Jaspamides

Jaspamide (17), previously mentioned in Section 17.3, is a modified peptide isolated from a Jaspis sponge. Jaspamide shows insecticidal activity against Heliothis virescens with an LCS0 of 4 ppm, as compared to 1 ppm for azadirachtin. Jaspamide (17), showed more than 72% mortality at 100 ppm to both southern com rootworm and tobacco budworm. Iso-domoic acids A (40), B, and C are novel amino acids from the red alga Chondria armata. They... 

Preparation of a mimetic of the cyclic peptide jaspamide was reported in 1988. 87 Compound 41 (Scheme 17) was designed to mimic the type-II (1-turn of the peptide, which contained the proposed pharmacophoric phenol and 2-bromoindole functional groups. This analogue displayed interesting insecticidal activity against the tobacco budworm, Heliothis vireseins. 

Zampella A, Giannini C, Debitus C, Roussakis C, D Auria MV (1999) New Jaspamide Derivatives from the Marine Sponge Jaspis splendans Collected in Vanuatu. J Nat Prod 62 332... 

Synthesis, Conformational Analysis, and Cytotoxicity of New Analogues of the Natural Cyclodepsipeptide Jaspamide. J Nat Prod 67 1325... 

Synthesis, Solution Structure, and Bioactivity of Six New Simplified Analogues of the Natural Cyclodepsipeptide Jaspamide. Bioorg Med Chem 13 5225... 

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... 

Tyr substructures are, moreover, found within several peptidic antibiotics, for example the edeines 57 from Bacillus brevis, or within cyclodepsipeptides that have been isolated from marine sponges, for example jaspamides A-C 59 [106] or geo-diamolides H-I 58 [107] (Scheme 1.5.9). The chondramides 60 are closely related antibiotics that have been obtained from the myxobacterium Chondromyces croca-tus. Within the edeine biosynthesis D-/ -Tyr 9 seems to be a real precursor [89]. The biosynthesis of the jaspamides, the geodiamolides, or the chondramides has not yet been investigated. 

Ethyl lactate has also been used as a chiral fragment for numerous other studies. Included are synthetic efforts relating to salenomycin, (-)-biopterin, (+)-polyoxamic acid, jaspamide, the enantiomeric 2-pentanols, pumilitoxin B, D-ristosamine, protomycinolide IV, and tirandamycin. ... 

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. 

Geodiamolide A (203) and jaspamide (204) are cytotoxic antifungal cyclic depsipeptides of marine sponge origin. The key component 207 required for their synthesis is achieved via coupling of acid 206 with amine 205 using DEPC.77... 

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