Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax

Noriyasu Hada, Taishi Nakashima, Suraj Prakash Shrestha, Ryo Masui, Yuuji Narukawa, Kayoko Tani, Tadahiro Takeda

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5912-5915
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number21
DOIs
Publication statusPublished - 2007 Nov 1

Fingerprint

Glycosphingolipids
Fucose
Porifera
Bioactivity
Trisaccharides
Galactosamine
Ceramides
Glucosamine
Glycolipids
Structure-Activity Relationship
Nitric Oxide
ceramide 3

Keywords

  • Aplysinella rhax
  • d-fucose
  • Glycosphingolipid
  • Nitric oxide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax. / Hada, Noriyasu; Nakashima, Taishi; Shrestha, Suraj Prakash; Masui, Ryo; Narukawa, Yuuji; Tani, Kayoko; Takeda, Tadahiro.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 17, No. 21, 01.11.2007, p. 5912-5915.

Research output: Contribution to journalArticle

Hada, Noriyasu ; Nakashima, Taishi ; Shrestha, Suraj Prakash ; Masui, Ryo ; Narukawa, Yuuji ; Tani, Kayoko ; Takeda, Tadahiro. / Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax. In: Bioorganic and Medicinal Chemistry Letters. 2007 ; Vol. 17, No. 21. pp. 5912-5915.
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