Abstract
The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D- Fucp(1→3)]-(3-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.
Original language | English |
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Pages (from-to) | 637-651 |
Number of pages | 15 |
Journal | Molecules |
Volume | 16 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2011 Jan |
Keywords
- Aplysinella rhax
- D-fucose
- Glycosphingolipid
- Nitric oxide
ASJC Scopus subject areas
- Analytical Chemistry
- Chemistry (miscellaneous)
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry