Synthesis and antiproliferative activity of helonioside A, 3',4',6'-tri-O-feruloylsucrose, lapathoside C and their analogs

Eur J Med Chem. 2012 Dec:58:418-30. doi: 10.1016/j.ejmech.2012.10.034. Epub 2012 Oct 27.

Abstract

The first total synthesis of natural phenylpropanoid sucrose esters (PSEs) helonioside A 1, 3',4',6'-tri-O-feruloylsucrose 2 and lapathoside C 3 along with 17 unnatural PSE analogs has been successfully accomplished in a short and simple synthetic route. A selected set of 17 synthesized PSEs were evaluated for the antiproliferative activity against human cervical epithelioid carcinoma (HeLa) cell lines using MTS assay method. Eleven (11) compounds showed significant antiproliferative activity with their IC(50)values ranging from 0.16 to 6.01 μM. The structure-activity-relationship studies revealed that the antiproliferative activity is influenced by the lipophilicity and number of feruloyl substituents on these compounds. The preliminary screening indicated that these compounds are potentially very valuable source for new lead chemotherapeutics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cinnamates / chemical synthesis
  • Cinnamates / chemistry
  • Cinnamates / pharmacology*
  • Coumaric Acids / chemical synthesis
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Sucrose / analogs & derivatives*
  • Sucrose / chemical synthesis
  • Sucrose / chemistry
  • Sucrose / pharmacology

Substances

  • 3',4',6'-tri-O-feruloylsucrose
  • 3',6'-di-O-feruloylsucrose
  • Antineoplastic Agents
  • Cinnamates
  • Coumaric Acids
  • lapathoside C
  • Sucrose