Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities

Bioorg Med Chem. 2010 May 1;18(9):3036-42. doi: 10.1016/j.bmc.2010.03.055. Epub 2010 Mar 27.

Abstract

A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity.

MeSH terms

  • 3T3-L1 Cells
  • Adipocytes / drug effects*
  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology*
  • Cell Differentiation
  • Cell Line
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Esters / pharmacology*
  • Fatty Acids / chemical synthesis
  • Fatty Acids / chemistry
  • Fatty Acids / pharmacology
  • Flavones / chemical synthesis
  • Flavones / chemistry
  • Flavones / pharmacology
  • Hypolipidemic Agents / chemical synthesis
  • Hypolipidemic Agents / chemistry
  • Hypolipidemic Agents / pharmacology
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Rats
  • Weight Loss / drug effects*

Substances

  • Anti-Obesity Agents
  • Esters
  • Fatty Acids
  • Flavones
  • Hypolipidemic Agents
  • flavone