Covalent polyphenol modification of a reactive cysteine in the major apple allergen Mal d 1

被引:13
|
作者
Unterhauser, Jana [1 ]
Ahammer, Linda [1 ]
Rainer, Tobias [1 ]
Eidelpes, Reiner [1 ]
Fuehrer, Sebastian [1 ]
Nothegger, Bettina [2 ]
Covaciu, Claudia E. [3 ]
Cova, Valentina [4 ]
Kamenik, Anna S. [5 ]
Liedl, Klaus R. [5 ]
Mueller, Thomas [1 ]
Breuker, Kathrin [1 ]
Eisendle, Klaus [3 ]
Reider, Norbert [2 ]
Letschka, Thomas [4 ]
Tollinger, Martin [1 ]
机构
[1] Univ Innsbruck, Inst Organ Chem, Ctr Mol Biosci Innsbruck CMBI, Innsbruck, Austria
[2] Med Univ Innsbruck, Dept Dermatol Venerol & Allergol, Innsbruck, Austria
[3] Cent Teaching Hosp, Dept Dermatol Venerol & Allergol, Bolzano, Italy
[4] Laimburg Res Ctr, Dept Mol Biol & Microbiol, Ora Auer, Italy
[5] Univ Innsbruck, Inst Gen Inorgan & Theoret Chem, Ctr Mol Biosci Innsbruck CMBI, Innsbruck, Austria
基金
奥地利科学基金会;
关键词
Chlorogenic acid; Chemical modification; Mass spectrometry; Three-dimensional structure; Antigen binding epitope; IGE-BINDING; MASS; CULTIVARS; MAL-D-1; OLD;
D O I
10.1016/j.foodchem.2022.135374
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Naturally occurring polyphenols can modify the molecular properties of food allergens. For the major apple allergen Mal d 1 it has been postulated that chemical reactions with polyphenols cause permanent changes in the tertiary structure, causing a loss of conformational IgE epitopes and reducing allergenicity. In our study, we investigated the effect that reactions with oxidized polyphenols have on the structure of Mal d 1 by mass spectrometry and NMR spectroscopy. We showed that a surface-exposed cysteine residue in this allergen spontaneously reacts with oxidized polyphenols under formation of a defined covalent adduct. Chemical modification of Mal d 1 did not destabilize or perturb the three-dimensional fold, nor did it interfere with ligand binding to its internal pocket. A structural model of the chemically modified apple allergen is presented, which reveals that the bound polyphenol partially covers a conformational IgE epitope on the protein surface.
引用
收藏
页数:9
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