TY - JOUR
T1 - Discovery of taste modulating octadecadien-12-ynoic acids in golden chanterelles (Cantharellus cibarius)
AU - Mittermeier, Verena Karolin
AU - Dunkel, Andreas
AU - Hofmann, Thomas
N1 - Publisher Copyright:
© 2018 Elsevier Ltd
PY - 2018/12/15
Y1 - 2018/12/15
N2 - 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 18 -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.
AB - 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 18 -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.
KW - Acetylenic acid
KW - Cantharellus cibarius
KW - Comparative taste dilution analysis
KW - Kokumi
KW - Taste dilution analysis
KW - Taste modulation
UR - https://www.scopus.com/pages/publications/85049322520
U2 - 10.1016/j.foodchem.2018.06.123
DO - 10.1016/j.foodchem.2018.06.123
M3 - Article
C2 - 30100470
AN - SCOPUS:85049322520
SN - 0308-8146
VL - 269
SP - 53
EP - 62
JO - Food Chemistry
JF - Food Chemistry
ER -