Abstract
Shelf-life of dietary products and the need for health supporting functional ingredients often require components with high anti-oxidative properties. The study aimed at the characterisation of peptides with antioxidant properties from enzymatically hydrolysed soybean protein isolate. Soybean protein isolate was hydrolysed with a food grade pancreatic trypsin/chymotrypsin for industrial applications, ultrafiltered and the permeate was fractionated by size exclusion chromatography. Anti-oxidative properties of these fractions were tested in a Trolox®-equivalent-anti-oxidative capacity assay, which is based on the absorbance suppression of 2,2′-azinobis(3-ethyl benzothiazoline-6-sulfonate) radical cations by anti-oxidative substances at λ 414 nm. The amino acid compositions and sequences of the peptide fractions were determined by liquid chromatography and mass spectrometry analysis. Compared to the intact soybean protein isolate a peptide fraction with an anti-oxidative capacity of 113 mg TEAC/g was obtained. This fraction was shown to be enriched in peptides smaller than 1 kDa with prevailing aromatic amino acid residues. Nine peptides derived from glycinin and β-conglycinin were sequenced by tandem mass spectrometry. The particular sequences were synthesized and assayed. The synthetic peptide analogue TTYY (β-conglycinin fragment 291–294) revealed significant radical scavenging properties of 13.6 up to 59.6% with 0.18–18 mM in a concentration dependent manner. Peptides from soybean protein isolate were shown to possess anti-oxidative capacities which might be linked to the presence of carboxy terminal tyrosine. These findings offer new functional application possibilities in nutrition, cosmetics and pharmaceuticals.
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Abbreviations
- ESI-MS:
-
Electrospray ionisation mass spectrometry
- HILIC:
-
Hydrophilic interaction liquid chromatography
- LC–ESI-MS/MS:
-
Liquid chromatography–electrospray ionisation tandem mass spectrometry
- NMWCO:
-
Nominal molecular weight cut-off
- OPA:
-
o-Phthaldialdehyde
- PES:
-
Polyethersulfone
- RP-HPLC:
-
Reversed-phase high performance liquid chromatography
- SEC:
-
Size exclusion chromatography
- TEAC:
-
Trolox® equivalent anti-oxidative capacity
References
Rodrigo R, Guichard C, Charles R (2007) Clinical pharmacology and therapeutic use of antioxidant vitamins. Fundam Clin Pharmacol 21(2):111–127
Victor VM, Rocha M (2007) Targeting antioxidants to mitochondria: a potential new therapeutic strategy for cardiovascular diseases. Curr Pharm Des 13(8):845–863
Bilska A, Wlodek L (2005) Lipoic acid: the drug of the futures? Acta Biochim Pol 52:656–671
Shoji H, Koletzko B (2007) Oxidative stress and antioxidant protection in the perinatal period. Curr Opin Clin Nutr Metab Care 10(3):324–328
Bounous G, Molson JH (2003) The antioxidant system. Anticancer Res 23(2B):1411–1415
Atmaca G (2004) Antioxidant effects of sulfur-containing amino acids. Yonsei Med J 45(5):776–788
Iwaniak A, Minkiewicz P (2007) Proteins as the source of physiologically and functionally active peptides. Acta Sci Pol Technol Aliment 6(3):5–15
Kitts DD, Weiler K (2003) Bioactive proteins and peptides from food sources. Applications of bioprocessess used in isolation and recovery. Curr Pharm Des 9(16):1309–1323
Maruyama N, Mohamed Salleh MR, Takahashi K, Yagasaki K, Goto H, Hontani N (2002) Structure-physicochemical function relationships of soybean beta-conglyxcinin heterotrimers. J Agric Food Chem 50:4323–4326
Pena-Ramos EA, Xiong YL (2001) Anti-oxidative activity of whey protein hydrolysates in a liposomal system. J Dairy Sci 84:2577–2583
Yokomizo A, Takenaka Y, Takenaka T (2002) Antioxidative activity of peptides prepared from okara protein. Food Sci Technol Res 8(4):357–359
Chen HM, Muramoto K, Yamauchi F, Nokihara K (1996) Antioxidant activity of designed peptides based on the antioxidant peptide isolated from digests of a soybean protein. J Agric Food Chem 44:2619–2623
Korhonen H, Pihlanto A (2003) Food-derived bioactive peptides-opportunities for designing future foods. Curr Pharm Des 9(16):1297–1308
Yamamoto N, Ejiri M, Mizuno S (2003) Biogenic peptides and their potential use. Curr Pharm Des 9(16):1345–1355
Chen I-C, Chang HC, Yang HW, Chen GL (2004) Evaluation of total antioxidant activity of several popular vegetables and Chinese herbs: a fast approach with ABTS/H2O2/HRP system in microplates. J Food Drug Anal 12(1):29–33
Georgi G, Pietsch C, Sawatzki G (1993) High-performance liquid chromatographic determination of amino acids in protein hydrolysates and in plasma using automated pre-column derivatization with o-phthaldialdehyde/2-mercaptoethanol. J Chromatogr 613:35–42
Cole RD, Stein WH, Moore S (1958) On the cysteine content of human hemoglobin. J Biol Chem 233(6):1359–1363
Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85(14):2149–2154
Van Overveld FW, Haenen GR, Rhemrev J, Vermeiden JP, Bast A (2000) Tyrosine as important contributor to the antioxidant capacity of seminal plasma. Chem Biol Interact 127(2):151–161
Chen HM, Muramoto K, Yamauchi F, Fujimoto K, Nokihara K (1998) Anti-oxidative properties of histidine-containing peptides designed from peptide fragments found in the digests of soybean proteins. J Agric Food Chem 46:49–53
Nguyen SD, Jeong TS, Kim MR, Sok DE (2006) Broad-spectrum antioxidant peptides derived from His residue-containing sequences present in human paraoxonase 1. Free Radic Res 40(4):349–358
Deneke SM (2000) Thiol-based antioxidants. Curr Top Cell Regul 36:151–180
Wang W, Gonzalez de Mejia E (2005) A new frontier in soy bioactive peptides that may preventage-related chronic diseases. Compr Rev Food Sci Technol 4:63–78
Erdmann K, Cheung BW, Schröder H (2008) The possible roles of food-derived bioactive peptides in reducing the risk of cardiovascular disease. J Nutr Biochem 19(10):643–654
Block KI, Koch AC, Mead MN, Tothy PK, Newman RA, Gyllenhaal C (2007) Impact of antioxidant supplementation on chemotherapeutic efficacy: a systematic review of the evidence from randomized controlled trials. Cancer Treat Rev 33(5):407–418
Acknowledgment
We are grateful to acknowledge Mrs. Monika Klapperich, and Mr. Michael Möbius (Danone Research, Friedrichsdorf, Germany) for their excellent technical assistance.
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Beermann, C., Euler, M., Herzberg, J. et al. Anti-oxidative capacity of enzymatically released peptides from soybean protein isolate. Eur Food Res Technol 229, 637–644 (2009). https://doi.org/10.1007/s00217-009-1093-1
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DOI: https://doi.org/10.1007/s00217-009-1093-1