Polyhydroxysteroid glycosides

Eight new polyhydroxysteroid glycosides (32a-32e, 33a-33c), Fig. (11), glycosylated at C-28 and C-29, and the C-24 glycosides Certonardosides H3 and H4 (34 and 35), Fig. (12), together with twenty two new polyhydroxysteroids were further isolated from the brine shrimp active fraction of the starfish Certonardoa semiregularis [42, 43]. 

A reinvestigation of the polar extractives from starfish Culcita novaeguineae (120) has led to the isolation of eleven polyhydroxysteroid glycosides and five polyhydroxysteroids (Fig. 13). One of them has been identified as culcitoside (128), previously isolated from the same organism by Kicha... 

Andersson, L, Bohlin, L, Ricdo, R., and Minale, L. (1987a) Studies of Swedish marine organisms. Part 8. Three novel minor polyhydroxysteroid glycosides from the starfish Crossaster papposus. J. Chem. Res. (S), 246. 

A new polyhydroxysteroidal glycoside from the starfish Anthenea chinensis. Chin. Chem. Lett., 20,1231-1234. 

Polyhydroxysteroidal glycosides from the starfish Anthenea chinensis. J. Nat. Prod., 73, 590-597. 

Iorizzi, M., Minale, L., Riccio, R., Higa, T., and Tanaka, J., Starfish saponins, part 46. Steroidal glycosides and polyhydroxysteroids from the starfish Culcita novaguineae, J. Nat. Prod., 54, 12254, 1991. 

Riccio, R., Iorizzi, M., and Minale, L., Starfish saponins XXX. Isolation of sixteen steroidal glycosides and three polyhydroxysteroids from the Mediterranean starfish Coscinasterias tenuispina, Bull. Soc. Chim. Belg., 95, 869, 1986. 

More than one hundred polyhydroxylated steroidal glycosides have been characterized but only few reports on their biological activity have been published. Recently, several examples of new bioactive mono- and diglycosides of polyhydroxysteroids as well as biological studies on known compounds have been reported. 

Asterosaponins are usually considered to be responsible for the general toxicity of starfish. However, this investigation showed that sterols and another class of minor chemical components, such as glycosides of polyhydroxysteroids also play an important role in the general toxicity. 

Fig. 4. Glycosides of polyhydroxysteroids and related polar steroids from the starfish Coscinasterias tenuispina (55).

More recent additions to the list of the glycosides of polyhydroxysteroids are the related pycnopodiosides A (77), B (78) and C (79) from Pycnopodia heliantoides (58), miniatoside A (80) and B (81) minor glycosides from Patiria miniata (101), and the twelve steroidal glycosides (Fig. 11)... 

Fig. 9. Some representative glycosides of polyhydroxysteroids from starfishes.

Fig. 11. Asterosaponin and glycosides of polyhydroxysteroids from the starfish Henricia laeviuscola...

Fig. 12. Glycosides of polyhydroxysteroids from the starfish Echimster brasiliensis (94).

Fig. 13. Glycosides and polyhydroxysteroids isolated from the starfish Culcita novaeguineae (120).

Fig. 15. New glycosides and polyhydroxysteroids from the starfish Myxoderma platyacanthum (89).

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