Abstract
Gamma-glutamyl-amino acids, lactoyl-amino acids and pyroglutamyl-amino acids, collectively named Non-Proteolytic Aminoacyl Derivatives (NPADs) are unusual aminoacyl derivatives of non-proteolytic origins found in consistent amount in several cheeses. Although their enzymatic origin arising from lactic acid bacteria has been demonstrated, the exact enzymes originating them, the ones eventually degrading them and also their resistance to digestive enzymes in the human gastrointestinal tract and in the blood serum after eventual absorption are still unknown. In this paper, pure enzymes and biological media were tested on NPAD and their aminoacidic precursors, for identifying the conditions favoring bioproduction and biodegradation of these compounds. Pure gamma-glutamyl-phenylalanine and its precursor (glutamic acid and phenylalanine), also in the isotopically labeled forms, were tested with Parmigiano-Reggiano extracts, blood serum and different pure enzymes, including typical digestion enzymes (pepsin, trypsin and chymotrypsin), gamma-glutamyl transpeptidase and carboxypeptidase. The data suggested that their production in cheese, and also their partial degradation, might be due to the action of peptidases and gamma-glutamyl transpeptidase. Anyway, under simulated gastrointestinal digestion and in blood serum these compounds turned out to be perfectly stable, suggesting a potential to be absorbed as such and possibly being transported to the body tissues.
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Fallico V, McSweeney PLH, Horne J, Pediliggieri C, Hannon JA, Carpino S, Licitra G (2005) Evaluation of bitterness in Ragusano cheese. J Dairy Sci 88:1288–1300. doi:10.3168/jds.S0022-0302(05)72795-8
Forde A, Fitzgerald GF (2000) Biotechnological approaches to the understanding and improvement of mature cheese flavour. Curr Opin Biotechnol 5:484–489. doi:10.1016/S0958-1669(00)00130-0
Hu X, Legler PM, Khavrutskii I, Scorpio A, Compton JR, Robertson KL, Friedlander AM, Wallqvist A (2012) Probing the donor and acceptor substrate specificity of the γ-glutamyltranspeptidase. Biochemistry 51:1199–1212. doi:10.1021/bi200987b
Kuroda M, Kato Y, Yamazaki J, Kageyama N, Mizukoshi T, Miyano H, Eto Y (2012a) Determination of γ-glutamyl–valyl–glycine in raw scallop and processed scallop products using high pressure liquid chromatography–tandem mass spectrometry. Food Chem 134:1640–1644. doi:10.1016/j.foodchem.2012.03.048
Kuroda M, Kato Y, Yamazaki J, Kai Y, Mizukoshi T, Miyano H, Eto Y (2012b) Determination of γ-glutamyl–valyl–glycine in commercial fish sauces. J Agric Food Chem 60:7291–7296. doi:10.1021/jf3012932
Prandi B, Bencivenni M, Tedeschi T, Marchelli R, Dossena A, Galaverna G, Sforza S (2012) Common wheat determination in durum wheat samples through LC/MS analysis of gluten peptide. Anal Bioanal Chem 403(10):2909–2914. doi:10.1007/s00216-012-5731-2
Roundot-Algaron F, Kerhoas L, Le Bars D, Einhorn J, Gripon JC (1994) Isolation of γ-glutamyl peptides from Comtè cheese. J Dairy Sci 77:1161–1166. doi:10.3168/jds.S0022-0302(94)77053-3
Sforza S, Cavatorta V, Galaverna G, Dossena A, Marchelli R (2009) Accumulation of non-proteolytica aminoacyl derivatives in Parmigiano Reggiano cheese during ripening. Int Dairy J 19:582–587. doi:10.16/j.idairyj.2009.04.009
Sforza S, Cavatorta V, Lambertini F, Galaverna G, Dossena A, Marchelli R (2012) Cheese peptidomics: a detailed study on the evolution of the oligopeptide fraction in Parmigiano-Reggiano cheese from curd to 24 months of aging. J Dairy Sci 95:3514–3526. doi:10.3168/jds.2011-5046
Sgarbi E, Lazzi C, Iacopino L, Bottesini C, Lambertini F, Sforza S, Gatti M (2013) Microbial origin of non proteolytic aminoacyl derivatives in long ripened cheeses. Food Microbiol 35:116–120. doi:10.1016/j.fm.2013.02.013
Suzuki H, Kajimoto Y, Kumagai H (2005) Improvement of the bitter taste of amino acids through the transpeptidation reaction of bacterial γ-glutamyltranspeptidase. J Agric Food Chem 50:313–318. doi:10.1021/jf010726u
Toelstede S, Hofmann T (2009) Kokumi-Active Glutamyl Peptides in Cheeses and their biogeneration by Penicillium roqueforti. J Agric Food Chem 57:3738–3748. doi:10.1021/jf900280j
Versantwoort CHM, Oomen AG, Van de Kamp E, Rompelberg CJM, Sips AJAM (2005) Applicability of an in vitro digestion model in assessing the bioaccessibility of mycotoxins from food. Food Chem Toxicol 43:31–40. doi:10.1016/j.fct.2004.08.007
Acknowledgments
Ajinomoto Inc. is gratefully acknowledged for its support to this research through the Ajinomoto Amino Acids Research Program (“Identification of microorganisms and conditions for optimal bioproduction of gamma-glutamyl aminoacids as new flavoring agents”).
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Bottesini, C., Tedeschi, T., Dossena, A. et al. Enzymatic production and degradation of cheese-derived non-proteolytic aminoacyl derivatives. Amino Acids 46, 441–447 (2014). https://doi.org/10.1007/s00726-013-1637-3
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DOI: https://doi.org/10.1007/s00726-013-1637-3