食品多酚与蛋白相互作用及其对多酚生物可利用性影响的研究进展
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摘要
多酚和蛋白质的相互作用是近几十年来多酚类化合物与生物大分子作用研究的重点。食品多酚具有多种功能活性,但是由于受其他食品组分、加工条件和消化环境等各种因素的影响,其生物可利用率较低,对人体的健康功效受到严重影响。因此,该文综述了近些年来国内外关于食品多酚与蛋白的相互作用类型及其对多酚生物可利用性影响的研究进展,以期为提高多酚类食品的健康功能品质提供一定的指导依据。
The polyphenol-protein interaction is a research focus in terms of studies on interactions between polyphenols and biological macromolecules in recent decades. Food polyphenols possess many functional activities,but their bioavailability is very low due to various interferential factors,such as formulation matrixes,processing conditions,and digestive environment etc. Consequently,their health effects on human body are seriously impaired.Therefore,this paper reviewed recent researches on the interactions between food polyphenols and proteins and their effects on the bioavailability of polyphenols,aimed to provide a basis for improving the health effects and functional qualities of food products rich in polyphenols.
The polyphenol-protein interaction is a research focus in terms of studies on interactions between polyphenols and biological macromolecules in recent decades. Food polyphenols possess many functional activities,but their bioavailability is very low due to various interferential factors,such as formulation matrixes,processing conditions,and digestive environment etc. Consequently,their health effects on human body are seriously impaired.Therefore,this paper reviewed recent researches on the interactions between food polyphenols and proteins and their effects on the bioavailability of polyphenols,aimed to provide a basis for improving the health effects and functional qualities of food products rich in polyphenols.
引文
[1]吴建华,吴志瑰,裴建国,等.多酚类化合物的研究进展[J].中国现代中药,2015,17(6):630-636.
[2]HOSSEN M S,ALI M Y,JAHURUL M,et al. Beneficial roles of honeypolyphenols against some human degenerative diseases:A review[J]. Pharmacological Reports,2017,69(6):1 194-1 205.
[3]BUITIMEACANTúA N E, GUTIéRREZURIBE J A,SERNASALDíVAR S O. Phenolic-protein interactions:Effects on food properties and health benefits[J]. Journal of Medicinal Food,2018,21(2):188-198.
[4]KROLL J,RAWEL H M,ROHN S. Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds[J]. Foodence&Technology Research,2007,9(3):205-218.
[5]敖自华,莫茂松,罗昌荣.饮料中蛋白质-多酚的作用机制(续)[J].江苏食品与发酵,2000,4:29-32.
[6]CANON F,PATéF,MEUDEC E,et al. Characterization,stoichiometry,and stability of salivary protein-tannin complexes by ESI-MS and ESI-MS/MS[J]. Analytical&Bioanalytical Chemistry,2009,395(8):2 535-2 545.
[7]ULRIH N P. Analytical techniques for the study ofpolyphenol and protein interactions[J]. C R C Critical Reviews in Food Technology,2017,57(10):2 144-2 161.
[8]SHI C,TANG H,XIAO J,et al. Small-angle X-ray scattering study of protein complexes with teapolyphenols[J].Journal of Agricultural&Food Chemistry,2017,65(3):656-665.
[9]SáNCHEZMILLA M,PASTOR I,MALY M,et al. Study of non-covalent interactions ondendriplex formation:Influence of hydrophobic,electrostatic and hydrogen bonds interactions[J]. Colloids&Surfaces B Biointerfaces,2017,162:380-388.
[10]刘夫国,马翠翠,王迪,等.蛋白质与多酚相互作用研究进展[J].食品与发酵工业,2016,42(2):282-288.
[11]HASLAM E. Plantpolyphenols:Vegetable tannins revisited[J]. Quarterly Review of Biology,1989,29(7):187-189.
[12]刘勤勤,郭晓娜,彭伟,等.茶多酚与大豆分离蛋白的相互作用[J].食品科学,2015,36(17):43-47.
[13]肖建波.多酚类化合物与血清白蛋白相互作用的结构-结合力关系、理论模型和应用研究[D].长沙:中南大学,2009.
[14]綦菁华,蔡同一,庞美霞,等.影响蛋白质-酚类聚合物形成的因素研究[J].中国食品学报,2009,9(6):78-82.
[15]O’CONNELL J E,FOX P F. Effects of phenolic compounds on the heat stability of milk and concentrated milk[J].Journal of Dairy Research,1999,66(3):399-407.
[16]PRIGENT S V,GRUPPEN H,VISSER A J,et al.Effects of non-covalent interactions with 5-O-caffeoylquinic acid(chlorogenic acid)on the heat denaturation and solubility of globular proteins[J]. Journal of Agricultural&Food Chemistry,2003,51(17):5 088-5 095.
[17]陶亚丹.加工过程和配料对果汁多酚生物可及性的影响[D].无锡:江南大学,2015.
[18]徐洁琼,曾茂茂,秦昉,等.热加工处理对β-乳球蛋白与茶多酚间相互作用的影响[J].食品与发酵工业,2017,43(8):96-102.
[19]CZUBINSKI J,DWIECKI K. A review of methods used for investigation of protein-phenolic compound interactions[J]. International Journal of Food Science&Technology,2017,52(3):1-13.
[20]NIKIFORIDIS C,KAREFYLLAKIS D,SALAKOU S,et al. Covalent bonding of chlorogenic acid induces structural modifications on sunflower proteins[J]. Chemphyschem,2018,19:459-468.
[21]WILDE S C,KEPPLER J K,PALANI K,et al.β-Lactoglobulin as nanotransporter for allicin:Sensory properties and applicability in food[J]. Food Chemistry,2016,199:667-674.
[22]BUDRYN G,PA?ECZ B,RACHWA?-ROSIAK D,et al. Effect of inclusion of hydroxycinnamic and chlorogenic acids from green coffee bean inβ-cyclodextrin on their interactions with whey,egg white and soy protein isolates[J]. Food Chemistry,2015,168:276-287.
[23]PRIGENT S V,VORAGEN A G,VISSER A J,et al.Covalent interactions between proteins and oxidation products of caffeoylquinic acid(chlorogenic acid)[J]. Journal of the Science of Food&Agriculture,2010,87(13):2 502-2 510.
[24]WU X,LU Y,XU H,et al. Reducing the allergenic capacity ofβ-lactoglobulin by covalent conjugation with dietary polyphenols[J]. Food Chemistry,2018,256:427-434.
[25]SUI X,SUN H,QI B,et al. Functional and conformational changes to soy proteins accompanying anthocyanins:Focus on covalent and non-covalent interactions[J]. Food Chemistry,2017,245:871-878.
[26]O’CONNELL J E,FOX P F. Significance and applications of phenolic compounds in the production and quality of milk and dairy products:A review[J]. International Dairy Journal,2001,11(3):103-120.
[27]LIU F,MA C,MCCLEMENTS D J,et al. A comparative study of covalent and non-covalent interactions between zein and polyphenols in ethanol-water solution[J]. Food Hydrocolloids,2017,63:625-634.
[28]REIN M J,RENOUF M,CRUZHERNANDEZ C,et al.Bioavailability of bioactive food compounds:A challenging journey to bioefficacy[J]. British Journal of Clinical Pharmacology,2013,75(3):588-602.
[29]CHANG Y L. Challenges in providing credible scientific evidence of health benefits of dietarypolyphenols[J].Journal of Functional Foods,2013,5(1):524-526.
[30]王丽颖,李福香,杨雅轩,等.多糖与多酚相互作用机制及其对多酚特性的影响研究进展[J].食品科学,2017,38(11):276-282.
[31]任霞霞,刘连亮,张鑫,等.酚类化合物与食品大分子互作代谢研究进展[J].食品工业科技,2017,38(14):321-325.
[32]BOUAYED J,DEUβER H,HOFFMANN L,et al. Bioaccessible and dialysable polyphenols in selected apple varieties following in vitro digestion vs. their native patterns[J]. Food Chemistry,2012,131(4):1 466-1 472.
[33]CROZIER A,DEL R D,CLIFFORD M N. Bioavailability of dietaryflavonoids and phenolic compounds[J]. Molecular Aspects of Medicine,2010,31(6):446-467.
[34]OZDAL T,SELA D A,XIAO J,et al. The reciprocal interactions betweenpolyphenols and gut microbiota and effects on bioaccessibility[J]. Nutrients,2016,8(2):78-114.
[35]XIAO Y,CHEN X,YANG L,et al. Preparation and oral bioavailability study ofcurcuminoid-loaded microemulsion[J]. Journal of Agricultural&Food Chemistry,2013,61(15):3 654-3 660.
[36]HUANG Y C,KUO T H. O-carboxymethyl chitosan/fucoidan nanoparticles increase cellular curcumin uptake[J]. Food Hydrocolloids,2016,53:261-269.
[37]LIU Y,LIU D,ZHU L,et al. Temperature-dependent structure stability and in vitro release of chitosan-coated curcumin liposome[J]. Food Research International,2015,74:97-105.
[38]HITHAMANI G,SRINIVASAN K. Effect of domestic processing on the polyphenol content and bioaccessibility in finger millet(Eleusine coracana)and pearl millet(Pennisetum glaucum)[J]. Food Chemistry,2014,164:55-62.
[39]刘婵,何志勇,秦昉,等.多酚与蛋白质、消化酶相互作用的研究进展[J].食品与发酵工业,2015,41(11):256-260.
[40]DUFOUR C,LOONIS M,DELOSIèRE M,et al. The matrix of fruit&vegetables modulates the gastrointestinalbioaccessibility of polyphenols and their impact on dietary protein digestibility[J]. Food Chemistry,2017,240:314-322.
[41]LAMOTHE S,AZIMY N,BAZINET L,et al. Interaction of green tea polyphenols with dairy matrices in a simulated gastrointestinal environment[J]. Food&Function,2014,5(10):2 621-2 631.
[42]HELAL A,TAGLIAZUCCHI D,VERZELLONI E,et al.Bioaccessibility of polyphenols and cinnamaldehyde in cinnamon beverages subjected to in vitro,gastro-pancreatic digestion[J]. Journal of Functional Foods,2014,7(1):506-516.
[43]ROURA E,ANDRéSLACUEVA C,ESTRUCH R,et al.Milk does not affect the bioavailability of cocoa powderflavonoid in healthy human[J]. Annals of Nutrition&Metabolism,2007,51(6):493-498.
[44]GREEN R J,MURPHY A S,SCHULZ B,et al. Common tea formulations modulate in vitro digestive recovery of green teacatechins[J]. Molecular Nutrition and Food Research,2007,51(9):1 152-1 162.
[45]CHANPHAI P,BOURASSA P,KANAKIS C D,et al.Review on the loading efficacy of dietary teapolyphenols with milk proteins[J]. Food Hydrocolloids,2018,77:322-328.
[46]YILDIRIMELIKOGLU S,ERDEM Y K. Interactions between milk proteins and polyphenols:Binding mechanisms,related changes and the future trends in dairy industry[J]. Food Reviews International,2017,34(7):665-697.
[47]XIE Y,KOSI SKA A,XU H,et al. Milk enhances intestinal absorption of green tea catechins in in vitro digestion/Caco-2 cells model[J]. Food Research International,2013,53(2):793-800.
[2]HOSSEN M S,ALI M Y,JAHURUL M,et al. Beneficial roles of honeypolyphenols against some human degenerative diseases:A review[J]. Pharmacological Reports,2017,69(6):1 194-1 205.
[3]BUITIMEACANTúA N E, GUTIéRREZURIBE J A,SERNASALDíVAR S O. Phenolic-protein interactions:Effects on food properties and health benefits[J]. Journal of Medicinal Food,2018,21(2):188-198.
[4]KROLL J,RAWEL H M,ROHN S. Reactions of plant phenolics with food proteins and enzymes under special consideration of covalent bonds[J]. Foodence&Technology Research,2007,9(3):205-218.
[5]敖自华,莫茂松,罗昌荣.饮料中蛋白质-多酚的作用机制(续)[J].江苏食品与发酵,2000,4:29-32.
[6]CANON F,PATéF,MEUDEC E,et al. Characterization,stoichiometry,and stability of salivary protein-tannin complexes by ESI-MS and ESI-MS/MS[J]. Analytical&Bioanalytical Chemistry,2009,395(8):2 535-2 545.
[7]ULRIH N P. Analytical techniques for the study ofpolyphenol and protein interactions[J]. C R C Critical Reviews in Food Technology,2017,57(10):2 144-2 161.
[8]SHI C,TANG H,XIAO J,et al. Small-angle X-ray scattering study of protein complexes with teapolyphenols[J].Journal of Agricultural&Food Chemistry,2017,65(3):656-665.
[9]SáNCHEZMILLA M,PASTOR I,MALY M,et al. Study of non-covalent interactions ondendriplex formation:Influence of hydrophobic,electrostatic and hydrogen bonds interactions[J]. Colloids&Surfaces B Biointerfaces,2017,162:380-388.
[10]刘夫国,马翠翠,王迪,等.蛋白质与多酚相互作用研究进展[J].食品与发酵工业,2016,42(2):282-288.
[11]HASLAM E. Plantpolyphenols:Vegetable tannins revisited[J]. Quarterly Review of Biology,1989,29(7):187-189.
[12]刘勤勤,郭晓娜,彭伟,等.茶多酚与大豆分离蛋白的相互作用[J].食品科学,2015,36(17):43-47.
[13]肖建波.多酚类化合物与血清白蛋白相互作用的结构-结合力关系、理论模型和应用研究[D].长沙:中南大学,2009.
[14]綦菁华,蔡同一,庞美霞,等.影响蛋白质-酚类聚合物形成的因素研究[J].中国食品学报,2009,9(6):78-82.
[15]O’CONNELL J E,FOX P F. Effects of phenolic compounds on the heat stability of milk and concentrated milk[J].Journal of Dairy Research,1999,66(3):399-407.
[16]PRIGENT S V,GRUPPEN H,VISSER A J,et al.Effects of non-covalent interactions with 5-O-caffeoylquinic acid(chlorogenic acid)on the heat denaturation and solubility of globular proteins[J]. Journal of Agricultural&Food Chemistry,2003,51(17):5 088-5 095.
[17]陶亚丹.加工过程和配料对果汁多酚生物可及性的影响[D].无锡:江南大学,2015.
[18]徐洁琼,曾茂茂,秦昉,等.热加工处理对β-乳球蛋白与茶多酚间相互作用的影响[J].食品与发酵工业,2017,43(8):96-102.
[19]CZUBINSKI J,DWIECKI K. A review of methods used for investigation of protein-phenolic compound interactions[J]. International Journal of Food Science&Technology,2017,52(3):1-13.
[20]NIKIFORIDIS C,KAREFYLLAKIS D,SALAKOU S,et al. Covalent bonding of chlorogenic acid induces structural modifications on sunflower proteins[J]. Chemphyschem,2018,19:459-468.
[21]WILDE S C,KEPPLER J K,PALANI K,et al.β-Lactoglobulin as nanotransporter for allicin:Sensory properties and applicability in food[J]. Food Chemistry,2016,199:667-674.
[22]BUDRYN G,PA?ECZ B,RACHWA?-ROSIAK D,et al. Effect of inclusion of hydroxycinnamic and chlorogenic acids from green coffee bean inβ-cyclodextrin on their interactions with whey,egg white and soy protein isolates[J]. Food Chemistry,2015,168:276-287.
[23]PRIGENT S V,VORAGEN A G,VISSER A J,et al.Covalent interactions between proteins and oxidation products of caffeoylquinic acid(chlorogenic acid)[J]. Journal of the Science of Food&Agriculture,2010,87(13):2 502-2 510.
[24]WU X,LU Y,XU H,et al. Reducing the allergenic capacity ofβ-lactoglobulin by covalent conjugation with dietary polyphenols[J]. Food Chemistry,2018,256:427-434.
[25]SUI X,SUN H,QI B,et al. Functional and conformational changes to soy proteins accompanying anthocyanins:Focus on covalent and non-covalent interactions[J]. Food Chemistry,2017,245:871-878.
[26]O’CONNELL J E,FOX P F. Significance and applications of phenolic compounds in the production and quality of milk and dairy products:A review[J]. International Dairy Journal,2001,11(3):103-120.
[27]LIU F,MA C,MCCLEMENTS D J,et al. A comparative study of covalent and non-covalent interactions between zein and polyphenols in ethanol-water solution[J]. Food Hydrocolloids,2017,63:625-634.
[28]REIN M J,RENOUF M,CRUZHERNANDEZ C,et al.Bioavailability of bioactive food compounds:A challenging journey to bioefficacy[J]. British Journal of Clinical Pharmacology,2013,75(3):588-602.
[29]CHANG Y L. Challenges in providing credible scientific evidence of health benefits of dietarypolyphenols[J].Journal of Functional Foods,2013,5(1):524-526.
[30]王丽颖,李福香,杨雅轩,等.多糖与多酚相互作用机制及其对多酚特性的影响研究进展[J].食品科学,2017,38(11):276-282.
[31]任霞霞,刘连亮,张鑫,等.酚类化合物与食品大分子互作代谢研究进展[J].食品工业科技,2017,38(14):321-325.
[32]BOUAYED J,DEUβER H,HOFFMANN L,et al. Bioaccessible and dialysable polyphenols in selected apple varieties following in vitro digestion vs. their native patterns[J]. Food Chemistry,2012,131(4):1 466-1 472.
[33]CROZIER A,DEL R D,CLIFFORD M N. Bioavailability of dietaryflavonoids and phenolic compounds[J]. Molecular Aspects of Medicine,2010,31(6):446-467.
[34]OZDAL T,SELA D A,XIAO J,et al. The reciprocal interactions betweenpolyphenols and gut microbiota and effects on bioaccessibility[J]. Nutrients,2016,8(2):78-114.
[35]XIAO Y,CHEN X,YANG L,et al. Preparation and oral bioavailability study ofcurcuminoid-loaded microemulsion[J]. Journal of Agricultural&Food Chemistry,2013,61(15):3 654-3 660.
[36]HUANG Y C,KUO T H. O-carboxymethyl chitosan/fucoidan nanoparticles increase cellular curcumin uptake[J]. Food Hydrocolloids,2016,53:261-269.
[37]LIU Y,LIU D,ZHU L,et al. Temperature-dependent structure stability and in vitro release of chitosan-coated curcumin liposome[J]. Food Research International,2015,74:97-105.
[38]HITHAMANI G,SRINIVASAN K. Effect of domestic processing on the polyphenol content and bioaccessibility in finger millet(Eleusine coracana)and pearl millet(Pennisetum glaucum)[J]. Food Chemistry,2014,164:55-62.
[39]刘婵,何志勇,秦昉,等.多酚与蛋白质、消化酶相互作用的研究进展[J].食品与发酵工业,2015,41(11):256-260.
[40]DUFOUR C,LOONIS M,DELOSIèRE M,et al. The matrix of fruit&vegetables modulates the gastrointestinalbioaccessibility of polyphenols and their impact on dietary protein digestibility[J]. Food Chemistry,2017,240:314-322.
[41]LAMOTHE S,AZIMY N,BAZINET L,et al. Interaction of green tea polyphenols with dairy matrices in a simulated gastrointestinal environment[J]. Food&Function,2014,5(10):2 621-2 631.
[42]HELAL A,TAGLIAZUCCHI D,VERZELLONI E,et al.Bioaccessibility of polyphenols and cinnamaldehyde in cinnamon beverages subjected to in vitro,gastro-pancreatic digestion[J]. Journal of Functional Foods,2014,7(1):506-516.
[43]ROURA E,ANDRéSLACUEVA C,ESTRUCH R,et al.Milk does not affect the bioavailability of cocoa powderflavonoid in healthy human[J]. Annals of Nutrition&Metabolism,2007,51(6):493-498.
[44]GREEN R J,MURPHY A S,SCHULZ B,et al. Common tea formulations modulate in vitro digestive recovery of green teacatechins[J]. Molecular Nutrition and Food Research,2007,51(9):1 152-1 162.
[45]CHANPHAI P,BOURASSA P,KANAKIS C D,et al.Review on the loading efficacy of dietary teapolyphenols with milk proteins[J]. Food Hydrocolloids,2018,77:322-328.
[46]YILDIRIMELIKOGLU S,ERDEM Y K. Interactions between milk proteins and polyphenols:Binding mechanisms,related changes and the future trends in dairy industry[J]. Food Reviews International,2017,34(7):665-697.
[47]XIE Y,KOSI SKA A,XU H,et al. Milk enhances intestinal absorption of green tea catechins in in vitro digestion/Caco-2 cells model[J]. Food Research International,2013,53(2):793-800.