Epigynumgenane-type pregnane glycosides from Epigynum cochinchinensis and their immunosuppressive activity

Phytochemistry. 2019 Dec:168:112127. doi: 10.1016/j.phytochem.2019.112127. Epub 2019 Sep 21.

Abstract

Five undescribed C21 pregnane glycosides, epigycosides D-H, together with four known analogues, two lignans, and a flavonoid have been isolated from the stems of Epigynum cochinchinensis. The structures of pregnane glycosides were elucidated using spectroscopic techniques and acid hydrolysis. The in vitro immunological activities were assessed against Con A-stimulated proliferation of mice splenocytes. The C21 pregnane glycosides showed immunosuppressive activity in a concentration-dependent manner. Moreover, epigycoside E exhibited a potent immunosuppressive effect, and the IC50 value on Con A-stimulated mice splenocytes was 22.1 ± 6.4 μM. Epigycoside E also caused G0/G1 arrest, and inhibited TNF-α and IL-2 production.

Keywords: Cytokines; Epigycoside E; Epigynum cochinchinensis (Apocynaceae); Immunosuppressive; Pregnane glycosides.

MeSH terms

  • Animals
  • Apocynaceae / chemistry*
  • Cell Cycle / drug effects
  • Cell Proliferation / drug effects
  • Concanavalin A / antagonists & inhibitors
  • Concanavalin A / pharmacology
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification*
  • Immunosuppressive Agents / pharmacology*
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Models, Molecular
  • Molecular Structure
  • Plant Stems / chemistry
  • Pregnanes / chemistry
  • Pregnanes / isolation & purification*
  • Pregnanes / pharmacology*
  • Spleen / drug effects*
  • Spleen / immunology*
  • Structure-Activity Relationship
  • T-Lymphocytes / drug effects

Substances

  • Glycosides
  • Immunosuppressive Agents
  • Pregnanes
  • pregnane glycoside
  • Concanavalin A