Topsentia sponge

Halistanol sulfate (532) from Halichondria cf. moorei is a tris-sodium sulfate salt, which possesses antimicrobial, hemolytic, and ichthyotoxic activity [444]. It was later isolated from two sponges of the genus Topsentia as the free sterol and found to inhibit pp60v-src protein tyrosine kinase activity [445]. The tris(2-aminoimidazolium) salt of halistanol sulfate (533) was isolated from Topsentia sp. from Japan and is also antimicrobial [446]. 

Additional unusual steroid derivatives have been isolated from marine sponges, eg., polymastiamides, steroid/aminoacid conjugates isolated from Polymastia boletiformis, a Norwegian marine sponge [180], and an aminoimidazolium salt of steroid trisulfate from Topsentia sp. [181], Some of these marine sterols are being reproduced by chemical synthesis in the laboratory [182],... 

Recently, bromodeoxytopsentin (76) and isobromodeoxytopsentin (77) have been isolated from the Korean sponge Topsentia genitrix. They exhibit cytotoxicity against the human leukemic cell line K-562 (LC50 0.6 and 2.1 pg/ml, respectively) [69]. 

Topsentinols A through J, ten new 7-hydroxy sterols with unusual polyalkylated side chains, have been isolated from the Okinawan marine sponge Topsentia sp. 

Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Isolation of an unusual 2-aminoimidazolium salt of steroid trisulfate from a marine sponge Topsentia sp., Fish. Sci., 63, 310, 1997. 

This compound also occurs in a number of related Haplosclerid sponges, such as Topsentia spp., Monanthus ciocalyptoides, Foliolina sp., mdiXestospongia spp., as well as from Aaptos sp., Trachyopsis sp., and two species of Pseudaxynissa... 

G., and Ottinger, R. (1987) Topsentins, new toxic bis-indole alkaloids from the marine sponge Topsentia genitrix. Can. J. Ghent. 65,2118-2121. 

McKee, T., Cardellina, J. H., Tischler, M., Snader, K. M., Boyd, M. R. (1993) Ibisterol sulfate, a novel HIV-inhibitory sulfated sterol from the deep water sponge Topsentia sp. J. Nat. Prod. 34, 389-392. 

The cytotoxic T. and nortopsentins are isolated from the Mediterranean sponge Topsentia genitrix as well as from deep-sea sponges of the genus Spongosorites. The T. are active against P388 leukemia cells and B16 melanoma cells. 

Calderon, G.J., Castellanos, L, Duque, C., Echigo, S Hara, N and Fujimoto, Y. (2004) OphirasteroL a new C31 sterol from the marine sponge Topsentia ophiraphidites. Steroids, 69,93-100. 

J, new sterols with highly branched side chains from marine sponge Topsentia sp. Chem. Pharm. Bull., 45,1435-1438. 

Fusetani, N., Takahashi, M., and Matsunaga, S. (1994a) Biochemical marine metabolites. 61. Topsentiatriol sulfates, antimicrobial sterol sulfates possessing novel side chains, from a marine sponge, Topsentia sp. Tetrahedron, 50, 7765-7770. 

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. 

Guzii, A.G., Makarieva, T.N., Denisenko, VA., Dmitrenok, P.S., Burtseva, Y.V., Krasokhm, V.B., and Stonik, VA (2008) Topsentiasterol sulfates with novel iodinated and chlorinated side chains from the marine sponge Topsentia sp. Tetrahedron Lett., 49, 7191-7193. 

Ibisterol sulfate, a novel HIV-inhibitory sulfated sterol from the deep water sponge Topsentia sp. Tetrahedron Lett., 34, 389-392. 

Braekman, J.C., Daloze, D., and Stoller, C. (1987) Synthesis of topsentin-A, a bisindole alkaloid of the marine sponge Topsentia genitrix. Bull. Soc. Chim. Belg., 96,809-812. 

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