New insight into umami receptor, umami/umami-enhancing peptides and their derivatives: A review

Trends in Food Science and Technology

Volumn 88, Issue , 2019, Pages 429-438

  Zhang, Jianan ^a,b   Sun Waterhouse, Dongxiao ^a,b   Su, Guowan ^a,b   Zhao, Mouming ^a,b  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b Guangdong Food Green Processing and Nutrition Regulation Technologies Research Center   (China)

Author keywords

Derivatives; Enzymatic treatment; Maillard reaction; Receptor; Umami umami enhancing peptide

Indexed keywords

BINDING SITES; CHEMICAL REACTIONS; DERIVATIVES; GLYCOSYLATION; HYDROPHILICITY;

AMINO ACID COMPOSITIONS; DIFFERENT MECHANISMS; ENZYMATIC TREATMENTS; MAILLARD REACTION; RECEPTOR; SENSING MECHANISM; SPATIAL STRUCTURE; STRUCTURAL CHARACTERISTICS;

PEPTIDES;

EID: 85067951959     PISSN: 09242244     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tifs.2019.04.008     Document Type: Review

References (78)

1. Amino, Y., Nakazawa, M., Kaneko, M., Miyaki, T., Miyamura, N., Maruyama, Y., et al. Structure-CaSR-activity relation of kokumi gamma-glutamyl peptides. Chemical and Pharmaceutical Bulletin 64:8 (2016), 1181–1189.
2. Assadi-Porter, F.M., Tonelli, M., Maillet, E.L., Markley, J.L., Max, M., Interactions between the human sweet-sensing T1R2-T1R3 receptor and sweeteners detected by saturation transfer difference NMR spectroscopy. Biochimica et Biophysica Acta 1798:2 (2010), 82–86.
3. Banerjee, R., Tudu, B., Bandyopadhyay, R., Bhattacharyya, N., A review on combined odor and taste sensor systems. Journal of Food Engineering 190 (2016), 10–21.
4. Behrens, M., Meyerhof, W., Briand, L., de March, C.A., Matsunami, H., Yamashita, A., et al. Structure–function relationships of olfactory and taste receptors. Chemical Senses 43:2 (2018), 81–87.
5. Beksan, E., Schieberle, P., Robert, F., Blank, I., Fay, L.B., Schlichtherle-Cerny, H., et al. Synthesis and sensory characterization of novel umami-tasting glutamate glycoconjugates. Journal of Agricultural and Food Chemistry 51:18 (2003), 5428–5436.
6. Bystrova, M.F., Romanov, R.A., Rogachevskaja, O.A., Churbanov, G.D., Kolesnikov, S.S., Functional expression of the extracellular-Ca2+-sensing receptor in mouse taste cells. Journal of Cell Science 123:Pt 6 (2010), 972–982.
7. Chandrashekar, J., Hoon, M.A., Ryba, N.J.P., Zuker, C.S., The receptors and cells for mammalian taste. Nature, 444, 2006, 288.
8. Chaudhari, N., Landin, A.M., Roper, S.D., A metabotropic glutamate receptor variant functions as a taste receptor. Nature Neuroscience 3:2 (2000), 113–119.
9. Cutts, R.J., Howlin, B.J., Mulholland, F., Webb, G.A., Low-energy conformations of delicious peptide, a food flavor. Study by quenched molecular dynamics and NMR. Journal of Agricultural and Food Chemistry 44:6 (1996), 1409–1415.
10. Dang, Y., Gao, X., Xie, A., Wu, X., Ma, F., Interaction between umami peptide and taste receptor T1R1/T1R3. Cell Biochemistry and Biophysics 70:3 (2014), 1841–1848.
11. Dang, Y., Hao, L., Cao, J., Sun, Y., Zeng, X., Wu, Z., et al. Molecular docking and simulation of the synergistic effect between umami peptides, monosodium glutamate and taste receptor T1R1/T1R3. Food Chemistry 271 (2019), 697–706.
12. Davaasuren, M., Matsumoto, J., Chinzorig, C., Nakamura, T., Takamura, Y., Patrono, E., et al. The effects of intragastric infusion of umami solutions on amygdalar and lateral hypothalamic neurons in rats. Physiological Reports, 3(10), 2015, e12545.
13. Doornbos, M.L.J., Pérez-Benito, L., Tresadern, G., Mulder-Krieger, T., Biesmans, I., Trabanco, A.A., et al. Molecular mechanism of positive allosteric modulation of the metabotropic glutamate receptor 2 by JNJ-46281222. British Journal of Pharmacology 173:3 (2016), 588–600.
14. Feng, Z., Ma, S., Hu, G., Xie, X., Allosteric binding site and activation mechanism of class C G-protein coupled receptors: Metabotropic glutamate receptor family. The AAPS Journal 17:3 (2015), 737–753.
15. Feng, Y., Su, G., Zhao, H., Cai, Y., Cui, C., Sun-Waterhouse, D., et al. Characterisation of aroma profiles of commercial soy sauce by odour activity value and omission test. Food Chemistry 167 (2015), 220–228.
16. Frerot, E., Chen, T., Identification and quantitation of new glutamic acid derivatives in soy sauce by UPLC/MS/MS. Chemistry & Biodiversity 10:10 (2013), 1842–1850.
17. Freund, J.R., Lee, R.J., Taste receptors in the upper airway. World Journal of Otorhinolaryngology - Head and Neck Surgery 4:1 (2018), 67–76.
18. Gabriella, M., Angela, B., Temussi, P.A., From small sweeteners to sweet proteins: Anatomy of the binding sites of the human T1R2_T1R3 receptor. Journal of Medicinal Chemistry 48:17 (2005), 5520–5529.
19. Greg, N., Jayaram, C., Hoon, M.A., Luxin, F., Grace, Z., Ryba, N.J.P., et al. An amino-acid taste receptor. Nature 416:6877 (2002), 199–202.
20. Haid, D., Widmayer, P., Voigt, A., Chaudhari, N., Boehm, U., Breer, H., Gustatory sensory cells express a receptor responsive to protein breakdown products (GPR92). Histochemistry and Cell Biology 140:2 (2013), 137–145.
21. Higaki-Sato, N., Sato, K., Esumi, Y., Okumura, T., Yoshikawa, H., Tanaka-Kuwajima, C., et al. Isolation and identification of indigestible pyroglutamyl peptides in an Eenzymatic hydrolysate of wheat gluten prepared on an industrial scale. Journal of Agricultural and Food Chemistry 51:1 (2003), 8–13.
22. Huang, S., Cao, J., Jiang, M., Labesse, G., Liu, J., Pin, J., et al. Interdomain movements in metabotropic glutamate receptor activation. Proceedings of the National Academy of Sciences of the United States of America 108:37 (2011), 15480–15485.
23. Iwaniak, A., Hrynkiewicz, M., Bucholska, J., Minkiewicz, P., Darewicz, M., Understanding the nature of bitter-taste di- and tripeptides derived from food proteins based on chemometric analysis. Journal of Food Biochemistry, 43(1), 2019, e12500.
24. Iwasaki, T., Miyamura, N., Kuroda, M., & Kohmura, M. (2007). European Patent Application EP20,040,728,395.
25. Jianbo, Tong, Lingxiao, Li, Kangnan, Li, Bai, Min, Peptide drugs QSAR study based on topomer CoMFA. Letters in Drug Design & Discovery 14:10 (2017), 1114–1121.
26. Kaneko, S., Kumazawa, K., Nishimura, O., Isolation and identification of the umami enhancing compounds in Japanese soy sauce. Bioscience, Biotechnology, and Biochemistry 75:7 (2011), 1275–1282.
27. Kim, M.J., Son, H.J., Kim, Y., Misaka, T., Rhyu, M., Umami–bitter interactions: The suppression of bitterness by umami peptides via human bitter taste receptor. Biochemical and Biophysical Research Communications 456:2 (2015), 586–590.
28. Kiyono, T., Hirooka, K., Yamamoto, Y., Kuniishi, S., Ohtsuka, M., Kimura, S., et al. Identification of pyroglutamyl peptides in Japanese rice wine (sake): Presence of hepatoprotective PyroGlu-Leu. Journal of Agricultural and Food Chemistry 61:47 (2013), 11660–11667.
29. Kuroda, M., Kato, Y., Yamazaki, J., Kai, Y., Mizukoshi, T., Miyano, H., et al. Determination and quantification of the kokumi peptide, γ-glutamyl-valyl-glycine, in commercial soy sauces. Food Chemistry 141:2 (2013), 823–828.
30. Leach, K., Gregory, K.J., Molecular insights into allosteric modulation of Class C G protein-coupled receptors. Pharmacological Research 116 (2017), 105–118.
31. Lee, D.K., Nguyen, T., Lynch, K.R., Cheng, R., Vanti, W.B., Arkhitko, O., Lewis, T., Evans, J.F., George, S.R., O'Dowd, B.F., Discovery and mapping of ten novel G protein-coupled receptor genes. Gene 275:1 (2001), 83–91.
32. Linscott, T.D., Lim, J., Retronasal odor enhancement by salty and umami tastes. Food Quality and Preference 48 (2016), 1–10.
33. López Cascales, J.J., Oliveira Costa, S.D., de Groot, B.L., Walters, D.E., Binding of glutamate to the umami receptor. Biophysical Chemistry 152:1 (2010), 139–144.
34. Maehashi, K., Matsuzaki, M., Yamamoto, Y., Udaka, S., Isolation of peptides from an enzymatic hydrolysate of food proteins and characterization of their taste properties. Bioscience Biotechnology & Biochemistry 63:3 (1999), 555–559.
35. Maruyama, Y., Yasuda, R., Kuroda, M., Eto, Y., Kokumi substances, enhancers of basic tastes, induce responses in calcium-sensing receptor expressing taste cells. PLoS One, 7(4), 2012, e34489.
36. Mouritsen, O.G., Khandelia, H., Molecular mechanism of the allosteric enhancement of the umami taste sensation. The FEBS Journal 279:17 (2012), 3112–3120.
37. Mucchetti, G., Locci, F., Massara, P., Vitale, R., Neviani, E., Production of pyroglutamic acid by thermophilic lactic acid bacteria in hard-cooked mini-cheeses. Journal of Dairy Science 85:10 (2002), 2489–2496.
38. Nango, E., Akiyama, S., Maki-Yonekura, S., Ashikawa, Y., Kusakabe, Y., Krayukhina, E., et al. Taste substance binding elicits conformational change of taste receptor T1r heterodimer extracellular domains. Scientific Reports, 6, 2016, 25745.
39. Narukawa, M., Toda, Y., Nakagita, T., Hayashi, Y., Misaka, T., l-Theanine elicits umami taste via the T1R1 + T1R3 umami taste receptor. Amino Acids 46:6 (2014), 1583–1587.
40. Nelson, G., Chandrashekar, J., Hoon, M.A., Feng, L., Zhao, G., Ryba, N.J.P., Zuker, C.S., An amino-acid taste receptor. Nature, 416, 2002, 199.
41. Niimi, J., Eddy, A.I., Overington, A.R., Heenan, S.P., Silcock, P., Bremer, P.J., et al. Aroma-taste interactions between a model cheese aroma and five basic tastes in solution. Food Quality and Preference 31 (2014), 1–9.
42. Nuemket, N., Yasui, N., Kusakabe, Y., Nomura, Y., Atsumi, N., Akiyama, S., et al. Structural basis for perception of diverse chemical substances by T1r taste receptors. Nature Communications, 8, 2017, 15530.
43. Ottinger, H., Hofmann, T., Identification of the taste enhancer Alapyridaine in beef broth and evaluation of its sensory impact by taste reconstitution experiments. Journal of Agricultural and Food Chemistry 51:23 (2003), 6791–6796.
44. Rae, C.D., Williams, S.R., Glutathione in the human brain: Review of its roles and measurement by magnetic resonance spectroscopy. Analytical Biochemistry 529 (2017), 127–143.
45. Ribeiro, F.M., Vieira, L.B., Pires, R.G.W., Olmo, R.P., Ferguson, S.S.G., Metabotropic glutamate receptors and neurodegenerative diseases. Pharmacological Research 115 (2017), 179–191.
46. Roper, S.D., Chaudhari, N., Taste buds: Cells, signals and synapses. Nature Reviews Neuroscience 18:8 (2017), 485–497.
47. San Gabriel, A., Uneyama, H., Yoshie, S., Torii, K., Cloning and characterization of a novel mGluR1 variant from vallate papillae that functions as a receptor for l-glutamate stimuli. Chemical Senses, 30(suppl_1), 2005, i25.
48. Schlichtherle-Cerny, H., Amadò, R., Analysis of taste-active compounds in an enzymatic hydrolysate of deamidated wheat gluten. Journal of Agricultural and Food Chemistry 50:6 (2002), 1515–1522.
49. Sgarbi, E., Lazzi, C., Iacopino, L., Bottesini, C., Lambertini, F., Sforza, S., et al. Microbial origin of non proteolytic aminoacyl derivatives in long ripened cheeses. Food Microbiology 35:2 (2013), 116–120.
50. Shigemura, N., Ninomiya, Y., Chapter three - recent advances in molecular mechanisms of taste signaling and modifying. Jeon, K.W., (eds.) International review of cell and molecular biology, 2016, Academic Press, Cambridge, 71–106.
51. Soldo, T., Blank, I., Hofmann, T., (+)-(S)-Alapyridaine—a general taste enhancer?. Chemical Senses 28:5 (2003), 371–379.
52. Su, G., Cui, C., Zheng, L., Yang, B., Ren, J., Zhao, M., Isolation and identification of two novel umami and umami-enhancing peptides from peanut hydrolysate by consecutive chromatography and MALDI-TOF/TOF MS. Food Chemistry 135:2 (2012), 479–485.
53. Suzuki, H., Izuka, S., Minami, H., Miyakawa, N., Ishihara, S., Kumagai, H., Use of bacterial gamma-glutamyltranspeptidase for enzymatic synthesis of gamma-D-glutamyl compounds. Applied and Environmental Microbiology 69:11 (2003), 6399–6404.
54. Takashi, T., Yuji, S., Shinji, K., Hidemitsu, H., Takahiko, M., Shintaro, K., et al. Expression of the metabotropic glutamate receptor, mGluR4a, in the taste hairs of taste buds in rat gustatory papillae. Archives of Histology & Cytology 65:1 (2002), 91–96.
55. Temussi, P.A., Why are sweet proteins sweet? Interaction of brazzein, monellin and thaumatin with the T1R2-T1R3 receptor. FEBS Letters 526:1–3 (2002), 1–4.
56. Temussi, P.A., The good taste of peptides. Journal of Peptide Science 18:2 (2012), 73–82.
57. Toda, Y., Nakagita, T., Hayakawa, T., Okada, S., Narukawa, M., Imai, H., et al. Two distinct determinants of ligand specificity in T1R1/T1R3 (the umami taste receptor). Journal of Biological Chemistry 288:52 (2013), 36863–36877.
58. Toda, Y., Nakagita, T., Hirokawa, T., Yamashita, Y., Nakajima, A., Narukawa, M., et al. Positive/negative allosteric modulation switching in an umami taste receptor (T1R1/T1R3) by a natural flavor compound, methional. Scientific Reports, 8(1), 2018, 11796.
59. Toyono, T., Seta, Y., Kataoka, S., Harada, H., Morotomi, T., Kawano, S., Shigemoto, R., Toyoshima, K., Expression of the metabotropic glutamate receptor, mGluR4a, in the taste hairs of taste buds in rat gustatory papillae. Archives of Histology and Cytology 65:1 (2002), 91–96.
60. Toyono, T., Seta, Y., Kataoka, S., Kawano, S., Shigemoto, R., Toyoshima, K., Expression of metabotropic glutamate receptor group I in rat gustatory papillae. Cell & Tissue Research 313:1 (2003), 29–35.
61. Trinnaman, Laurence, Liu, Zhihua, Psota-kelty Linda Ann, Chen, Zhen. (2015). U.S. Patent No. 2,009,143,488. Washington, DC: U.S. Patent and Trademark Office.
62. Türközü, D., Şanlier, N., L-theanine, unique amino acid of tea, and its metabolism, health effects, and safety. Critical Reviews in Food Science and Nutrition 57:8 (2017), 1681–1687.
63. Villard, R., Robert, F., Blank, I., Bernardinelli, G., Soldo, T., Hofmann, T., Racemic and enantiopure synthesis and physicochemical characterization of the novel taste enhancer N-(1-Carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol inner salt. Journal of Agricultural and Food Chemistry 51:14 (2003), 4040–4045.
64. Weiss, I.M., Muth, C., Drumm, R., Kirchner, H.O.K., Thermal decomposition of the amino acids glycine, cysteine, aspartic acid, asparagine, glutamic acid, glutamine, arginine and histidine. BMC Biophysics, 11(1), 2018, 2.
65. Wellendorph, P., Bräuner-Osborne, H., Molecular cloning, expression, and sequence analysis of GPRC6A, a novel family C G-protein-coupled receptor. Gene 335 (2004), 37–46.
66. Winkel, C., de Klerk, A., Visser, J., de Rijke, E., Bakker, J., Koenig, T., et al. New developments in umami (enhancing) molecules. Chemistry & Biodiversity 5:6 (2008), 1195–1203.
67. Xue, L., Rovira, X., Scholler, P., Zhao, H., Liu, J., Pin, J., et al. Major ligand-induced rearrangement of the heptahelical domain interface in a GPCR dimer. Nature Chemical Biology, 11, 2014, 134.
68. Xu, H., Staszewski, L., Tang, H., Adler, E., Zoller, M., Li, X., Different functional roles of T1R subunits in the heteromeric taste receptors. Proceedings of the National Academy of Sciences of the United States of America, 101(39), 2004, 14258.
69. Yamasaki, Y., Maekawa, K., A peptide with delicious taste. Agricultural and Biological Chemistry 42:9 (1978), 1761–1765.
70. Yu, X., Zhang, L., Miao, X., Li, Y., Liu, Y., The structure features of umami hexapeptides for the T1R1/T1R3 receptor. Food Chemistry 221 (2017), 599–605.
71. Zhang, F., Klebansky, B., Fine, R.M., Xu, H., Pronin, A., Liu, H., et al. Molecular mechanism for the umami taste synergism. Proceedings of the National Academy of Sciences, 105(52), 2008, 20930.
72. Zhang, X.C., Liu, J., Jiang, D., Why is dimerization essential for class-C GPCR function? New insights from mGluR1 crystal structure analysis. Protein & Cell 5:7 (2014), 492–495.
73. Zhang, J., Sun-Waterhouse, D., Feng, Y., Su, G., Zhao, M., Lin, L., The umami intensity enhancement of peanut protein isolate hydrolysate and its derived factions and peptides by Maillard reaction and the analysis of peptide (EP) Maillard products. Food Research International, 2018 https://doi.org/10.1016/j.foodres.2018.11.055.
74. Zhang, Y., Venkitasamy, C., Pan, Z., Liu, W., Zhao, L., Novel umami ingredients: Umami peptides and their taste. Journal of Food Science 82:1 (2017), 16–23.
75. Zhang, J., Zhao, M., Su, G., Lin, L., Identification and taste characteristics of novel umami and umami-enhancing peptides separated from peanut protein isolate hydrolysate by consecutive chromatography and UPLC–ESI–QTOF–MS/MS. Food Chemistry 278 (2019), 674–682.
76. Zhao, C.J., Schieber, A., Gänzle, M.G., Formation of taste-active amino acids, amino acid derivatives and peptides in food fermentations–A review. Food Research International 89 (2016), 39–47.
77. Zhao, Mouming, Su, Guowan, Zhao, Qiangzhong, Zhao, Rongzhong, Lin, Lianzhu, U.S. Patent No. 20,170,145,360. 2017, U.S. Patent and Trademark Office, Washington, DC.
78. Zhuang, M., Lin, L., Zhao, M., Dong, Y., Sun-Waterhouse, D., Chen, H., et al. Sequence, taste and umami-enhancing effect of the peptides separated from soy sauce. Food Chemistry 206 (2016), 174–181.