Stereospecificity in hydroxyl radical scavenging activities of four ginsenosides produced by heat processing

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5028-31. doi: 10.1016/j.bmcl.2006.07.071. Epub 2006 Aug 9.

Abstract

The activity-guided fractionation of sun ginseng (SG, heat processed Panax ginseng C. A. Meyer at 120 degrees C) was carried out to identify its main active hydroxyl radical (*OH) scavenging components. As a result, the n-BuOH fraction mainly consisting of ginsenosides showed the strongest activity. Of several ginsenosides of SG, the *OH scavenging activities of relatively high contents of 20(S)-Rg(3), 20(R)-Rg(3), Rk(1), and Rg(5) were compared. Rg(5) and 20(S)-Rg(3) showed strong *OH scavenging IC(50) values of 0.15 and 0.44 mM, respectively, and these activities were prominently higher than each of their respective isomers. Therefore, stereospecificity exists in the *OH scavenging activities of ginsenosides produced by heat processing. Especially, the double bond at carbon-20(22) or the OH group at carbon-20 geometrically close to OH at carbon-12 is thought to increase the *OH scavenging activity of ginsenosides.

MeSH terms

  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / pharmacology
  • Ginsenosides / chemistry*
  • Ginsenosides / pharmacology
  • Hot Temperature
  • Hydroxyl Radical / chemistry*
  • Hydroxyl Radical / pharmacology
  • Inhibitory Concentration 50
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Free Radical Scavengers
  • Ginsenosides
  • Hydroxyl Radical