Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography
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<sup>®</sup> XAD<sup>®</sup>-2 extract obtained from a...
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5378 |
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| author | Recep Gök Pia Selhorst Mats Kiene Theresa Noske Michael Ziegler Ulrich Fischer Peter Winterhalter |
| author_facet | Recep Gök Pia Selhorst Mats Kiene Theresa Noske Michael Ziegler Ulrich Fischer Peter Winterhalter |
| author_sort | Recep Gök |
| collection | DOAJ |
| description | 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<sup>®</sup> XAD<sup>®</sup>-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-<i>O</i>-rutinoside and 3,4-dihydroxy-7,8-dihydro-β-ionone 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-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. |
| first_indexed | 2024-03-10T01:31:18Z |
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| id | doaj.art-10f75b6fc2db4f0eb73246c5c6862954 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:31:18Z |
| publishDate | 2022-08-01 |
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| series | Molecules |
| spelling | doaj.art-10f75b6fc2db4f0eb73246c5c68629542023-11-23T13:40:57ZengMDPI AGMolecules1420-30492022-08-012717537810.3390/molecules27175378Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent ChromatographyRecep Gök0Pia Selhorst1Mats Kiene2Theresa Noske3Michael Ziegler4Ulrich Fischer5Peter Winterhalter6Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, GermanyInstitute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, GermanyInstitute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, GermanyInstitute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, GermanyInstitute for Viticulture and Oenology, Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, 67435 Neustadt an der Weinstraße, GermanyInstitute for Viticulture and Oenology, Dienstleistungszentrum Ländlicher Raum (DLR) Rheinpfalz, 67435 Neustadt an der Weinstraße, GermanyInstitute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, GermanyHigh-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<sup>®</sup> XAD<sup>®</sup>-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-<i>O</i>-rutinoside and 3,4-dihydroxy-7,8-dihydro-β-ionone 3-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-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.https://www.mdpi.com/1420-3049/27/17/53781,1,6-trimethyl-1,2-dihydronaphthalene (TDN)glycosidesaroma precursorsisolationpetrol notekerosene off-flavor |
| spellingShingle | Recep Gök Pia Selhorst Mats Kiene Theresa Noske Michael Ziegler Ulrich Fischer Peter Winterhalter Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography Molecules 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) glycosides aroma precursors isolation petrol note kerosene off-flavor |
| title | Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography |
| title_full | Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography |
| title_fullStr | Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography |
| title_full_unstemmed | Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography |
| title_short | Target-Guided Isolation of Progenitors of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) from Riesling Wine by High-Performance Countercurrent Chromatography |
| title_sort | target guided isolation of progenitors of 1 1 6 trimethyl 1 2 dihydronaphthalene tdn from riesling wine by high performance countercurrent chromatography |
| topic | 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) glycosides aroma precursors isolation petrol note kerosene off-flavor |
| url | https://www.mdpi.com/1420-3049/27/17/5378 |
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