Selective release of ACE-inhibiting tryptophan-containing dipeptides from food proteins by enzymatic hydrolysis

European Food Research and Technology

Volumn 237, Issue 1, 2013, Pages 27-37

  Lunow, Diana ^a   Kaiser, Susanne ^a   Brückner, Stephan ^a   Gotsch, Astrid ^a   Henle, Thomas ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Angiotensin converting enzyme (ACE); Bioactive peptides; Enzyme inhibitors; Functional food; Lysozyme; Protein hydrolysate

Indexed keywords

AMINO ACIDS; BLOOD PRESSURE; ENZYME INHIBITION; ENZYMES; FUNCTIONAL FOOD; HYDROLYSIS; PEPTIDES; PROTEINS;

ANGIOTENSIN I-CONVERTING ENZYME; ANGIOTENSIN-CONVERTING ENZYME; BIOACTIVE PEPTIDES; ENZYME INHIBITORS; GASTROINTESTINAL DIGESTION; HEN EGG WHITE LYSOZYME; HYDROLYSIS CONDITIONS; PROTEIN HYDROLYSATE;

ENZYMATIC HYDROLYSIS;

EID: 84878005615     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-013-2014-x     Document Type: Article

References (44)

1. Kearney PM, Whelton M, Reynolds K, Muntner P, Whelton PK, He J (2005) Global burden of hypertension: analysis of worldwide data. Lancet 365: 217-223
2. Skeggs LT, Kahn JR, Shumway NP (1956) The preparation and function of the hypertension-converting enzyme. J Exp Med 103: 295
3. Ondetti M, Rubin B, Cushman D (1977) Design of specific inhibitors of angiotensin-converting enzyme: new class of orally active antihypertensive agents. Science 196: 441-444
4. Dicpinigaitis PV (2006) Angiotensin-converting enzyme inhibitor-induced cough: ACCP evidence-based clinical practice guidelines. Chest 129: 169-173
5. Brantl V, Teschemacher H, Henschen A (1981) Opioid activities of b-casomorphins. Life Sci 28: 1903-1909
6. Haque E, Chand R (2007) Antihypertensive and antimicrobial bioactive peptides from milk proteins. Eur Food Res Technol 227: 7-15
7. Phelan M, Aherne A, FitzGerald RJ, O’Brien NM (2009) Casein-derived bioactive peptides: biological effects, industrial uses, safety aspects and regulatory status. Int Dairy J 19: 643-654
8. Cheung HS, Wang FL, Ondetti MA, Sabo EF, Cushman DW (1980) Binding of peptide substrates and inhibitors of angiotensin-converting enzyme. Importance of the COOH-terminal dipeptide sequence. J Biol Chem 255: 401-407
9. Nakamura Y, Yamamoto N, Sakai K, Okubo A, Yamazaki S, Takano T (1995) Purification and characterization of angiotensin I-converting enzyme inhibitors from sour milk. J Dairy Sci 78: 777-783
10. Nakamura T, Mizutani J, Ohki K, Yamada K, Yamamoto N, Takeshi M, Takazawa K (2011) Casein hydrolysate containing Val-Pro-Pro and Ile-Pro-Pro improves central blood pressure and arterial stiffness in hypertensive subjects: a randomized, doubleblind, placebo-controlled trial. Atherosclerosis 219: 298-303
11. Xu J-Y, Qin L-Q, Wang P-Y, Li W, Chang C (2008) Effect of milk tripeptides on blood pressure: a meta-analysis of randomized controlled trials. Nutrition 24: 933-940
12. Wuerzner G, Peyrard S, Blanchard A, Lalanne F, Azizi M (2009) The lactotripeptides isoleucine-proline-proline and valine-proline-proline do not inhibit the N-terminal or C-terminal angiotensin converting enzyme active sites in humans. J Hypertens 27: 1404-1409
13. Engberink MF, Schouten EG, Kok FJ, Van Mierlo LAJ, Brouwer IA, Geleijnse JM (2008) Lactotripeptides show no effect on human blood pressure: results from a double-blind randomized controlled trial. Hypertension 51: 399-405
14. Geleijnse JM, Engberink MF (2010) Lactopeptides and human blood pressure. Curr Opin Lipidol 21: 58-63
15. Miguel M, Aleixandre MA, Ramos M, López-Fandiño R (2006) Effect of simulated gastrointestinal digestion on the antihypertensive properties of ACE-inhibitory peptides derived from ovalbumin. J Agric Food Chem 54: 726-731
16. Miguel M, Manso M, Aleixandre A, Alonso MJ, Salaices M, López-Fandiño R (2007) Vascular effects, angiotensin I-converting enzyme (ACE)-inhibitory activity, and antihypertensive properties of peptides derived from egg white. J Agric Food Chem 55: 10615-10621
17. Miguel M, Aleixandre A (2006) Antihypertensive peptides derived from egg proteins. J Nutr 136: 1457-1460
18. Fujita H, Usui H, Kurahashi K, Yoshikawa M (1995) Isolation and characterization of ovokinin, a bradykinin B1 agonist peptide derived from ovalbumin. Peptides 16: 785-790
19. Fujita H (2000) Classification and antihypertensive activity of angiotensin I-converting enzyme inhibitory peptides derived from food proteins. J Food Sci 65: 564-569
20. Miguel M, Recio I, Gómez-Ruiz JA, Ramos M, López-Fandiño R (2004) Angiotensin I-converting enzyme inhibitory activity of peptides derived from egg white proteins by enzymatic hydrolysis. J Food Protect 67: 1914-1920
21. Asoodeh A, Yazdi M (2011) Purification and characterization of angiotensin I converting enzyme inhibitory peptides from lysozyme hydrolysates. Food Chem 131: 291-295
22. Rao S-Q, Ju T, Sun J, Su Y-J, Xu R-R, Yang Y-J (2012) Purification and characterization of angiotensin I-converting enzyme inhibitory peptides from enzymatic hydrolysate of hen egg white lysozyme. Food Res Int 46: 127-134
23. Martin M, Wellner A, Ossowski I, Henle T (2008) Identification and quantification of inhibitors for Angiotensin-converting enzyme in hypoallergenic infant milk formulas. J Agric Food Chem 56: 6333-6338
24. Krigbaum WR, Kügler FR (1970) Molecular conformation of egg-white lysozyme and bovine alpha-lactalbumin in solution. Biochemistry 9: 1216-1223
25. Copeland RA (2000) Enzymes: a practical introduction to structure, mechanism, and data analysis, 2nd edn, Wiley-VCH, New York
26. DIN 19738 (2004) German industrial standard 19738. Bodenbeschaffenheit-resorptionsverfügbarkeit von organischen und anorganischen schadstoffen aus kontaminiertem bodenmaterial
27. Matthews BW, Weaver LH, Kester WR (1974) The conformation of thermolysin. J Biol Chem 249: 8030-8044
28. Pfeil W, Privalov PL (1976) Thermodynamic investigations of proteins. Biophys Chem 4: 33-40
29. Wu J, Aluko RE, Nakai S (2006) Structural requirements of angiotensin I-converting enzyme inhibitory peptides: quantitative structure-activity relationship study of di- and tripeptides. J Agric Food Chem 54: 732-738
30. Norris R, Casey F, FitzGerald RJ, Shields D, Mooney C (2012) Predictive modelling of angiotensin converting enzyme inhibitory dipeptides. Food Chem 133: 1349-1354
31. Wilkins MR, Gasteiger E, Bairoch A, Sanchez JC, Williams KL, Appel RD, Hochstrasser DF (1999) Protein identification and analysis tools in the ExPASy server. Meth Mol Biol (Clifton, NJ) 112: 531-552
32. Sato M, Hosokawa T, Yamaguchi T, Nakano T, Muramoto K, Kahara T, Funayama K, Kobayashi A, Nakano T (2002) Angiotensin I-converting enzyme inhibitory peptides derived from wakame (Undaria pinnatifida) and their antihypertensive effect in spontaneously hypertensive rats. J Agric Food Chem 50: 6245-6252
33. Ono S, Hosokawa M, Miyashita K, Takahashi K (2006) Inhibition properties of dipeptides from salmon muscle hydrolysate on angiotensin I-converting enzyme. Int J Food Sci Technol 41: 383-386
34. Morihara K, Tsuzuki H (1970) Thermolysin: kinetic study with oligopeptides. Eur J Biochem 15: 374-380
35. Appel W (1986) Chymotrypsin: molecular and catalytic properties. Clin Biochem 19: 317-322
36. Riordan JF (2003) Protein family review angiotensin-I-converting enzyme and its relatives. Genome Biol 4: 225
37. Blumberger J, Lamoureux G, Klein ML (2007) Peptide hydrolysis in thermolysin: Ab initio QM/MM investigation of the Glu143-assisted water addition mechanism. J Chem Theory Comput 3: 1837-1850
38. Foltz M, van der Pijl P (2010) Current in vitro testing of bioactive peptides is not valuable. J Nutr 140: 117-118
39. Hernández-Ledesma B, Amigo L, Ramos M, Recio I (2004) Release of angiotensin converting enzyme-inhibitory peptides by simulated gastrointestinal digestion of infant formulas. Int Dairy J 14: 889-898
40. Vermeirssen V, Van Camp J, Verstraete W (2007) Bioavailability of angiotensin I converting enzyme inhibitory peptides. Brit J Nutr 92(03):357
41. Roufik S, Gauthier SF, Turgeon SL (2006) In vitro digestibility of bioactive peptides derived from bovine b-lactoglobulin. Int Dairy J 16: 294-302
42. Adibi SA (1971) Intestinal transport of dipeptides in man: relative importance of hydrolysis and intact absorption. J Clin Invest 50: 2266-2275
43. Foltz M, Van Buren L, Klaffke W, Duchateau GSMJE (2009) Modeling of the relationship between dipeptide structure and dipeptide stability, permeability, and ACE inhibitory activity. J Food Sci 74: 243-251
44. Laureto PPDE, Frare E, Gottardo R, Dael HVAN, Fontana A (2002) Partly folded states of members of the lysozyme/lactalbumin superfamily: a comparative study by circular dichroism spectroscopy and limited proteolysis. Protein Sci 11: 2932-2946