title: The Brassica epithionitrile 1-cyano-2,3-epithiopropane triggers cell death in human liver cancer cells in vitro.
abstract: METHODS
  Glucosinolates are secondary metabolites present in Brassica vegetables. Alkenyl glucosinolates are enzymatically degraded forming nitriles or isothiocyanates, but in the presence of epithiospecifier protein, epithionitriles are released. However, studies on the occurrence of epithionitriles in Brassica food and knowledge about their biological effects are scarce.
  
  
  RESULTS
  Epithionitrile formation from glucosinolates of seven Brassica vegetables was analyzed using GC-MS and HPLC-DAD. Bioactivity of synthetic and plant-derived 1-cyano-2,3-epithiopropane (CETP) - the predominant epithionitrile in Brassica vegetables - in three human hepatocellular carcinoma (HCC) cell lines and primary murine hepatocytes was also evaluated. The majority of the Brassica vegetables were producers of nitriles or epithionitriles as hydrolysis products and not of isothiocyanates. For example, Brussels sprouts and savoy cabbage contained up to 0.8 μmol CETP/g vegetable. Using formazan dye assays, concentrations of 380-1500 nM CETP were observed to inhibit the mitochondrial dehydrogenase activity of human HCC cells without impairment of cell growth. At 100-fold higher CETP concentrations, cell death was observed. Presence of plant matrix increased CETP-based toxicity.
  
  
  CONCLUSIONS
  These in vitro data provide no indication that epithionitriles will severely affect human health by Brassica consumption. In contrast to isothiocyanates, no evidence of selective toxicity against HCC cells was found.
authors.affiliation: Department of Quality, Leibniz-Institute of Vegetable and Ornamental Crops Großbeeren and Erfurt e.V, Großbeeren, Germany.
authors.forename: Franziska S
authors.initials: FS
authors.lastname: Hanschen
authors.affiliation: Environmental Health Sciences, University Medical Center Freiburg, Freiburg i.Br, Germany.
authors.forename: Corinna
authors.initials: C
authors.lastname: Herz
authors.affiliation: Environmental Health Sciences, University Medical Center Freiburg, Freiburg i.Br, Germany.
authors.forename: Nina
authors.initials: N
authors.lastname: Schlotz
authors.affiliation: Environmental Health Sciences, University Medical Center Freiburg, Freiburg i.Br, Germany.|Institute of Food Chemistry, Hamburg School of Food Science, University of Hamburg, Hamburg, Germany.
authors.forename: Franziska
authors.initials: F
authors.lastname: Kupke
authors.affiliation: Clinic for Internal Medicine II, Molecular Biology, University Medical Center Freiburg, Freiburg i.Br, Germany.
authors.forename: María M
authors.initials: MM
authors.lastname: Bartolomé Rodríguez
authors.affiliation: Department of Quality, Leibniz-Institute of Vegetable and Ornamental Crops Großbeeren and Erfurt e.V, Großbeeren, Germany.
authors.forename: Monika
authors.initials: M
authors.lastname: Schreiner
authors.affiliation: Institute of Food Chemistry, Hamburg School of Food Science, University of Hamburg, Hamburg, Germany.
authors.forename: Sascha
authors.initials: S
authors.lastname: Rohn
authors.affiliation: Environmental Health Sciences, University Medical Center Freiburg, Freiburg i.Br, Germany.
authors.forename: Evelyn
authors.initials: E
authors.lastname: Lamy
mesh_terms: D017209:Apoptosis / Q000187:drug effects*; D001937:Brassica / Q000378:metabolism*; D002453:Cell Cycle / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D056945:Hep G2 Cells; D022781:Hepatocytes / Q000187:drug effects; D006801:Humans; D008113:Liver Neoplasms / Q000188:drug therapy* / Q000473:pathology; D009336:Necrosis; D009570:Nitriles / Q000032:analysis / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000032:analysis; D011407:Propane / Q000031:analogs & derivatives* / Q000032:analysis / Q000494:pharmacology; D013438:Sulfhydryl Compounds / Q000032:analysis / Q000494:pharmacology*
chemical_list: C544438:1-cyano-2,3-epithiopropane; D009570:Nitriles; D010936:Plant Extracts; D013438:Sulfhydryl Compounds; D011407:Propane
keywords: Bioactivity; Brassica vegetables; Epithionitriles; Glucosinolates; Human hepatocarcinoma cells