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

doi:10.3390/molecules16010637

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

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	637-651
Number of pages	15
Journal	Molecules
Volume	16
Issue number	1
DOIs	https://doi.org/10.3390/molecules16010637
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

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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 journal › Article › peer-review

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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.",

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AU - Schweizer, Frank

AU - Takeda, Tadahiro

AU - Kiuchi, Fumiyuki

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AB - 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.

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

Abstract

Keywords

ASJC Scopus subject areas

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