Abstract
High-performance countercurrent chromatography (HPCCC) was used for the target-guided isolation of precursors of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) from Riesling wine. In separated HPCCC fractions of an Amberlite® XAD®-2 extract obtained from a German Riesling, TDN-generating fractions were identified by the acid-catalyzed hydrolysis of the progenitors at pH 3.0 and subsequent HS-GC-MS/MS analysis. The presence of multiple TDN-generating precursors in Riesling wine could be confirmed. From polar HPCCC fractions (11–13 and 14–16), 3,4-dihydroxy-7,8-dihydro-β-ionone 3-O-rutinoside and 3,4-dihydroxy-7,8-dihydro-β-ionone 3-O-β-d-glucopyranoside were isolated as major TDN-precursors at a sufficient amount for structure elucidation by NMR spectroscopic studies. In the medium polar HPCCC factions (27–35), enzymatic hydrolysis liberated the aglycones 3-hydroxy-β-ionone and 3-hydroxy-TDN in minor amounts. In further less polar TDN-generation fractions (36–44 and 45–50), glycosidic progenitors were absent; instead, a minor TDN formation most likely from non-conjugated constituents was observed.
Funder
Open Access Publication Funds of Technische Universität Braunschweig
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
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