Theonella swinhoei

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...

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... 

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

Doi, M. Ishida, T. Kobayashi, M. Kitagawa, I. (1991) Molecular confcnmation of swinholide A, a potent cytotoxic dimo ic macrolide from the Okinawan marine sponge Theonella swinhoei. J. Org. Chem., 56, 3629-32. 

Marine sponges of the genus Haliclona contain a diverse array of active secondary metabolites, including highly potent cytotoxic macrolides, e g., halichondrin and related compounds, Fig. (56) [468], and salicylihalamides A and B, Fig. (57) [469], New macrolides chemically related to salicylihalamides, apicularens A and B, were recently isolated from the myxobacteria Chondromyces sp. [470], From marine bacteria, other cytotoxic macrolides have been isolated, such as octalactin A, Fig. (58) and B, which have been shown as a cell cycle-specific anticancer drug [471], and swinholide, Fig. (59), isolated from symbiotic cyanobacteria with the marine sponge Theonella swinhoei [472]. 

Following the first report of tumor promotion by okadaic acid, additional tumor promoters of the okadaic acid activity class have been identified, e.g., microcystin [513,514], and calyculin derivatives, Fig. (63) reported in marine sponges such as Discodermia calyx [515] and Theonella swinhoei [516] as potent inhibitors of tumor cell proliferation. A two-sponge association, Poecillastra sp. and Jaspis sp., yielded cytotoxic toxins which exhibited selective activity against several tumoral cell lines [517],... 

Theonellamides A-E (1104-1108), which are analogs of the previously isolated theonellamide F (7), were characterized from the Japanese sponge Theonella sp. (7725). The related theopalauamide (= P951) (1109) was isolated from Theonella swinhoei found in both Palau and Mozambique (1126,1127). It should be noted that a minor structural correction (misplaced methyl group) has been reported for the previously known theonegramide (1128). 

Ratnayake AS, Davis RA, Harper MK, Veltri CA, Andjelic CD, Barrows LR, Ireland CM (2005) Aurantosides G, H, and I Three New Tetramic Acid Glycosides from a Papua New Guinea Theonella swinhoei. J Nat Prod 68 104... 

Bewley CA, Holland ND, Faulkner DJ (1996) Two Classes of Metabolites from Theonella swinhoei are Localized in Distinct Populations of Bacterial Symbionts. Experientia 52 716... 

Schmidt EW, Bewley CA, Faulkner DJ (1998) Theopalauamide, a Bicyclic Glycopeptide from Filamentous Bacterial Symbionts of the Lithistid Sponge Theonella swinhoei from Palau and Mozambique. J Org Chem 63 1254... 

Bewley CA, Faulkner DJ (1995) Theonegramide, an Antifungal Glycopeptide from the Philippine Lithistid Sponge Theonella swinhoei. J Org Chem 60 2644... 

Clark DP, Carroll J, Naylor S, Crews P (1998) An Antifungal Cyclodepsipeptide, Cyclolithistide A, from the Sponge Theonella swinhoei. J Org Chem 63 8757... 

This strategy was employed by Semple and co-workers [29] in the synthesis of the N(10)-C(17) fragment of cyclotheonamides, a family of 19-membered cyclic penta-peptides isolated from the sponge Theonella swinhoei, which are serine protease inhibitors. 

Niphatynes A (418) and B (419) are pyridine derivatives with alkyne and methoxylamine functionalities isolated from the Fijian sponge Niphates sp. (344). Niphatyne A (418) exhibits cytotoxic activity. Theonelladins A-D (420-423) are other pyridine alkaloids obtained from the Okinawan sponge Theonella swinhoei and exhibit antineoplastic activity (345). These... 

Over half of the compounds reported for lithistid sponges were isolated from Theonella (family Theonellidae). Theonella species have been reported to contain a wide variety of cyclic and linear peptides and polyketides, as well as 3-alkyl piperidine derivatives nearly identical to those reported from the order Haplosclerida.58 There is also a single report of cyano- and isothiocyano-sesquiter-penes similar to those isolated from Axinellidae (order Halichondrida).42 Bewley et al. performed a cellular localization study on Theonella swinhoei in which several types of microorganisms were separated from the sponge cells. Chemical analysis of the extracts from the separated cells indicated that the bicyclic peptide theopalauamide was found exclusively in filamentous bacteria while the polyketide swinholide A was localized to a mixed population of unicellular bacteria.59... 

Kobayashi, J., Murayama, T., and Ohizumi, Y., Theonelladins A-D, novel antineoplastic pyridine alkaloids from the Okinawan sponge Theonella swinhoei, Tetrahedron Lett., 30, 4833, 1989. 

Bewley, C. A., Holland, N. D., and Faulkner, D. J., Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts, Experientia, 52, 716, 1996. 

Schmidt, E.W., Bewley C.A., and Faulkner, D.J., Theopalauamide, a bicyclic glycopeptide from filamentous bacterial symbionts of the lithistid sponge Theonella Swinhoei from Palau and Mozambique, J. Org. Chem., 63, 1254, 1998. 

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