Structure-activity relationships of resveratrol and derivatives in breast cancer cells

Rosamaria Lappano, Camillo Rosano, Antonio Madeo, Lidia Albanito, Pierluigi Plastina, Bartolo Gabriele, Luca Forti, Lucia Anna Stivala, Domenico Iacopetta, Vincenza Dolce, Sebastiano Andò, Vincenzo Pezzi, Marcello Maggiolini

Research output: Contribution to journalArticlepeer-review


Resveratrol (RSV) is classified as a phytoestrogen due to its ability to interact with estrogen receptors (ERs). We assessed structure-activity relationships of RSV and the analogs 4,4'-dihydroxystilbene (4,4'-DHS), 3,5-dihydroxystilbene (3,5-DHS), 3,4'-dihydroxystilbene (3,4'-DHS), 4-hydroxystilbene (4-HS) using as model systems the ERα-positive and negative MCF7 and SkBr3 breast cancer cells, respectively. In binding assays and transfection experiments RSV and the analogs showed the following order of agonism for ERa: 3,4'-DHS A 4,4'-DHS A 4-HS A RSV, while 3,5-DHS did not elicit any ligand properties. Computational docking analysis and real-time PCR revealed for each analog a distinct ERα binding orientation and estrogen target gene expression profile. Interestingly, the aforementioned order of ligand activity was confirmed in proliferation assays which also showed the lack of growth stimulation by 3,5-DHS. Our data suggest that subtle changes in the structure of the RSV derivatives examined may be responsible for the different ERα-mediated biological responses observed in estrogen-sensitive cancer cells.

Original languageEnglish
Pages (from-to)845-858
Number of pages14
JournalMolecular Nutrition and Food Research
Issue number7
Publication statusPublished - Jul 2009


  • Breast cancer
  • Docking analysis
  • Estrogen receptor
  • Hydroxystilbenes
  • Resveratrol

ASJC Scopus subject areas

  • Food Science
  • Biotechnology


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