Molecules (Jan 2011)

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

  • Naohiro Ohshima,
  • Ai Hasegawa,
  • Frank Schweizer,
  • Tadahiro Takeda,
  • Fumiyuki Kiuchi,
  • Noriyasu Hada,
  • Yuzo Fujita

DOI
https://doi.org/10.3390/molecules16010637
Journal volume & issue
Vol. 16, no. 1
pp. 637 – 651

Abstract

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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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