Synthesis of fungal glycolipid asperamide B and investigation of its ability to stimulate natural killer T cells

Org Lett. 2013 Oct 18;15(20):5242-5. doi: 10.1021/ol4024375. Epub 2013 Oct 10.

Abstract

The relationship between mold and asthma has been recognized for decades, but the molecular triggers of asthma generated by molds have not been fully elucidated. A glycolipid generated by Aspergillus species has recently been identified that triggers airway hyperreactivity via natural killer T cell activation. The synthesis of this glycolipid and structural variants designed to allow identification of the features of this glycolipid required for recognition by natural killer T cells is described.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Aspergillus / chemistry*
  • Dendritic Cells / drug effects
  • Dose-Response Relationship, Drug
  • Enzyme-Linked Immunosorbent Assay
  • Interferon-gamma / analysis
  • Interleukin-4 / analysis
  • Mice
  • Molecular Conformation
  • Natural Killer T-Cells / drug effects*
  • Sphingolipids / chemical synthesis*
  • Sphingolipids / chemistry
  • Sphingolipids / pharmacology*
  • Structure-Activity Relationship

Substances

  • 1-O-beta-D-glucopyranosyl-(2S,2'R,3R,3'E,4E,8E)-N-(2'-hydroxy-3'-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol
  • Sphingolipids
  • Interleukin-4
  • Interferon-gamma