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

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

6 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
Externally published	Yes

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules16010637

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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 - Fujita, Yuzo

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AU - Hasegawa, Ai

AU - Schweizer, Frank

AU - Takeda, Tadahiro

AU - Kiuchi, Fumiyuki

AU - Hada, Noriyasu

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N2 - 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.

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

UN SDGs

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