TY - JOUR
T1 - Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax
AU - Hada, Noriyasu
AU - Nakashima, Taishi
AU - Shrestha, Suraj Prakash
AU - Masui, Ryo
AU - Narukawa, Yuji
AU - Tani, Kayoko
AU - Takeda, Tadahiro
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (No. 19590011) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and the (MEXT) High-Tech Research Center project.
PY - 2007/11/1
Y1 - 2007/11/1
N2 - A novel glycosphingolipid, β-d-GalNAcp(1 → 4)[α-d- Fucp(1 → 3)]-β-d-GlcNAcp(1→)Cer (1), isolated from the marine sponge Aplysinella rhax, has a unique structure, with d-fucose and N-acetyl-d-galactosamine attached to a reducing-end N-acetyl-d-glucosamine through an α1 → 3 and β1 → 4 linkage, respectively. We synthesized glycolipid analogues carrying a 2-branched fatty alkyl residue or a 2-trimethylsilyl ethyl residue in place of ceramide (2 and 3), non-natural type trisaccharide analogue containing an l-fucose residue (4), and other analogues (5 and 6). Among these prepared compounds, 2 showed the most potent nitric oxide (NO) production inhibitory activity against LPS-activated J774.1 cells. In addition, their structure-activity relationships were established.
AB - A novel glycosphingolipid, β-d-GalNAcp(1 → 4)[α-d- Fucp(1 → 3)]-β-d-GlcNAcp(1→)Cer (1), isolated from the marine sponge Aplysinella rhax, has a unique structure, with d-fucose and N-acetyl-d-galactosamine attached to a reducing-end N-acetyl-d-glucosamine through an α1 → 3 and β1 → 4 linkage, respectively. We synthesized glycolipid analogues carrying a 2-branched fatty alkyl residue or a 2-trimethylsilyl ethyl residue in place of ceramide (2 and 3), non-natural type trisaccharide analogue containing an l-fucose residue (4), and other analogues (5 and 6). Among these prepared compounds, 2 showed the most potent nitric oxide (NO) production inhibitory activity against LPS-activated J774.1 cells. In addition, their structure-activity relationships were established.
KW - Aplysinella rhax
KW - Glycosphingolipid
KW - Nitric oxide
KW - d-fucose
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U2 - 10.1016/j.bmcl.2007.07.108
DO - 10.1016/j.bmcl.2007.07.108
M3 - Article
C2 - 17827010
AN - SCOPUS:34548813646
SN - 0960-894X
VL - 17
SP - 5912
EP - 5915
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 21
ER -
