Steroid Compounds from the Far East Starfish Pteraster Obscurus and the Ophiura Asteronyx Loveni

E. V. Levina^1 #, A. I. Kalinovsky¹ and P. S. Dmitrenok¹

^#Fax: (423-2) 31- 40-50; e-mail: levina@piboc.dvo.ru

¹Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, pr. Stoletiya Vladivostoka 159, Vladivostok, 690022, Russia

Received: 13 June 2006;  in final form: July,  20  2006

Abstract.  Seven sulfated polyhydroxysteroids were isolated from the Far East starfish Pteraster obscurus and the ophiura (snake star) Asteronyx loveni (collected in the Sea of Okhotsk) and characterized: disodium and sodium salts of (20R)-24-methyl-2β-hydroxycholesta-5,24(28)-diene-3α,21-diyl disulfate, (20R)-5α-cholestane-3β,21-diyl disulfate, (20R)-3β-hydroxy-5α-cholestan-21-yl sulfate, (20R)-cholest-5-ene-3β,21-diyl disulfate, (20R)-2β-hydroxycholest-5-ene-3α,21-diyl disulfate, (20R)-cholest-5-en-3β-yl sulfate, and (20R)-5α-cholestan-3β-yl sulfate. The first four compounds turned out to be new, whereas the others were identical to the known compounds. Structures of the isolated steroids were identified by two-dimensional NMR spectroscopy and other physicochemical methods. The compounds isolated from starfish are structurally similar to typical ophiuroid metabolites, which support the opinion of some taxonomists that starfish and ophiuroids are phylogenetically related classes.

Key words:  MALIDI TOF mass spectra, NMR spectra, ophiura Asteronyx loveni, starfish Pteraster obscurus, sulfated polyhydroxysteroids

Russian Journal of Bioorganic Chemistry 2007, 33 (3): 341-346