Sponges steroid sulfates

An Acanthodendrilla sp. from Japan contained ten steroidal sulfates, acanthosterol sulfates A-J (561-570). Acanthosterol sulfates I (569) and J (570) showed antifungal activity against Saccharomyces cervisiae and its mutants [463]. Clathsterol (571), was isolated from the Red Sea sponge Clathria sp. The structure was established mainly by interpretation of spectral data and a chemical transformation. Clathsterol (571) was active against HIV-1 reverse transcriptase (RT) at a concentration of 10 iM [464]. Toxadocia zumi contains three sterol sulfates (572-574) that are antimicrobial, cytotoxic, ichthyotoxic and larvicidal [465]. 

Additionally, sulfated sterols have been described from a wide variety of marine organisms, particularly sponges and echinoderms, and several of these steroidal sulfates have exhibited a broad range of activities. Halistanol sulfates are a group of sulfated polyhydroxysteroids from... 

D Auria MV, Giannini C, Zampella A, Minale L, Deditus C, Roussakis C (1998) Crellastatin A A Cytotoxic Bis-Steroid Sulfate from the Vanuatu Marine Sponge Crella sp. J Org Chem 63 7382... 

Sun, H.H. Cross, S.S. Gunasekera, M. Koehn, F.E. Weinbersterol Disulfates A and B, Antiviral Steroid Sulfates from The Sponge Petrosia weinbergi. Tetrahedron, 1991, 47, 1185-1190. 

Fusetani, N., S. Matsunaga, and S. Konosu Bioactive Marine Metabolites. II. Halistanol sulfate, an Antimicrobial Novel Steroid Sulfate from the Marine Sponge Halichondria CF. moorei Bergquist. Tetrahedron Lett. 22, 1985 (1981). 

D Auria, M.V., Giannini, C., Zampella, A., Minale, L., Debitus, C., and Roussakis, C. (1998) Crellastatin A a cytotoxic bis-steroid sulfate from the Vanuatu marine sponge Crella sp. J. Org. Chem., 63, 7382-7388. 

Li, H.-Y, Matstmaga, S., Fusetani, N Fujiki, H Murphy, P.T., Willis, R.H., and Baker, J.T. (1993) Echinoclasterol sulfate phenethylammonimn salt, a unique steroid sulfate from the marine sponge Echinoclathria subhispida. Tetrahedron Lett., 34, 5733-5736. 

Boonlarppradab, C. and Faulkner, D.J. (2007) Eurysterols A and B, cytotoxic and antifungal steroidal sulfates from a marine sponge of the genus Euryspor a. J. Nat. Prod., 70, 846-848. 

Gunasekera, S.P., Sennett, S.H., Kelly-Borges, M., and Bryant, R.W. (1994a) Ophirapstanol trisulfate, a new biologically active steroid sulfate from the deep water marine sponge Topsentia ophiraphidites. J. Nat. Prod., 57,1751-1754. 

Kanazawa, S., Fusetani, N., and Matsunaga, S. (1992) Halistanol sulfates A-E, new steroid sulfates from a marine sponge, Epipolasis sp. Tetrahedron, 48, 5467-5472. 

Fusetani, N., Matsunaga, S., and Konosu, S. (1981) Bioactive marine metabolites. 11. Halistanol sulfate, an antimicrobial novel steroid sulfate from the marine sponge Halichondria cf moorei Bergquist. Tetrahedron Lett., 22, 1985-1988. 

The structure of sokotrasterol sulfate (548), isolated from sponges of the family Halichondriidae was determined by X-ray analysis [453-455]. The steroid, 26-norsokotrasterol sulfate (549), was isolated from the marine sponge Trachyopsis halichondrioides and was identified by NMR spectroscopic analysis [456]. 

An unusual 6a-sterol sulfate (557) was isolated from Dysidea fragilis, from the Venetian lagoon and displayed cytotoxicity against two different tumour cell lines in vitro [460]. Tamosterone sulfates (558-559) are a C14 epimeric pair of polyhydroxylated sterols isolated from a new species of Oceanapia [461]. The Japanese marine sponge Epipolasis sp. contained the steroid polasterol B sulfate (560) along with the known compound halistanol sulfate (532). The structure of compound 560 was determined on the basis of spectroscopic evidence and a chemical conversion [462]. 

Echinoclasterol sulfate phenethylammonium salt (585), an antifungal and cytotoxic steroid, was isolated from the South Australian sponge Echinoclathria subhispida [472]. 

Several sulfated polyhydroxysterols have been recently isolated from sponges. Most of these natural products are characterized by the 2p,3a,6a-tri-0-sulfate functions together with additional alkylation in the side chain. These steroids are of interest not only because of their structures but... 

Makarieva, T.N., L.K. Shubina, A.I. Kalinovsky, V.A. Stonik, and G.B. Elyakov Steroids in Porifera. II. Steroid Derivatives from two Sponges of the Family Halichondriidae. Sokotrasterol sulfate, a Marine Steroid with a New Pattern of Side Chain Alkylation. Steroids 42, 267 (1983). 

Gabant, M., Schmitz-Afonso, 1., Galard, J.-F., Menou, J.-L., Lament, D Debitus, C and Al-Mourabit, A. (2009a) Sulfated steroids Ptilosteroids A-C and ptilosaponosides A and B from the Solomon marine sponge Ptilocaulis spiculifer. J. Nat. Prod., 72, 760-763. 

Makarieva, T.N., Shubina, L.K., Kalinovskii, A.I., and Storuk, V.A. (1985) Steroidal compounds from marine sponges. V. 24 25-dimethyl-5-cholesten-2p,3a-diol diammonium sulfate, a novel polyhydroxylated steroid from sponges of Hcdichondria sp. Khim. Prir. Soedin., 272-273. 

Makarieva, T.N., Dmitrenok, P.S., and Stonik, V.A. (1988) Steroidal compounds of marine sponges. X. 26-nor-sokostrasterol sulfate, a new steroid from the sponge Trachyopsis halichondroides. Khim. Prir. Soedin., 371-375. 

Makarieva, T.N., Stonik, V.A., D yachuk, O., and Dmitrenok, P.S. (1995a) Annasterol sulfate, a novel marine sulfated steroid, inhibitor of glucanase activity from the deep water sponge Poecillastra laminaris. Tetrahedron Lett., 36,129—132. 

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