蛋白质糖基化接枝改性研究进展
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摘要
食品蛋白质的糖基化改性可通过美拉德反应使蛋白质分子的ε-氨基与糖分子的还原性羰基进行共价结合而实现,该过程不需任何化学催化剂参与,是一种绿色有效的化学改性方法。文章系统介绍了蛋白质糖基化的反应机理、反应标志物、改性方法以及功能特性,并对糖基化的研究方向进行了探讨。
Glycosylation modification of food proteins with reducing sugars allows covalent attachment of theε-amino group of the protein to the reducing carbonyl group of the sugar by Maillard reaction,which does not require any chemical catalyst,and is a green and effective chemical modification method.We systematically introduced the reaction mechanism,reaction markers, modification methods and functional properties of protein glycosylation,and discussed the research direction of protein glycosylation.
Glycosylation modification of food proteins with reducing sugars allows covalent attachment of theε-amino group of the protein to the reducing carbonyl group of the sugar by Maillard reaction,which does not require any chemical catalyst,and is a green and effective chemical modification method.We systematically introduced the reaction mechanism,reaction markers, modification methods and functional properties of protein glycosylation,and discussed the research direction of protein glycosylation.
引文
[1]DE OLIVEIRA F C,COIMBRA J S,DE OLIVEIRA E B,et al.Food protein-polysaccharide conjugates obtained via the Maillard reaction:A Review[J].Crit Rev Food Sci Nutr,2016,56(7):1 108-1 125.
[2]LIU Jian-hua,RU Qiao-mei,DING Yu-ting.Glycation a promising method for food protein modification:Physicochemical properties and structure,a review[J].Food Research International,2012,49(1):170-183.
[3]KETNAWA S,LICEAGA A M.Effect of microwave treatments on antioxidant activity and antigenicity of fish frame protein hydrolysates[J].Food and Bioprocess Technology,2017,10(3):582-591.
[4]ZHANG Zi-ye,REGENSTEIN J M,ZHOU Peng,et al.Effects of high intensity ultrasound modification on physicochemical property and water in myofibrillar protein gel[J].Ultrasonics Sonochemistry,2017,34:960-967.
[5]AKHTAR M,DING R.Covalently cross-linked proteins&polysaccharides:Formation,characterisation and potential applications[J].Current Opinion in Colloid&Interface Science,2017,28:31-36.
[6]ZHOU Quan-cheng,LIU Na,FENG Chuan-xing.Research on the effect of papain co-extrusion on pea protein and enzymolysis antioxidant peptides[J].Journal of Food Processing and Preservation,2017,DOI:10.1111/jfpp.13301.
[7]SPOTTI M J,PERDUCA M J,PIAGENTINI A,et al.Gel mechanical properties of milk whey protein-dextran conjugates obtained by Maillard reaction[J].Food Hydrocolloids,2013,31(1):26-32.
[8]HELLWIG M,HENLE T.Baking,Ageing,Diabetes:Ashort history of the Maillard reaction[J].Angewandte Chemie-International Edition,2014,53(39):10 316-10 329.
[9]ECHAVARRIA A P,PAGAN J,IBARZ A.Melanoidins formed by Maillard reaction in food and their biological activity[J].Food Engineering Reviews,2012,4(4):203-223.
[10]LUND M N,RAY C A.Control of Maillard reactions in foods:strategies and chemical mechanisms[J].J Agric Food Chem,2017,65(23):4 537-4 552.
[11]LIANG Chun-xuan,YUAN Fang,LIU Fu-guo,et al.Structure and antimicrobial mechanism of epsilon-polylysine-chitosan conjugates through Maillard reaction[J].International Journal of Biological Macromolecules,2014,70:427-434.
[12]PERUSKO M,AL-HANISH A,CIRKOVIC VELICKO-VIC T,et al.Macromolecular crowding conditions enhance glycation and oxidation of whey proteins in ultrasound-induced Maillard reaction[J].Food Chem,2015,177:248-257.
[13]YU Ai-nong,ZHOU Yong-yan,YANG Yi-ni.Kinetics of browning and correlations between browning degree and pyrazine compounds in l-ascorbic acid/acidic amino acid model systems[J].Food Chem,2017,221:1 678-1 684.
[14]SUN Wei-wei,YU Shu-juan,YANG Xiao-quan,et al.Study on the rheological properties of heat-induced whey protein isolate-dextran conjugate gel[J].Food Research International,2011,44(10):3 259-3 263.
[15]HAN Miao-miao,YI Yang,WANG Hong-xun,et al.Investigation of the Maillard reaction between polysaccharides and proteins from Longan Pulp and the improvement in activities[J].Molecules,2017,DOI:10.3390/molecules22060938.
[16]O'CHAROEN S,HAYAKAWA S,OGAWA M.Food properties of egg white protein modified by rare ketohexoses through Maillard reaction[J].International Journal of Food Science And Technology,2015,50(1):194-202.
[17]SHENG Long,SU Peng,HAN Ke,et al.Synthesis and structural characterization of lysozyme-pullulan conjugates obtained by the Maillard reaction[J].Food Hydrocolloids,2017,71:1-7.
[18]HAN Zhong-hui,GAO Jian-xin,WANG Xiao-min,et al.Formation and alterations of the Potentially Harmful Maillard reaction products during the production and storage of brown fermented milk[J].Molecules,2019,DOI:10.3390/molecules24020272.
[19]YAMAGUCHI K,NOMI Y,HOMMA T,et al.Determination of furosine and fluorescence as markers of the Maillard reaction for the evaluation of meat products during actual cooking conditions[J].Food Science and Technology Research,2012,18(1):67-76.
[20]OH M J,KIM Y,HOON LEE S,et al.Prediction of CMLcontents in the Maillard reaction products for casein-monosaccharides model[J].Food Chem,2018,267:271-276.
[21]COUREL M,AIT-AMEUR L,CAPUANO E,et al.Effects of formulation and baking conditions on neo-formed contaminants in model cookies[J].Czech Journal of Food Sciences,2009,27:93-95.
[22]BRAUN M K,GRIMALDO M,ROOSEN-RUNGE F,et al.Crowding-controlled cluster size in concentrated aqueous protein solutions:structure,self-and collective diffusion[J].Journal of Physical Chemistry Letters,2017,8(12):2 590-2 596.
[23]KATO A M K,KOBAYASHI K.Preparation and characterization of ovalbumin-dextran conjugate having excellent emulsifying properties[J].Journal of Agricultural&Food Chemistry,1988(3):421-425.
[24]CORTES Yá1ez D A,GAGNETEN M,LEIVA G E,et al.Antioxidant activity developed at the different stages of Maillard reaction with milk proteins[J].Lwt,2018,89:344-349.
[25]MULCAHY E M,PARK C W,DRAKE M,et al.Enhancement of the functional properties of whey protein by conjugation with maltodextrin under dry-heating conditions[J].International Journal of Dairy Technology,2018,71(1):216-225.
[26]MUHOZA B,ZHANG Y,XIA S,et al.Improved stability and controlled release of lutein-loaded micelles based on glycosylated casein via Maillard reaction[J].Journal of Functional Foods,2018,45:1-9.
[27]BOOSTANI S,AMINLARI M,MOOSAVI-NASAB M,et al.Fabrication and characterisation of soy protein isolategrafted dextran biopolymer:A novel ingredient in spraydried soy beverage formulation[J].Int J Biol Macromol,2017,102:297-307.
[28]WENG Jing-yi,QI Jun-ru,YIN Shou-wei,et al.Fractionation and characterization of soy beta-conglycinin-dextran conjugates via macromolecular crowding environment and dry heating[J].Food Chem,2016,196:1 264-1 271.
[29]WANG Yong-quan,GAN Jing,LI Yang,et al.Conformation and emulsifying properties of deamidated wheat glutenmaltodextrin/citrus pectin conjugates and their abilities to stabilize beta-carotene emulsions[J].Food Hydrocolloids,2019,87:129-141.
[30]DU Yan-xue,SHI Su-hua,JIANG Yan,et al.Physicochemical properties and emulsion stabilization of rice dreg glutelin conjugated with kappa-carrageenan through Maillard reaction[J].J Sci Food Agric,2013,93(1):125-133.
[31]MENG Jun,KANG Ting-ting,WANG Hui-fang,et al.Physicochemical properties of casein-dextran nanoparticles prepared by controlled dry and wet heating[J].Int J Biol Macromol,2018,107(Pt B):2 604-2 610.
[32]LI Yue,ZHONG Fang,JI Wei,et al.Functional properties of Maillard reaction products of rice protein hydrolysates with mono-,oligo-and polysaccharides[J].Food Hydrocolloids,2013,30(1):53-60.
[33]BI Wei-wei,GE Wei,LI Xiao-dong,et al.Effects of ultrasonic pretreatment and glycosylation on functional properties of casein grafted with glucose[J].Journal of Food Processing and Preservation,2017,DOI:10.1111/jfpp.13177.
[34]YU H,SEOW Y-X,ONG P K C,et al.Kinetic study of high-intensity ultrasound-assisted Maillard reaction in a model system of D-glucose and glycine[J].Food Chemistry,2018,269:628-637.
[35]NASROLLAHZADEH F,VARIDI M,KOOCHEKI A,et al.Effect of microwave and conventional heating on structural,functional and antioxidant properties of bovine serum albumin-maltodextrin conjugates through Maillard reaction[J].Food Res Int,2017,100(2):289-297.
[36]LI He,WU Chun-jian,YU Shu-juan.Impact of microwaveassisted heating on the pH value,Color,and flavor compounds in Glucose-Ammonium Model System[J].Food and Bioprocess Technology,2018,11(6):1 248-1 258.
[37]RUIZ G A,XI B,MINOR M,et al.High-Pressure-High-Temperature Processing Reduces Maillard Reaction and Viscosity in Whey Protein-Sugar Solutions[J].Journal of Agricultural and Food Chemistry,2016,64(38):7 208-7 215.
[38]WANG Zhong-jiang,HAN Fei-fei,SUI Xiao-nan,et al.Effect of ultrasound treatment on the wet heating Maillard reaction between mung bean[Vigna radiate(L.)]protein isolates and glucose and on structural and physico-chemical properties of conjugates[J].J Sci Food Agric,2016,96(5):1 532-1 540.
[39]MU Li-xia,ZHAO Hai-feng,ZHAO Mou-ming,et al.Physicochemical properties of soy protein isolates-acacia gum conjugates[J].Czech Journal of Food Sciences,2011,29(2):129-136.
[40]MULCAHY E M,PARK C W,DRAKE M,et al.Improvement of the functional properties of whey protein hydrolysate by conjugation with maltodextrin[J].International Dairy Journal,2016,60:47-54.
[41]ZHONG Lei,MA Ning,WU Yi-liang,et al.Characterization and functional evaluation of oat protein isolatePleurotus ostreatusβ-glucan conjugates formed via Maillard reaction[J].Food Hydrocolloids,2019,87:459-469.
[42]CHENG Yun-hui,TANG Wen-juan,XU Zhou,et al.Structure and functional properties of rice protein-dextran conjugates prepared by the Maillard reaction[J].International Journal of Food Science And Technology,2018,53(2):372-380.
[43]KASRAN M,CUI S W,GOFF H D.Emulsifying properties of soy whey protein isolate-fenugreek gum conjugates in oil-in-water emulsion model system[J].Food Hydrocolloids,2013,30(2):691-697.
[44]ALVAREZ C,GARCIA V,RENDUELES M,et al.Functional properties of isolated porcine blood proteins modified by Maillard's reaction[J].Food Hydrocolloids,2012,28(2):267-274.
[45]OLIVER C M,MELTON L D,STANLEY R A.Creating proteins with novel functionality via the Maillard reaction:A review[J].Critical Reviews in Food Science and Nutrition,2006,46(4):337-350.
[46]RU Qiao-mei,CHO Younghee,HUANG Qing-rong.Biopolymer-stabilized emulsions on the basis of interactions betweenβ-lactoglobulin andι-carrageenan[J].Frontiers of Chemical Engineering in China,2009,3(4):399-406.
[47]CASTEL V,RUBIOLO A C,CARRARA C R.Improvement of emulsifying properties of Brea gum by controlled thermal treatment[J].Food Hydrocolloids,2018,85:93-101.
[48]LI Wei-wei,ZHAO Hai-bo,HE Zhi-yong,et al.Modification of soy protein hydrolysates by Maillard reaction:Effects of carbohydrate chain length on structural and interfacial properties[J].Colloids Surf B Biointerfaces,2016,138:70-77.
[49]PIRESTANI S,NASIRPOUR A,KERAMAT J,et al.Effect of glycosylation with gum Arabic by Maillard reaction in a liquid system on the emulsifying properties of canola protein isolate[J].Carbohydr Polym,2017,157:1 620-1 627.
[50]JIAN Wen-jie,HE Jing,SUN Yuan-ming,et al.Comparative studies on physicochemical properties of bovine serum albumin-glucose and bovine serum albumin-mannose conjugates formed via Maillard reaction[J].LWT-Food Science and Technology,2016,69:358-364.
[51]OLIVER C M,MELTON L D,STANLEY R A.Functional properties of caseinate glycoconjugates prepared by controlled heating in the‘dry’state[J].Journal of the Science of Food and Agriculture,2006,86(5):732-740.
[52]FRANCISCO J Morales,SALVIO Jimeanezpearez.Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence[J].Food Chemistry,2001,72:119-125.
[53]LIU Qian,KONG Bao-hua,HAN Jian-chun,et al.Structure and antioxidant activity of whey protein isolate conjugated with glucose via the Maillard reaction under dry-heating conditions[J].Food Structure,2014,1(2):145-154.
[54]TAGLIAZUCCHI D,VERZELLONI E.Relationship between the chemical composition and the biological activities of food melanoidins[J].Food Science and Biotechnology,2014,23(2):561-568.
[55]HABINSHUTI I,CHEN X,YU J,et al.Antimicrobial,antioxidant and sensory properties of Maillard reaction products(MRPs)derived from sunflower,soybean and corn meal hydrolysates[J].Lwt,2019,101:694-702.
[56]HASHEMI M M,AMINLARI M,MOOSAVINASAB M.Preparation of and studies on the functional properties and bactericidal activity of the lysozyme-xanthan gum conjugate[J].LWT-Food Science and Technology,2014,57(2):594-602.
[2]LIU Jian-hua,RU Qiao-mei,DING Yu-ting.Glycation a promising method for food protein modification:Physicochemical properties and structure,a review[J].Food Research International,2012,49(1):170-183.
[3]KETNAWA S,LICEAGA A M.Effect of microwave treatments on antioxidant activity and antigenicity of fish frame protein hydrolysates[J].Food and Bioprocess Technology,2017,10(3):582-591.
[4]ZHANG Zi-ye,REGENSTEIN J M,ZHOU Peng,et al.Effects of high intensity ultrasound modification on physicochemical property and water in myofibrillar protein gel[J].Ultrasonics Sonochemistry,2017,34:960-967.
[5]AKHTAR M,DING R.Covalently cross-linked proteins&polysaccharides:Formation,characterisation and potential applications[J].Current Opinion in Colloid&Interface Science,2017,28:31-36.
[6]ZHOU Quan-cheng,LIU Na,FENG Chuan-xing.Research on the effect of papain co-extrusion on pea protein and enzymolysis antioxidant peptides[J].Journal of Food Processing and Preservation,2017,DOI:10.1111/jfpp.13301.
[7]SPOTTI M J,PERDUCA M J,PIAGENTINI A,et al.Gel mechanical properties of milk whey protein-dextran conjugates obtained by Maillard reaction[J].Food Hydrocolloids,2013,31(1):26-32.
[8]HELLWIG M,HENLE T.Baking,Ageing,Diabetes:Ashort history of the Maillard reaction[J].Angewandte Chemie-International Edition,2014,53(39):10 316-10 329.
[9]ECHAVARRIA A P,PAGAN J,IBARZ A.Melanoidins formed by Maillard reaction in food and their biological activity[J].Food Engineering Reviews,2012,4(4):203-223.
[10]LUND M N,RAY C A.Control of Maillard reactions in foods:strategies and chemical mechanisms[J].J Agric Food Chem,2017,65(23):4 537-4 552.
[11]LIANG Chun-xuan,YUAN Fang,LIU Fu-guo,et al.Structure and antimicrobial mechanism of epsilon-polylysine-chitosan conjugates through Maillard reaction[J].International Journal of Biological Macromolecules,2014,70:427-434.
[12]PERUSKO M,AL-HANISH A,CIRKOVIC VELICKO-VIC T,et al.Macromolecular crowding conditions enhance glycation and oxidation of whey proteins in ultrasound-induced Maillard reaction[J].Food Chem,2015,177:248-257.
[13]YU Ai-nong,ZHOU Yong-yan,YANG Yi-ni.Kinetics of browning and correlations between browning degree and pyrazine compounds in l-ascorbic acid/acidic amino acid model systems[J].Food Chem,2017,221:1 678-1 684.
[14]SUN Wei-wei,YU Shu-juan,YANG Xiao-quan,et al.Study on the rheological properties of heat-induced whey protein isolate-dextran conjugate gel[J].Food Research International,2011,44(10):3 259-3 263.
[15]HAN Miao-miao,YI Yang,WANG Hong-xun,et al.Investigation of the Maillard reaction between polysaccharides and proteins from Longan Pulp and the improvement in activities[J].Molecules,2017,DOI:10.3390/molecules22060938.
[16]O'CHAROEN S,HAYAKAWA S,OGAWA M.Food properties of egg white protein modified by rare ketohexoses through Maillard reaction[J].International Journal of Food Science And Technology,2015,50(1):194-202.
[17]SHENG Long,SU Peng,HAN Ke,et al.Synthesis and structural characterization of lysozyme-pullulan conjugates obtained by the Maillard reaction[J].Food Hydrocolloids,2017,71:1-7.
[18]HAN Zhong-hui,GAO Jian-xin,WANG Xiao-min,et al.Formation and alterations of the Potentially Harmful Maillard reaction products during the production and storage of brown fermented milk[J].Molecules,2019,DOI:10.3390/molecules24020272.
[19]YAMAGUCHI K,NOMI Y,HOMMA T,et al.Determination of furosine and fluorescence as markers of the Maillard reaction for the evaluation of meat products during actual cooking conditions[J].Food Science and Technology Research,2012,18(1):67-76.
[20]OH M J,KIM Y,HOON LEE S,et al.Prediction of CMLcontents in the Maillard reaction products for casein-monosaccharides model[J].Food Chem,2018,267:271-276.
[21]COUREL M,AIT-AMEUR L,CAPUANO E,et al.Effects of formulation and baking conditions on neo-formed contaminants in model cookies[J].Czech Journal of Food Sciences,2009,27:93-95.
[22]BRAUN M K,GRIMALDO M,ROOSEN-RUNGE F,et al.Crowding-controlled cluster size in concentrated aqueous protein solutions:structure,self-and collective diffusion[J].Journal of Physical Chemistry Letters,2017,8(12):2 590-2 596.
[23]KATO A M K,KOBAYASHI K.Preparation and characterization of ovalbumin-dextran conjugate having excellent emulsifying properties[J].Journal of Agricultural&Food Chemistry,1988(3):421-425.
[24]CORTES Yá1ez D A,GAGNETEN M,LEIVA G E,et al.Antioxidant activity developed at the different stages of Maillard reaction with milk proteins[J].Lwt,2018,89:344-349.
[25]MULCAHY E M,PARK C W,DRAKE M,et al.Enhancement of the functional properties of whey protein by conjugation with maltodextrin under dry-heating conditions[J].International Journal of Dairy Technology,2018,71(1):216-225.
[26]MUHOZA B,ZHANG Y,XIA S,et al.Improved stability and controlled release of lutein-loaded micelles based on glycosylated casein via Maillard reaction[J].Journal of Functional Foods,2018,45:1-9.
[27]BOOSTANI S,AMINLARI M,MOOSAVI-NASAB M,et al.Fabrication and characterisation of soy protein isolategrafted dextran biopolymer:A novel ingredient in spraydried soy beverage formulation[J].Int J Biol Macromol,2017,102:297-307.
[28]WENG Jing-yi,QI Jun-ru,YIN Shou-wei,et al.Fractionation and characterization of soy beta-conglycinin-dextran conjugates via macromolecular crowding environment and dry heating[J].Food Chem,2016,196:1 264-1 271.
[29]WANG Yong-quan,GAN Jing,LI Yang,et al.Conformation and emulsifying properties of deamidated wheat glutenmaltodextrin/citrus pectin conjugates and their abilities to stabilize beta-carotene emulsions[J].Food Hydrocolloids,2019,87:129-141.
[30]DU Yan-xue,SHI Su-hua,JIANG Yan,et al.Physicochemical properties and emulsion stabilization of rice dreg glutelin conjugated with kappa-carrageenan through Maillard reaction[J].J Sci Food Agric,2013,93(1):125-133.
[31]MENG Jun,KANG Ting-ting,WANG Hui-fang,et al.Physicochemical properties of casein-dextran nanoparticles prepared by controlled dry and wet heating[J].Int J Biol Macromol,2018,107(Pt B):2 604-2 610.
[32]LI Yue,ZHONG Fang,JI Wei,et al.Functional properties of Maillard reaction products of rice protein hydrolysates with mono-,oligo-and polysaccharides[J].Food Hydrocolloids,2013,30(1):53-60.
[33]BI Wei-wei,GE Wei,LI Xiao-dong,et al.Effects of ultrasonic pretreatment and glycosylation on functional properties of casein grafted with glucose[J].Journal of Food Processing and Preservation,2017,DOI:10.1111/jfpp.13177.
[34]YU H,SEOW Y-X,ONG P K C,et al.Kinetic study of high-intensity ultrasound-assisted Maillard reaction in a model system of D-glucose and glycine[J].Food Chemistry,2018,269:628-637.
[35]NASROLLAHZADEH F,VARIDI M,KOOCHEKI A,et al.Effect of microwave and conventional heating on structural,functional and antioxidant properties of bovine serum albumin-maltodextrin conjugates through Maillard reaction[J].Food Res Int,2017,100(2):289-297.
[36]LI He,WU Chun-jian,YU Shu-juan.Impact of microwaveassisted heating on the pH value,Color,and flavor compounds in Glucose-Ammonium Model System[J].Food and Bioprocess Technology,2018,11(6):1 248-1 258.
[37]RUIZ G A,XI B,MINOR M,et al.High-Pressure-High-Temperature Processing Reduces Maillard Reaction and Viscosity in Whey Protein-Sugar Solutions[J].Journal of Agricultural and Food Chemistry,2016,64(38):7 208-7 215.
[38]WANG Zhong-jiang,HAN Fei-fei,SUI Xiao-nan,et al.Effect of ultrasound treatment on the wet heating Maillard reaction between mung bean[Vigna radiate(L.)]protein isolates and glucose and on structural and physico-chemical properties of conjugates[J].J Sci Food Agric,2016,96(5):1 532-1 540.
[39]MU Li-xia,ZHAO Hai-feng,ZHAO Mou-ming,et al.Physicochemical properties of soy protein isolates-acacia gum conjugates[J].Czech Journal of Food Sciences,2011,29(2):129-136.
[40]MULCAHY E M,PARK C W,DRAKE M,et al.Improvement of the functional properties of whey protein hydrolysate by conjugation with maltodextrin[J].International Dairy Journal,2016,60:47-54.
[41]ZHONG Lei,MA Ning,WU Yi-liang,et al.Characterization and functional evaluation of oat protein isolatePleurotus ostreatusβ-glucan conjugates formed via Maillard reaction[J].Food Hydrocolloids,2019,87:459-469.
[42]CHENG Yun-hui,TANG Wen-juan,XU Zhou,et al.Structure and functional properties of rice protein-dextran conjugates prepared by the Maillard reaction[J].International Journal of Food Science And Technology,2018,53(2):372-380.
[43]KASRAN M,CUI S W,GOFF H D.Emulsifying properties of soy whey protein isolate-fenugreek gum conjugates in oil-in-water emulsion model system[J].Food Hydrocolloids,2013,30(2):691-697.
[44]ALVAREZ C,GARCIA V,RENDUELES M,et al.Functional properties of isolated porcine blood proteins modified by Maillard's reaction[J].Food Hydrocolloids,2012,28(2):267-274.
[45]OLIVER C M,MELTON L D,STANLEY R A.Creating proteins with novel functionality via the Maillard reaction:A review[J].Critical Reviews in Food Science and Nutrition,2006,46(4):337-350.
[46]RU Qiao-mei,CHO Younghee,HUANG Qing-rong.Biopolymer-stabilized emulsions on the basis of interactions betweenβ-lactoglobulin andι-carrageenan[J].Frontiers of Chemical Engineering in China,2009,3(4):399-406.
[47]CASTEL V,RUBIOLO A C,CARRARA C R.Improvement of emulsifying properties of Brea gum by controlled thermal treatment[J].Food Hydrocolloids,2018,85:93-101.
[48]LI Wei-wei,ZHAO Hai-bo,HE Zhi-yong,et al.Modification of soy protein hydrolysates by Maillard reaction:Effects of carbohydrate chain length on structural and interfacial properties[J].Colloids Surf B Biointerfaces,2016,138:70-77.
[49]PIRESTANI S,NASIRPOUR A,KERAMAT J,et al.Effect of glycosylation with gum Arabic by Maillard reaction in a liquid system on the emulsifying properties of canola protein isolate[J].Carbohydr Polym,2017,157:1 620-1 627.
[50]JIAN Wen-jie,HE Jing,SUN Yuan-ming,et al.Comparative studies on physicochemical properties of bovine serum albumin-glucose and bovine serum albumin-mannose conjugates formed via Maillard reaction[J].LWT-Food Science and Technology,2016,69:358-364.
[51]OLIVER C M,MELTON L D,STANLEY R A.Functional properties of caseinate glycoconjugates prepared by controlled heating in the‘dry’state[J].Journal of the Science of Food and Agriculture,2006,86(5):732-740.
[52]FRANCISCO J Morales,SALVIO Jimeanezpearez.Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence[J].Food Chemistry,2001,72:119-125.
[53]LIU Qian,KONG Bao-hua,HAN Jian-chun,et al.Structure and antioxidant activity of whey protein isolate conjugated with glucose via the Maillard reaction under dry-heating conditions[J].Food Structure,2014,1(2):145-154.
[54]TAGLIAZUCCHI D,VERZELLONI E.Relationship between the chemical composition and the biological activities of food melanoidins[J].Food Science and Biotechnology,2014,23(2):561-568.
[55]HABINSHUTI I,CHEN X,YU J,et al.Antimicrobial,antioxidant and sensory properties of Maillard reaction products(MRPs)derived from sunflower,soybean and corn meal hydrolysates[J].Lwt,2019,101:694-702.
[56]HASHEMI M M,AMINLARI M,MOOSAVINASAB M.Preparation of and studies on the functional properties and bactericidal activity of the lysozyme-xanthan gum conjugate[J].LWT-Food Science and Technology,2014,57(2):594-602.