2. Academic Validation
  3. Comprehensive structure-activity-relationship studies of sensory active compounds in licorice (Glycyrrhiza glabra)

Comprehensive structure-activity-relationship studies of sensory active compounds in licorice (Glycyrrhiza glabra)

  • Food Chem. 2021 Dec 1;364:130420. doi: 10.1016/j.foodchem.2021.130420.
Christian Schmid 1,  Anne Brockhoff 2,  Yaron Ben Shoshan-Galeczki 3,  Maximilian Kranz 1,  Timo D Stark 1,  Rukiye Erkaya 1,  Wolfgang Meyerhof 4,  Masha Y Niv 3,  Corinna Dawid 5,  Thomas Hofmann 6
Affiliations

Affiliations

  • 1 Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner-Str. 34, 85354 Freising, Germany.
  • 2 Department of Molecular Genetics, German Institute of Human Nutrition Potsdam-Rehbrücke (DIfE), Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
  • 3 The Institute of Biochemistry, Food and Nutrition, The Robert H Smith Faculty of Agriculture, Food and Environment, The Hebrew University, 76100 Rehovot and The Fritz Haber Center for Molecular Dynamics, The Hebrew University, Jerusalem 91904, Israel.
  • 4 German Institute of Human Nutrition Potsdam-Rehbruecke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany; Center for Integrative Physiology and Molecular Medicine, Saarland University, Kirrberger Straße 100, 66421 Homburg, Germany.
  • 5 Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner-Str. 34, 85354 Freising, Germany. Electronic address: [email protected].
  • 6 Food Chemistry and Molecular Sensory Science, Technical University of Munich, Lise-Meitner-Str. 34, 85354 Freising, Germany. Electronic address: [email protected].
PMID: 34182369 DOI: 10.1016/j.foodchem.2021.130420
Abstract

Licorice saponins, the main constituents of Glycyrrhiza glabra L. roots, are highly appreciated by the consumer for their pleasant sweet and long lasting licorice taste. The objective of the present study was to understand the molecular features that contribute to bitter, sweet and licorice sensation of licorice roots, and whether individual compounds elicit more than one of these sensations. Therefore, a sensomics approach was conducted, followed by purification of the compounds with highest sensory impact, and by synthesis as well as full characterization via HRESIMS, ESIMS/MS and 1D/2D-NMR experiments. This led to the discovery and structure determination of 28 sweet, bitter and licorice tasting key phytochemicals, including two unknown compounds. A combination of sensorial, cell-based and computational analysis revealed distinct structural features, such as spatial arrangement of functional groups in the triterpenoid E-ring, driving to different taste sensations and sweet receptor hTAS1R2/R3 stimulation.

Keywords

Glycyrrhizin; Modelling; SAR; Saponin; Sensomics; Taste receptor.

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