Determination of diastereomerization barrier of some flavanones by high-performance liquid chromatography methods.
The rate constants and activation energy barriers DeltaG# of diastereomerization reaction of flavanones: naringin, narirutin, hesperidin and neohesperidin were determined. The stopped-flow HPLC (SFM-HPLC), dynamic HPLC (D-HPLC) and enantioselective HPLC combined with the classical kinetic method were applied for determination of these parameters. It was found that the rate constants of diastereomerization were about eight times higher for naringin and narirutin (1.9 x 10(-5) s(-1)) than for hesperidin and neohesperidin (2.4 x 10(-6) s(-1)). No significant differences in the rate of diastereomerization were found between neohesperidosides and corresponding rutinosides.
Asztemborska
Monika
M
Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. monika@ichf.edu.pl
Zukowski
Janusz
J
D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000737:chemistry; D044950:Flavanones / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry*; D006569:Hesperidin / Q000737:chemistry; D007700:Kinetics; D013237:Stereoisomerism
D004187:Disaccharides; D044950:Flavanones; D005419:Flavonoids; C500601:narirutin; D006569:Hesperidin; C005274:naringin