[en] BACKGROUND: Zanthoxylum bungeanum Maxim. (Z. bungeanum) is widely applied in the processing of stewed beef with spices (SBS) to improve sensory quality, yet the processing-induced interactions between its flavonol glycosides and myofibrillar protein (MP) and their role in taste modulation remain poorly understood. In particular, the structural basis and binding behavior underlying protein-flavonol interactions during stewing, as well as their contribution to taste regulation. In this study, metabolomics combined with random forest modeling was employed to screen key taste-active compounds in SBS. The structure-affinity relationship and the mechanism underlying the interaction between flavonol glycosides and MP were investigated using fluorescence spectroscopy, Fourier transform infrared spectroscopy, and molecular docking. RESULTS: The top 15 key taste compounds were identified by a random forest model as significant contributors to flavor enhancement. A subsequent investigation focused on isoquercetin and astragalin due to their notably high variable importance scores and acknowledged chemical relevance. E-tongue results suggest that MP exhibits strong bitterness-masking activity. The interaction of flavonol glycosides (isoquercetin and astragalin) with MP in higher pH environments caused fluorescence quenching. Molecular docking results indicate that variations in the molecular geometries of isoquercetin and astragalin contribute to their distinct binding interactions with bitter taste receptor TAS2R14. CONCLUSIONS: These findings provide mechanistic insight into processing-induced protein-flavonol interactions and offer theoretical guidance for optimizing spice-assisted meat processing strategies and taste quality regulation.
Disciplines :
Agriculture & agronomy Chemistry
Author, co-author :
Wang, Jingfan ; Université de Liège - ULiège > TERRA Research Centre
Jiang, 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
Qiang, Yu; 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
Yang, Ping; ACK Company, XinJiang Uygur Autonomous Region, Ürümqi, China
Huang, Feng ; 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
Chisoro, Prince; 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; Jiangsu Chaoyue Agricultural Development Co. Ltd, Taixing, China
Qi, Chenchen; ACK Company, XinJiang Uygur Autonomous Region, Ürümqi, China
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Département GxABT > Chemistry for Sustainable Food and Environmental Systems (CSFES)
Purcaro, Giorgia ; Université de Liège - ULiège > Département GxABT > Chemistry for Sustainable Food and Environmental Systems (CSFES)
Xia, Shuangmei; Testing Center for Quality Supervision on Agro-Products and Foods, Ministry of Agriculture and Rural Affairs, Beijing, China
Zhang, Chunhui; Jiangsu Huaguoshan Food Co. Ltd, Lianyungang, China
Zhou C-Y, Bai Y, Wang C, Li C-B, Xu X-L, Pan D-D et al., 1H NMR-based metabolomics and sensory evaluation characterize taste substances of Jinhua ham with traditional and modern processing procedures. Food Control 126:107873 (2021).
Ribeiro-Santos R, Andrade M, Madella D, Martinazzo AP, de Aquino Garcia Moura L, de Melo NR et al., Revisiting an ancient spice with medicinal purposes: cinnamon. Trends Food Sci Technol 62:154–169 (2017).
Bader M, Stark TD, Dawid C, Lösch S and Hofmann T, All-trans-configuration in zanthoxylum alkylamides swaps the tingling with a numbing sensation and diminishes salivation. J Agric Food Chem 62:2479–2488 (2014).
Luo J, Ke J, Hou X, Li S, Luo Q, Wu H et al., Composition, structure and flavor mechanism of numbing substances in Chinese prickly ash in the genus Zanthoxylum: a review. Food Chem 373:131454 (2022).
Ke J, Cheng J, Luo Q, Wu H, Shen G and Zhang Z, Identification of two bitter components in Zanthoxylum bungeanum Maxim. and exploration of their bitter taste mechanism through receptor hTAS2R14. Food Chem 338:127816 (2021).
Hu X, Ao W, Gao M, Wu L, Pei Y, Liu S et al., Bitter taste TAS2R14 activation by intracellular tastants and cholesterol. Nature 631:459–466 (2024).
Yang Q, Mei X, Wang Z, Chen X, Zhang R, Chen Q et al., Comprehensive identification of non-volatile bitter-tasting compounds in Zanthoxylum bungeanum Maxim. by untargeted metabolomics combined with sensory-guided fractionation technique. Food Chem 347:129085 (2021).
Li S, Tian Y, Jiang P, Lin Y and Yang H, Recent advances in the application of metabolomics for food safety control and food quality analyses. Crit Rev Food Sci Nutr 61:1448–1469 (2020).
Weckwerth W, Metabolomics in systems biology. Annu Rev Plant Biol 54:669–689 (2003).
Shen N, Wang T, Gan Q, Liu S, Wang L and Jin B, Plant flavonoids: classification, distribution, biosynthesis, and antioxidant activity. Food Chem 383:132531 (2022).
Ma C-M, Zhang N and Zhao X-H, Impact of covalent grafting of two flavonols (kaemperol and quercetin) to caseinate on in vitro digestibility and emulsifying properties of the caseinate-flavonol grafts. Food Chem 390:133210 (2022).
Soares S, Kohl S, Thalmann S, Mateus N, Meyerhof W and De Freitas V, Different phenolic compounds activate distinct human bitter taste receptors. J Agric Food Chem 61:1525–1533 (2013).
Roland WSU, van Buren L, Gruppen H, Driesse M, Gouka RJ, Smit G et al., Bitter taste receptor activation by flavonoids and isoflavonoids: modeled structural requirements for activation of hTAS2R14 and hTAS2R39. J Agric Food Chem 61:10454–10466 (2013).
Homma R, Yamashita H, Funaki J, Ueda R, Sakurai T, Ishimaru Y et al., Identification of bitterness-masking compounds from cheese. J Agric Food Chem 60:4492–4499 (2012).
Tenney K, Hayes J, Euston S, Elias R and Coupland J, Binding of caffeine and quinine by whey protein and the effect on bitterness. J Food Sci 82:509–516 (2017).
Yang Y, Sun Y, Pan D, Wang Y and Cao J, Effects of high pressure treatment on lipolysis-oxidation and volatiles of marinated pork meat in soy sauce. Meat Sci 145:186–194 (2018).
Zhang B, Zhang J, Yu X, Peng J, Pan L and Tu K, Evaluation of the adsorption capacity and mechanism of soy protein isolate for volatile flavor compounds: role of different oxygen-containing functional groups. Food Chem 386:132745 (2022).
He Y, Zhou C, Li C and Zhou G, Effect of incubation temperature on the binding capacity of flavor compounds to myosin. Food Chem 346:128976 (2021).
Sun X, Saleh ASM, Wang Z, Yu Y, Li W and Zhang D, Insights into the interactions between etheric compounds and myofibrillar proteins using multi-spectroscopy, molecular docking, and molecular dynamics simulation. Food Res Int 175:113787 (2024).
Bertram HC, Kristensen M and Andersen HJ, Functionality of myofibrillar proteins as affected by pH, ionic strength and heat treatment – a low-field NMR study. Meat Sci 68:249–256 (2004).
Liu R, Zhao S, Xiong S, Xie B and Qin L, Role of secondary structures in the gelation of porcine myosin at different pH values. Meat Sci 80:632–639 (2008).
Shen H, Zhao M and Sun W, Effect of pH on the interaction of porcine myofibrillar proteins with pyrazine compounds. Food Chem 287:93–99 (2019).
Jinfeng W, Ziyao J, Zhihao Z, Yutong W, Xi L, Linghua W et al., Analysis of chemical constituents of Melastoma dodecandrum lour. by UPLC-ESI-Q-Exactive focus-MS/MS. Molecules 22:476 (2017).
Pang Z, Xu L, Viau C, Lu Y, Salavati R, Basu N et al., MetaboAnalystR 4.0: a unified LC-MS workflow for global metabolomics. Nat Commun 15:3675 (2024).
Li X, Xie X, Wang J, Xu Y, Yi S, Zhu W et al., Identification, taste characteristics and molecular docking study of novel umami peptides derived from the aqueous extract of the clam Meretrix meretrix Linnaeus. Food Chem 312:126053 (2020).
Wang T, Han D, Zhao L, Huang F, Yang P and Zhang C, 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 71:17860–17873 (2023).
Pan X, Liu R, Qin P, Wang L and Zhao X, Spectroscopic studies on the interaction of acid yellow with bovine serum albumin. J Lumin 130:611–617 (2010).
Liu Y, Yang X, Gan J, Chen S, Xiao Z-X and Cao Y, CB-Dock2: improved protein-ligand blind docking by integrating cavity detection, docking and homologous template fitting. Nucleic Acids Res 50:W159–W164 (2022).
Zhang Y, Wang D, Yang L, Zhou D and Zhang J, Purification and characterization of flavonoids from the leaves of Zanthoxylum bungeanum and correlation between their structure and antioxidant activity. PLoS One 9:e105725 (2014).
Drewnowski A and Gomez-Carneros C, Bitter taste, phytonutrients, and the consumer: a review. Am J Clin Nutr 72:1424–1435 (2000).
Dixon RA and Paiva NL, Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085–1097 (1995).
Siddique MAB, Maresca P, Pataro G and Ferrari G, Effect of pulsed light treatment on structural and functional properties of whey protein isolate. Food Res Int 87:189–196 (2016).
Rawel HM, Czajka D, Rohn S and Kroll J, Interactions of different phenolic acids and flavonoids with soy proteins. Int J Biol Macromol 30:137–150 (2002).
Zhang D, Li H, Emara AM, Hu Y, Wang Z, Wang M et al., Effect of in vitro oxidation on the water retention mechanism of myofibrillar proteins gel from pork muscles. Food Chem 315:126226 (2020).
Du X, Chang P, Tian J, Kong B, Sun F and Xia X, Effect of ice structuring protein on the quality, thermal stability and oxidation of mirror carp (Cyprinus carpio L.) induced by freeze-thaw cycles. LWT 124:109140 (2020).
Acevedo W, González-Nilo F and Agosin E, Docking and molecular dynamics of Steviol glycoside–human bitter receptor interactions. J Agric Food Chem 64:7585–7596 (2016).
Huang F, Pan F, Wang L, Xiao Z, He J, Yan M et al., The interaction between citronellol and bovine serum albumin: spectroscopic, computational and thermal imaging studies. J Mol Struct 1251:131986 (2022).
Barallat-Pérez C, Janssen H-G, Martins S, Fogliano V and Oliviero T, Unraveling the role of flavor structure and physicochemical properties in the binding phenomenon with commercial food protein isolates. J Agric Food Chem 71:20274–20284 (2023).
Zhao S, Yang L, Hei M, Zhao Y, Zhu M, Wang H et al., Conformation and functional modification of porcine myofibrillar protein by pepper leaf polyphenols under oxidative condition. LWT 198:116017 (2024).
Cheng J, Zhu M and Liu X, Insight into the conformational and functional properties of myofibrillar protein modified by mulberry polyphenols. Food Chem 308:125592 (2020).
He C, Bai L, Liu D and Liu B, Interaction mechanism of okra (Abelmoschus esculentus L.) seed protein and flavonoids: fluorescent and 3D-QSAR studies. Food Chem X 20:101023 (2023).
Fu M, Gao L, Geng Q, Li T, Dai T, Liu C et al., Noncovalent interaction mechanism and functional properties of flavonoid glycoside-β-lactoglobulin complexes. Food Funct 14:1357–1368 (2023).
Chen J, He Z, Qin F, Chen J and Zeng M, Formation of free and protein-bound heterocyclic amines in roast beef patties assessed by UPLC-MS/MS. J Agric Food Chem 65:4493–4499 (2017).
Takeuchi K and Wagner G, NMR studies of protein interactions. Curr Opin Struct Biol 16:109–117 (2006).
Leavitt S and Freire E, Direct measurement of protein binding energetics by isothermal titration calorimetry. Curr Opin Struct Biol 11:560–566 (2001).
Richter P, Sebald K, Fischer K, Behrens M, Schnieke A and Somoza V, Bitter peptides YFYPEL, VAPFPEVF, and YQEPVLGPVRGPFPIIV, released during gastric digestion of casein, stimulate mechanisms of gastric acid secretion via bitter taste receptors TAS2R16 and TAS2R38. J Agric Food Chem 70:11591–11602 (2022).