title: Separation of chlorinated diastereomers of decarboxy-betacyanins in myeloperoxidase catalyzed chlorinated Beta vulgaris L. extract.
abstract: A comparative chromatographic evaluation of chlorinated decarboxylated betanins and betanidins generated under activity of hypochlorous acid exerted upon these highly antioxidative potent decarboxylated pigments derived from natural sources was performed by LC-DAD-ESI-MS/MS. Comparison of the chromatographic profiles of the chlorinated pigments revealed two different directions of retention changes in relation to the corresponding substrates. Chlorination of all betacyanins that are decarboxylated at carbon C-17 results in an increase of their retention times. In contrast, all other pigments (the non-decarboxylated betacyanins as well as 2-decarboxy- and 15-decarboxy-derivatives) exhibit lower retention after chlorination. During further chromatographic experiments based upon chemical transformation of the related pigments (decarboxylation and deglucosylation), the compounds' structures were confirmed. The elaborated method for determination of chlorinated pigments enabled analysis of a chlorinated red beet root extract that was submitted to the MPO/H2O2/Cl-system acting under inflammation-like conditions (pH 5). This indicates a promising possibility for measurement of these chlorinated pigments as indicators of specific inflammatory states wherein betacyanins and decarboxylated betacyanins act as hypochlorite scavengers.
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. Electronic address: swybran@chemia.pk.edu.pl.
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: Department of Chemistry, NMR Div, Jagiellonian University, ul. Ingardena 3, 31-007 Cracow, Poland.
authors.forename: Edward
authors.initials: E
authors.lastname: Szneler
authors.affiliation: Applied BioClinical Labs., 16259 Laguna Canyon Rd, Irvine, CA 92618, USA.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Pietrzkowski
mesh_terms: D027461:Beta vulgaris / Q000737:chemistry*; D050859:Betacyanins / Q000032:analysis* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D054879:Halogenation; D010936:Plant Extracts / Q000032:analysis* / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry / Q000379:methods
chemical_list: D050859:Betacyanins; D010936:Plant Extracts
keywords: Betalains; Betanin; Hypochlorite; Inflammation; Myeloperoxidase; Red beet extract