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Halipeptins A and B: Two Novel Potent Anti-inflammatory Cyclic Depsipeptides from the Vanuatu Marine Sponge Haliclona species
journal contribution
posted on 2001-10-13, 00:00 authored by Antonio Randazzo, Giuseppe Bifulco, Clelia Giannini, Mariarosaria Bucci, Cécile Debitus, Giuseppe Cirino, Luigi Gomez-PalomaTwo 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-δ-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 μg/kg (i.p.).