Bioactive sponge peptides

Fusetani N, Matsunaga S. Bioactive sponge peptides. Chem. Rev. 1993 93 1793-1806. 

Gerwick WH, Tan LT, Sitachitta N (2001) Alkaloids of marine cyanobacteria. In Cordell GA (ed) The Alkaloids, vol 57. Academic Press, San Diego, p 75 Fusetani N, Matsunaga S (1993) Bioactive sponge peptides. Chem Rev 93 1793 Shimizu Y (1993) Microalgal metabolites. Chem Rev 93 1685... 

Bioactive cyclic peptides and peptides containing O-heterocyclic fragments from sponges 93CRV1793. 

HO-./ T V-NH Blue-green algae -Anabaena laxa Marine sponge -Callyspongia abnormis Laxaphycins A and E -antifungal peptides Callynormine A - no bioactivity has been reported 246-248 249... 

Marine sponges contain a host of bioactive compounds, particularly small molecules, and also contain a range of peptides that are non-ribosomally synthesised, often containing non-native amino acids. However, there are examples of peptides of ribosomal origin, including, for example, asteropine A isolated from the sponge Asteropus simplex.133 This peptide comprises 36 residues and three disulphide bonds. It has potent sialidase inhibitory activity and thus has applications in the design of novel viral inhibitors. Structural analysis of asteropine A with NMR spectroscopy revealed a cystine-knot motif, similar to that already described for plant toxins. This observation emphasises the fact that the cystine-knot motif is extremely prevalent in disulphide-rich peptides.134 Asteropine A, discovered in 2006, was the first reported cystine-knot peptide isolated from marine invertebrates other than from cone snails, which are described in more detail below. 

In addition to ribosomal peptides, some of which exhibit interesting bioactivities as is the case of conotoxins, marine organisms in particular, sponges and tunicates contain a wide variety of nonribosomal peptides, many of which contain unusual or unprecedented amino acids. It should be noted that these peptides show a range of biological activities. 

The bioactIve secondary metabolites from several marine sources, sponges and tunica-tes (Kobayashl/lshibashi), sea plumes (Katz/Adamczeski) and ascidians (Bowdem) cover a broad range of different chemical structures, terpenoids, unsaturated fatty acids, steroids, alkaloids, cyclic peptides and polysaccharides. 

Matsunaga, S., Fusetani, N., Konosu, S., (1985). Bioactive marine metabolites, IV. Isolation and the amino acid composition of discodermin A, an antimicrobial peptide, from the marine sponge Discodermia kiiensis. J. Nat. Prod. 48, 236-241. 

Matsunaga, S., Fusetam, N., and Konosu, S. (1985a) Bioactive marine metabolites VII. Structures of discodermins B, C, and D antimicrobial peptides from the marine sponge Discodermia kiiensis. Tetrahedron Lett., 26,855-856. 

D Auria, M.V., Zampella, A., Paloma, L.G., Minale, L., Debitus, C., Roussakis, C., and Lebert, V. (1996) Calhpeltins B and C bioactive peptides from a marine hthistida sponge Callipelta sp. Tetrahedron, 52,9589-9596. 

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