Separation of amaranthine-type betacyanins by ion-pair high-speed countercurrent chromatography.
Betacyanins, red-violet plant pigments, were fractionated by ion-pair high-speed countercurrent chromatography (IP-HSCCC) from leaves extract of Iresine lindenii Van Houtte, an ornamental plant of the family Amaranthaceae. An HSCCC solvent system consisting of TBME-1-BuOH-ACN-H2O (1:3:1:5, v/v/v/v) was applied using ion-pair forming heptafluorobutyric acid (HFBA). Significantly different elution profiles of betacyanin diastereomeric pairs (derivatives based on betanidin and isobetanidin) observed in the HSCCC in comparison to HPLC systems indicate a complementarity of both techniques' fractionation capabilities. The numerous diastereomeric pairs can be selectively separated from each other using the HSCCC system simplifying the pigment purification process. Apart from the three well known highly abundant pigments (amaranthine, betanin and iresinin I) together with their isoforms, three new acylated (feruloylated and sinapoylated) betacyanins as well as known pigment hylocerenin (previously isolated from cacti fruits) were characterized in the plant for the first time and they are new for the whole Amaranthaceae family.
Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.
Gerold
G
Jerz
Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.
Nadine
N
Gebers
Faculty of Analytical Chemistry, Institute C-1, Department of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland.
Dominika
D
Szot
Joint Laboratory of Biotechnology and Enzyme Catalysis at Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, ul. Niezapominajek 8, 30-239 Cracow, Poland.
Maciej
M
Szaleniec
Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.
Peter
P
Winterhalter
Faculty of Analytical Chemistry, Institute C-1, Department of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, Cracow 31-155, Poland. Electronic address: swybran@chemia.pk.edu.pl.
Slawomir
S
Wybraniec
D027703:Amaranthaceae / Q000737:chemistry*; D050859:Betacyanins / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003377:Countercurrent Distribution / Q000379:methods; D005466:Fluorocarbons / Q000737:chemistry; D007202:Indicators and Reagents; D007477:Ions; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
D050859:Betacyanins; D005466:Fluorocarbons; D007202:Indicators and Reagents; D007477:Ions; D010936:Plant Extracts; D012997:Solvents; C033094:perfluorobutyric acid
Acylated betacyanins; Betalains; Betanin; IP-HSCCC; Ion-pair countercurrent chromatography; Iresinin