Time filter

Source Type

Tashiro T.,Glycosphingolipid Synthesis Group | Moriy K.,Glycosphingolipid Synthesis Group
Bioscience, Biotechnology and Biochemistry

Esterified ceramides, (2S,3R,4E)-2-[(300-stearoyloxy) triacontanamido] octadec-4-ene-1,3-diol (2) and (2S,3R,4E,6R)-2-[(300-stearoyloxy) triacontanamido]octadec- 4-ene-1,3,6-triol (4), are minor components of the human stratum corneum. We synthesized these ceramides by employing olefin cross metathesis as the key reaction for constructing their !-hydroxytriacontanoyl part (13). Source

Tashiro T.,Glycosphingolipid Synthesis Group | Mori K.,Glycosphingolipid Synthesis Group
Studies in Natural Products Chemistry

Noncytotoxic anticancer α-galactosphingolipid agelasphin-9b (1) was isolated in 1993 from an Okinawan marine sponge. Since then, a large number of natural and synthetic glycolipids were bioassayed as immunostimulants, which activate natural killer T cells to generate cytokines such as interferon γ (IFN-γ) and interleukin 4 (IL-4). Some of them (2-6) are known to be drug candidates for autoimmune disease or cancer. Our chapter will review the methods used for the synthesis of these compounds, and also the structure-activity relationships among them. Recent biological and X-ray crystallographic studies show that each of the glycolipids is a ligand to make a complex with CD1d protein, and the complex can be recognized by T-cell receptor to induce the generation of cytokines such as IFN-γ and IL-4. Accordingly, it is important to identify the naturally occurring ligand(s) in animal bodies. In 2011, 7 (β-GluCer) was proposed as the natural and endogenous ligand. Synthesis and bioassay of 7 and its relatives will also be reviewed. Finally, future clinical application of these noncytotoxic immunostimulants will be discussed. (for a previous review please, see K. Mori, T. Tashiro, Heterocycles, 2011, 83, 951-1003.) © 2014 Elsevier B.V. Source

Discover hidden collaborations