Semi-synthesis of Twelve Known 20Z/E Pseudo-Ginsenosides and Their Comparative Study of Antioxidative Activity in Free Radical Induced Hemolysis of Rabbit Erythrocytes

Chem Pharm Bull (Tokyo). 2018 May 1;66(5):535-540. doi: 10.1248/cpb.c17-00779. Epub 2018 Mar 7.

Abstract

Twelve pseudo-ginsenosides were synthesized under a mild condition, via a simple three-step called acetylation, elimination-addition and saponification. The inhibitory effects of these twelve pseudo-ginsenosides were screened on the hemolysis of rabbit erythrocytes caused by 2,2'-azobis (2-amidinopropane hydrochloride) (AAPH). It was found that the IC50 values followed the sequence of (20Z) pseudo-protopanaxatriol (pseudo-PPT)<(20Z) pseudo-protopanaxadiol (pseudo-PPD)<(20Z) pseudo-Rh2<(20E) pseudo-PPT<(20E) pseudo-PPD<(20E) pseudo-Rh2<(20Z) pseudo-Rg2<(20E) pseudo-Rg2<Rb1<(20Z) pseudo-Rh1<Rg2<(20E) pseudo-Rh1. These compounds can be divided into three groups: accelerate the hemolysis group (7, 8), weak group (2, 11, 12) and strong group (others). Moreover, we also find that most of the Z configuration has better antioxidative activity than E configuration and the number and type of sugar moieties to the ring of triterpene dammarane influence the antioxidative activity.

Keywords: antioxidant; free radical; ginsenoside; hemolysis; prooxidant; pseudo ginsenoside.

Publication types

  • Comparative Study

MeSH terms

  • Amidines / antagonists & inhibitors
  • Amidines / pharmacology
  • Animals
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Dose-Response Relationship, Drug
  • Erythrocytes / drug effects*
  • Free Radicals / chemistry
  • Ginsenosides / chemical synthesis*
  • Ginsenosides / chemistry
  • Ginsenosides / pharmacology*
  • Hemolysis / drug effects
  • Molecular Conformation
  • Rabbits
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Amidines
  • Antioxidants
  • Free Radicals
  • Ginsenosides
  • 2,2'-azobis(2-amidinopropane)