Enantioselective analysis of free and glycosidically bound monoterpene polyols in Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel: evidence for an oxidative monoterpene metabolism in grapes.
The enantiomeric ratios of various free and glycosidically bound monoterpene polyols in musts of the aromatic grapes Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel were determined by means of enantioselective multidimensional gas chromatography-mass spectrometry. Reference compounds of defined stereochemistry were synthesized and permitted the unequivocal determination of the elution order of the target compounds on chiral columns with modified cyclodextrins as stationary phases. It could be shown for the first time that the linalool-derived polyol 3,7-dimethylocta-1,7-dien-3,6-diol occurs predominately as the (3S,6S)-configured stereoisomer, providing evidence that this compound is generated by an enzymatic process in grape berries. The involvement of a cytochrome P450 monooxygenase in the oxidative metabolism of monoterpenes in grapes is dicussed.
Luan
Fang
F
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität Frankfurt am Main, Marie-Curie-Strasse 9, D-60439 Frankfurt (Main), Germany.
Hampel
Daniela
D
Mosandl
Armin
A
Wüst
Matthias
M
D000080462:Acyclic Monoterpenes; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D005638:Fruit / Q000737:chemistry* / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006027:Glycosides / Q000378:metabolism; D039821:Monoterpenes / Q000032:analysis* / Q000378:metabolism*; D010084:Oxidation-Reduction; D011108:Polymers / Q000378:metabolism; D013237:Stereoisomerism; D013729:Terpenes / Q000378:metabolism; D027843:Vitis / Q000737:chemistry*
D000080462:Acyclic Monoterpenes; D006027:Glycosides; D039821:Monoterpenes; D011108:Polymers; D013729:Terpenes; C024617:polyol; D003577:Cytochrome P-450 Enzyme System; C018584:linalool; C007836:geraniol