Jasplakinolide/jaspamide

Hirai, Y, Yokota, K., and Momose, T. (1994) Studies on the novel cyclodepsipeptides. A total synthesis of (+)-jasplakinolide (jaspamide). Heterocycles, 39, 603-612. 

From sponges of the genus Jaspis collected at Fiji (300,301), Palau (300), and Papua New Guinea (302), jaspamide (jasplakinolide, 372) was isolated the compound shows potent insecticidal, antifungal, anthelminthic, and ichthyotoxic activity. The structure was determined by X-ray analysis (300). The solution conformation of372 was reported using NMR, molecular mechanics, and dynamics calculations (303). A complexation study was carried out with 372 and the univalent metal ions Li ", Na+, and K+. Li+ binding was observed, and the complex was characterized by NMR and molecular mechanics calculations (304). Jaspamide (372) has potent in... 

A similar enantioconvergent strategy is used for the construction of the hydroxy acid of the biologically active peptides geodiamolide A or jaspamide (jasplakinolide), isolated from lower marine organisms (sponges)442. 

Posey and Bierer, 1999 Okada, Sanders, and Crews, 2000). Most jaspamides/jasplakinolides have potent q to-toxic activities against HT-29, HCT-116, and MCF-7 cancer cell lines with IC50 values less than 1 pM, but jaspamides F, H, N, and P have only moderate activities with IC50 values greater than 10 pM (Ebada et al, 2009 Gala et al, 2009 Robinson et al, 2010). 

Kato, S., Hamada, Y., and Shioiri, T. (1988) A practical synthesis of the peptide part of jaspamide (jasplakinolide), a cydodepsipeptide from a marine sponge. Tetrahedron Lett., 29, 6465-6466. 

Schmidt, U., Siegel, W., and Mundinger, K. (1988) Total syntheses of jaspamide (jasplakinolide) and geodiamolide A and B —1. Stereoselective synthesis of (2S,4E,6R,8E)-8-hydroxy-2,4,6-trimethyl-4-nonenoic. Tetrahedron Lett., 29,1269-1270. 

Geodiamolides and jaspamides are closely related cyclic depsipeptides isolated from a variety of tropical marine sponges. Jaspamide (259), also named jasplakinolide, obtained independently from Jaspis sp. collected in Palau (156) and Fiji (157), was the first member of this group of depsipeptides to be reported. 

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