Interaction study between wheat-derived peptides and procyanidin B3 by mass spectrometry

被引:23
作者
Dias, Ricardo [1 ]
Perez-Gregorio, Maria Rosa [1 ]
Mateus, Nuno [1 ]
De Freitas, Victor [1 ]
机构
[1] Univ Porto, Fac Ciencias, Dept Quim & Bioquim, LAQV REQUIMTE, P-4169007 Oporto, Portugal
关键词
Celiac Disease; Gliadin; Tannin; Procyanidin B3; Tannin-protein non-covalent complexes; CELIAC-DISEASE; CONDENSED TANNINS; SALIVARY PROTEINS; GLUTEN; ASTRINGENCY; PROANTHOCYANIDIN; IDENTIFICATION; PRECIPITATION; INTOLERANCE; MECHANISMS;
D O I
10.1016/j.foodchem.2015.08.108
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Tannins have the ability to complex and precipitate proteins, being particularly reactive towards the proline-rich ones. The main structural feature of the wheat peptides responsible for the onset of Celiac Disease (CD) is their high content in proline residues. The aim of this work was to characterize the binding between a common food tannin (procyanidin B3) and different wheat-derived peptidic fractions. For this, seven peptide mixtures were obtained after in vitro digestion of a wheat gliadins crude extract and further characterized by LC-ESI-MS/MS. Several soluble B3-peptide complexes were identified by ESI-MS. The peptides involved in complex formation varied in terms of their size and diversity in CD epitopes. Although binding selectivity of procyanidin B3 towards peptides containing CD epitopes was not found, the major complexes contained or could contain immunoreactive peptides. This study highlights the potential beneficial effects of food polyphenols as a nutritional approach in the modulation of CD. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1304 / 1312
页数:9
相关论文
共 32 条
[1]   The molecular basis for oat intolerance in patients with Celiac disease [J].
Arentz-Hansen, H ;
Fleckenstein, B ;
Molberg, O ;
Scott, H ;
Koning, F ;
Jung, G ;
Roepstorff, P ;
Lundin, KEA ;
Sollid, LM .
PLOS MEDICINE, 2004, 1 (01) :84-92
[2]   FLAVONOID COMPOUNDS IN FOODS [J].
BATESMITH, EC .
ADVANCES IN FOOD RESEARCH, 1954, 5 :261-300
[3]   Inflammatory Disease Processes and Interactions with Nutrition [J].
Calder, P. C. ;
Albers, R. ;
Antoine, J. -M. ;
Blum, S. ;
Bourdet-Sicard, R. ;
Ferns, G. A. ;
Folkerts, G. ;
Friedmann, P. S. ;
Frost, G. S. ;
Guarner, F. ;
Lovik, M. ;
Macfarlane, S. ;
Meyer, P. D. ;
M'Rabet, L. ;
Serafini, M. ;
van Eden, W. ;
van Loo, J. ;
Dias, W. Vas ;
Vidry, S. ;
Winklhofer-Roob, B. M. ;
Zhao, J. .
BRITISH JOURNAL OF NUTRITION, 2009, 101 :S1-+
[4]  
Camarca Alessandra, 2012, Endocrine Metabolic & Immune Disorders-Drug Targets, V12, P207
[5]   Aggregation of the Salivary Proline-Rich Protein IB5 in the Presence of the Tannin EgCG [J].
Canon, Francis ;
Pate, Franck ;
Cheynier, Veronique ;
Sarni-Manchado, Pascale ;
Giuliani, Alexandre ;
Perez, Javier ;
Durand, Dominique ;
Li, Joaquim ;
Cabane, Bernard .
LANGMUIR, 2013, 29 (06) :1926-1937
[6]   Characterization, stoichiometry, and stability of salivary protein-tannin complexes by ESI-MS and ESI-MS/MS [J].
Canon, Francis ;
Pate, Franck ;
Meudec, Emmanuelle ;
Marlin, Therese ;
Cheynier, Veronique ;
Giuliani, Alexandre ;
Sarni-Manchado, Pascale .
ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2009, 395 (08) :2535-2545
[7]   Polyphenol/peptide binding and precipitation [J].
Charlton, AJ ;
Baxter, NJ ;
Khan, ML ;
Moir, AJG ;
Haslam, E ;
Davies, AP ;
Williamson, MP .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (06) :1593-1601
[8]   Structural features of procyanidin interactions with salivary proteins [J].
de Freitas, V ;
Mateus, N .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (02) :940-945
[9]   Protein/Polyphenol Interactions: Past and Present Contributions. Mechanisms of Astringency Perception [J].
de Freitas, Victor ;
Mateus, Nuno .
CURRENT ORGANIC CHEMISTRY, 2012, 16 (06) :724-746
[10]   SYNTHESIS OF CONDENSED TANNINS .9. THE CONDENSATION SEQUENCE OF LEUCOCYANIDIN WITH (+)-CATECHIN AND WITH THE RESULTANT PROCYANIDINS [J].
DELCOUR, JA ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1711-1717