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

The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D-Fucp(1→3)]-β-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, respec...

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Autores principales: Fujita, Yuzo, Ohshima, Naohiro, Hasegawa, Ai, Schweizer, Frank, Takeda, Tadahiro, Kiuchi, Fumiyuki, Hada, Noriyasu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259274/
https://www.ncbi.nlm.nih.gov/pubmed/21242943
http://dx.doi.org/10.3390/molecules16010637
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author Fujita, Yuzo
Ohshima, Naohiro
Hasegawa, Ai
Schweizer, Frank
Takeda, Tadahiro
Kiuchi, Fumiyuki
Hada, Noriyasu
author_facet Fujita, Yuzo
Ohshima, Naohiro
Hasegawa, Ai
Schweizer, Frank
Takeda, Tadahiro
Kiuchi, Fumiyuki
Hada, Noriyasu
author_sort Fujita, Yuzo
collection PubMed
description The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D-Fucp(1→3)]-β-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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spelling pubmed-62592742018-12-07 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 Molecules Article The novel glycosphingolipid, β-D-GalNAcp(1→4)[α-D-Fucp(1→3)]-β-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. MDPI 2011-01-17 /pmc/articles/PMC6259274/ /pubmed/21242943 http://dx.doi.org/10.3390/molecules16010637 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
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
title Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
title_full Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
title_fullStr Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
title_full_unstemmed Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
title_short Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues
title_sort synthesis, inhibitory effects on nitric oxide and structure-activity relationships of a glycosphingolipid from the marine sponge aplysinella rhax and its analogues
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259274/
https://www.ncbi.nlm.nih.gov/pubmed/21242943
http://dx.doi.org/10.3390/molecules16010637
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