[en] This investigation aimed to clarify the binding mechanisms between six aldehydes and myofibrillar proteins (MPs), with a structural explanation in response to stage-heating treatments. The conformational intermediates of MPs, which form during heat processing, were systematically characterized to elucidate their role in aldehyde binding and flavor retention. Machine learning results suggested that high-temperature boiling promoted extensive protein denaturation and aggregation, while subsequent low-temperature stewing induced partial rearrangement. Thermodynamic parameters indicated that hexanal–MPs formation was primarily driven by hydrogen bonding, whereas other longer-chain and unsaturated aldehydes penetrated hydrophobic pockets. Proteomics revealed that saturated aldehydes predominantly formed Schiff bases with the lysine ε-amino group. Unsaturated aldehydes, especially (E, E)-2,4-decadienal, undergo both Schiff base reactions and Michael addition with cysteine, histidine, and tryptophan residues. The retention/release behavior of aldehydes during processing is determined by covalent and non-covalent interactions. These results provide a scientific basis for precisely controlling flavor quality in meat products.
Disciplines :
Agriculture & agronomy Chemistry
Author, co-author :
Wang, Jingfan ; Université de Liège - ULiège > TERRA Research Centre ; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Wang, Tianze
Yang, Ping; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Han, Dong; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Zhang, Chunhui; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Jia, Wei; Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, China
Purcaro, Giorgia ; Université de Liège - ULiège > Département GxABT > Chemistry for Sustainable Food and Environmental Systems (CSFES)
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Département GxABT > Chemistry for Sustainable Food and Environmental Systems (CSFES)
Language :
English
Title :
Novel insights into the binding mechanisms of selected aldehydes during heat-induced protein unfolding S
Wang J et al. Study of the flavor dissipation mechanism of soy-sauce-marinated beef using flavor matrices Food Chem. 2024 437 1:CAS:528:DC%2BB3sXitlWkur%2FO 10.1016/j.foodchem.2023.137890 37926031 137890
Sohail A et al. Aroma compounds identified in cooked meat: a review Food Res. Int. 2022 157 1:CAS:528:DC%2BB38XitF2lu7bN 10.1016/j.foodres.2022.111385 35761641 111385
Bleicher J Ebner EE Bak KH Formation and analysis of volatile and odor compounds in meat—A review Molecules 2022 27 6703 1:CAS:528:DC%2BB38Xis1ymu7bK 10.3390/molecules27196703 36235239 9572956
Dou P Feng X Cheng X Guan Q Chen L Binding of aldehyde flavour compounds to beef myofibrillar proteins and the effect of nonenzymatic glycation with glucose and glucosamine LWT Food Sci. Technol. 2021 144 111198 1:CAS:528:DC%2BB3MXms1Kkt7Y%3D 10.1016/j.lwt.2021.111198
Lv T et al. Effect of trypsin treatments on the structure and binding capacity of volatile compounds of myosin Food Chem. 2017 214 710 716 1:CAS:528:DC%2BC28Xht1Glt7rF 10.1016/j.foodchem.2016.07.115 27507529
Di C Jia W Capture modes evaluation of four flavor constituents in β-lactoglobulin by high-resolution mass spectrometry and molecular dynamics simulation approaches Food Hydrocoll. 2023 145 109157 1:CAS:528:DC%2BB3sXhs1Gqt7%2FO 10.1016/j.foodhyd.2023.109157
Wang, T. et al. Binding of selected aroma compounds to myofibrillar protein, sarcoplasmic protein, and collagen during thermal treatment: role of conformational changes and degradation of proteins. J. Agric. Food Chem. https://doi.org/10.1021/acs.jafc.3c02618 (2023).
He Y Zhou C Li C Zhou G Effect of incubation temperature on the binding capacity of flavor compounds to myosin Food Chem. 2021 346 128976 1:CAS:528:DC%2BB3MXhsVGktbg%3D 10.1016/j.foodchem.2020.128976 33476948
Zhang, J., Kang, D., Zhang, W. & Lorenzo, J. M. Recent advantage of interactions of protein-flavor in foods: Perspective of theoretical models, protein properties and extrinsic factors. Trends Food Sci. Technol.111, 405–425 (2021).
Anantharamkrishnan V Hoye T Reineccius GA Covalent adduct formation between flavor compounds of various functional group classes and the model protein β-lactoglobulin J. Agric. Food Chem. 2020 68 6395 6402 1:CAS:528:DC%2BB3cXovFyhu7Y%3D 10.1021/acs.jafc.0c01925 32390422
Wang T et al. Unraveling the covalent binding mechanisms of aroma compounds with porcine proteins: a mass spectrometry, proteomics, and conformational analysis approach Food Chem. 2025 493 145913 1:CAS:528:DC%2BB2MXitVaqurbJ 10.1016/j.foodchem.2025.145913 40840383
Wang K Arntfield SD Modification of interactions between selected volatile flavour compounds and salt-extracted pea protein isolates using chemical and enzymatic approaches Food Hydrocoll. 2016 61 567 577 1:CAS:528:DC%2BC28XhtVagsL3F 10.1016/j.foodhyd.2016.05.040
Lund MN Heinonen M Baron CP Estévez M Protein oxidation in muscle foods: a review Mol. Nutr. Food Res. 2011 55 83 95 1:CAS:528:DC%2BC3MXpvVSk 10.1002/mnfr.201000453 21207515
Jackson PA Widen JC Harki DA Brummond KM Covalent modifiers: a chemical perspective on the reactivity of α,β-unsaturated carbonyls with thiols via hetero-michael addition reactions J. Med Chem. 2017 60 839 885 1:CAS:528:DC%2BC28XitV2rtbnM 10.1021/acs.jmedchem.6b00788 27996267
Ouellette, R. J. & Rawn, J. D. Aldehydes and ketones. in Organic Chemistry 629–657 https://doi.org/10.1016/B978-0-12-800780-8.00019-X (Elsevier, 2014).
Chen L et al. Production of branched-chain flavor compounds from hydrolysis of pork myofibrillar protein by optimizing the inoculation of Limosilactobacillus fermentum YZU-06 and Staphylococcus saprophyticus CGMCC 3475 LWT 2023 189 1:CAS:528:DC%2BB3sXisVSntrrJ 10.1016/j.lwt.2023.115512 115512
Wang J Zhao M Qiu C Sun W Effect of malondialdehyde modification on the binding of aroma compounds to soy protein isolates Food Res. Int. 2018 105 150 158 1:CAS:528:DC%2BC2sXhvVCjsrjN 10.1016/j.foodres.2017.11.001 29433202
Xu L et al. A structural explanation for enhanced binding behaviors between β-lactoglobulin and alkene-aldehydes upon heat- and ultrasonication-induced protein unfolding Food Hydrocoll. 2022 130 1:CAS:528:DC%2BB38XosFymu7c%3D 10.1016/j.foodhyd.2022.107682 107682
Ju Q et al. Heat-induced aggregation of subunits/polypeptides of soybean protein: structural and physicochemical properties Food Chem. 2023 405 1:CAS:528:DC%2BB38XivVegt7rP 10.1016/j.foodchem.2022.134774 36370559 134774
Chen H et al. Exploring in vitro gastrointestinal digestion of myofibrillar proteins at different heating temperatures Food Chem. 2023 414 1:CAS:528:DC%2BB3sXjsFGgsr8%3D 10.1016/j.foodchem.2023.135694 36808027 135694
Dockal M Carter DC Rüker F Conformational transitions of the three recombinant domains of human serum albumin depending on pH* J. Biol. Chem. 2000 275 3042 3050 1:CAS:528:DC%2BD3cXhtVyhtLw%3D 10.1074/jbc.275.5.3042 10652284
Hendy A et al. Enhancement of biological properties in casein protein through functionalization with cinnamaldehyde via Schiff base bonding: antibacterial and antioxidant effects RSC Adv. 2025 15 27300 27310 1:CAS:528:DC%2BB2MXhvVSnsbbK 10.1039/D5RA00852B 40746786 12312107
Kobayashi Y Mayer SG Park JW Gelation properties of tilapia fish protein isolate and surimi pre- and post-rigor: Rigor condition of tilapia FPI and surimi Food Biosci. 2017 17 17 23 1:CAS:528:DC%2BC2sXnt1Gisrc%3D 10.1016/j.fbio.2016.11.001
Cao H et al. Microwave irradiation promotes aggregation behavior of myosin through conformation changes Food Hydrocoll. 2019 96 11 19 1:CAS:528:DC%2BC1MXptlagsbs%3D 10.1016/j.foodhyd.2019.05.002
Zhou F Zhao M Cui C Sun W Influence of linoleic acid-induced oxidative modifications on physicochemical changes and in vitro digestibility of porcine myofibrillar proteins LWT Food Sci. Technol. 2015 61 414 421 1:CAS:528:DC%2BC2MXkslaqsw%3D%3D 10.1016/j.lwt.2014.12.037
Yang QL et al. Effect of pH on the interaction of volatile compounds with the myofibrillar proteins of duck meat Poult. Sci. 2017 96 1963 1969 1:CAS:528:DC%2BC1cXitFSnur3E 10.3382/ps/pew413 27915269
Bortnowska G Aroma compounds retention and release from protein-polysaccharide-based bilayer emulsion gels: a thermodynamic and kinetic study Food Hydrocoll. 2024 150 1:CAS:528:DC%2BB3sXis1yks7%2FF 10.1016/j.foodhyd.2023.109648 109648
Yu, Y. et al. Exploring the interaction between myofibrillar proteins and pyrazine compounds: Based on molecular docking, molecular dynamics simulation, and multi-spectroscopy techniques. Int. J. Biol. Macromol.253, 126844 (2023).
Rahman N et al. Multispectroscopic and molecular docking studies on the interaction of diltiazem hydrochloride with bovine serum albumin and its application to the quantitative determination of diltiazem hydrochloride J. King Saud. Univ. Sci. 2022 34 10.1016/j.jksus.2022.102267 102267
Wei M et al. Investigating the interactions between selected heterocyclic flavor compounds and beef myofibrillar proteins using SPME-GC–MS, spectroscopic, and molecular docking approaches J. Mol. Liq. 2024 403 1:CAS:528:DC%2BB2cXpvFOhurs%3D 10.1016/j.molliq.2024.124878 124878
Bi S et al. Non-covalent interactions of selected flavors with pea protein: Role of molecular structure of flavor compounds Food Chem. 2022 389 1:CAS:528:DC%2BB38XhtFGntr7N 10.1016/j.foodchem.2022.133044 35489259 133044
Bi K et al. Exploring the off-flavour removal mechanism of d-limonene, geraniol and acetophenone in perilla leaves from the perspective of molecular structure and kinetic properties Food Chem. 2025 480 1:CAS:528:DC%2BB2MXntV2nurw%3D 10.1016/j.foodchem.2025.143938 40138830 143938
Li C Xiong YL Chen J Oxidation-induced unfolding facilitates Myosin cross-linking in myofibrillar protein by microbial transglutaminase J. Agric Food Chem. 2012 60 8020 8027 1:CAS:528:DC%2BC38XhtVeqtrjO 10.1021/jf302150h 22809283
Yang T et al. Novel insights into interfacial effects on α, β-unsaturated aldehyde-induced modifications of milk proteins and polyphenol interventions in multiphase food systems Food Hydrocoll. 2026 172 1:CAS:528:DC%2BB2MXitlaksr7M 10.1016/j.foodhyd.2025.111962 111962
Snel SJE et al. Flavor-protein interactions for four plant protein isolates and whey protein isolate with aldehydes LWT 2023 185 1:CAS:528:DC%2BB3sXhslSlsr7M 10.1016/j.lwt.2023.115177 115177
Li W Wu Y Li C Zhu L Effect of (E,E)-2,4-decadienal on side-chain modification, conformation change, and aggregation of bovine serum albumin Eur. J. Lipid Sci. Technol. 2022 124 2100066 1:CAS:528:DC%2BB3MXisFGjt7nP 10.1002/ejlt.202100066
Chu Y Ding Z Xie J Molecular mechanism of the impact of lipid oxidation products (2,4-decadienal) on the conformation of grouper (Epinephelus coioides) myofibrillar proteins during refrigeration and its implications on the overall protein flavor Food Bioprocess Technol. 2024 17 5299 5311 1:CAS:528:DC%2BB2cXht1Git7%2FF 10.1007/s11947-024-03439-4
Wang K Arntfield SD Probing the molecular forces involved in binding of selected volatile flavour compounds to salt-extracted pea proteins Food Chem. 2016 211 235 242 1:CAS:528:DC%2BC28XotFalsrs%3D 10.1016/j.foodchem.2016.05.062 27283627
Gong S et al. Study on the interaction mechanism of purple potato anthocyanins with casein and whey protein Food Hydrocoll. 2021 111 1:CAS:528:DC%2BB3cXhs1KkurzE 10.1016/j.foodhyd.2020.106223 106223
Anantharamkrishnan V Reineccius GA Influence of pH, temperature, and water activity on covalent adduct formation between selected flavor compounds and model protein βlactoglobulin J. Agric. Food Chem. 2020 68 13833 13843 1:CAS:528:DC%2BB3cXit1ynsb%2FO 10.1021/acs.jafc.0c06752 33170688
Yu Y et al. Spice aldehydes improve emulsification stability of β-carotene by Schiff base reaction binding sodium caseinate as emulsion surface stabilizer Food Chem. 2025 475 1:CAS:528:DC%2BB2MXjsFOmtrk%3D 10.1016/j.foodchem.2025.143305 39946924 143305
Miles AJ Ramalli SG Wallace BA DichroWeb, a website for calculating protein secondary structure from circular dichroism spectroscopic data Protein Sci. 2022 31 37 46 1:CAS:528:DC%2BB3MXhs1Shtb%2FO 10.1002/pro.4153 34216059
Wang J et al. Elucidation of molecular interactions between selected phenylpropanoids and myofibrillar protein: Conformational remodeling and machine learning analysis Food Res. Int. 2026 228 1:CAS:528:DC%2BB28XhtFCqtbY%3D 10.1016/j.foodres.2025.118268 41703802 118268
Ewald JD et al. Web-based multi-omics integration using the Analyst software suite Nat. Protoc. 2024 19 1467 1497 1:CAS:528:DC%2BB2cXjs1amu78%3D 10.1038/s41596-023-00950-4 38355833