For the accurate quantitation of kokumi-enhancing and bitter-tasting octadecadien-12-ynoic and octadecadienoic acids in chanterelles ( Fr.), a sensitive ultra-high-performance liquid chromatography-differential ion mobility spectrometry-tandem mass spectrometry method was developed. On the basis of these quantitative data and the taste thresholds, dose-over-threshold factors were calculated to determine the contribution of these sensometabolites to the kokumi and bitter taste of chanterelles; e.g., 14,15-dehydrocrepenynic acid () and (9,15)-14-oxooctadeca-9,15-dien-12-ynoic acid () were identified as key kokumi substances in raw chanterelles. Quantitative profiling of these compounds in various mushroom species demonstrated a unique accumulation of octadecadien-12-ynoic acids in . Furthermore, storage experiments highlighted dynamic processes, including the biosynthesis of these substances as a result of lipid peroxidation mechanisms.
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Ion-Mobility-Based Liquid Chromatography-Mass Spectrometry Quantitation of Taste-Enhancing Octadecadien-12-ynoic Acids in Mushrooms.
J Agric Food Chem
May 2020
Chair of Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner-Straße 34, D-85354 Freising, Germany.
For the accurate quantitation of kokumi-enhancing and bitter-tasting octadecadien-12-ynoic and octadecadienoic acids in chanterelles ( Fr.), a sensitive ultra-high-performance liquid chromatography-differential ion mobility spectrometry-tandem mass spectrometry method was developed. On the basis of these quantitative data and the taste thresholds, dose-over-threshold factors were calculated to determine the contribution of these sensometabolites to the kokumi and bitter taste of chanterelles; e.
View Article and Find Full Text PDFDiscovery of taste modulating octadecadien-12-ynoic acids in golden chanterelles (Cantharellus cibarius).
Food Chem
December 2018
Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner Str. 34, D-85354 Freising, Germany; Leibniz-Institute for Food Systems Biology at the Technical University of Munich, Lise-Meitner Str. 34, D-85354 Freising, Germany. Electronic address:
Activity-guided fractionation in combination with taste dilution and comparative taste dilution analysis, followed by LC-MS and 1D/2D-NMR experiments, enabled the identification of several C-acetylenic acids in chanterelles among which (9Z,15E)-14,17,18-trihydroxy-9,15-octadecadien-12-ynoic acid, (9Z,15E)-14-oxo-9,15-octadecadien-12-ynoic acid, (10E,15E)-9-hydroxy-14-oxo-10,15-octadecadien-12-ynoic acid, (10E,15E)-9-hydroperoxy-14-oxo-10,15-octadecadien-12-ynoic acid, (10E,15E)-9,14-dioxo-10,15-octadecadien-12-ynoic acid, (9Z,15E)-14-oxo-9,15-octadecadien-12-ynoic acid methyl ester, (9Z,15E)-17(18)-epoxy-14-oxo-9,15-octadecadien-12-ynoic acid methyl ester and (10E,14Z)-9-hydroperoxy-10,14-octadecadien-12-ynoic acid have not yet been reported in literature. Sensory evaluation in a basic taste recombinant revealed taste modulating thresholds for the octadecadien-12-ynoic acids in the range of 19-105 µmol/l. In comparison, three isolated octadecadienoic acids, namely (10E,14Z)-12-hydroxy-10,14-octadecadienoic acid, (9Z,11Z)-14,18-dihydroxy-9,11-octadecadienoic acid, and (9Z,11Z)-14,17,18-trihydroxy-9,11-octadecadienoic acid, respectively, did not show any taste modulating activity, thus pinpointing the putative key role of the acetylene moiety for kokumi enhancement.
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