New silibinin glyco-conjugates: synthesis and evaluation of antioxidant properties

Bioorg Med Chem Lett. 2014 Nov 15;24(22):5147-9. doi: 10.1016/j.bmcl.2014.10.023. Epub 2014 Oct 14.

Abstract

New silibinin glyco-conjugates have been synthesized by efficient method and in short time. Exploiting our solution phase strategy, several structurally diverse silibinin glyco-conjugates (gluco, manno, galacto, and lacto-) were successfully realized in very good yields and in short time. In preliminary study to evaluate their antioxidant and neuroprotective activities new derivatives were subjected to DPPH free radical scavenging assay and the Xanthine oxidase (XO) inhibition models assay. Irrespective of the sugar moiety examined, new glyco-conjugates are more than 50 times water-soluble of silibinin. In the other hand they exhibit a radical scavenging activities slightly higher than to silibinin and XO inhibition at least as silibinin.

Keywords: Glyco-conjugates; Natural products; Phosphoramidite chemistry; Silibinin; Silybin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / pharmacology
  • Cell Death / drug effects
  • Cell Death / physiology
  • Cell Line, Tumor
  • Drug Evaluation / methods
  • Free Radical Scavengers / chemical synthesis
  • Free Radical Scavengers / pharmacology
  • Glycogen / chemical synthesis*
  • Glycogen / pharmacology
  • Humans
  • Silybin
  • Silybum marianum*
  • Silymarin / chemical synthesis*
  • Silymarin / pharmacology

Substances

  • Antioxidants
  • Free Radical Scavengers
  • Silymarin
  • Silybin
  • Glycogen