Synthesis of novel derivatives of esculentoside A and its aglycone phytolaccagenin, and evaluation of their haemolytic activity and inhibition of lipopolysaccharide-induced nitric oxide production

Chem Biodivers. 2011 Oct;8(10):1833-52. doi: 10.1002/cbdv.201000339.

Abstract

A series of 46 compounds derived from esculentoside A and its aglycone were synthesized and characterized. The effect of these compounds on lipopolysaccharide (LPS)-induced NO production, haemolytic activity, and cell viability was evaluated. Structure-activity relationship was established by comparing the derivatives of esculentoside A with its aglycone derivatives. Both the aglycone and its derivatives showed higher inhibitory effects on LPS-induced NO production, and lower haemolytic activities than esculentoside A and its derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Drug Evaluation, Preclinical
  • Erythrocytes / drug effects
  • Hemolytic Agents / chemistry*
  • Hemolytic Agents / pharmacology*
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemical synthesis
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology
  • Phytolacca / chemistry
  • Rabbits
  • Saponins / chemical synthesis*
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Hemolytic Agents
  • Lipopolysaccharides
  • Saponins
  • phytolaccoside B
  • Nitric Oxide
  • esculentoside A
  • Oleanolic Acid