Two new metabolites, named halipeptins A and B, have been isolated from the marine sponge Haliclona sp. Their structures were determined by extensive use of one- and two-dimensional NMR experiments, mass spectrometry, and UV and IR spectroscopy. Halipeptin A is a novel 17-membered cyclic depsipeptide, consisting of five residues including two alanines (with L stereochemistry) and three new residues that appear to be previously undescribed from natural sources: 1,2-oxazetidine-4-methyl-4-carboxylic acid, 3-hydroxy-2,2,4-trimethyl-7-methoxydecanoic acid (HTMMD), and N-methyl-delta-hydroxyisoleucine. The HTMMD residue is substituted with 3-hydroxy-2,2,4-trimethyl-7-hydroxydecanoic acid in halipeptin B. Halipeptin A was found to possess very potent anti-inflammatory activity in vivo, causing about 60% inhibition of edema in mice at the dose of 300 microg/kg (i.p.).
Halipeptins A and B : Two Novel Potent Anti-inflammatory Cyclic Depsipeptides from the Vanuatu Marine Sponge Haliclona species / A. Randazzo, G. Bifulco, C. Giannini, M. Bucci, C. Debitus, G. Cirino, L. Gomez-Paloma. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 123:44(2001), pp. 10870-10876.
|Titolo:||Halipeptins A and B : Two Novel Potent Anti-inflammatory Cyclic Depsipeptides from the Vanuatu Marine Sponge Haliclona species|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2001|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1021/ja010015c|
|Appare nelle tipologie:||01 - Articolo su periodico|