Synthesis, inhibitory effects on nitric oxide and structure-activity relationships of a glycosphingolipid from the marine sponge Aplysinella rhax and its analogues

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

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 languageEnglish
Pages (from-to)637-651
Number of pages15
JournalMolecules
Volume16
Issue number1
DOIs
Publication statusPublished - 2011 Jan

Fingerprint

Glycosphingolipids
Fucose
Porifera
Structure-Activity Relationship
nitric oxide
linkages
Nitric Oxide
analogs
Trisaccharides
Acetylgalactosamine
Acetylglucosamine
Ceramides
Glycolipids
synthesis
cells

Keywords

  • Aplysinella rhax
  • D-fucose
  • Glycosphingolipid
  • Nitric oxide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, inhibitory effects on nitric oxide and structure-activity relationships of a glycosphingolipid from the marine sponge Aplysinella rhax and its analogues. / Fujita, Yuzo; Ohshima, Naohiro; Hasegawa, Ai; Schweizer, Frank; Takeda, Tadahiro; Kiuchi, Fumiyuki; Hada, Noriyasu.

In: Molecules, Vol. 16, No. 1, 01.2011, p. 637-651.

Research output: Contribution to journalArticle

Fujita, Yuzo ; Ohshima, Naohiro ; Hasegawa, Ai ; Schweizer, Frank ; Takeda, Tadahiro ; Kiuchi, Fumiyuki ; Hada, Noriyasu. / Synthesis, inhibitory effects on nitric oxide and structure-activity relationships of a glycosphingolipid from the marine sponge Aplysinella rhax and its analogues. In: Molecules. 2011 ; Vol. 16, No. 1. pp. 637-651.
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