Tomensides A-D, new antiproliferative phenylpropanoid sucrose esters from Prunus tomentosa leaves

Bioorg Med Chem Lett. 2014 Jun 1;24(11):2459-62. doi: 10.1016/j.bmcl.2014.04.018. Epub 2014 Apr 13.

Abstract

To search for novel cytotoxic constituents against cancer cells as lead structures for drug development, four new 3-phenylpropanoid-triacetyl sucrose esters, named tomensides A-D (1-4), and three known analogs (5-7) were isolated from the leaves of Prunus tomentosa. Their structures were elucidated by spectroscopic analyses (1D, 2D NMR, CD and HRESIMS). The cytotoxic activities of all isolates against four human cancer cell lines (MCF-7, A549, HeLa and HT-29) were assayed, and the results showed that these isolates displayed stronger inhibitory activities compared with positive control 5-fluorouracil. Tomenside A (1) was the most active compound with IC50 values of 0.11-0.62 μM against the four tested cell lines. The structure-activity relationship (SAR) of the isolates was also discussed. The primary screening results indicated that these 3-phenylpropanoid-triacetyl sucrose esters might be valuable source for new potent anticancer drug candidates.

Keywords: 3-Phenylpropanoid-triacetyl sucrose esters; Cytotoxicities; Prunus tomentosa; Structure–activity relationships (SAR).

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification
  • Coumaric Acids / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • HeLa Cells
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Plant Leaves / chemistry*
  • Prunus / chemistry*
  • Structure-Activity Relationship
  • Sucrose / analogs & derivatives*
  • Sucrose / chemistry
  • Sucrose / isolation & purification
  • Sucrose / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Coumaric Acids
  • tomenside A
  • Sucrose