Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues

Autor: Naohiro Ohshima, Ai Hasegawa, Frank Schweizer, Tadahiro Takeda, Fumiyuki Kiuchi, Noriyasu Hada, Yuzo Fujita
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Molecules, Vol 16, Iss 1, Pp 637-651 (2011)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules16010637
Popis: The novel glycosphingolipid, b-D-GalNAcp(1®4)[a-D-Fucp(1®3)]-b-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 a1®3 and b1®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-Fuca1-3GlcNAc-linkage and the ceramide aglycon portion are crucial for optimal NO inhibition.
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