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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, 1, 1, 2, 1, 1 and 1,*
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 / Revised: 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 glycosphingolipid; Aplysinella rhax; D-fucose; nitric oxide
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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