Isolation and structural elucidation of different geometrical isomers of lycopene.
Five geometrical isomers of lycopene were isolated from a photoisomerized mixture on a semi-preparative C30 column and characterized by UV-vis spectroscopy, mass spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. 1H NMR and 2D NMR measurements were used to unambiguously assign the double bond configuration of five isomers: (5Z,9'Z)-, (9Z)-, (5Z,9Z)-, (all-E)-, and (5Z)-lycopene. This will allow other laboratories to use the results for their C30 HPLC. In addition, it is possible to investigate structure-activity relationships for these lycopene isomers which will improve the understanding of their physiological role in biological tissues.
Fröhlich
Kati
K
Institute of Nutrition, Friedrich Schiller University Jena, Dornburger Strasse 25-29, Jena, Germany.
Conrad
Jürgen
J
Schmid
Antje
A
Breithaupt
Dietmar E
DE
Böhm
Volker
V
D002338:Carotenoids / Q000737:chemistry* / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D007536:Isomerism; D000077276:Lycopene; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D013057:Spectrum Analysis / Q000379:methods
D002338:Carotenoids; D000077276:Lycopene