Chemoenzymatic synthesis and antitumor promoting activity of 6'- and 3-esters of 2-O-beta-D-glucosylglycerol

Bioorg Med Chem. 1999 Sep;7(9):1867-71. doi: 10.1016/s0968-0896(99)00137-6.

Abstract

Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anticarcinogenic Agents / chemical synthesis*
  • Anticarcinogenic Agents / pharmacology*
  • Antigens, Viral / drug effects
  • Antigens, Viral / immunology
  • Cell Line
  • Esters
  • Glycerides / chemical synthesis*
  • Glycerides / pharmacology*
  • Glycosides / chemical synthesis*
  • Glycosides / pharmacology*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry

Substances

  • Anticarcinogenic Agents
  • Antigens, Viral
  • Epstein-Barr virus early antigen
  • Esters
  • Glycerides
  • Glycosides