Theonella sponges

Kobayashi J, Itagaki F, Shigemori H, Takao T, Shimonishi Y (1995) Keramamides E, G, H, and J, New Cyclic Peptides Containing an Oxazole or a Thiazole Ring from a Theonella sponge. Tetrahedron 51 2525... 

Uemoto H, Yahiro Y, Shigemori H, Tsuda M, Takao T, Shimonishi Y, Kobayashi J (1998) Keramamides K and L, New Cyclic Peptides Containing Unusual Tryptophan Residue from Theonella Sponge. Tetrahedron 54 6719... 

In the last of their reports on the characterization of marine natural products to appear in 1999, Fu et al.120 reported the characterization of a series of acetylenic swinholides from a previously undescribed specie of Theonella sponge. The structure of one of the new compounds, pellynol E (57), is shown. In general, the analogs isolated and characterized differed in the central region of the long methylene chain of 57. 

Analysis of the extracts of different collections of Theonella sponge resulted in the isolation of the first example of marine occurring brominated benzyl tetrahydroprotoberberine alkaloid, theoneberine (81)... 

Fu, X., Schmitz, F.J., and Kelly, M. (1999b) Swinholides and new acetylenic compounds from an undescribed species of Theonella sponge. /. Nat. Prod., 62,1336-1338. 

Uemoto, H., Yahiro, Y, Shigemori, H., Tsuda, M., Takao, T, Shimonishi, Y, and Kobayashi, J. (1998) Keramamides K and L, new cyclic peptides containing unusual tryptophane residue from Theonella sponge. Tetrahedron, 54, 6719-6724. 

More recently, miraziridine A (113) was isolated from a marine sponge related to Theonella mirabilis and shown to inhibit the cysteine protease cathepsin B. It has been shown that the aziridine ring plays a key role in this biological activity and gives rise to irreversible inhibition of cathepsins B and L, presumably through... 

Swinholide A, isolated from the marine sponge Theonella swinhoei, sequesters actin dimers and induces their formation. One molecule of swinholide A binds to one dimer. In addition, swinholide A can sever F-actin by binding to the neighbouring protomers. Increased depolymerization of F-actin has also been reported. 

Scheme 20 Lobophorolide (72) from the brown alga Lobophora variegata, and structurally similar natural products from cyanobacteria and the sponge Theonella swinhoei...

Several examples of the monocyclic isothiocyano sesquiterpenoids having the bisabolane (83) skeleton are known. Along with the hydrocarbon theonellin (84), isothiocyanate 86 and formamide 87 were obtained from the Okinawan sponge Theonella cf. swinhoei. It seems remarkable, but not unusual, that not only was the amide the major constituent, but the isonitrile 85 was the missing member of the triad [57], Relative stereostructures were indicated by NMR analysis of theonellin formamide (87) and its transformation products. 

Todd JS, Alvi KA, Crews P (1992) The isolation of a monomeric carboxylic acid of swinholide A from the Indo-Pacific sponge, Theonella swinhoei. Tetrahedron Lett 33 441 142... 

Tsukamoto S, Ishibashi M, Sasaki T, Kobayashi J (1991) New congeners of swinholides from the Okinawan marine sponge Theonella sp. J Chem Soc Perk Trans 1 3185-3188... 

The toxic effect of various species of rove beetles pertaining to the genus Paederus on the skin and eyes of mammals, including man, are due to the presence in their hemolymph of three vesicant amides pederin (104), pederone (105) and pseudopederin (106) (Fig. 18) [94,95], pederin being the major and most active of the three compounds. Their structure determination [96, 97] revealed rather unique substances until similar natural products with comparable biological activities were isolated from sponges of the genera Mycale [98,99], Stylinos [100] and Theonella [101-104]. 

Marine sponge - Theonella Cyclollthlstide A - antifungal peptide 14, 32... 

Nonribosomai peptides from marine sponge -Theonella sp. 

Marine sponge - Discodermia sp. Marine sponge - Theonella sp. 

Nonribosomal peptide from sponge - Theonella mirabllls and Theonella swinhoel... 

Nonribosomai peptide from sponge -Theonella mirabilis and Theonella swinhoei... 

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