Peptides sponges

A novel natural product has been isolated from the Micronesian sponge Dysidea herbacea. This material is the zwitterionic pyrroloimidazopyridine 293 and is claimed to be the first example of a simple peptide with an N,N-aminal linkage <2004JOC1180>. 

Many of the listed nonprotein amino acids have been identified as components of nonribosomal peptides from fungi and sponges. Hence, they tend to exhibit antifungal and antimicrobial properties, and in some cases potent cytotoxicity is observed. Specific details on known nonprotein amino acids are given in Table 1. 

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

Generally, most of the nonprotein amino acids containing aryl or functionalized aryl side chains are part of nonribosomal peptides isolated from hacteria, fungi, and sponges. These peptides exhibit interesting biological activities that include antimicrobial, antitumor, antifungal, and other inhibitory activities. Table 3 describes many of these types of amino acids. 

Nonribosomai peptides from marine sponge -Theonella sp. 

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

H2N0C- C02H Sponge -Aciculites orientalis Acicuiitins and acicuiitamides - antifungai peptides 14, 75... 

H2NOC C02H isoiated from theoneiiid sponges Theoneiiamides - cytotoxic, antifungai peptide 14, 128... 

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

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... 

Talpir R, Benayahu Y, Kashman Y. Pannell L, Schleyer M. (1994) Hemiasterlin and geodiamolide TA two new cytotoxic peptides from the marine sponge HemiastereUa minor (Kirkpatrick). Tetrahedron Lett 35 4453 456. 

The marine sponge-derived HDAC inhibitors can be classified as cyclic peptides or bicyclic depsipeptides. 

Gunasekera, S.P. Pomponi, S.A. McCarthy, P.J. (1994A) Discobahamins A and B, new peptides from the Bahamian deep water marine sponge Discodermia sp. J. Nat. Prod., 57, 79-83. 

Qureshi, A. Colin, P.L. Faulkner, D.J. (2000) Microsclerodermins F-I, antitumor and antifungal cyclic peptides from the lithistid sponge Microscleroderma sp. Tetrahedron, 56, 3679-85. 

Dolastatin 10 has been evaluated with promising results in a phase I clinical study in patients with solid tumors. Subsequently, its noticeable antitumor activity was well documented in various in vitro and in vivo tumor models (Madden et al., 2000). More than a dozen dolastatin peptides have been isolated to date. Recent studies have shown, for example, that the depsipeptide dolastatin 11 arrests cells at cytokinesis by causing a rapid and massive rearrangement of the cellular actin filament network and induces the hyperpolymerization of purified actin (Bai et al., 2001). The effects of dolastatin 11 were similar to those of the sponge-derived depsipeptide jasplakinolide however, dolastatin 11 exhibited threefold more cytotoxicity than jasplakinolide in the cells studied. 

Zang et al. developed a peptide-based polyurethane scaffold for tissue engineering. LDI was reacted with glycerol and upon reaction with water produced a porous sponge due to liberation of CO2. Initial cell growth studies with rabbit bone marrow stromal cells showed that the polymer supported cell growth. 

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... 

Besides peptides, marine organisms have been reported to produce biologically active proteins, which are probably involved in the protection of organisms against physiological and stress conditions. Recently, these molecules have been cloned from sponges [324] and marine microorganisms [325],... 

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