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Bioorg Khim ; 35(1): 134-41, 2009.
Article in Russian | MEDLINE | ID: mdl-19377532

ABSTRACT

Three new steroid glycosides (evasteriosides C, D, and E), along with six known compounds, were isolated from two Pacific starfish of the genus Evasterias. Evasterioside C from E. retifera collected from the Sea of Japan was identified as (20R,22E)-3-O-(beta-D-xylopyranosyl)-24-nor-5alpha-cholest-22-ene-3beta,6beta,8,15alpha,26-pentaol 26-sulfate sodium salt. The structures of evasterioside D and E from E. echinosoma (collected from the Gulf of Shelichov, the Sea of Okhotsk) were established as (20R,24S)-24-O-(beta-D-glucopyranosyl)-5alpha-cholestane-3beta,6alpha,8,15beta,24-pentaol and (20R,24S)-3,24-di-O-(beta-D-xylopyranosyl)-cholest-4-ene-3beta,6beta,8,15alpha,24-pentaol, respectively. In addition, the known compounds pycnopodiosides A and C, luridoside A, 5alpha-cholestane-3beta,6alpha,8,15beta,16beta,26-hexaol, 5alpha-cholestane-3beta,6alpha,8,15beta,24-pentaol 24-sulfate sodium salt, and marthasterone sulfate sodium salt were identified in E. echinosoma. The structures of the isolated compounds were established on the basis of spectroscopic analyses using 1D and 2D NMR techniques, mass spectrometry, and some chemical transformations.


Subject(s)
Starfish/metabolism , Steroids/isolation & purification , Animals , Magnetic Resonance Spectroscopy , Mass Spectrometry , Stereoisomerism , Steroids/chemistry , Steroids/pharmacology
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