title: Chlorination of Betacyanins in Several Hypochlorous Acid Systems.
abstract: This study presents a comparative evaluation of chlorination of betanin, betanidin, and neobetanin exposed to sodium hypochlorite and myeloperoxidase (MPO)/H2O2/Cl(-) systems. For betanin/betanidin, the chlorination takes place at the aglycone unit, but for neobetanin, no chlorinated products in the reaction mixtures can be detected. In the RP-HPLC system, monochloro-betanin/-betanidin were eluted earlier than their corresponding nonchlorinated substrates. An influence of Cl(-) concentration on betanin/betanidin chlorination efficiency in sodium hypochlorite and MPO systems was investigated. At pH 3-5, the yields of formed monochloro-betanin/-betanidin decrease dramatically at higher Cl(-) concentrations, indicating that generated Cl2 is not the chlorinating agent in the presence of sodium hypochlorite. The intriguing low activity of Cl2 in betanin/betanidin chlorination compared to HOCl and/or Cl2O can be explained by a special position of the attack by molecules of HOCl and/or Cl2O. In the MPO/H2O2/Cl(-) system, the highest efficiency of monochloro-betanin/-betanidin generation is observed at pH 5.
authors.affiliation: Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology , ul. Warszawska 24, Cracow 31-155, Poland.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Wybraniec
authors.affiliation: Department of Analytical Chemistry, Institute C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology , ul. Warszawska 24, Cracow 31-155, Poland.
authors.forename: Karolina
authors.initials: K
authors.lastname: Starzak
authors.affiliation: FutureCeuticals, Inc. , 16259 Laguna Canyon Road, Irvine, California 92618, United States.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Pietrzkowski
mesh_terms: D027461:Beta vulgaris / Q000737:chemistry; D050859:Betacyanins / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry; D054879:Halogenation; D006863:Hydrogen-Ion Concentration; D006997:Hypochlorous Acid / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D050859:Betacyanins; D002713:Chlorine; D006997:Hypochlorous Acid
keywords: MPO; betacyanins; betalains; betanidin; betanin; chlorination; hypochlorite; inflammation; myeloperoxidase; neobetanin; neutrophils