Discovery of taste modulating octadecadien-12-ynoic acids in golden chanterelles (Cantharellus cibarius). (15th December 2018)

• Record Type: Journal Article
• Authors: Mittermeier, Verena Karolin; Dunkel, Andreas; Hofmann, Thomas
• Is Part Of: Food chemistry. Volume 269(2018)
• Page Start: 53
• Page End: 62
• Publication Date: 2018-12-15
• Subjects: Cantharellus cibarius -- Acetylenic acid -- Kokumi -- Taste dilution analysis -- Comparative taste dilution analysis -- Taste modulation; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2018.06.123
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Taste active octadecadien-12-ynoic acids and octadecadienoic acids were isolated from chanterelles. Long-chain acetylenic acids showed kokumi activity at sub-bitter threshold concentrations. Octadecadienoic acids only exhibited bitter taste, but no taste modulating activity. Abstract: 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 C18 -acetylenic acids in chanterelles among which (9 Z, 15 E )-14, 17, 18-trihydroxy-9, 15-octadecadien-12-ynoic acid, (9 Z, 15 E )-14-oxo-9, 15-octadecadien-12-ynoic acid, (10 E, 15 E )-9-hydroxy-14-oxo-10, 15-octadecadien-12-ynoic acid, (10 E, 15 E )-9-hydroperoxy-14-oxo-10, 15-octadecadien-12-ynoic acid, (10 E, 15 E )-9, 14-dioxo-10, 15-octadecadien-12-ynoic acid, (9 Z, 15 E )-14-oxo-9, 15-octadecadien-12-ynoic acid methyl ester, (9 Z, 15 E )-17(18)-epoxy-14-oxo-9, 15-octadecadien-12-ynoic acid methyl ester and (10 E, 14 Z )-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 (10 E, 14 Z )-12-hydroxy-10, 14-octadecadienoic acid, (9 Z, 11 Z )-14, 18-dihydroxy-9, 11-octadecadienoic acid, and (9 Z, 11 Z )-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.