Bioactive Sterols from the StarfishCertonardoasemiregularis

Abstract

Thirteen new polyhydroxysterols (1-5, 7-12, 14, 15) and two known polyhydroxysterols (6, 13) were isolated from the brine shrimp active fraction of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical derivatization. These compounds displayed considerable cytotoxicity against a small panel of human solid tumor cell lines. These compounds were also evaluated for antibacterial activity against 20 clinically isolated strains. Most of the compounds showed weak antibacterial activity against Streptococcus pyogenes 308A, Pseudomonas aeruginosa 1771, and Pseudomonas aeruginosa 1771M.

Chemical Constituents and Bioactivities of Starfish

“…and F -M (50 -57, resp.) [24], as well as the known compound 58 [25]. Except 57, the other sterols exhibited modest in vitro cytotoxicities towards a panel of human tumor cell lines.…”

“…The Antarctic sea star Labidiaster annulatus contained a polyhydroxy sterol, 170 [57]. The starfish Certonardoa semiregularis, collected off Komun Island, Korea, afforded three polyhydroxy sterols, certonardosterols 171 -173 [24] [26]. The compounds exhibited modest in vitro cytotoxicities towards a panel of human tumor cell lines.…”

“…Main glycones of the glycosides from starfish positions 4b, 5a, and 7a. The side chain occasionally has OH groups at C(26) or C (24). Structural variations are ascribable to the hydroxylation pattern of steroidal nucleus, the functionalization of the side chain, and the nature and location of the saccharide moiety.…”

NewN-Acyl Taurine from the Sea UrchinGlyptocidaris crenularis

“…6) It has been reported that taurine derivatives were also found in starfish, 7) sponge 7,8) and shellfish. 9) Taurine derivatives with acyl moieties, eicosapentaenoic acid (EPA) and other C20 unsaturated fatty acids have been found in starfish and cold deep-water fishes.…”

“…9) Taurine derivatives with acyl moieties, eicosapentaenoic acid (EPA) and other C20 unsaturated fatty acids have been found in starfish and cold deep-water fishes. 7) Since EPA is widespread in many marine organisms, the new N-acyl taurine isolated might be derived from EPA and taurine on a certain biosynthetic pathway in the sea urchin, G. crenularis.…”