Binding of Caffeine and Quinine by Whey Protein and the Effect on Bitterness

Journal of Food Science

Volumn 82, Issue 2, 2017, Pages 509-516

  Tenney, Kelsey ^a   Hayes, John ^a   Euston, Stephen ^a   Elias, Ryan ^a   Coupland, John ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

binding; bitter; computer modeling; protein; sensory; taste masking

Indexed keywords

CAFFEINE; LACTOGLOBULIN; NITROGEN; QUININE; WHEY PROTEIN;

CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MOLECULAR MODEL; SALIVA; TASTE; THERMODYNAMICS;

CAFFEINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPUTER SIMULATION; HUMANS; LACTOGLOBULINS; MODELS, MOLECULAR; NITROGEN; QUININE; SALIVA; TASTE; TASTE PERCEPTION; THERMODYNAMICS; WHEY PROTEINS;

EID: 85011265983     PISSN: 00221147     EISSN: 17503841     Source Type: Journal    
DOI: 10.1111/1750-3841.13588     Document Type: Article

References (44)

1. Barzanti C, Evans R, Fouquet J, et al. 2007. Potentiometric determination of octanol-water and liposome-water partition coefficients (log P) of ionizable organic compounds. Tetrahedron Lett 48:3337–41.
2. Bello M, Portillo-Tellez MD, Garcia-Hernandez E. 2011. Energetics of ligand recognition and self-association of bovine β-lactoglobulin: differences between variants A and B. Biochemistry 50, 151–61.
3. Bennett SM, Zhou L, Hayes JE. 2012. Using milk fat to reduce the irritation and bitter taste of ibuprofen. Chemosens Percept 5:231–6.
4. Bohin MC, Roland WSU, Gruppen H, et al. 2013. Evaluation of the bitter-masking potential of food proteins for EGCG by a cell-based human bitter taste receptor assay and binding studies. J Agric Food Chem 61:10010–17.
5. Bohin MC, Vincken JP, Van Der Hijden HTWM, Gruppen H. 2012. Efficacy of food proteins as carriers for flavonoids. J Agric Food Chem 60:4136–43.
6. Chowdhry BZ, Harding SE. 2001. Protein-ligand interactions and their analysis In: Harding SE and Chowdhry BZ, editors. Protein–ligand interactions: hydrodynamics and calorimetry: a practical approach. Oxford University Press, Oxford, UK.
7. Coupland JN, Hayes JE. 2014. Physical approaches to masking bitter taste: lessons from food and pharmaceuticals. Pharm Res 31:2921–39.
8. Davies EH, Tuleu C. 2008. Medicines for children: a matter of taste. J Pediatr 153:599–604.
9. de Wit J, Backx-Hontelez E, Adamse M. 1988. Evaluation of functional properties of whey protein concentrates and whey protein isolates, 3: functional properties in aqueous solution. Netherlands Milk Dairy J 42:155–72.
10. Drewnowski A, Gomez-Carneros C. 2000. Bitter taste, phyonutrients, and the consumer: a review. Am J Clin Nutr 72:1424–35.
11. Dsamou M, Palicki O, Septier C, et al. 2012. Salivary protein profiles and sensitivity to the bitter taste of caffeine. Chem Senses 37:87–95.
12. Floriano WB, Hall S, Vaidehi N, et al. 2006. Modeling the human PTC bitter-taste receptor interactions with bitter tastants. J Mol Model 12:931–41.
13. Guichard E, Langourieux S. 2000. Interactions between beta-lactoglobulin and flavour compounds. Food Chem 71:301–8.
14. Homma R, Yamashita H, Funaki J, et al. 2012. Identification of bitterness-masking compounds from cheese. J Agric Food Chem 60:4492–9.
15. Huey R, Morris GM, Olson AJ, Goodsell DS. 2007. A semiempirical free energy force field with charge-based desolvation. J. Comput. Chem 28:1145–52.
16. Humphrey SP, Williamson RT. 2001. A review of saliva: normal composition, flow, and function. J Prosthet Dent 85:162–9.
17. Jovanović S, Bara M, Ma O. 2005. Whey proteins-properties and possibility of application. Mljekarstvo 55:215–33.
18. Keast RSJ. 2008. Modification of the bitterness of caffeine. Food Qual Prefer 19:465–72.
19. Keast RSJ, Roper J. 2007. A complex relationship among chemical concentration, detection threshold, and suprathreshold intensity of bitter compounds. Chem Senses 32:245–53.
20. Klebanov GS, Mednikova LN, Ovcharova AD. 1967. Extraction of caffeine from aqueous solutions. Pharm Chem J 1:221–3.
21. Kontopidis G, Holt C, Sawyer L. 2004. Invited review: β-lactoglobulin: binding properties, structure, and function. J Dairy Sci 87:785–96.
22. Loch JI, Polit A, Bonarek P Olszewska D, Kurpiewska K, Dziedzicka-Wasylewska M, Lewinski K. 2012. Structural and thermodynamic studies of binding saturated fatty acids to bovine β-lactoglobulin. Intl J Biol Macromol 50, 1095–102.
23. Malde AK, Zuo L, Breeze M, Stroet M, Poger D, Nair PC, Oostenbrink C, Mark AE. 2011. An automated force field topology builder (ATB) and repository: version 1.0. J Chem Theory Comput 7:4026–37.
24. Matsuo R. 2000. Role of saliva in the maintenance of taste sensitivity. Crit Rev Oral Biol Med 11:216–29.
25. Mattes RD. 2007. Effects of linoleic acid on sweet, sour, salty, and bitter taste thresholds and intensity ratings of adults. Am J Physiol Gastrointest Liver Physiol 292:G1243–48.
26. Melis M, Aragoni MC, Arca M, et al. 2013. Marked increase in PROP taste responsiveness following oral supplementation with selected salivary proteins or their related free amino acids. PLoS One 8:e59810.
27. Mennella JA, Beauchamp GK. 2008. Optimizing oral medications for children. Clin Ther 30:2120–32.
28. Metcalf KL, Vickers ZM. 2001. Taste intensities of oil-in-water emulsions with varying fat content. J Sens Stud 17:379–90.
29. Morris GM, Goodsell DS, Halliday RS, Huey, R, Hart WE, Belew RK, Olson AJ. 1998. Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J. Computat. Chem. 19:1639–62.
30. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. 2009. Autodock4 and AutoDockTools4: automated docking with selective receptor flexiblity. J. Computat. Chem. 30:2785–91.
31. Morr CV, Foegeding EA. 1990. Composition and functionality of commercial whey and milk protein concentrates and isolates: a status report. Food Technol 44:100–12.
32. Mudgal S, Keresztes I, Feigenson GW, Rizvi SSH. 2016. Controlling the taste receptor accessible structure of rebaudioside A via binding to bovine serum albumin. Food Chem 197:84–91.
33. Muresan S, van der Bent A, de Wolf FA. 2001. Interaction of β-lactoglobulin with small hydrophobic ligands as monitored by fluorometry and equilibrium dialysis: nonlinear quenching effects related to protein-protein association. J Agric Food Chem 49:2609–18.
34. Negri R, Di Feola M, Di Domenico S, et al. 2012. Taste perception and food choices. J Pediatr Gastroenterol Nutr 54:624–9.
35. O'Neill TE, Kinsella JE. 1987. Binding of alkanone flavors to beta-lactoglobulin: effects of conformational and chemical modification. J Agric Food Chem 35:770–4.
36. Pelletier E, Sostmann K, Guichard E. 1998. Measurement of interactions between beta-lactoglobulin and flavor compounds (esters, acids, and pyrazines) by affinity and exclusion size chromatography. J Agric Food Chem 46:1506–9.
37. Qin BY, Bewley MC, Creamer LK, Baker HM, Baker EN, Jameson GB. 1998. Structural basis of the Tanford transition of bovine beta-lactoglobulin. Biochemistry 37:14014–23
38. Sawyer L, Kontopidis G. 2000. The core lipocalin, bovine beta-lactoglobulin. Biochim Biophys Acta 1482:136–48.
39. Shahiwala A. 2011. Formulation approaches in enhancement of patient compliance to oral drug therapy. Expert Opin Drug Deliv 8:1521–29.
40. Shpigelman A, Cohen Y, Livney YD. 2012. Thermally-induced β-lactoglobulin–EGCG nanovehicles: loading, stability, sensory and digestive-release study. Food Hydrocoll 29:57–67.
41. Shpigelman A, Israeli G, Livney YD. 2010. Thermally-induced protein-polyphenol co-assemblies: beta lactoglobulin-based nanocomplexes as protective nanovehicles for EGCG. Food Hydrocoll 24:735–43.
42. Thurgood JE, Martini S. 2010. Effects of three emulsion compositions on taste thresholds and intensity ratings of five taste compounds. J Sens Stud 25:861–75.
43. Tucker RM, Mattes RD, Running CA. 2014. Mechanisms and effects of fat taste in humans. BioFactors 40:313–26.
44. Wu SY, Pérez MD, Puyol P, Sawyer L. 1999. β-Lactoglobulin binds palmitate within its central cavity. J Biol Chem 274:170–4.