Semisynthesis and Biological Evaluation of Oleanolic Acid 3-O-β-d-Glucuronopyranoside Derivatives for Protecting H9c2 Cardiomyoblasts against H₂O₂-Induced Injury

Molecules. 2018 Jan 10;23(1):44. doi: 10.3390/molecules23010044.

Abstract

A series of novel oleanolic acid 3-O-β-d-glucuronopyranoside derivatives have been designed and synthesized. Biological evaluation has indicated that some of the synthesized compounds exhibit moderate to good activity against H₂O₂-induced injury in rat myocardial cells (H9c2). Particularly, derivative 28-N-isobutyl ursolic amide 3-O-β-d-galactopyranoside (8a) exhibited a greater protective effect than the positive control oleanolic acid 3-O-β-d-glucuronopyranoside, indicating that it possesses a great potential for further development as a cardiovascular disease modulator by structural modification.

Keywords: ">d-glucuronopyranoside; H2O2-induced; derivatives; oleanolic acid 3-O-β-; protective effect; semisynthesis.

Publication types

  • Evaluation Study

MeSH terms

  • Animals
  • Cell Line
  • Cell Survival
  • Humans
  • Hydrogen Peroxide / chemistry
  • Molecular Structure
  • Myoblasts, Cardiac / drug effects*
  • Myoblasts, Cardiac / pathology
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemical synthesis*
  • Oleanolic Acid / pharmacology
  • Protective Agents / chemical synthesis*
  • Protective Agents / pharmacology*
  • Rats
  • Structure-Activity Relationship

Substances

  • Protective Agents
  • Oleanolic Acid
  • Hydrogen Peroxide