Synthesis and anti-fungal activity of seven oleanolic acid glycosides

Molecules. 2011 Jan 26;16(2):1113-28. doi: 10.3390/molecules16021113.

Abstract

In order to develop potential anti-fungal agents, seven glycoconjugates composed of α-L-rhamnose, 6-deoxy-α-L-talose, β-D-galactose, α-D-mannose, β-D-xylose-(1→4)-6-deoxy-α-L-talose, β-D-galactose-(1→4)-α-L-rhamnose, β-D-galactose-(1→3)-β-D-xylose-(1→4)-6-deoxy-α-L-talose as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of the new compounds were confirmed by MS, ¹H-NMR and ¹³C-NMR.Preliminary studies based on means of mycelium growth rate, indicated that all the compounds possess certain fungicidal activity against Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn, Botrytis cinerea Pers and Phytophthora parasitica Dast.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Fungi / drug effects*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Sequence Data
  • Molecular Structure
  • Oleanolic Acid / chemistry*

Substances

  • Antifungal Agents
  • Glycosides
  • Oleanolic Acid