title: Separation of some chiral flavanones by micellar electrokinetic chromatography.
abstract: Micellar electrokinetic chromatography (MEKC) was applied for enantioseparation of selected flavanones, including naringin, hesperidin, neohesperidin, naringenin, hesperetin, pinostrobin, isosakuranetin, eriodictyol, and homoeriodictyol. gamma-Cyclodextrin (gamma-CD) and sodium cholate (SCh) were used as chiral modifiers inducing enantioselectivity to the background electrolyte. From among many investigated selectors only these two appeared to possess the best enantioselective properties in respect to studied flavanones. The mechanisms of their action are a little different; SCh used above critical micelle point concentration forms chiral micelles itself while gamma-CD is deprived of this property and requires addition of surfactants as, e.g., sodium dodecyl sulfate. It was found that SCh enables separation of flavanone glycosides diastereomers while separation of enantiomers of flavanone aglycones may be achieved with gamma-CD. Consideration of structural relation led to the suggestion that interaction of sugar moiety of glycosides with SCh micelles give rise to chiral recognition. MEKC appeared to be a suitable and efficient analytical tool to follow enantiomeric composition of flavanones.
authors.affiliation: Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, PL-01-224 Warsaw, Poland. monika@ichf.edu.pl
authors.forename: Monika
authors.initials: M
authors.lastname: Asztemborska
authors.forename: Magdalena
authors.initials: M
authors.lastname: Miśkiewicz
authors.forename: Danuta
authors.initials: D
authors.lastname: Sybilska
mesh_terms: D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D003505:Cyclodextrins; D044950:Flavanones / Q000302:isolation & purification*; D006027:Glycosides / Q000737:chemistry; D008823:Micelles; D020358:Sodium Cholate / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003505:Cyclodextrins; D044950:Flavanones; D006027:Glycosides; D008823:Micelles; D020358:Sodium Cholate