Marine polar steroids

Polar steroidal compounds from the Far-Eastern starfish Lethasterias fusca

“…In continu ation of our studies of physiologically active steroidal metabolites from Far Eastern starfishes, 3 we studied the steroid composition of the starfish Lethasterias fusca (order Forcipulatida, family Asteriidae) collected at the experimental Marine station of the Pacific Institute of Bioorganic Chemistry (Possiet Bay, Japanese Sea). As a result, nine steroidal compounds (1)(2)(3)(4)(5)(6)(7)(8)(9) were isolated, in particular, three new steroidal glycosides, fuscasides A (1) R = OSO 3 Na (1), OH (2) (2) and desulfated minutoside A (3), three known glycosides, viz., distolasterosides D 1 (4) and D 2 (5) and pycnopodioside A (6), two known polyhydroxysteroids, viz., 5α cholestan 3β,6α,8,15β,16β,26 hexol (7) and 5α cholestan 3β,4β,6α,7α,8,15β,16β,26 octol (8), and known native aglycon of the asterosaponin series, viz., sodium 24,25 dihydromarthasterone 3 sulfate (9).…”

“…As a rule, these include polyhydroxysteroids, polyhydroxysteroid mono and biosides, and toxic steroidal oligoglycosides called asterosaponins. 1, 2 The oxidized steroids are encountered in both free and sulfated forms. In continu ation of our studies of physiologically active steroidal metabolites from Far Eastern starfishes, 3 we studied the steroid composition of the starfish Lethasterias fusca (order Forcipulatida, family Asteriidae) collected at the experimental Marine station of the Pacific Institute of Bioorganic Chemistry (Possiet Bay, Japanese Sea).…”

Structures of new polar steroids from the Far-Eastern starfish Ctenodiscus crispatus

“…These compounds are of interest not only because of their un usual chemical structures but also due to their properties, including embriotoxic, fungicidal, bactericidal, antifoul ing, neuritogenic, and other types of physiological activi ties. 1 Earlier, 2 we have isolated four new polyhydroxylated steroids, two of which are sulfates, from the starfish Ctenodiscus crispatus (family Ctenodiscidae, the order Paxillosida) collected in the Japan Sea (the Posiet Bay). As part of continuing investigations of steroid metabolites from Far Eastern starfishes, 2,3 we studied the composi tion of a fraction of sulfated polyhydroxysteroids from this starfish, isolated several new steroids, and established the absolute configuration of the side chain of steroid 1, whose structure has been determined earlier without elu cidation of the stereochemical features of the side chain.…”

Polar steroidal compounds from the Antarctic starfish Diplasterias brucei

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NaO 3 SO O OH OH H RO OH NaO 3 SO OH OH H 2: R 1 = SO 3 Na 2a: R 1 = H 1 3 RO OH OH OH H O O OH R 1 O HO O OH HO HO = R 2, 2aStarfish, in contrast with many other marine animals, contain highly oxidized steroids that occur in the free, sulfated, and glycosylated states [1,2]. In continuation of our research on steroidal metabolites of starfish, we studied for the first time steroids from the Antarctic starfish Diplasterias brucei (Asteriidae, Forcipulatida) collected in 2000 near the shore of Ross Sea (Terra Nova Bay, Antarctica) under the auspices of the National Italian program Antarctic Research.

Starfish (460 g) was ground and extracted twice with ethanol (70%) with heating on a water bath.

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