Steroid Compounds from Far Eastern Starfishes Henricia aspera and H. tumida

Abstract

Six new natural compounds were isolated from two Far Eastern starfish species, Henricia aspera and H. tumida, collected in the Sea of Okhotsk. Two new glycosylated steroid polyols were obtained from H. aspera: asperoside A and asperoside B, which were shown to be (20R,24R,25S)-3-O-(2,3-di-O-methyl-beta-D-xylopyranosyl)-24-methyl-5alpha-cholest-4-ene-3beta,6beta,8,15a,16beta,26-hexaol and (20R,24R,25S,22E)-3-O-(2,4-di-O-methyl-beta-D-xylopyranosyl)-24-methyl-5alpha-cholest-22-ene-3beta,4beta,6beta,8,15alpha,26-hexaol, respectively. Two other glycosylated polyols, tumidoside A, with the structure elucidated as (20R,22E)-3-O-(2,4-di-O-methyl-beta-D-xylopyranosyl)-26,27-di-nor-24-methyl-5alpha-cholest-22-ene-3beta,4beta,6beta,8,15alpha,25-hexaol, and tumidoside B, whose structure was elucidated as (20R,24S)-3-O-(2,3-di-O-methyl-beta-D-xylopyranosyl)-5alpha-cholestan-3beta,4beta,6beta,8,15alpha,24-hexaol, were isolated from the two starfish species. (20R,24S)-Salpha-Cholestan-3beta,6beta,15alpha,24-tetraol and (20R,24S)-5alpha-cholestan-3beta,6beta,8,15alpha,24-pentaol were identified only in H. tumida. The known monoglycosides henricioside H1 and laeviuscolosides H and G were also identified in both species.

Marine natural products

“…Studies of two species of Far-Eastern starfishes, Henricia aspera and H. tumida led to identification of a number of new polyhydroxyl steroids and glycosides. 681 Henricia aspera was the source of asperosides A 837 and B 838, H. tumida the source of 839 and 840, while tumidosides A 841 and B 842 were isolated from both species. All six metabolites exhibited moderate cytostatic activity towards sea urchin eggs.…”

Chemical Constituents and Bioactivities of Starfish

“…The side-chain configuration of the known structurally-related sterol 178 [59] was determined as (24R,25R) [60]. Far Eastern starfish Henricia tumida was the source of 179 and 180, and both metabolites exhibited moderate cytostatic activity towards sea urchin eggs [61]. Four steroids, 181 -184, were isolated from the starfish H. leviuscula (Sea of Okhotsk, Russia) [62]; 182 induced haemolysis of erythrocytes.…”

“…Asteriidoside L (413), a moderately cytotoxic steroidal saponin, was isolated from an unidentified Antarctic starfish of the family Asteriidae [112]. The monoglycosylated steroid sanguinoside C (414) [58] [61]. Henricia aspera was the source of asperosides A and B (417 and 418, resp.…”

New Polar Steroids from Starfish

“…The tetraol 38 has an uncommon 3β,6β,15β-trihydroxysteroid nucleus, while 39 contains a rare 15-ketone fragment, like compounds 25-31. Two new polyhydroxy-steroids (40 and 41) were obtained from the Far Eastern starfish Henricia tumida [11]. These substances showed cytotoxic activities against fertilized eggs of the urchin Strongylocentrotus intermedius and inhibited their development with an IC min of 1.14×10 -7 and 1.16×10 -7 M, respectively.…”