The Odorant (R)-Citronellal Attenuates Caffeine Bitterness by Inhibiting the Bitter Receptors TAS2R43 and TAS2R46
- Barbara SuessBarbara SuessChair of Food Chemistry and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Straße 34, D-85354 Freising-Weihenstephan, GermanyMore by Barbara Suess,
- Anne BrockhoffAnne BrockhoffDepartment of Molecular Genetics, German Institute of Human Nutrition (DIFE) Potsdam-Rehbrücke, Arthur-Scheunert-Allee 114−116, 14558 Nuthetal, GermanyMore by Anne Brockhoff,
- Wolfgang MeyerhofWolfgang MeyerhofDepartment of Molecular Genetics, German Institute of Human Nutrition (DIFE) Potsdam-Rehbrücke, Arthur-Scheunert-Allee 114−116, 14558 Nuthetal, GermanyMore by Wolfgang Meyerhof, and
- Thomas Hofmann*Thomas Hofmann*(T.H.) Phone: +49 8161-71-2902. Fax: +49 8161-71-2949. E-mail: [email protected]Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Straße 34, D-85354 Freising-Weihenstephan, GermanyMore by Thomas Hofmann
Abstract
Sensory studies showed the volatile fraction of lemon grass and its main constituent, the odor-active citronellal, to significantly decrease the perceived bitterness of a black tea infusion as well as caffeine solutions. Seven citronellal-related derivatives were synthesized and shown to inhibit the perceived bitterness of caffeine in a structure-dependent manner. The aldehyde function at carbon 1, the (R)-configuration of the methyl-branched carbon 3, and a hydrophobic carbon chain were found to favor the bitter inhibitory activity of citronellal; for example, even low concentrations of 25 ppm were observed to reduce bitterness perception of caffeine solution (6 mmol/L) by 32%, whereas (R)-citronellic acid (100 pm) showed a reduction of only 21% and (R)-citronellol (100 pm) was completely inactive. Cell-based functional experiments, conducted with the human bitter taste receptors TAS2R7, TAS2R10, TAS2R14, TAS2R43, and TAS2R46 reported to be sensitive to caffeine, revealed (R)-citronellal to completely block caffeine-induced calcium signals in TAS2R43-expressing cells, and, to a lesser extent, in TAS2R46-expressing cells. Stimulation of TAS2R43-expressing cells with structurally different bitter agonists identified (R)-citronellal as a general allosteric inhibitor of TAS2R43. Further structure/activity studies indicated 3-methyl-branched aliphatic aldehydes with a carbon chain of ≥4 C atoms as best TAS2R43 antagonists. Whereas odor–taste interactions have been mainly interpreted in the literature to be caused by a central neuronal integration of odors and tastes, rather than by peripheral events at the level of reception, the findings of this study open up a new dimension regarding the interaction of the two chemical senses.
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- Raise Ahmad, Julie E. Dalziel. G Protein-Coupled Receptors in Taste Physiology and Pharmacology. Frontiers in Pharmacology 2020, 11 https://doi.org/10.3389/fphar.2020.587664
- Liang Zhang, Qing-Qing Cao, Daniel Granato, Yong-Quan Xu, Chi-Tang Ho. Association between chemistry and taste of tea: A review. Trends in Food Science & Technology 2020, 101 , 139-149. https://doi.org/10.1016/j.tifs.2020.05.015
- Maik Behrens. Bitter Taste. 2020, 231-246. https://doi.org/10.1016/B978-0-12-809324-5.23882-0
- Qingbiao Xu, Nisha Singh, Hui Hong, Xianghua Yan, Wenlin Yu, Xu Jiang, Prashen Chelikani, Jianping Wu. Hen protein-derived peptides as the blockers of human bitter taste receptors T2R4, T2R7 and T2R14. Food Chemistry 2019, 283 , 621-627. https://doi.org/10.1016/j.foodchem.2019.01.059
- Bilal Malik, Nadia Elkaddi, Jumanah Turkistani, Andrew I Spielman, Mehmet Hakan Ozdener. Mammalian Taste Cells Express Functional Olfactory Receptors. Chemical Senses 2019, 44 (5) , 289-301. https://doi.org/10.1093/chemse/bjz019
- Antonella Di Pizio, Maik Behrens, Dietmar Krautwurst. Beyond the Flavour: The Potential Druggability of Chemosensory G Protein-Coupled Receptors. International Journal of Molecular Sciences 2019, 20 (6) , 1402. https://doi.org/10.3390/ijms20061402
- Tomáš Pluskal, Jing-Ke Weng. Natural product modulators of human sensations and mood: molecular mechanisms and therapeutic potential. Chemical Society Reviews 2018, 47 (5) , 1592-1637. https://doi.org/10.1039/C7CS00411G
- Rachel L. Poole, Michael G. Tordoff. The Taste of Caffeine. Journal of Caffeine Research 2017, 7 (2) , 39-52. https://doi.org/10.1089/jcr.2016.0030
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