Abstract
The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D-Fucp(1→3)]-β-D-GlcNAcp(1→)Cer (A), isolated from the marine sponge Aplysinella rhax has a unique structure, with D-fucose and N-acetyl-D-galactosamine moieties attached to a reducing-end N-acetyl-D-glucosamine through an α1→3 and β1→4 linkage, respectively. We synthesized glycolipid 1 and some non-natural di- and trisaccharide analogues 2-6 containing a D-fucose residue. Among these compounds, the natural type showed the most potent nitric oxide (NO) production inhibitory activity against LPS-induced J774.1 cells. Our results indicate that both the presence of a D-Fucα1-3GlcNAc-linkage and the ceramide aglycon portion are crucial for optimal NO inhibition.
Highlights
Carbohydrates in the form of glycoconjugates, for example glycoproteins, glycolipids and proteoglycans, play an important role in many intracellular and extracellular events including cell-cellMolecules 2011, 16 adhesion, cell differentiation, signal transduction, cancer metastasis and immune responses [1]
Zollo et al isolated and characterized a novel neutral glycosphingolipid (A, Figure 1) from the marine sponge Aplysinella rhax which features a D-fucose and an N-acetyl-Dgalactosamine attached to a reducing-end N-acetyl-D-glucosamine through a α1→3 and a β1→4 linkages, respectively [14]
In order to study the structure-activity relationships of these compounds inhibiting nitric oxide (NO) release, we previously reported the synthesis of β-D-GalNAcp(1→4)[α-DFucp(1→3)]-β-D-GlcNAcp(1→)aglycon trisaccharide analogues, containing a 2-branched fatty alkyl residue and a 2-(trimethylsilyl)ethyl (TMS-Et) residue, respectively [6]
Summary
Carbohydrates in the form of glycoconjugates, for example glycoproteins, glycolipids and proteoglycans, play an important role in many intracellular and extracellular events including cell-cell. Molecules 2011, 16 adhesion, cell differentiation, signal transduction, cancer metastasis and immune responses [1] The majority of these studies have focused on higher animals and relatively little is known about the functions of glycoconjugates in lower animals [2]. Figure 1) from the marine sponge Aplysinella rhax which features a D-fucose and an N-acetyl-Dgalactosamine attached to a reducing-end N-acetyl-D-glucosamine through a α1→3 and a β1→4 linkages, respectively [14] This was the first report on glycolipids containing D-fucose. In order to study the structure-activity relationships of these compounds inhibiting NO release, we previously reported the synthesis of β-D-GalNAcp(1→4)[α-DFucp(1→3)]-β-D-GlcNAcp(1→)aglycon trisaccharide analogues, containing a 2-branched fatty alkyl residue and a 2-(trimethylsilyl)ethyl (TMS-Et) residue, respectively [6]. The NO-inhibitory affect of commercially available ceramide 7 and known trisaccharide 2 was included in these experiments for comparison
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