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Chemical compound From Wikipedia, the free encyclopedia
Onnamide A is a bioactive natural product found in Theonella swinhoei, a species of marine sponge whose genus is well known for yielding a diverse set of biologically active natural products, including the swinholides[1] and polytheonamides.[2] It bears structural similarities to the pederins, a family of compounds known to inhibit protein synthesis in eukaryotic cells. Onnamide A and its analogues have attracted academic interest due to their cytotoxicity and potential for combating the growth and proliferation of cancer cells.[3]
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Other names
(2S)-5-[(Diaminomethylene)amino]-2-({(2E,4E,6E,11R)-11-hydroxy-12-[(4S,4aS,6R,8S,8aR)-4-({(2S)-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl]acetyl}amino)-8-methox y-7,7-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]-2,4,6-dodecatrienoyl}amino)pentanoic acid | |
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Properties | |
C39H63N5O12 | |
Molar mass | 793.956 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Onnamide A was first isolated in 1988 from Theonella spp., a genus of marine sponges residing off the coast of Okinawa, Japan,[4] as part of a bioassay aimed at discovering novel marine natural products possessing antiviral activity. Eight analogues possessing similar structure, as well as cytotoxicity were reported in 1992.
Onnamide A is a complex biomolecule with a 39 unique carbon atoms and 11 degrees of unsaturation. Its core contains three rings, two of which comprise a dimeric lactone structure. It contains a long side chain that has a three conjugated trans- olefins that connects to an amide bond, terminating in an arginine residue. The stereochemical assignments of onnamide A have been extensively characterized by experimental and advanced NMR studies.[4][5]
Genomic studies suggest strong homology with Ped genes, which encode the production of pederins, structurally similar compounds synthesized by bacterial endosymbionts of Paederus beetles. This suggests that onnamide A is actually the product of bacterial endosymbionts of the marine sponges from which the compound was first isolated. Thus, the biosynthetic pathway of onnamide A is envisioned to undertake analogous steps as those that lead to pederin, utilizing a prokaryotic PKS-NRPS system.[6]
Onnamide A inhibits protein synthesis in cell lines, leading to induction of stress-activated protein kinases apoptosis in the affected cell.[3] Its derivatives have been found to be highly toxic towards leukemic cells of the P388 cell line.[7]
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