Stereoisomeric Separation of Flavanones and Flavanone-7-O-glycosides by Capillary Electrophoresis and Determination of Interconversion Barriers
The stereoisomeric separation of several flavanones and flavanone-7-O-glycosides has been achieved with capillary electrophoresis by adding native cyclodextrins or cyclodextrin derivatives to the background electrolyte. As an alternative method, micellar electrokinetic chromatography with sodium cho...
Saved in:
Published in | Analytical chemistry (Washington) Vol. 78; no. 10; pp. 3424 - 3433 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Washington, DC
American Chemical Society
15.05.2006
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | The stereoisomeric separation of several flavanones and flavanone-7-O-glycosides has been achieved with capillary electrophoresis by adding native cyclodextrins or cyclodextrin derivatives to the background electrolyte. As an alternative method, micellar electrokinetic chromatography with sodium cholate as a chiral surfactant has been used for the epimeric separation of two flavanone-7-O-glycosides. The effect of buffer systems containing mixtures of cyclodextrin with either sodium dodecyl sulfate or sodium cholate upon the chiral recognition of flavanones and flavanone-7-O-glycosides as well as the variation of the background electrolyte (concentration of buffer and surfactant, pH value, organic modifier), and its influence on the resolution factor R s was investigated. Temperature- and pH-dependent enantiomerization or epimerization barriers of several flavanones (naringenin, homoeriodictyol) and flavanone-7-O-glycosides (naringin, neohesperidin, prunin, narirutin) in basic media (pH values of 9−11) have been observed. Interconversion profiles featuring characteristic plateau formation of the elution pattern were observed at high pH and evaluated with the simulation software ChromWin to determine rate constants k(T) and Eyring activation parameters, ΔG #(T), ΔH #, and ΔS #. |
---|---|
Bibliography: | istex:7C16E5AC318F3C78C7029E2074180C529C906114 ark:/67375/TPS-2Q5K70DJ-5 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0003-2700 1520-6882 |
DOI: | 10.1021/ac0600499 |