Steroidal monoglycosides from the Far Eastern starfish Hippasteria kurilensis and hypothetic pathways of polyhydroxysteroid biosynthesis in starfish |
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Authors: | Alla A Kicha |
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Institution: | Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia |
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Abstract: | Five new steroidal monoglycosides, kurilensosides E (1), F (2), G (3), H (4) and 15-O-sulfate of echinasteroside C (5) were isolated along with the previously known echinasteroside C (6) from the alcoholic extract of the Far Eastern starfish Hippasteria kurilensis collected near Kuril Islands. Compounds 1-3 were determined to contain unusual polyhydroxysteroidal aglycons lacking 6-hydroxy group. Aglycon moiety of kurilensoside H (4) was shown to be the first case of marine polar steroids containing 4,5-epoxy functionality. Hypothetic pathways of the biosynthesis of polyhydroxysteroids and related glycosides in starfish and the existence of the late C-6 oxidation pathway in H. kurilensis are discussed. |
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Keywords: | Polyhydroxylated steroids Glycosides Starfish Hippasteria kurilensis Biosynthesis |
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