Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography
2022
Recep Gök | Pia Selhorst | Mats Kiene | Theresa Noske | Michael Ziegler | Ulrich Fischer | Peter Winterhalter
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&ndash:13 and 14&ndash:16), 3,4-dihydroxy-7,8-dihydro-&beta:-ionone 3-O-rutinoside and 3,4-dihydroxy-7,8-dihydro-&beta:-ionone 3-O-&beta:-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&ndash:35), enzymatic hydrolysis liberated the aglycones 3-hydroxy-&beta:-ionone and 3-hydroxy-TDN in minor amounts. In further less polar TDN-generation fractions (36&ndash:44 and 45&ndash:50), glycosidic progenitors were absent: instead, a minor TDN formation most likely from non-conjugated constituents was observed.
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