Formation of taste-active amino acids, amino acid derivatives and peptides in food fermentations – A review

Zhao, Cindy J.; Schieber, Andreas; Gänzle, Michael G.

doi:10.1016/j.foodres.2016.08.042

Cited by 790Protein Hydrolysis and Bioactive PeptidesBiochemical Analysis and Sensing TechniquesProbiotics and Fermented Foods

Formation of taste-active amino acids, amino acid derivatives and peptides in food fermentations – A review

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Zhao, Cindy J., Schieber, Andreas, Gänzle, Michael G.·2016·Food Research International

DOI 10.1016/j.foodres.2016.08.042

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Abstract

Fermented foods are valued for their rich and complex odour and taste. The metabolic activity of food-fermenting microorganisms determines food quality and generates odour and taste compounds. This communication reviews the formation of taste-active amino acids, amino acid derivatives and peptides in food fermentations. Pathways of the generation of taste compounds are presented for soy sauce, cheese, fermented meats, and bread. Proteolysis or autolysis during food fermentations generates taste-active amino acids and peptides; peptides derived from proteolysis particularly impart umami taste (e.g. α-glutamyl peptides) or bitter taste (e.g. hydrophobic peptides containing proline). Taste active peptide derivatives include pyroglutamyl peptides, γ-glutamyl peptides, and succinyl- or lactoyl amino acids. The influence of fermentation microbiota on proteolysis, and peptide hydrolysis, and the metabolism of glutamate and arginine is well understood, however, the understanding of microbial metabolic activities related to the formation of taste-active peptide derivatives is incomplete. Improved knowledge of the interactions between taste-active compounds will enable the development of novel fermentation strategies to develop tastier, less bitter, and low-salt food products, and may provide novel and "clean label" ingredients to improve the taste of other food products.

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A fine balance between proteolysis and peptidolysis avoids bitterness formation in cheese.
“Also, a fine balance between proteolysis and peptidolysis avoids bitterness formation in the cheese (Zhao et al. 2016).”
From Optimizing the acceleration of Cheddar cheese ripening using response surface methodology by microbial protease without altering its quality features (2021) · cites this paper as Zhao et al. 2016

Biochemical pathways for the production of flavour compounds in cheeses during ripening: A review
McSweeney, P. L. H., & Sousa, M. J. (2000) · Le Lait · doi:10.1051/lait:2000127 · Cited by 1,266 · cited 1× · see citing works
“Their composition of flavour active 177 compounds is strongly dependent on the technology used for cheese production and the 178 fermentation microbiota (McSweeney and Sousa, 2000).”
Background
The Molecular Receptive Ranges of Human TAS2R Bitter Taste Receptors
Meyerhof, W., Batram, C., Kühn, C., Brockhoff, A., Chudoba, E., Bufe, B., Appendino, G., & Behrens, M. (2009) · Chemical Senses · doi:10.1093/chemse/bjp092 · Cited by 1,146 · see citing works
Lactic metabolism revisited: metabolism of lactic acid bacteria in food fermentations and food spoilage.
Gänzle, M. G. (2015) · Current Opinion in Food Science · doi:10.1016/j.cofs.2015.03.001 · Cited by 936 · see citing works
Self-citation
Proteolytic systems of lactic acid bacteria.
Savijoki, K., Ingmer, H., & Varmanen, P. (2006) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-006-0427-1 · Cited by 717 · see citing works
Angiotensin I–converting enzyme inhibitory peptides derived from food proteins and their physiological and pharmacological effects
Li, G., Le, G., Shi, Y., & Shrestha, S. (2004) · Nutrition Research · doi:10.1016/j.nutres.2003.10.014 · Cited by 554 · see citing works
Changes in the Components of Dry-Fermented Sausages during Ripening
Pereda, J. A. O., Hierro, E. M., Bruna, J. M., et al. (1999) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408699991279204 · Cited by 501 · see citing works
Microbiology and Technology of Fermented Foods
(2006) · doi:10.1002/9780470277515 · Cited by 468 · see citing works
The Role of Muscle Proteases and Lipases in Flavor Development During the Processing of Dry-Cured Ham
Toldrá, F., & Flores, M. (1998) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408699891274237 · Cited by 467 · see citing works
Enzymatic and bacterial conversions during sourdough fermentation
Gänzle, M. G. (2014) · Food Microbiology · doi:10.1016/j.fm.2013.04.007 · Cited by 432 · cited 2× · see citing works
“239 3.4 Bread 240 Bread flavour is dependent on the activity of flour enzymes, and the metabolic activity of 241 yeasts and lactic acid bacteria (Gänzle, 2014).”
BackgroundInfluentialSelf-citation
Functional Properties of Wheat Glutenin
Weegels, P. L., Hamer, R. J., & Schofield, J. D. (1996) · Journal of Cereal Science · doi:10.1006/jcrs.1996.0001 · Cited by 420 · see citing works
Angiotensin I–converting enzyme inhibitory peptides derived from food proteins and their physiological and pharmacological effects
Geng, L., Le, G., Shi, Y., et al. (2004) · Nutrition Research · doi:10.1016/s0271-5317(04)00058-2 · Cited by 420 · see citing works
Role of Free Amino Acids and Peptides in Food Taste
Kato, H., Rhue, M. R., & Nishimura, T. (1989) · ACS symposium series · doi:10.1021/bk-1989-0388.ch013 · Cited by 387 · see citing works
Contribution of Sourdough Lactobacilli, Yeast, and Cereal Enzymes to the Generation of Amino Acids in Dough Relevant for Bread Flavor
Thiele, C., Gänzle, M. G., & Vogel, R. F. (2002) · Cereal Chemistry · doi:10.1094/cchem.2002.79.1.45 · Cited by 360 · see citing works
Self-citation
Proteolysis in sourdough fermentations: mechanisms and potential for improved bread quality
Gänzle, M. G., Loponen, J., & Gobbetti, M. (2008) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2008.04.002 · Cited by 356 · see citing works
Self-citation
Molecular and Sensory Studies on the Umami Taste of Japanese Green Tea
Kaneko, S., Kumazawa, K., Masuda, H., Henze, A., & Hofmann, T. F. (2006) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0525232 · Cited by 316 · see citing works
Characterization of proteolysis during the ripening of semi-dry fermented sausages
Hughes, M. C., Kerry, J. P., Arendt, E. K., Kenneally, P. M., McSweeney, P. L. H., & O’Neill, E. (2002) · Meat Science · doi:10.1016/s0309-1740(01)00248-0 · Cited by 312 · see citing works
Glutamate. Its applications in food and contribution to health
Jinap, S., & Hajeb, P. (2010) · Appetite · doi:10.1016/j.appet.2010.05.002 · Cited by 301 · see citing works
Sensory Property Relationships to Chemical Data of Italian‐type Dry‐cured Ham
Careri, M., Mangia, A., Barbieri, G., et al. (1993) · Journal of Food Science · doi:10.1111/j.1365-2621.1993.tb06090.x · Cited by 297 · see citing works
Major taste loss in carnivorous mammals
Jiang, P., Josue, J., Li, X., Gläser, D., Li, W., Brand, J. G., Margolskee, R. F., Reed, D. R., & Beauchamp, G. K. (2012) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1118360109 · Cited by 285 · see citing works
Oleogustus: The Unique Taste of Fat
Running, C. A., Craig, B. Α., & Mattes, R. D. (2015) · Chemical Senses · doi:10.1093/chemse/bjv036 · Cited by 262 · see citing works
A Series of Kokumi Peptides Impart the Long-Lasting Mouthfulness of Matured Gouda Cheese
Toelstede, S., Dunkel, A., & Hofmann, T. F. (2009) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf803376d · Cited by 260 · see citing works
A Genomic View of Lactobacilli and Pediococci Demonstrates that Phylogeny Matches Ecology and Physiology
Zheng, J., Ruan, L., Sun, M., & Gänzle, M. G. (2015) · Applied and Environmental Microbiology · doi:10.1128/aem.02116-15 · Cited by 236 · see citing works
Self-citation
New developments in meat starter cultures
Hammes, W. P., & Hertel, C. (1998) · Meat Science · doi:10.1016/s0309-1740(98)90043-2 · Cited by 234 · see citing works
Debittering of protein hydrolyzates
Badal Chandra, S. A. H. A., & Hayashi, K. (2001) · Biotechnology Advances · doi:10.1016/s0734-9750(01)00070-2 · Cited by 229 · see citing works
Flavor Characteristics of Glutathione in Raw and Cooked Foodstuffs
Ueda, Y., Yonemitsu, M., Tsubuku, T., et al. (1997) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.61.1977 · Cited by 221 · see citing works
Enzymatic debittering of food protein hydrolysates
Fitzgerald, R. J., & O’Cuinn, G. (2006) · Biotechnology Advances · doi:10.1016/j.biotechadv.2005.11.002 · Cited by 216 · see citing works
Umami–bitter interactions: The suppression of bitterness by umami peptides via human bitter taste receptor
Kim, M. J., Son, H. J., Kim, Y., Misaka, T., & Rhyu, M. (2014) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2014.11.114 · Cited by 216 · see citing works
Masking Bitter Taste by Molecules
Ley, J. P. (2008) · Chemosensory Perception · doi:10.1007/s12078-008-9008-2 · Cited by 212 · see citing works
Redox Reactions in Wheat Dough as Affected by Ascorbic Acid
Grosch, W., & Wieser, H. (1999) · Journal of Cereal Science · doi:10.1006/jcrs.1998.0218 · Cited by 208 · see citing works
Flavor chemistry: Trends and developments
Reineccius, G. A. (1990) · Journal of Controlled Release · doi:10.1016/0168-3659(90)90168-s · Cited by 203 · see citing works
Voraussage der Bitterkeit von Peptiden aus deren Aminosäurezu-sammensetzung
NEY, K. H. (1971) · European Food Research and Technology · doi:10.1007/bf01879606 · Cited by 195 · see citing works
Kokumi Substances, Enhancers of Basic Tastes, Induce Responses in Calcium-Sensing Receptor Expressing Taste Cells
Maruyama, Y., Yasuda, R., Kuroda, M., et al. (2012) · PLoS ONE · doi:10.1371/journal.pone.0034489 · Cited by 193 · see citing works
Pseudogenization of the Umami Taste Receptor Gene Tas1r1 in the Giant Panda Coincided with its Dietary Switch to Bamboo
Zhao, H., Yang, J., Xu, H., & Zhang, J. (2010) · Molecular Biology and Evolution · doi:10.1093/molbev/msq153 · Cited by 193 · see citing works
Sweet and Umami Taste: Natural Products, Their Chemosensory Targets, and Beyond
Behrens, M., Meyerhof, W., Hellfritsch, C., & Hofmann, T. F. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201002094 · Cited by 191 · see citing works
Lactobacilli — Their Enzymes and Role in Ripening and Spoilage of Cheese: A Review
Khalid, N. M., & Marth, E. H. (1990) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(90)78952-7 · Cited by 186 · see citing works
Composition and function of sourdough microbiota: From ecological theory to bread quality
Gänzle, M. G., & Ripari, V. (2016) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2016.05.004 · Cited by 183 · see citing works
Self-citation
Cathepsin B, D, H and L activities in the processing of dry‐cured ham
Toldrá, F., Rico, E., & Flores, J. (1993) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2740620208 · Cited by 173 · see citing works
Sensomics Mapping and Identification of the Key Bitter Metabolites in Gouda Cheese
Toelstede, S., & Hofmann, T. F. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf7036533 · Cited by 173 · see citing works
Discovery of Salt Taste Enhancing Arginyl Dipeptides in Protein Digests and Fermented Fish Sauces by Means of a Sensomics Approach
Schindler, A., Dunkel, A., Stähler, F., Backes, M., Ley, J. P., Meyerhof, W., & Hofmann, T. F. (2011) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf2041593 · Cited by 159 · see citing works
Quantitative Structure−Activity Relationship Study of Bitter Peptides
(2006) · doi:10.1021/jf062422j · Cited by 158 · see citing works
Generation of flavour compounds in fermented sausages—the influence of curing ingredients, Staphylococcus starter culture and ripening time
Olesen, P. T., Meyer, A. S., & Stahnke, L. H. (2003) · Meat Science · doi:10.1016/s0309-1740(03)00189-x · Cited by 157 · see citing works
Umami Taste Enhancement of MSG/NaCl Mixtures by Subthreshold L‐α‐Aromatic Amino Acids
Lioe, H. N., Apriyantono, A., Takara, K., Wada, K., & Yasuda, M. (2005) · Journal of Food Science · doi:10.1111/j.1365-2621.2005.tb11483.x · Cited by 149 · see citing works
Contribution of glutamate decarboxylase in Lactobacillus reuteri to acid resistance and persistence in sourdough fermentation
Su, M. S., Schlicht, S., & Gänzle, M. G. (2011) · Microbial Cell Factories · doi:10.1186/1475-2859-10-s1-s8 · Cited by 148 · see citing works
Self-citation
Soy Sauce and Its Umami Taste: A Link from the Past to Current Situation
Lioe, H. N., Selamat, J., & Yasuda, M. (2010) · Journal of Food Science · doi:10.1111/j.1750-3841.2010.01529.x · Cited by 142 · see citing works
Sourdough products for convenient use in baking
Brandt, M. (2006) · Food Microbiology · doi:10.1016/j.fm.2006.07.010 · Cited by 141 · see citing works
Identification of the Taste Enhancer Alapyridaine in Beef Broth and Evaluation of Its Sensory Impact by Taste Reconstitution Experiments
Ottinger, H., & Hofmann, T. F. (2003) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf034788r · Cited by 134 · see citing works
Sources of Umami Taste in Cheddar and Swiss Cheeses
Drake, S. L., Carunchia Whetstine, M. E., Drake, M. A., Courtney, P., Fligner, K., Jenkins, J., & Pruitt, C. (2007) · Journal of Food Science · doi:10.1111/j.1750-3841.2007.00402.x · Cited by 123 · see citing works
Evaluation of Peptide Contribution to the Intense Umami Taste of Japanese Soy Sauces
Lioe, H. N., Takara, K., & Yasuda, M. (2006) · Journal of Food Science · doi:10.1111/j.1365-2621.2006.tb15654.x · Cited by 123 · see citing works
Effect of selected strains of Debaryomyces hansenii on the volatile compound production of dry fermented sausage “salchichón”
Andrade, M. J., Córdoba, J. J., Casado, E. M., et al. (2010) · Meat Science · doi:10.1016/j.meatsci.2010.01.009 · Cited by 121 · see citing works
Kokumi-Active Glutamyl Peptides in Cheeses and Their Biogeneration by Penicillium roquefortii
Toelstede, S., & Hofmann, T. F. (2009) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf900280j · Cited by 119 · see citing works
Glutamine, glutamate, and arginine-based acid resistance in Lactobacillus reuteri
Teixeira, J. S., Seeras, A., Sánchez-Maldonado, A. F., Zhang, C., Su, M. S., & Gänzle, M. G. (2014) · Food Microbiology · doi:10.1016/j.fm.2014.03.015 · Cited by 117 · see citing works
Self-citation
Quantitative Studies and Taste Re-engineering Experiments toward the Decoding of the Nonvolatile Sensometabolome of Gouda Cheese
Toelstede, S., & Hofmann, T. F. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf800552n · Cited by 116 · see citing works
Identification of Small Peptides Generated in Spanish Dry‐cured Ham
Sentandreu, M. Á., Stoeva, S., Aristoy, M., et al. (2003) · Journal of Food Science · doi:10.1111/j.1365-2621.2003.tb14115.x · Cited by 114 · see citing works
Microbiology and physico-chemical changes of dry-cured ham during the post-salting stage as affected by partial replacement of NaCl by other salts
Blesa, E., Aliño, M., Baviera, J. M. B., et al. (2007) · Meat Science · doi:10.1016/j.meatsci.2007.07.008 · Cited by 114 · see citing works
Detection of Proteolytic Activity in Microorganisms Isolated from Dry‐Cured Ham
MOLINA, I., & Toldrá, F. (1992) · Journal of Food Science · doi:10.1111/j.1365-2621.1992.tb06843.x · Cited by 113 · see citing works
Synthesis and Sensory Characterization of Novel Umami-Tasting Glutamate Glycoconjugates
Beksan, E., Schieberle, P., Robert, F., et al. (2003) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0344441 · Cited by 112 · see citing works
Isolation and identification of acidic oligopeptides occurring in a flavor potentiating fraction from a fish protein hydrolysate
NOGUCHI, M., Arai, S., Yamashita, M., et al. (1975) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf60197a003 · Cited by 111 · see citing works
Low Molecular Weight Compounds Responsible for Savory Taste of Indonesian Soy Sauce
Lioe, H. N., Apriyantono, A., Takara, K., Wada, K., Naoki, H., & Yasuda, M. (2004) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf049230d · Cited by 110 · see citing works
Glutathione Reductase from Lactobacillus sanfranciscensis DSM20451 T : Contribution to Oxygen Tolerance and Thiol Exchange Reactions in Wheat Sourdoughs
Jänsch, A., Korakli, M., Vogel, R. F., & Gänzle, M. G. (2007) · Applied and Environmental Microbiology · doi:10.1128/aem.02322-06 · Cited by 110 · see citing works
Self-citation
Quantitation of Key Tastants and Re-engineering the Taste of Parmesan Cheese
Hillmann, H., & Hofmann, T. F. (2016) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.6b00112 · Cited by 104 · see citing works
Effect of ripening time and rearing system on amino acid-related flavour compounds of Iberian ham
Jurado, Á., Garcı́a, C., Timon, M. L., et al. (2006) · Meat Science · doi:10.1016/j.meatsci.2006.09.006 · Cited by 101 · see citing works
Modelling relationship between angiotensin-(I)-converting enzyme inhibition and the bitter taste of peptides
Pripp, A. H., & Ardö, Y. (2006) · Food Chemistry · doi:10.1016/j.foodchem.2006.06.026 · Cited by 98 · see citing works
Sensory interaction of umami substances with model food matrices and its hedonic effect
Barylko-Pikielna, N., & Kostyra, E. (2007) · Food Quality and Preference · doi:10.1016/j.foodqual.2007.01.002 · Cited by 97 · see citing works
Analysis of the correlation between dipeptides and taste differences among soy sauces by using metabolomics-based component profiling
Yamamoto, S., Shiga, K., Kodama, Y., Imamura, M., Uchida, R., Obata, A., Bamba, T., & Fukusaki, E. (2014) · Journal of Bioscience and Bioengineering · doi:10.1016/j.jbiosc.2013.12.019 · Cited by 95 · see citing works
Determination and quantification of the kokumi peptide, γ-glutamyl-valyl-glycine, in commercial soy sauces
Kuroda, M., KATO, Y. O., Yamazaki, J., et al. (2013) · Food Chemistry · doi:10.1016/j.foodchem.2013.03.070 · Cited by 94 · see citing works
Flavor Modification by Sodium Chloride and Monosodium Glutamate
Kemp, S. E., & Beauchamp, G. K. (1994) · Journal of Food Science · doi:10.1111/j.1365-2621.1994.tb05592.x · Cited by 92 · see citing works
Contribution of Lactococcus lactis Cell Envelope Proteinase Specificity to Peptide Accumulation and Bitterness in Reduced-Fat Cheddar Cheese
Broadbent, J. R., Barnes, M., Brennand, C., Strickland, M., Houck, K., Johnson, M. E., & Steele, J. L. (2002) · Applied and Environmental Microbiology · doi:10.1128/aem.68.4.1778-1785.2002 · Cited by 91 · see citing works
Effect of Extended Aging of Parma Dry-Cured Ham on the Content of Oligopeptides and Free Amino Acids
Sforza, S., Galaverna, G., Schivazappa, C., Marchelli, R., Dossena, A., & Virgili, R. (2006) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf061312+ · Cited by 89 · see citing works
Mechanism of the perception of “kokumi” substances and the sensory characteristics of the “kokumi” peptide, γ-Glu-Val-Gly
Kuroda, M., & Miyamura, N. (2015) · Flavour · doi:10.1186/2044-7248-4-11 · Cited by 89 · see citing works
Oligopeptides and free amino acids in Parma hams of known cathepsin B activity
Sforza, S., Pigazzani, A., Motti, M., et al. (2001) · Food Chemistry · doi:10.1016/s0308-8146(01)00224-2 · Cited by 88 · see citing works
Isolation and Identification of the Umami Enhancing Compounds in Japanese Soy Sauce
Kaneko, S., Kumazawa, K., & Nishimura, O. (2011) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.110041 · Cited by 83 · see citing works
Metabolic Profiling Approach To Explore Compounds Related to the Umami Intensity of Soy Sauce
Shiga, K., Yamamoto, S., Nakajima, A., Kodama, Y., Imamura, M., Sato, T., Uchida, R., Obata, A., Bamba, T., & Fukusaki, E. (2014) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf501173r · Cited by 83 · see citing works
Improvement of the Bitter Taste of Amino Acids through the Transpeptidation Reaction of Bacterial γ-Glutamyltranspeptidase
Suzuki, H., Kajimoto, Y., & Kumagai, H. (2001) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf010726u · Cited by 77 · see citing works
Effect of Glutamate Accumulation During Sourdough Fermentation with Lactobacillus reuteri on the Taste of Bread and Sodium‐Reduced Bread
Zhao, C. J., Kinner, M., Wismer, W. V., & Gänzle, M. G. (2014) · Cereal Chemistry · doi:10.1094/cchem-07-14-0149-r · Cited by 76 · see citing works
Self-citation
The relationship between taste and primary structure of "delicious peptide" (Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from beef soup.
Tamura, M., Nakatsuka, T., Tada, M., et al. (1989) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.53.319 · Cited by 75 · see citing works
Salt-tolerant γ-glutamyltranspeptidase from Bacillus subtilis 168 with glutaminase activity
Minami, H., Suzuki, H., & Kumagai, H. (2003) · Enzyme and Microbial Technology · doi:10.1016/s0141-0229(02)00314-9 · Cited by 72 · see citing works
Bitterness of Phenylalanine- and Tyrosine-containing Peptides
Ishibashi, N., Sadamori, K., Yamamoto, O., et al. (1987) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1987.10868574 · Cited by 71 · see citing works
Identification and Quantitation of New Glutamic Acid Derivatives in Soy Sauce by UPLC/MS/MS
Frérot, E., & Chen, T. (2013) · Chemistry & Biodiversity · doi:10.1002/cbdv.201300150 · Cited by 70 · see citing works
Bitterness of Leucine-containing Peptides
Ishibashi, N., Arita, Y., Kanehisa, H., et al. (1987) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1987.10868411 · Cited by 70 · see citing works
Glutamine deamidation by cereal-associated lactic acid bacteria
Vermeulen, N., Gänzle, M. G., & Vogel, R. F. (2007) · Journal of Applied Microbiology · doi:10.1111/j.1365-2672.2007.03333.x · Cited by 69 · see citing works
Self-citation
Formation of Kokumi-Enhancing γ-Glutamyl Dipeptides in Parmesan Cheese by Means of γ-Glutamyltransferase Activity and Stable Isotope Double-Labeling Studies
Hillmann, H., Behr, J., Ehrmann, M. A., et al. (2016) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.6b00113 · Cited by 67 · see citing works
Proteolysis and Bioconversion of Cereal Proteins to Glutamate and γ-Aminobutyrate (GABA) in Rye Malt Sourdoughs
Stromeck, A., Hu, Y., Chen, L., & Gänzle, M. G. (2011) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf103546t · Cited by 66 · see citing works
Self-citation
Isolation of γ-Glutamyl Peptides from Comté Cheese
Roudot-Algaron, F., Kerhoas, L., Bars, D. L., et al. (1994) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(94)77053-3 · Cited by 61 · see citing works
APPLYING PROTEOLYTIC ENZYMES ON SOYBEAN. 6. Deodorization Effect of Aspergillopeptidase A and Debittering Effect of Aspergillus Acid Carboxypeptidase
Arai, S., NOGUCHI, M., KUROSAWA, S., et al. (1970) · Journal of Food Science · doi:10.1111/j.1365-2621.1970.tb00940.x · Cited by 61 · see citing works
Identification of Endopeptidase Genes from the Genomic Sequence of Lactobacillus helveticus CNRZ32 and the Role of These Genes in Hydrolysis of Model Bitter Peptides
Sridhar, V. R., Hughes, J. E., Welker, D. L., Broadbent, J. R., & Steele, J. L. (2005) · Applied and Environmental Microbiology · doi:10.1128/aem.71.6.3025-3032.2005 · Cited by 61 · see citing works
Tastes of L -Glutamyl Oligopeptides in Relation to Their Chromatographic Properties
Arai, S., Yamashita, M., & NOGUCHI, M. (1973) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1973.10860638 · Cited by 58 · see citing works
Taste of Proline-containing Peptides
Ishibashi, N., Kubo, T., Chino, M., et al. (1988) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1988.10868632 · Cited by 58 · see citing works
Taste Properties and Synergisms of Beefy Meaty Peptide
Wang, K., Maga, J. A., & Bechtel, P. J. (1996) · Journal of Food Science · doi:10.1111/j.1365-2621.1996.tb12214.x · Cited by 57 · see citing works
New Developments in Umami (Enhancing) Molecules
Winkel, C., de Klerk, A., Visser, J., et al. (2008) · Chemistry & Biodiversity · doi:10.1002/cbdv.200890096 · Cited by 56 · see citing works
Food Flavors and Chemistry: Advances of the New Millennium
Aishima, T. (2002) · Food Research International · doi:10.1016/s0963-9969(02)00092-3 · Cited by 56 · see citing works
Sensory and Chromatographic Evaluations of Water Soluble Fractions from Dried Sausages
Henriksen, A. P., & Stahnke, L. H. (1997) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf960792+ · Cited by 51 · see citing works
Tastes and Structures of Bitter Peptide, Asparagine-Alanine-Leucine-Proline-Glutamate, and Its Synthetic Analogues
Kim, M.-R., Kawamura, Y., Kim, K. M., et al. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf7036664 · Cited by 51 · see citing works
Purification and Characterization of an Extracellular Protease from Penicillium chrysogenum Pg222 Active against Meat Proteins
Benito, M. J., Rodrı́guez, M., Núñez, F., et al. (2002) · Applied and Environmental Microbiology · doi:10.1128/aem.68.7.3532-3536.2002 · Cited by 51 · see citing works
Study of taste-active compounds in the water-soluble extract of mature Cheddar cheese
Andersen, L. T., Ardö, Y., & Bredie, W. L. P. (2010) · International Dairy Journal · doi:10.1016/j.idairyj.2010.02.009 · Cited by 50 · see citing works
Accumulation of non-proteolytic aminoacyl derivatives in Parmigiano-Reggiano cheese during ripening.
Sforza, S., Cavatorta, V., Galaverna, G., Dossena, A., & Marchelli, R. (2009) · International Dairy Journal · doi:10.1016/j.idairyj.2009.04.009 · Cited by 50 · see citing works
Glutamyl Oligopeptides as Factors Responsible for Tastes of a Proteinase-modified Soybean Protein
Arai, S., Yamashita, M., & Fujimaki, M. (1972) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1972.10860400 · Cited by 49 · see citing works
From gene to function: Metabolic traits of starter cultures for improved quality of cereal foods
Gänzle, M. G. (2009) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2009.05.018 · Cited by 47 · see citing works
Self-citation
Pyroglutamic Acid in Cheese: Presence, Origin, and Correlation with Ripening Time of Grana Padano Cheese
Mucchetti, G., Locci, F., Gatti, M., Neviani, E., Addeo, F., Dossena, A., & Marchelli, R. (2000) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(00)74926-5 · Cited by 45 · see citing works
Production of Pyroglutamic Acid by Thermophilic Lactic Acid Bacteria in Hard-cooked Mini-Cheeses
Mucchetti, G., Locci, F., Massara, P., Vitale, R., & Neviani, E. (2002) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(02)74331-2 · Cited by 45 · see citing works
A mutantBacillus subtilisγ-glutamyltranspeptidase specialized in hydrolysis activity
Minami, H., Suzuki, H., & Kumagai, H. (2003) · FEMS Microbiology Letters · doi:10.1016/s0378-1097(03)00456-7 · Cited by 45 · see citing works
Evaluation of Bitterness in Ragusano Cheese
Fallico, V., McSweeney, P. L. H., Horne, J., Pediliggieri, C., Hannon, J. A., Carpino, S., & Licitra, G. (2005) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(05)72795-8 · Cited by 44 · see citing works
Novel Brothy Taste Modifier Isolated from Beef Broth
Shima, K., Yamada, N., Suzuki, E., et al. (1998) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9708709 · Cited by 44 · see citing works
Microbial origin of non proteolytic aminoacyl derivatives in long ripened cheeses
Sgarbi, E., Lazzi, C., Iacopino, L., Bottesini, C., Lambertini, F., Sforza, S., & Gatti, M. (2013) · Food Microbiology · doi:10.1016/j.fm.2013.02.013 · Cited by 40 · see citing works
Identification of the Glutaminase Genes ofAspergillus sojaeInvolved in Glutamate Production during Soy Sauce Fermentation
Ito, K., Koyama, Y., & Hanya, Y. (2013) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.130151 · Cited by 39 · see citing works
Determination of taste-active compounds of a bitter Camembert cheese by omission tests
Engel, E., Septier, C., Leconte, N., et al. (2001) · Journal of Dairy Research · doi:10.1017/s0022029901005209 · Cited by 39 · see citing works
Sweet-bitter and umami-bitter taste interactions in single parabrachial neurons in C57BL/6J mice
Tokita, K., & Boughter, J. D. (2012) · Journal of Neurophysiology · doi:10.1152/jn.00465.2012 · Cited by 38 · see citing works
Availability of essential amino acids in dry-cured ham
Toldrá, F., & Aristoy, M. (1993) · International Journal of Food Sciences and Nutrition · doi:10.3109/09637489309017442 · Cited by 36 · see citing works
Evolution of the Composition of a Selected Bitter Camembert Cheese during Ripening: Release and Migration of Taste-Active Compounds
Engel, E., Tournier, C., Salles, C., et al. (2001) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf000966u · Cited by 35 · see citing works
Enzymatic Synthesis of γ-Glutamylvaline to Improve the Bitter Taste of Valine
Suzuki, H., Kato, K. H., & Kumagai, H. (2004) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0347564 · Cited by 34 · see citing works
Debittering and Hydrolysis of a Tryptic Hydrolysate of β‐casein with Purified General and Proline Specific Aminopeptidases from Lactococcus lactis ssp. cremoris AM2
Bouchier, P., O’Cuinn, G., Harrington, D., et al. (2001) · Journal of Food Science · doi:10.1111/j.1365-2621.2001.tb15179.x · Cited by 33 · see citing works
Comparison of different IlvE aminotransferases in Lactobacillus sakei and investigation of their contribution to aroma formation from branched chain amino acids
Freiding, S., Ehrmann, M. A., & Vogel, R. F. (2011) · Food Microbiology · doi:10.1016/j.fm.2011.07.008 · Cited by 29 · see citing works
Use of bacterial extracts to enhance amino acid breakdown in dry fermented sausages
Herranz, B., Fernández, M., de la Hoz, L., et al. (2005) · Meat Science · doi:10.1016/j.meatsci.2005.08.002 · Cited by 28 · see citing works
Amino acid and nucleotide contents and sensory traits of dry-cured products from pigs with different genotypes
Reina, R., del Pulgar, J. S., López‐Buesa, P., et al. (2013) · Meat Science · doi:10.1016/j.meatsci.2013.07.006 · Cited by 27 · see citing works
Mechanism for the Bitter Tasting Potency of Peptides UsingO-Aminoacyl Sugars as Model Compounds+
Tamura, M., Miyoshi, T., Mori, N., Kinomura, K., Kawaguchi, M., Ishibashi, N., & Okai, H. (1990) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1990.10870166 · Cited by 27 · see citing works
Isolation and Characterization of Neutral Peptides in Soy Sauce
Oka, S., & Nagata, K. (1974) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1974.10861305 · Cited by 22 · see citing works
Isolation and Characterization of Acidic Peptides in Soy Sauce
Oka, S., & Nagata, K. (1974) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.38.1195 · Cited by 22 · see citing works
Role of nonvolatile compounds in bread flavor
Johnson, J. A., & El-Dash, A. A. (1969) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf60164a029 · Cited by 20 · see citing works
Contents and Compositions of Free Sugars, Organic Acids, Free Amino Acids and Oligopeptides in Soy Sauce and Soy Paste Produced in Korea and Japan.
KANEKO, K., TSUJI, K., Kim, C.-H., et al. (1994) · NIPPON SHOKUHIN KOGYO GAKKAISHI · doi:10.3136/nskkk1962.41.148 · Cited by 20 · see citing works
Proteolytic Enzymes of Lactic Acid Bacteria and Their Influence on Bitterness in Bacterial-Ripened Cheeses
Broadbent, J. R., & Steele, J. L. (2007) · ACS symposium series · doi:10.1021/bk-2007-0971.ch011 · Cited by 16 · see citing works
PYROGLUTAMYL DIPEPTIDES IN MUSHROOM, AGARICUS CAMPESTRIS
Altamura, M. R., Andreotti, R. E., Bazinet, M. L., et al. (1970) · Journal of Food Science · doi:10.1111/j.1365-2621.1970.tb12122.x · Cited by 16 · see citing works
Hydrolytic activity of Penicillium chrysogenum Pg222 on pork myofibrillar proteins
Benito, M. J., Córdoba, J. J., Alonso, M., et al. (2003) · International Journal of Food Microbiology · doi:10.1016/s0168-1605(03)00117-x · Cited by 16 · see citing works
Degradation of a Bitter Peptide Derived from Casein by Lactic Acid Bacterial Peptidase
Shimamura, T., NISHIMURA, T., IWASAKI, A., et al. (2009) · Food Science and Technology Research · doi:10.3136/fstr.15.191 · Cited by 11 · see citing works
Transformation of Glutamyl Dipeptides by Heating in Aqueous Solution
Kasai, T., Nishitoba, T., & Sakamura, S. (1983) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1983.10866007 · Cited by 8 · see citing works
Isolation and Characterization of Acidic Peptides in Soy Sauce
Oka, S., & Nagata, K. (1974) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1974.10861306 · Cited by 7 · see citing works
A Hydrolase from Lactobacillus sakei Moonlights as a Transaminase
Sinz, Q., Freiding, S., Vogel, R. F., et al. (2013) · Applied and Environmental Microbiology · doi:10.1128/aem.03762-12 · Cited by 6 · see citing works
Application of Bacterial γ-Glutamyl-Transpeptidase to Improve the Taste of Food
Suzuki, H., & Kumagai, H. (2003) · ACS symposium series · doi:10.1021/bk-2003-0867.ch015 · Cited by 6 · see citing works
Determination of taste-active compounds in a bitter camembert cheese and evolution of their impact on taste during ripening
Engel, E., Septier, C., Feyen, V., et al. (2007) · Special publication - Royal Society of Chemistry/Special publication · doi:10.1039/9781847550859-00130 · Cited by 3 · see citing works
Transformation of glutamyl dipeptides by heating in aqueous solution.
Kasai, T., Nishitoba, T., & Sakamura, S. (1983) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.47.2647 · Cited by 3 · see citing works
Changes in the Content of Inosinic Acid and Glutamic Acid Contribute to the Taste of Fermented Bread.
Fujisawa, K., & Yoshino, M. (1995) · Nippon Eiyo Shokuryo Gakkaishi · doi:10.4327/jsnfs.48.494 · Cited by 2 · see citing works

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Authors: Zhao, C. J., Schieber, A., & Gänzle, M. G.
Affiliations: University of Alberta (CA)
University of Bonn (DE)
Corresponding author: Gänzle, Michael G.
ORCID: Schieber, Andreas
Gänzle, Michael G.
Venue: Food Research International
Publisher: Elsevier BV
Published: 2016-11
Volume: 89
Issue: Pt 1
Pages: 39-47
ISSN: 0963-9969 (ISSN-L)
DOI: 10.1016/j.foodres.2016.08.042
OpenAlex: W2512514802
Cited by: 790
References: 129
Citations by year: 2026: 131 · 2025: 137 · 2024: 120 · 2023: 113 · 2022: 78 · 2021: 73 · 2020: 64 · 2019: 38 · 2018: 24 · 2017: 10 · 2016: 1
FWCI: 2.17
Type: journal article
Language: en
Open access: green
doi.org
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Food Research International (publishedVersion)
PubMed (publishedVersion)
ERA: Education and Research Archive (University of Alberta)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Hydrolysis and Bioactive Peptides
Health Sciences › Nursing › Nutrition and Dietetics › Biochemical Analysis and Sensing Techniques
Life Sciences › Agricultural and Biological Sciences › Food Science › Probiotics and Fermented Foods
Keywords: amino acid derivatives, food fermentation, fermented foods, umami taste, bitter taste, proteolysis, autolysis, soy sauce, cheese, fermented meat products, bread, γ-glutamyl peptides, glutamate metabolism, arginine metabolism, fermentation microbiota, low-salt foods, clean-label ingredients

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Formation of taste-active amino acids, amino acid derivatives and peptides in food fermentations – A review

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