Four new asterosaponins, hippasteriosides A - D, from the Far Eastern starfish Hippasteria kurilensis.
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.
Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok, Russia. kicha@piboc.dvo.ru
Alla A
AA
Kicha
Anatoly I
AI
Kalinovsky
Natalia V
NV
Ivanchina
Timofey V
TV
Malyarenko
Pavel S
PS
Dmitrenok
Svetlana P
SP
Ermakova
Valentin A
VA
Stonik
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D019073:HT29 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D013215:Starfish / Q000737:chemistry*
D000970:Antineoplastic Agents; D012503:Saponins