Studies on the stereoselective synthesis and immunosuppressive activity of dihydroartemisinin-O-glycoside derivatives

Bioorg Med Chem Lett. 2020 Aug 15;30(16):127338. doi: 10.1016/j.bmcl.2020.127338. Epub 2020 Jun 10.

Abstract

Eight new dihydroartemisinin-O-glycosides were synthesized with their relative configurations were determined based on NMR spectrum. In vitro immunosuppressive assay showed that 10α-dihydroartemisinin-β-O-d-mannoside (19a) demonstrate 88% inhibition towards T cells proliferation and 98% reduction in IFN-γ levels in cell media. These results suggest that dihydroartemisinin-O-glycoside as a potential lead for further in vivo evaluation.

Keywords: Dihydroartemisinin; Glycoside; Immunosuppressive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Artemisinins / chemical synthesis
  • Artemisinins / chemistry
  • Artemisinins / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Glycosides / chemical synthesis
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Humans
  • Immunosuppressive Agents / chemical synthesis
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology*
  • Interferon-gamma / antagonists & inhibitors*
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship
  • T-Lymphocytes / drug effects*

Substances

  • Artemisinins
  • Glycosides
  • Immunosuppressive Agents
  • artenimol
  • Interferon-gamma