscopy , biochemistry , in vitro , biology , ecology
Four new sulfated steroidal glycosides (asterosaponins), hippasteriosides A–D ( 1 – 4 , resp.), were isolated from the alcoholic extract of the Far Eastern starfish Hippasteria kurilensis , collected in the Sea of Okhotsk near Kuril Islands. Compounds 1 – 4 were determined to contain the same unprecedented hexasaccharide moiety, β ‐ D ‐xylopyranosyl‐(1→3)‐ β ‐ D ‐fucopyranosyl‐(1→2)‐ β ‐ D ‐quinovopyranosyl‐(1→4)‐[ β ‐ D ‐quinovopyranosyl‐(1→2)]‐ β ‐ D ‐xylopyranosyl‐(1→3)‐ β ‐ D ‐quinovopyranosyl, linked to C(6) of 3 ‐O ‐sulfonylated steroidal aglycons, which differ from each other in their side‐chain structures. Structures 1 – 4 were elucidated by extensive NMR and MS techniques, and chemical transformations. Not all the asterosaponins show a prominent cytotoxic activity against human colon tumor HT‐29 cells, but some of them, especially compound 4 demonstrate a remarkable inhibition of the HT‐29 colony formation in soft‐agar clonogenic assay, suggesting its anticancerogenic properties.