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- Title
Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues.
- Authors
Fujita, Yuzo; Ohshima, Naohiro; Hasegawa, Ai; Schweizer, Frank; Takeda, Tadahiro; Kiuchi, Fumiyuki; Hada, Noriyasu
- Abstract
The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D-Fucp(1→3)]-β-DGlcNAcp( 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.
- Subjects
GLYCOSPHINGOLIPIDS; CHEMICAL reactions; CHEMICAL structure; NITRIC oxide; GLYCOLIPIDS
- Publication
Molecules, 2011, Vol 16, Issue 1, p637
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules16010637