Bitter taste receptor activation by flavonoids and isoflavonoids: Modeled structural requirements for activation of hTAS2R14 and hTAS2R39

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 44, 2013, Pages 10454-10466

  Roland, Wibke S U ^a   Van Buren, Leo ^b   Gruppen, Harry ^a   Driesse, Marianne ^a   Gouka, Robin J ^b   Smit, Gerrit ^a,c   Vincken, Jean Paul ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

^c VALIO LTD   (Finland)

Author keywords

bitterness; flavonoids; hTAS2R; modeling; pharmacophore; T2R; TAS2R

Indexed keywords

BITTERNESS; HTAS2R; PHARMACOPHORES; T2R; TAS2R;

FLAVONOIDS; HYDROGEN BONDS; HYDROPHOBICITY; LIGANDS; MODELS; PHARMACODYNAMICS; RADIOACTIVITY LOGGING;

THREE DIMENSIONAL;

CELL SURFACE RECEPTOR; FLAVONOID; G PROTEIN COUPLED RECEPTOR; ISOFLAVONE DERIVATIVE; TAS2R39 PROTEIN, HUMAN; TASTE RECEPTORS, TYPE 2;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; KINETICS; METABOLISM; PROTEIN BINDING; PROTEIN MOTIF; TASTE;

AMINO ACID MOTIFS; BINDING SITES; FLAVONOIDS; HUMANS; ISOFLAVONES; KINETICS; MODELS, MOLECULAR; PROTEIN BINDING; RECEPTORS, CELL SURFACE; RECEPTORS, G-PROTEIN-COUPLED; TASTE;

EID: 84887705499     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf403387p     Document Type: Article

References (34)

1. Setchell, K. D. R.; Cassidy, A. Dietary isoflavones: biological effects and relevance to human health J. Nutr. 1999, 129 (3) 758S-767S
2. Manach, C.; Scalbert, A.; Morand, C.; Rémésy, C.; Jiménez, L. Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 2004, 79 (5) 727-747
3. Soto-Vaca, A.; Gutierrez, A.; Losso, J. N.; Xu, Z.; Finley, J. W. Evolution of phenolic compounds from color and flavor problems to health benefits J. Agric. Food Chem. 2012, 60 (27) 6658-6677
4. Drewnowski, A.; Gomez-Carneros, C. Bitter taste, phytonutrients, and the consumer: a review Am. J. Clin. Nutr. 2000, 72 (6) 1424-1435
5. Aldin, E.; Reitmeier, C. A.; Murphy, P. Bitterness of soy extracts containing isoflavones and saponins J. Food Sci. 2006, 71 (3) S211-S215
6. Okubo, K.; Iijima, M.; Kobayashi, Y.; Yoshokoshi, M.; Uchida, T.; Kudou, S. Components responsible for the undesirable taste of soybean seeds Biosci., Biotechnol., Biochem. 1992, 56 (1) 99-103
7. Roland, W. S. U.; Vincken, J. P.; Gouka, R. J.; van Buren, L.; Gruppen, H.; Smit, G. Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39 J. Agric. Food Chem. 2011, 59 (21) 11764-11771
8. Behrens, M.; Brockhoff, A.; Kuhn, C.; Bufe, B.; Winnig, M.; Meyerhof, W. The human taste receptor hTAS2R14 responds to a variety of different bitter compounds Biochem. Biophys. Res. Commun. 2004, 319 (2) 479-485
9. Meyerhof, W.; Batram, C.; Kuhn, C.; Brockhoff, A.; Chudoba, E.; Bufe, B.; Appendino, G.; Behrens, M. The molecular receptive ranges of human TAS2R bitter taste receptors Chem. Senses 2010, 35 (2) 157-170
10. Intelmann, D.; Batram, C.; Kuhn, C.; Haseleu, G.; Meyerhof, W.; Hofmann, T. Three TAS2R bitter taste receptors mediate the psychophysical responses to bitter compounds of hops (Humulus lupulus L.) and beer Chemosens. Percept. 2009, 2 (3) 118-132
11. Le Neve, B.; Foltz, M.; Daniel, H.; Gouka, R. The steroid glycoside H.g.-12 from Hoodia gordonii activates the human bitter receptor TAS2R14 and induces CCK release from HuTu-80 cells Am. J. Physiol.-Gastrointest. Liver Physiol. 2010, 299 (6) G1368-G1375
12. Maehashi, K.; Matano, M.; Wang, H.; Vo, L. A.; Yamamoto, Y.; Huang, L. Bitter peptides activate hTAS2Rs, the human bitter receptors Biochem. Biophys. Res. Commun. 2008, 365 (4) 851-855
13. Hellfritsch, C.; Brockhoff, A.; Stähler, F.; Meyerhof, W.; Hofmann, T. Human psychometric and taste receptor responses to steviol glycosides J. Agric. Food Chem. 2012, 60 (27) 6782-6793
14. Narukawa, M.; Noga, C.; Ueno, Y.; Sato, T.; Misaka, T.; Watanabe, T. Evaluation of the bitterness of green tea catechins by a cell-based assay with the human bitter taste receptor hTAS2R39 Biochem. Biophys. Res. Commun. 2011, 405 (4) 620-625
15. Ueno, Y.; Sakurai, T.; Okada, S.; Abe, K.; Misaka, T. Human bitter taste receptors hTAS2R8 and hTAS2R39 with differential functions to recognize bitter peptides Biosci., Biotechnol., Biochem. 2011, 75 (6) 1188-1190
16. Soares, S.; Kohl, S.; Thalmann, S.; Mateus, N.; Meyerhof, W.; De Freitas, V. Different phenolic compounds activate distinct human bitter taste receptors J. Agric. Food Chem. 2013, 61 (7) 1525-1533
17. Kohl, S.; Behrens, M.; Dunkel, A.; Hofmann, T.; Meyerhof, W. Amino acids and peptides activate at least five members of the human bitter taste receptor family J. Agric. Food Chem. 2013, 61 (1) 53-60
18. Martinez-Mayorga, K.; Medina-Franco, J. L. Chemoinformatics-applications in food chemistry. In Advances in Food and Nutrition Research, 58 th ed.; Academic Press: Burlington, MA, 2009; pp 33-56.
19. Glen, R. C.; Bender, A.; Arnby, C. H.; Carlsson, L.; Boyer, S.; Smith, J. Circular fingerprints: flexible molecular descriptors with applications from physical chemistry to ADME IDrugs 2006, 9 (3) 199-204
20. Wermuth, C. G.; Ganellin, C. R.; Lindberg, P.; Mitscher, L. A. Glossary of terms used in medicinal chemistry (IUPAC Recommendations 1998) Pure Appl. Chem. 1998, 70 (5) 1129-1143
21. Van Drie, J. H. Monty Kier and the origin of the pharmacophore concept Internet Electron. J. Mol. Des. 2007, 6 (9) 271-279
22. Ley, J. P.; Dessoy, M.; Paetz, S.; Blings, M.; Hoffmann-Lücke, P.; Reichelt, K. V.; Krammer, G. E.; Pienkny, S.; Brandt, W.; Wessjohann, L. Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol J. Agric. Food Chem. 2012, 60 (25) 6303-6311
23. Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Odds and trends: recent developments in the chemistry of odorants Angew. Chem.-Int. Ed. 2000, 39 (17) 2981-3010
24. Tromelin, A.; Guichard, E. Use of catalyst in a 3D-QSAR study of the interactions between flavor compounds and β-lactoglobulin J. Agric. Food Chem. 2003, 51 (7) 1977-1983
25. Chandrashekar, J.; Mueller, K. L.; Hoon, M. A.; Adler, E.; Feng, L.; Guo, W.; Zuker, C. S.; Ryba, N. J. P. T2Rs function as bitter taste receptors Cell 2000, 100 (6) 703-711
26. Kuhn, C.; Bufe, B.; Winnig, M.; Hofmann, T.; Frank, O.; Behrens, M.; Lewtschenko, T.; Slack, J. P.; Ward, C. D.; Meyerhof, W. Bitter taste receptors for saccharin and acesulfame K J. Neurosci. 2004, 24 (45) 10260-10265
27. Hawkins, D. M.; Basak, S. C.; Mills, D. Assessing model fit by cross-validation J. Chem. Inf. Comput. Sci. 2003, 43 (2) 579-586
28. Clifford, M. N. Anthocyanins-nature, occurrence and dietary burden J. Sci. Food Agric. 2000, 80 (7) 1063-1072
29. Awika, J. M. Behavior of 3-deoxyanthocyanidins in the presence of phenolic copigments Food Res. Int. 2008, 41 (5) 532-538
30. Fang, H.; Tong, W.; Perkins, R.; Soto, A. M.; Prechtl, N. V.; Sheehan, D. M. Quantitative comparisons of in vitro assays for estrogenic activities Environ. Health Perspect. 2000, 108 (8) 723-729
31. Ley, J. P.; Krammer, G.; Reinders, G.; Gatfield, I. L.; Bertram, H. J. Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. & A.) Torr., Hydrophyllaceae) J. Agric. Food Chem. 2005, 53 (15) 6061-6066
32. Brockhoff, A.; Behrens, M.; Roudnitzky, N.; Appendino, G.; Avonto, C.; Meyerhof, W. Receptor agonism and antagonism of dietary bitter compounds J. Neurosci. 2011, 31 (41) 14775-14872
33. Bufe, B.; Hofmann, T.; Krautwurst, D.; Raguse, J. D.; Meyerhof, W. The human TAS2R16 receptor mediates bitter taste in response to β- glucopyranosides Nat. Genetics 2002, 32 (3) 397-401
34. Wiener, A.; Shudler, M.; Levit, A.; Niv, M. Y. BitterDB: a database of bitter compounds Nucleic Acids Res. 2012, 40 (D1) D413-D419