Abstract
Four polyhydroxylated steroids, new (20R)-5α-cholestan-3β,6α,8,15α,24,26-hexaol (I) and known (20R,25S)-5α-cholestan-3β,6α,8,15β,16β,26-hexaol, (20R,25S)-5α-cholestan-3β,6α,15β,16β,26-pentaol, and marthasterone sulfate were isolated from the Solaster endeca starfish inhabiting the Sea of Okhotsk and characterized. Steroid (I) contains a 24,26-dihydroxylated side chain, which is unique for starfish polyols. The isolated steroids and related metabolites from two starfish species of the Evasterias genus (in total, 15 compounds) were weakly cytotoxic in a human HeLa cell culture and some of them were inhibitors of non-specific esterase from mouse Ehrlich carcinoma. The effects of these compounds on the p53 protein activity were studied in a yeast two-hybrid test system and both inhibitors and stimulators of this activity were found among them.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Stonik, V.A., Usp. Khim., 2001, vol. 70, pp. 673–715.
Kicha, A.A., Ivanchina, N.V., Kalinovsky, A.I., Dmitrenok, P.S., Palyanova, N.V., Pankova, T.M., Starostina, M.V., Gavagnin, M., and Stonik, V.A., Nat. Prod. Com, 2007, vol. 2, pp. 41–46.
Levina, E.V., Kalinovsky, A.I., Andriyashshenko, P.V., Menzorova, N.I., and Dmitrenok, R.S., Bioorg. Khim., 2007, vol. 33, pp. 357–364 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2007, vol. 33, pp. 334–340].
Levina, E.V., Kalinovskii, A.I., Andriyashchenko, P.V., and Dmitrenok, P.S., Izv. Akad. Nauk, Ser. Khim., 2008, no. 11, pp. 2380–2385.
Levina, E.V., Kalinovsky, A.I., and Dmitrenok, P.S., Bioorg. Khim., 2009, vol. 35, pp. 134–141 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2009, vol. 35, pp. 123–130].
Iorizzi, M., Bifulco, G., De Riccardis, F., Minale, L., Riccio, R., and Zollo, F., J. Nat. Prod., 1995, vol. 58, pp. 10–26.
Riccio, R., Iorizzi, M., and Minale, L., Bull. Soc. Chim. Belg., 1986, vol. 95, pp. 869–893.
Iorizzi, M., Minale, L., Riccio, R., Debray, M., and Menou, J.L., J. Nat. Prod., 1986, vol. 49, pp. 67–78.
Levina, E.V., Andriyashchenko, P.V., Kalinovskii, A.I., Stonik, V.A., Dmitrenok, P.S., and Prokof’eva, N.G., Izv. Akad. Nauk, Ser. Khim., 2002, no. 3, pp. 497–500.
Kicha, A.A., Kalinovskii, A.I., and Stonik, V.A., Izv. Akad. Nauk, Ser. Khim., 1997, no. 1, pp. 190–196.
Wang, W., Hong, J., Lee, C.-O., Im, K.S., Choi, J.S., and Jung, J.H., J. Nat. Prod., 2004, vol. 67, pp. 584–591.
Minale, L., Riccio, R., and Zollo, F., Steroidal Oligoglycosides and Polyhydroxysteroids from Echinoderms. Progress in the Chemistry of Organic Natural Products, Herz, W., Kirby, G.W., Moore, R.E., Steglich, W., and Wien Tamm, Ch., Eds., New York: Springer-Verlag, 1993, vol. 62, pp. 75–308.
Fedorov, S.N., Shubina, L.K., Kicha, A.A., Ivanchina, N.V., Kwak, J.Y., Jun, O.J., and Stonik, V.A., Natur. Prod. Commun., 2008, vol. 3, pp. 1575–1580.
Baltrop, J.A., Owen, T.C., Cory, A.H., and Cory, J.G., Bioorg. Med. Chem. Lett., 1991, vol. 1, pp. 611–614.
Kovalchuk, S.N., Kozhemyako, V.B., Atopkina, L.N., Silchenko, A.S., Avilov, S.A., Kalinin, V.I., Rasskazov, V.A., and Aminin, D.L., J. Steroid Biochem. Mol. Biol., 2006, vol. 101, pp. 4–5.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.V. Levina, D.L. Aminin, S.N. Kovalchuk, V.B. Kozhemyako, S.A. Dyshlovoi, A.I. Kalinovskii, P.S. Dmitrenok, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 2, pp. 251–258.
Rights and permissions
About this article
Cite this article
Levina, E.V., Aminin, D.L., Kovalchuk, S.N. et al. Polar steroids from Solaster endeca starfish and the physiological activity of polar steroids from three starfish species. Russ J Bioorg Chem 36, 233–239 (2010). https://doi.org/10.1134/S1068162010020135
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162010020135