Molecules 2011, 16(1), 637-651; doi:10.3390/molecules16010637
Article

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

1 Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan. 2 Department of Chemistry and Medical Microbiology, University of Manitoba, Winnipeg, Manitoba, R3T 2N2, Canada
* Author to whom correspondence should be addressed.
Received: 9 December 2010; in revised form: 29 December 2010 / Accepted: 14 January 2011 / Published: 17 January 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract: The novel glycosphingolipid, b-D-GalNAcp(1®4)[a-D-Fucp(1®3)]-b-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 a1®3 and b1®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-Fuca1-3GlcNAc-linkage and the ceramide aglycon portion are crucial for optimal NO inhibition.
Keywords: glycosphingolipid; Aplysinella rhax; D-fucose; nitric oxide

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MDPI and ACS Style

Fujita, Y.; Ohshima, N.; Hasegawa, A.; Schweizer, F.; Takeda, T.; Kiuchi, F.; Hada, N. Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues. Molecules 2011, 16, 637-651.

AMA Style

Fujita Y, Ohshima N, Hasegawa A, Schweizer F, Takeda T, Kiuchi F, Hada N. Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues. Molecules. 2011; 16(1):637-651.

Chicago/Turabian Style

Fujita, Yuzo; Ohshima, Naohiro; Hasegawa, Ai; Schweizer, Frank; Takeda, Tadahiro; Kiuchi, Fumiyuki; Hada, Noriyasu. 2011. "Synthesis, Inhibitory Effects on Nitric Oxide and Structure-Activity Relationships of a Glycosphingolipid from the Marine Sponge Aplysinella rhax and Its Analogues." Molecules 16, no. 1: 637-651.

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