Sequestered fulvinol-related polyacetylenes in Peltodoris atromaculata.

The Mediterranean dorid nudibranch Peltodoris atromaculata that had been collected while feeding on Haliclona fulva was shown to sequester long-chain fulvinol-like polyacetylene metabolites (compounds 2-5) from the prey. They were isolated along with previously reported bromorenierins from the diethyl ether extracts of both the mollusk and the sponge. Their structures were elucidated by NMR spectroscopy and tandem FABMS analysis. Compound 5 exhibited in vitro growth inhibitory effects against the SKMEL-28 melanoma cell line.

[1]  Genoveffa Nuzzo,et al.  Fulvynes, antimicrobial polyoxygenated acetylenes from the Mediterranean sponge Haliclona fulva , 2012 .

[2]  R. Kiss,et al.  Evaluation of the antiproliferative activity of diterpene isonitriles from the sponge Pseudoaxinella flava in apoptosis-sensitive and apoptosis-resistant cancer cell lines. , 2011, Journal of natural products.

[3]  R. Kiss,et al.  Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells. , 2010, Journal of natural products.

[4]  T. Hoye,et al.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons , 2007, Nature Protocols.

[5]  S. D. Rosa,et al.  Polyacetylenes from the spongePetrosia ficiformis found in dark caves , 1981, Experientia.

[6]  S. Gemballa,et al.  Cytotoxic haplosclerid sponges preferred: a field study on the diet of the dotted sea slug Peltodoris atromaculata (Doridoidea: Nudibranchia) , 2004 .

[7]  M. Ghiselin,et al.  Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs (Mollusca: Gastropoda: Opisthobranchia) , 1999, CHEMOECOLOGY.

[8]  M. Ortega,et al.  Fulvinol, a New Long-Chain Diacetylenic Metabolite from the Sponge Reniera fulva , 1996 .

[9]  M. Gavagnin,et al.  Further Structural Studies on the Petroformynes , 1995 .

[10]  M. Gavagnin,et al.  Absolute stereochemistry of petroformynes, high molecular polyacetylenes from the marine sponge Petrosia ficiformis , 1994 .

[11]  V. Marzo,et al.  Minor Bioactive Polyacetylenes from Petrosia ficiformis , 1990 .

[12]  V. Marzo,et al.  High molecular weight polyacetylenes from Petrosia ficiformis: Further structural analysis and biological activity , 1989 .

[13]  S. D. Rosa,et al.  Further High Molecular Weight Polyacetylenes from the Sponge Petrosia ficiformis , 1985 .

[14]  S. D. Rosa,et al.  High molecular weight polyacetylenes from the nudibranch Peltodoris actromaculata and the sponge Petrosia ficiformis , 1980 .

[15]  G. Cimino,et al.  New acetylenic compounds from the sponge reniera fulva , 1977 .

[16]  J. Matiskella,et al.  2,2,2-trichloroethyl chloroformate: A general reagent for demethylation of tertiary methylamines , 1974 .