植物多酚与蛋白质互作机制表征方法研究进展
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摘要
多酚化合物是食物中对人体健康有促进作用的功能活性成分,其功能作用的发挥与食物中其他营养成分(如蛋白质、多糖)之间的相互作用密切相关。为深入研究食品加工过程中功能营养成分的相互作用与变化,本文综述了多酚与蛋白质的相互作用机制及表征方法,包括荧光光谱法、傅里叶变换红外光谱法、拉曼光谱法、圆二色谱、等温滴定量热法、核磁共振法、原子力显微镜、激光扫描共聚焦显微镜、分子对接和分子动态模拟等。多酚与蛋白质之间的相互作用主要是氢键、疏水相互作用、静电相互作用和范德华力,应用多种表征方法可全面地解析植物多酚与蛋白质相互作用机制。
Polyphenols are functional active ingredients in foods that promote human health. Their functional roles are closely related to their interactions between other nutrients in food,such as proteins and polysaccharides. In order to study interactions and changes in functional nutrients during food processing,this paper reviewed interactions between polyphenols and proteins,as well as the interaction mechanisms and characterization methods,including fluorescence spectroscopy,FT-IR,raman spectroscopy,circular dichroism spectroscopy,isothermal titration calorimetry,nuclear magnetic resonance,atomic force microscopy,laser scanning confocal microscope,molecular docking,and molecular dynamic simulation,etc. The review found that interactions between polyphenols and proteins are mainly by hydrogen bonds,hydrophobic interactions,electrostatic interactions,and van der Waals force. Besides,using a variety of characterization methods can fully analyze the mechanisms between plant polyphenols and proteins.
Polyphenols are functional active ingredients in foods that promote human health. Their functional roles are closely related to their interactions between other nutrients in food,such as proteins and polysaccharides. In order to study interactions and changes in functional nutrients during food processing,this paper reviewed interactions between polyphenols and proteins,as well as the interaction mechanisms and characterization methods,including fluorescence spectroscopy,FT-IR,raman spectroscopy,circular dichroism spectroscopy,isothermal titration calorimetry,nuclear magnetic resonance,atomic force microscopy,laser scanning confocal microscope,molecular docking,and molecular dynamic simulation,etc. The review found that interactions between polyphenols and proteins are mainly by hydrogen bonds,hydrophobic interactions,electrostatic interactions,and van der Waals force. Besides,using a variety of characterization methods can fully analyze the mechanisms between plant polyphenols and proteins.
引文
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[11]JAKOBEK L.Interactions of polyphenols with carbohydrates,lipids and proteins[J].Food Chemistry,2015,175:556-567.
[12]ISHII T,MORI T,TANAKA T,et al.Covalent modification of proteins by green tea polyphenol(-)-epigallocatechin-3-gallate through autoxidation[J].Free Radical Biology and Medicine,2008,45:1 384-1 394.
[13]JALDAPPAGARI S,BALAKRISHNAN S,HEGDE A H,et al.Interactions of polyphenols with plasma proteins:insights from analytical techniques[J].Current Drug Metabolism,2013,14:456-473.
[14]XIAO Jianbo,KAI Guoyin.A review of dietary polyphenol-plasma protein interactions:characterization,influence on the bioactivity,and structure-affinity relationship[J].Food Science and Nutrition,2012,52:85-101.
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[16]JIA Jingjing,GAO Xin,HAO Minghao,et al.Comparison of binding interaction betweenβ-lactoglobulin and three common polyphenols using multi-spectroscopy and modeling methods[J].Food Chemistry,2017,228:143-151.
[17]KONG Jilie,YU Shaoning.Fourier transform infrared spectroscopic analysis of protein secondary structures[J].Acta Biochimica et Biophysica Sinica,2007,39(8):549-559.
[18]BYLER D M,BROUILLETTE J N,SUS H.Quantitative studies of protein structure by FT-IR spectra deconvolution and curve-fitting[J].Spectroscopy,1986,1(3):29-32.
[19]ZOU Yuan,GUO Jian,YIN Shouwei,et al.Pickering emulsion gels prepared by hydrogen-bonded zein/tannic acid complex colloidal particles[J].Journal of Agriculture and Food Chemistry,2015,63(33):7 405-7 414.
[20]ZHOU Changyan,ZHANG Huiping,YAN Ying,et al.17O NMR and raman spectroscopies of green tea infusion with nanomaterial to investigate their properties[J].Journal of Aoac International,2016,99(5):1 377-1 380.
[21]LIU Fuguo,MA Da,LUO Xiang,et al.Fabrication and characterization of protein-phenolic conjugate nanoparticles for co-delivery of curcumin and resveratrol[J].Food Hydrocolloids,2018,79:450-461.
[22]XU Lihui,TU Sidong,CHEN Congheng,et al.Effect of EGCG on Fe(III)-induced conformational transition of silk fibroin,a model of protein related to neurodegenerative diseases[J].Biopolymers,2016,105(2):100-107.
[23]ULRIH N P.Analytical techniques for the study of polyphenol-protein interactions[J].Critical Reviews in Food Science and Nutrition,2017,57(10):2 144-2 161.
[24]YAO Han,WYNENDAELE E,XU Xiaolong,et al.Circular dichroism in functional quality evaluation of medicines[J].Journal of Pharmaceutical and Biomedical A-nalysis,2018,147:50-64.
[25]TANG Jianhong,LIAN Ning.Simple and sensitive spectrofluorometric method for the determination of protein using an europium-thenoyl-trifluoroacetone probe[J].Analytical Science,2009,25:1 237-1 242.
[26]ALULA M T,MENGESHA Z T,MWENESONGOLE E,Advances in surface-enhanced Raman spectroscopy for analysis of pharmaceuticals:A review[J].Vibrational Spectroscopy,2018,98:50-63.
[27]MURRAY N J,WILLIAMSON M P,LILLEY T H,et al.Study of the interaction between salivary proline-rich proteins and a polyphenol by1H-NMR spectroscopy[J].European Journal of Biochemistry,1994,219:923-935.
[28]SIMARD J R,ZUNSZAIN P A,BHAGAVAN N V,et al.Locating high-affinity fatty acid-binding sites on albumin by x-ray crystallography and NMR spectroscopy[J].Proceedings of the National Academy of Sciences,2005,102(179):58-63.
[29]DELIUS J,FRANK O,HOFMANN T.Label-free quantitative 1H NMR spectroscopy to study low-affinity ligandprotein interactions in solution:A contribution to the mechanism of polyphenol-mediated astringency[J].Plos One,2017,12(9):e0184487.
[30]樊艳华.表面等离子共振技术和荧光光谱法研究生物分子相互作用[D].太原:山西大学,2011.
[31]CANOA P,RIVADULLA M L,POPPLEWELL J,et al.Use of surface plasmon resonance in the binding study of vitamin D,metabolites and analogues with vitamin Dbinding protein[J].Analytical&Bioanalytical Chemistry,2017,409(10):2 547-2 558.
[32]KHANSILI N,RATTU G,KRISHNA P M.Label-free optical biosensors for food and biological sensor applications[J].Sensors&Actuators B Chemical,2018,265:35-49.
[33]PARK J Y,YUK H J,RYU H W,et al.Evaluation of polyphenols from Broussonetia papyriferaas coronavirus protease inhibitors[J].Journal of Enzyme Inhibition&Medicinal Chemistry,2017,32(1):504-512.
[34]SABOURY A A.A review on the ligand binding studies by isothermal titration calorimetry[J].Journal of the Iranian Chemical Society,2006,3(1):1-21.
[35]FARAH J S,SILVA M C,CRUZ A G,et al.Differential calorimetry scanning:current background and application in authenticity of dairy products[J].Current Opinion in Food Science,2018,22:88-94.
[36]SUN Lijun,GIDLEY M J,WARREN F J.The mechanism of interactions between tea polyphenols and porcine pancreatic alpha-amylase:Analysis by inhibition kinetics,fluorescence quenching,differential scanning calorimetry and isothermal titration calorimetry[J].Molecular Nutrition and Food Research,2017,61(10):1-13.
[37]BINNIG G,QUATE C F,GERBER C.Atomic force microscope[J].Physical Review Letters,1986,56:930-933.
[38]张曼,王岸娜,吴立根,等.蛋白质、多糖和多酚间相互作用及研究方法[J].粮食与油脂,2015,28(4):42-46.
[39]SUN Cuixia,XU Chenqi,MAO Like,et al.Preparation,characterization and stability of curcumin-loaded zeinshellac composite colloidal particles[J].Food Chemistry,2017,228:656-667.
[40]刘淑萍.现代仪器分析方法及应用[M].北京:中国质检出版社,2013.
[41]SNEDDON G C,TRIMBY P W,CAIRNEY J M.Transmission Kikuchi diffraction in a scanning electron microscope:A review[J].Materials Science&Engineering RReports,2016,110:1-12.
[42]刘海学.现代仪器分析技术[M].北京:中国农业出版社,2011.
[43]MERSON E,DANILOV V,MERSON D,et al.Confocal laser scanning microscopy:The technique for quantitative fractographic analysis[J].Engineering Fracture Mechanics,2017,183:147-158.
[44]PYGALL S R,WHETSTONE J,TIMMINS P,et al.Pharmaceutical applications of confocal laser scanning microscopy:the physical characterisation of pharmaceutical systems[J].Advanced Drug Delivery Reviews,2007,59(14):1 434-1 452.
[45]庄绪静,曹雅忠,李克斌,等.同源建模和分子对接方法的应用与发展[C].中国植物保护学会2011年学术年会,2011.
[46]GUPTA M,SHARMA R,SINGH M,et al.Docking techniques in pharmacology:How much promising?[J].Computational Biology and Chemistry,2018,76:210-217.
[47]LI Ti,HU Peng,DAI Taotao,et al.Comparing the binding interaction betweenβ-lactoglobulin and flavonoids with different structure by multi-spectroscopy analysis and molecular docking[J].Spectrochimica Acta Part A Molecular&Biomolecular Spectroscopy,2018,201:197-206.
[48]HOLLINGSWORTH,SCOTT A D,RON O,Molecular dynamics simulation for all[J].Neuron,2018,99(6):1 129-1 143.
[49]MITSUTAKE A,TAKANO H.Relaxation mode analysis for molecular dynamics simulations of proteins[J].Biophysical Reviews,2018,10(2):375-389.
[50]ZHANG Jingxiao,ZHANG Lilei,XU Yangcheng,et al.Deciphering the binding behavior of flavonoids to the cyclin dependent kinase 6/cyclin D complex[J].PLo S One,2018,13(5):1-18.
[2]LUO Wei,XIAO Gao,TIAN Fan,et al.Engineering robust metal-phenolic network membranes for uranium extraction from seawater[J].Energy&Environmental Science,2019,DOI:10.1039/c8ee01438h.
[3]GUO Junling,PING Yuan,EJIMA H,et al.Engineering multifunctional capsules through the assembly of metal-phenolic networks[J].Angewandte Chemie,2014,126(22):5 652-5 657.
[4]石碧,狄莹.植物多酚[M].北京:中国科学技术出版社,2000.
[5]KASPCHAK E,MAFRA L I,MAFRA M R.Effect of heating and ionic strength on the interaction of bovine serum albumin and the antinutrients tannic and phytic acids,and its influence on in vitro protein digestibility[J].Food Chemistry,2018,252:1-8.
[6]AL-SHABIB N A,KHAN J M,MALIK A,et al.Molecular insight into binding behavior of polyphenol(rutin)with beta lactoglobulin:Spectroscopic,molecular docking and MD simulation studies[J].Journal of Molecular Liquids,2018,269:511-520.
[7]GUO Nihong,WANG Cailian,SHANG Chao,et al.Integrated study of the mechanism of tyrosinase inhibition by baicalein using kinetic,multispectroscopic and computational simulation analyses[J].International Journal of Biological Macromolecules,2018,118:57-68.
[8]PRODPRAN T,BENJAKUL S,PHATECHARAT S.Effect of phenolic compounds on protein cross-linking and properties of film from fish myofibrillar protein[J].International Journal of Biological Macromolecules,2012,51:774-782.
[9]SUI Xiaonan,SUN Hongbo,QI Baokun,et al.Functional and conformational changes to soy proteins accompanying anthocyanins:Focus on covalent and non-covalent interactions[J].Food Chemistry,2018,245:871-878.
[10]ASANO K,SHINAGAGAWA K,HASHIMOTO N.Characterization of haze-forming proteins of beer and their roles in chill haze formation[J].Journal of the American Society of Brewing Chemists,1982,40:147-154.
[11]JAKOBEK L.Interactions of polyphenols with carbohydrates,lipids and proteins[J].Food Chemistry,2015,175:556-567.
[12]ISHII T,MORI T,TANAKA T,et al.Covalent modification of proteins by green tea polyphenol(-)-epigallocatechin-3-gallate through autoxidation[J].Free Radical Biology and Medicine,2008,45:1 384-1 394.
[13]JALDAPPAGARI S,BALAKRISHNAN S,HEGDE A H,et al.Interactions of polyphenols with plasma proteins:insights from analytical techniques[J].Current Drug Metabolism,2013,14:456-473.
[14]XIAO Jianbo,KAI Guoyin.A review of dietary polyphenol-plasma protein interactions:characterization,influence on the bioactivity,and structure-affinity relationship[J].Food Science and Nutrition,2012,52:85-101.
[15]姜涌明,罗贵民,李惟,等.蛋白质分子基础(第二版)[M].北京:人民教育出版社,1982.
[16]JIA Jingjing,GAO Xin,HAO Minghao,et al.Comparison of binding interaction betweenβ-lactoglobulin and three common polyphenols using multi-spectroscopy and modeling methods[J].Food Chemistry,2017,228:143-151.
[17]KONG Jilie,YU Shaoning.Fourier transform infrared spectroscopic analysis of protein secondary structures[J].Acta Biochimica et Biophysica Sinica,2007,39(8):549-559.
[18]BYLER D M,BROUILLETTE J N,SUS H.Quantitative studies of protein structure by FT-IR spectra deconvolution and curve-fitting[J].Spectroscopy,1986,1(3):29-32.
[19]ZOU Yuan,GUO Jian,YIN Shouwei,et al.Pickering emulsion gels prepared by hydrogen-bonded zein/tannic acid complex colloidal particles[J].Journal of Agriculture and Food Chemistry,2015,63(33):7 405-7 414.
[20]ZHOU Changyan,ZHANG Huiping,YAN Ying,et al.17O NMR and raman spectroscopies of green tea infusion with nanomaterial to investigate their properties[J].Journal of Aoac International,2016,99(5):1 377-1 380.
[21]LIU Fuguo,MA Da,LUO Xiang,et al.Fabrication and characterization of protein-phenolic conjugate nanoparticles for co-delivery of curcumin and resveratrol[J].Food Hydrocolloids,2018,79:450-461.
[22]XU Lihui,TU Sidong,CHEN Congheng,et al.Effect of EGCG on Fe(III)-induced conformational transition of silk fibroin,a model of protein related to neurodegenerative diseases[J].Biopolymers,2016,105(2):100-107.
[23]ULRIH N P.Analytical techniques for the study of polyphenol-protein interactions[J].Critical Reviews in Food Science and Nutrition,2017,57(10):2 144-2 161.
[24]YAO Han,WYNENDAELE E,XU Xiaolong,et al.Circular dichroism in functional quality evaluation of medicines[J].Journal of Pharmaceutical and Biomedical A-nalysis,2018,147:50-64.
[25]TANG Jianhong,LIAN Ning.Simple and sensitive spectrofluorometric method for the determination of protein using an europium-thenoyl-trifluoroacetone probe[J].Analytical Science,2009,25:1 237-1 242.
[26]ALULA M T,MENGESHA Z T,MWENESONGOLE E,Advances in surface-enhanced Raman spectroscopy for analysis of pharmaceuticals:A review[J].Vibrational Spectroscopy,2018,98:50-63.
[27]MURRAY N J,WILLIAMSON M P,LILLEY T H,et al.Study of the interaction between salivary proline-rich proteins and a polyphenol by1H-NMR spectroscopy[J].European Journal of Biochemistry,1994,219:923-935.
[28]SIMARD J R,ZUNSZAIN P A,BHAGAVAN N V,et al.Locating high-affinity fatty acid-binding sites on albumin by x-ray crystallography and NMR spectroscopy[J].Proceedings of the National Academy of Sciences,2005,102(179):58-63.
[29]DELIUS J,FRANK O,HOFMANN T.Label-free quantitative 1H NMR spectroscopy to study low-affinity ligandprotein interactions in solution:A contribution to the mechanism of polyphenol-mediated astringency[J].Plos One,2017,12(9):e0184487.
[30]樊艳华.表面等离子共振技术和荧光光谱法研究生物分子相互作用[D].太原:山西大学,2011.
[31]CANOA P,RIVADULLA M L,POPPLEWELL J,et al.Use of surface plasmon resonance in the binding study of vitamin D,metabolites and analogues with vitamin Dbinding protein[J].Analytical&Bioanalytical Chemistry,2017,409(10):2 547-2 558.
[32]KHANSILI N,RATTU G,KRISHNA P M.Label-free optical biosensors for food and biological sensor applications[J].Sensors&Actuators B Chemical,2018,265:35-49.
[33]PARK J Y,YUK H J,RYU H W,et al.Evaluation of polyphenols from Broussonetia papyriferaas coronavirus protease inhibitors[J].Journal of Enzyme Inhibition&Medicinal Chemistry,2017,32(1):504-512.
[34]SABOURY A A.A review on the ligand binding studies by isothermal titration calorimetry[J].Journal of the Iranian Chemical Society,2006,3(1):1-21.
[35]FARAH J S,SILVA M C,CRUZ A G,et al.Differential calorimetry scanning:current background and application in authenticity of dairy products[J].Current Opinion in Food Science,2018,22:88-94.
[36]SUN Lijun,GIDLEY M J,WARREN F J.The mechanism of interactions between tea polyphenols and porcine pancreatic alpha-amylase:Analysis by inhibition kinetics,fluorescence quenching,differential scanning calorimetry and isothermal titration calorimetry[J].Molecular Nutrition and Food Research,2017,61(10):1-13.
[37]BINNIG G,QUATE C F,GERBER C.Atomic force microscope[J].Physical Review Letters,1986,56:930-933.
[38]张曼,王岸娜,吴立根,等.蛋白质、多糖和多酚间相互作用及研究方法[J].粮食与油脂,2015,28(4):42-46.
[39]SUN Cuixia,XU Chenqi,MAO Like,et al.Preparation,characterization and stability of curcumin-loaded zeinshellac composite colloidal particles[J].Food Chemistry,2017,228:656-667.
[40]刘淑萍.现代仪器分析方法及应用[M].北京:中国质检出版社,2013.
[41]SNEDDON G C,TRIMBY P W,CAIRNEY J M.Transmission Kikuchi diffraction in a scanning electron microscope:A review[J].Materials Science&Engineering RReports,2016,110:1-12.
[42]刘海学.现代仪器分析技术[M].北京:中国农业出版社,2011.
[43]MERSON E,DANILOV V,MERSON D,et al.Confocal laser scanning microscopy:The technique for quantitative fractographic analysis[J].Engineering Fracture Mechanics,2017,183:147-158.
[44]PYGALL S R,WHETSTONE J,TIMMINS P,et al.Pharmaceutical applications of confocal laser scanning microscopy:the physical characterisation of pharmaceutical systems[J].Advanced Drug Delivery Reviews,2007,59(14):1 434-1 452.
[45]庄绪静,曹雅忠,李克斌,等.同源建模和分子对接方法的应用与发展[C].中国植物保护学会2011年学术年会,2011.
[46]GUPTA M,SHARMA R,SINGH M,et al.Docking techniques in pharmacology:How much promising?[J].Computational Biology and Chemistry,2018,76:210-217.
[47]LI Ti,HU Peng,DAI Taotao,et al.Comparing the binding interaction betweenβ-lactoglobulin and flavonoids with different structure by multi-spectroscopy analysis and molecular docking[J].Spectrochimica Acta Part A Molecular&Biomolecular Spectroscopy,2018,201:197-206.
[48]HOLLINGSWORTH,SCOTT A D,RON O,Molecular dynamics simulation for all[J].Neuron,2018,99(6):1 129-1 143.
[49]MITSUTAKE A,TAKANO H.Relaxation mode analysis for molecular dynamics simulations of proteins[J].Biophysical Reviews,2018,10(2):375-389.
[50]ZHANG Jingxiao,ZHANG Lilei,XU Yangcheng,et al.Deciphering the binding behavior of flavonoids to the cyclin dependent kinase 6/cyclin D complex[J].PLo S One,2018,13(5):1-18.