title: Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene.
abstract: OBJECTIVE
  Oxidative stress is related to a number of autoimmune diseases, e.g. rheumatoid arthritis, cancer, etc. The main source of pathologically working reactive oxygen species (ROS) are activated polymorphonuclear leukocytes (PMNL).
  
  
  OBJECTIVE
  There are some papers comparing structure - pharmacological efficiency relationship of vegetal substances from the stilbenoid group. We compared the effect of trans-resveratrol, which is well-known by its antioxidative activity, with the effect of pinosylvin and pterostilbene.
  
  
  METHODS
  Luminol-enhanced chemiluminescence (CL) was used to study the antioxidative action. The effect was observed in whole blood and in isolated PMNL. The concentrations of substances tested were 0.01-100 microM. Due to the different abilities of luminol and isoluminol to pass through the cell membrane, we studied the effect of the substances tested on intracellular and extracellular ROS. To stimulate the production of ROS we used phorbol-myristate-acetate (PMA), which activates PMNL via protein kinase C.
  
  
  RESULTS
  Resveratrol, pinosylvin and pterostilbene inhibited significantly the CL of whole blood and extra- and intracellular CL of isolated PMNL in a dosedependent manner. Depending on different functional groups of the stilbene molecule, resveratrol inhibited CL of whole blood and isolated PMNL, whereas pinosylvin influenced mainly intracellular CL and pterostilbene extracellular CL.
  
  
  CONCLUSIONS
  The presence of different functional groups in the molecules of stilbenoids influence their antioxidative effect. Modification of these functional groups may result in derivatives with required antioxidative properties, targeting mainly extracellular ROS which are responsible for tissue damage during chronic inflammation.
authors.affiliation: Institute of Experimental Pharmacology, Slovak Academy of Sciences, Bratislava, Slovakia. tomas.perecko@savba.sk
authors.forename: Tomas
authors.initials: T
authors.lastname: Perecko
authors.forename: Viera
authors.initials: V
authors.lastname: Jancinova
authors.forename: Katarina
authors.initials: K
authors.lastname: Drabikova
authors.forename: Radomir
authors.initials: R
authors.lastname: Nosal
authors.forename: Juraj
authors.initials: J
authors.lastname: Harmatha
mesh_terms: D000255:Adenosine Triphosphate / Q000378:metabolism; D000975:Antioxidants / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006801:Humans; D049449:Luminescence; D009504:Neutrophils / Q000187:drug effects; D017382:Reactive Oxygen Species / Q000378:metabolism; D000077185:Resveratrol; D013267:Stilbenes / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D000094162:Phytoalexins
chemical_list: D000255:Adenosine Triphosphate; D000975:Antioxidants; D017382:Reactive Oxygen Species; D000077185:Resveratrol; D013267:Stilbenes; C107773:pterostilbene; C049032:pinosylvin; D000094162:Phytoalexins