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 | |
| Publication status | Published - 2011 Jan |
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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 journal › Article
}
TY - JOUR
T1 - Synthesis, inhibitory effects on nitric oxide and structure-activity relationships of a glycosphingolipid from the marine sponge Aplysinella rhax and its analogues
AU - Fujita, Yuzo
AU - Ohshima, Naohiro
AU - Hasegawa, Ai
AU - Schweizer, Frank
AU - Takeda, Tadahiro
AU - Kiuchi, Fumiyuki
AU - Hada, Noriyasu
PY - 2011/1
Y1 - 2011/1
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.
KW - Aplysinella rhax
KW - D-fucose
KW - Glycosphingolipid
KW - Nitric oxide
UR - http://www.scopus.com/inward/record.url?scp=79251512333&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79251512333&partnerID=8YFLogxK
U2 - 10.3390/molecules16010637
DO - 10.3390/molecules16010637
M3 - Article
C2 - 21242943
AN - SCOPUS:79251512333
VL - 16
SP - 637
EP - 651
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 1
ER -