纤维二糖2-差向异构酶的酶学性质及在乳制品中的应用
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摘要
近年来,对纤维二糖2-差向异构酶(CE)的研究取得了许多突破性的进展。针对不同的寡糖,CE表现出不同程度的差向异构化和异构化活性,催化乳糖生成的依匹乳糖和乳果糖,两种都是有益生元性质的乳糖衍生物,在保健食品及药品中具有非常广阔的前景。因此,CE在工业应用的中游和下游工艺越来越引起重视,来自嗜温和嗜热微生物的CE也被应用于不同需求的生产中。尤其是嗜温微生物来源的CE能在较低温中保持活性,推进了CE在乳制品行业中的应用。作者针对性总结了CE的酶学性质和催化产物的最新研究进展,及其在乳制品行业中的发展。
In recent years,many substantial advances have been made in the research of cellobiose2-epimerase(CE). For different oligosaccharides,CE shows different levels of epimerization and isomerization activities,converting lactose into epilactose and lactulose,respectively. Both of them are lactose derivatives with prebiotic properties and show wide application prospects in food and pharmaceutical industries. Therefore,more and more attention has been attracted to the middle and downstream processes of industrial applications of CE. CEs from mesophilic and thermophilic microorganisms have also been applied to satisfy different needs in production. In particular,CE of mesophilic microorganisms can maintain activity at lower temperatures,facilitating the applications of CE in dairy industry. In this paper,we summarized the recent progress in the enzymatic properties,catalytic products,and dairy industrial development of CE.
In recent years,many substantial advances have been made in the research of cellobiose2-epimerase(CE). For different oligosaccharides,CE shows different levels of epimerization and isomerization activities,converting lactose into epilactose and lactulose,respectively. Both of them are lactose derivatives with prebiotic properties and show wide application prospects in food and pharmaceutical industries. Therefore,more and more attention has been attracted to the middle and downstream processes of industrial applications of CE. CEs from mesophilic and thermophilic microorganisms have also been applied to satisfy different needs in production. In particular,CE of mesophilic microorganisms can maintain activity at lower temperatures,facilitating the applications of CE in dairy industry. In this paper,we summarized the recent progress in the enzymatic properties,catalytic products,and dairy industrial development of CE.
引文
[1]CHEN Q,LEVIN R,ZHANG W,et al.Characterisation of a novel cellobiose 2-epimerase from thermophilic Caldicellulosiruptor obsidiansis for lactulose production[J].Journal of the Science of Food and Agriculture,2017,97(10):3095-3105.
[2]IZUMORI K.Izumoring:A strategy for bioproduction of all hexoses[J].Journal of Biotechnology,2006,124(4):717-722.
[3]MU W,LI Q,FAN C,et al.Recent advances on physiological functions and biotechnological production of epilactose[J].Applied Microbiology and Biotechnology,2013,97(5):1821-1827.
[4]TYLER T R,LEATHERWOOD J M.Epimerization of disaccharides by enzyme preparations from Ruminococcus albus[J].Archives of Biochemistry and Biophysics,1967,119(1):363-367.
[5]ITO S,HAMADA S,YAMAGUCHI K,et al.Cloning and sequencing of the cellobiose 2-epimerase gene from an obligatory anaerobe,Ruminococcus albus[J].Biochemical and Biophysical Research Communications,2007,360(3):640-645.
[6]ITO S,TAGUCHI H,HAMADA S,et al.Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme[J].Applied Microbiology and Biotechnology,2008,79(3):433-441.
[7]KIM J-E,KIM Y-S,KANG L-W,et al.Characterization of a recombinant cellobiose 2-epimerase from Dictyoglomus turgidum that epimerizes and isomerizesβ-1,4-andα-1,4-gluco-oligosaccharides[J].Biotechnology Letters,2012,34(11):2061-2068.
[8]SENOURA T,TAGUCHI H,ITO S,et al.Identification of the cellobiose 2-epimerase gene in the genome of Bacteroides fragilis NCTC 9343[J].Bioscience,Biotechnology&Biochemistry,2009,73(2):400-406.
[9]PARK C S,KIM J E,CHOI J G,et al.Characterization of a recombinant cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus and its application in the production of mannose from glucose[J].Applied Microbiology and Biotechnology,2011,92(6):1187-1196.
[10]KREWINKEL M,KAISER J,MERZ M,et al.Novel cellobiose 2-epimerases for the production of epilactose from milk ultrafiltrate containing lactose[J].Journal of Dairy Science,2015,98(6):3665-3678.
[11]SABURI W,TANAKA Y,MUTO H,et al.Functional reassignment of Cellvibrio vulgaris EpiA to cellobiose 2-epimerase and an evaluation of the biochemical functions of the 4-O-β-D-mannosyl-D-glucose phosphorylase-like protein,UnkA[J].Bioscience,Biotechnology&Biochemistry,2015,79(6):969-977.
[12]OJIMA T,SABURI W,YAMAMOTO T,et al.Identification and characterization of cellobiose 2-epimerases from various aerobes[J].Bioscience,Biotechnology&Biochemistry,2013,77(1):189-193.
[13]TAGUCHI H,SENOURA T,HAMADA S,et al.Cloning and sequencing of the gene for cellobiose 2-epimerase from a ruminal strain of Eubacterium cellulosolvens[J].FEMS Microbiology Letters,2008,287(1):34-40.
[14]OJIMA T,SABURI W,SATO H,et al.Biochemical characterization of a thermophilic cellobiose 2-epimerase from a thermohalophilic bacterium,Rhodothermus marinus JCM9785[J].Bioscience,Biotechnology&Biochemistry,2011,75(11):2162-2168.
[15]RENTSCHLER E,SCHUH K,KREWINKEL M,et al.Enzymatic production of lactulose and epilactose in milk[J].Journal of Dairy Science,2015,98(10):6767-6775.
[16]CHEN Q M,ZHANG W L,ZHANG T,et al.Characterization of an epilactose-producing cellobiose 2-epimerase from Thermoanaerobacterium saccharolyticum[J].Journal of Molecular Catalysis B-Enzymatic,2015,116:39-44.
[17]FUJIWARA T,SABURI W,INOUE S,et al.Crystal structure of Ruminococcus albus cellobiose 2-epimerase:Structural insights into epimerization of unmodified sugar[J].FEBS Letters,2013,587(7):840-846.
[18]FUJIWARA T,SABURI W,MATSUI H,et al.Structural insights into the epimerization ofβ-1,4-linked oligosaccharides catalyzed by cellobiose 2-epimerase,the sole enzyme epimerizing non-anomeric hydroxyl groups of unmodified sugars[J].Journal of Biological Chemistry,2014,289(6):3405-3415.
[19]NELOFAR A,LAGHARI A H,YASMIN A.Validated HPLC-RI method for the determination of lactulose and its process related impurities in syrup[J].Indian Journal of Pharmaceutical Sciences,2010,72(2):255-258.
[20]SATO H,SABURI W,OJIMA T,et al.Immobilization of a thermostable cellobiose 2-epimerase from Rhodothermus marinus JCM9785 and continuous production of epilactose[J].Bioscience,Biotechnology,&Biochemistry,2012,76(8):1584-1587.
[21]SABURI W,YAMAMOTO T,TAGUCHI H,et al.Practical preparation of epilactose produced with cellobiose 2-epimerase from Ruminococcus albus NE1[J].Journal of the Agricultural Chemical Society of Japan,2010,74(8):1736-1737.
[22]RENTSCHLER E,KUSCHEL B,KREWINKEL M,et al.Quantification of lactulose and epilactose in the presence of lactose in milk using a dual HPLC analysis[J].Food Analytical Methods,2016,9(8):2210-2222.
[23]MIYASATO M,AJISAKA K.Regioselectivity in beta-galactosidase-catalyzed transglycosylation for the enzymatic assembly of D-galactosyl-D-mannose[J].Bioscience,Biotechnology,&Biochemistry,2004,68(10):2086-2090.
[24]ITO S,TAGUCHI H,HAMADA S,et al.Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme[J].Applied Microbiology and Biotechnology,2008,79(3):433-441.
[25]WATANABE J,NISHIMUKAI M,TAGUCHI H,et al.Prebiotic properties of epilactose[J].Journal of Dairy Science,2008,91(12):4518-4526.
[26]SUZUKI T,NISHIMUKAI M,SHINOKI A,et al.Ingestion of epilactose,a non-digestible disaccharide,improves postgastrectomy osteopenia and anemia in rats through the promotion of intestinal calcium and iron absorption[J].Journal of Agricultural&Food Chemistry,2010,58(19):10787-10792.
[27]SUZUKI T,NISHIMUKAI M,TAKECHI M,et al.The nondigestible disaccharide epilactose increases paracellular Ca absorption via rho-associated kinase-and myosin light chain kinase-dependent mechanisms in rat small intestines[J].Journal of Agricultural&Food Chemistry,2010,58(3):1927-1932.
[28]NISHIMUKAI M,WATANABE J,TAGUCHI H,et al.Effects of epilactose on calcium absorption and serum lipid metabolism in rats[J].Journal of Agricultural&Food Chemistry,2008,56(21):10340-10345.
[29]MURAKAMI Y,OJIMA-KATO T,SABURI W,et al.Supplemental epilactose prevents metabolic disorders through uncoupling protein-1 induction in the skeletal muscle of mice fed high-fat diets[J].British Journal of Nutrition,2015,114(11):1774-1783.
[30]WANG Jiayao,JIANG Rui,LIANG Xiaomei,et al.Efficient synthesis of epilactose[J].Chinese Journal of Organic Chemistry,2017,37(2):375-384.(in Chinese)
[31]SABURI W,YAMAMOTO T,TAGUCHI H,et al.Practical preparation of epilactose produced with cellobiose 2-epimerase from Ruminococcus albus NE1[J].Bioscience,Biotechnology&Biochemistry,2010,74(8):1736-1737.
[32]KUSCHEL B,RIEMER F,PFOST D,et al.Large-scale purification of epilactose using a semi-preparative HPLC system[J].European Food Research and Technology,2016,243(3):391-402.
[33]CHEN Q,HE W,YAN X,et al.Construction of an enzymatic route using a food-grade recombinant Bacillus subtilis for the production and purification of epilactose from lactose[J].Journal of Dairy Science,2018,101(3):1872-1882.
[34]CARDELLE-COBAS A,CORZO N,OLANO A,et al.Galactooligosaccharides derived from lactose and lactulose:Influence of structure on Lactobacillus,Streptococcus and Bifidobacterium growth[J].International Journal of Food Microbiology,2011,149(1):81-87.
[35]SAARELA M,HALLAMAA K,MARRILASANDHOLM T,et al.The effect of lactose derivatives lactulose,lactitol and lactobionic acid on the functional and technological properties of potentially probiotic Lactobacillus strains[J].International Dairy Journal,2003,13(4):291-302.
[36]AIT-AISSA A,AIDER M.Lactulose:production and use in functional food,medical and pharmaceutical applications.Practical and critical review[J].International Journal of Food Science and Technology,2014,49(5):1245-1253.
[37]FINN R D,COGGILL P,EBERHARDT R Y,et al.The Pfam protein families database:towards a more sustainable future[J].Nucleic Acids Research,2016,44(D1):D279-285.
[38]SIDHU S S,GOYAL O,PARKER R A,et al.Rifaximin vs.lactulose in treatment of minimal hepatic encephalopathy[J].Liver International,2016,36(3):378-385.
[39]GLUUD L L,DAM G,BORRE M,et al.Lactulose,rifaximin or branched chain amino acids for hepatic encephalopathy:what is the evidence?[J].Metabolic Brain Disease,2013,28(2):221-225.
[40]PLAYNE M J,CRITTENDEN R G.Galacto-oligosaccharides and other products derived from lactose[J].Advanced Dairy Chemistry,2009,3:121-201.
[41]KIM Y S,OH D K.Lactulose production from lactose as a single substrate by a thermostable cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Bioresource Technology,2012,104:668-672.
[42]KIM Y S,KIM J E,OH D K.Borate enhances the production of lactulose from lactose by cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Bioresource Technology,2013,128(1):809-812.
[43]SHEN Q,ZHANG Y,YANG R,et al.Enhancement of isomerization activity and lactulose production of cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Food Chemistry,2016,207:60-67.
[44]KUSCHEL B,SEITL I,GLUCK C,et al.Hidden reaction:mesophilic cellobiose 2-epimerases produce lactulose[J].Journal of Agricultural&Food Chemistry,2017,65(12):2530-2539.
[45]LI Meiling,JIANG Bo,ZHANG Tao,et al.Synthesis of galactooligosaccharides form lactose byβ-galactosidase[J].Journal of Food Science and Biotechnology,2016,35(3):156-158.(in Chinese)
[46]KREWINKEL M,GOSCH M,RENTSCHLER E,et al.Epilactose production by 2 cellobiose 2-epimerases in natural milk[J].Journal of Dairy Science,2014,97(1):155-161.
[47]KREWINKEL M,KAISER J,MERZ M,et al.Novel cellobiose 2-epimerases for the production of epilactose from milk ultrafiltrate containing lactose[J].Journal of Dairy Science,2015,98(6):3665-3678.
[2]IZUMORI K.Izumoring:A strategy for bioproduction of all hexoses[J].Journal of Biotechnology,2006,124(4):717-722.
[3]MU W,LI Q,FAN C,et al.Recent advances on physiological functions and biotechnological production of epilactose[J].Applied Microbiology and Biotechnology,2013,97(5):1821-1827.
[4]TYLER T R,LEATHERWOOD J M.Epimerization of disaccharides by enzyme preparations from Ruminococcus albus[J].Archives of Biochemistry and Biophysics,1967,119(1):363-367.
[5]ITO S,HAMADA S,YAMAGUCHI K,et al.Cloning and sequencing of the cellobiose 2-epimerase gene from an obligatory anaerobe,Ruminococcus albus[J].Biochemical and Biophysical Research Communications,2007,360(3):640-645.
[6]ITO S,TAGUCHI H,HAMADA S,et al.Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme[J].Applied Microbiology and Biotechnology,2008,79(3):433-441.
[7]KIM J-E,KIM Y-S,KANG L-W,et al.Characterization of a recombinant cellobiose 2-epimerase from Dictyoglomus turgidum that epimerizes and isomerizesβ-1,4-andα-1,4-gluco-oligosaccharides[J].Biotechnology Letters,2012,34(11):2061-2068.
[8]SENOURA T,TAGUCHI H,ITO S,et al.Identification of the cellobiose 2-epimerase gene in the genome of Bacteroides fragilis NCTC 9343[J].Bioscience,Biotechnology&Biochemistry,2009,73(2):400-406.
[9]PARK C S,KIM J E,CHOI J G,et al.Characterization of a recombinant cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus and its application in the production of mannose from glucose[J].Applied Microbiology and Biotechnology,2011,92(6):1187-1196.
[10]KREWINKEL M,KAISER J,MERZ M,et al.Novel cellobiose 2-epimerases for the production of epilactose from milk ultrafiltrate containing lactose[J].Journal of Dairy Science,2015,98(6):3665-3678.
[11]SABURI W,TANAKA Y,MUTO H,et al.Functional reassignment of Cellvibrio vulgaris EpiA to cellobiose 2-epimerase and an evaluation of the biochemical functions of the 4-O-β-D-mannosyl-D-glucose phosphorylase-like protein,UnkA[J].Bioscience,Biotechnology&Biochemistry,2015,79(6):969-977.
[12]OJIMA T,SABURI W,YAMAMOTO T,et al.Identification and characterization of cellobiose 2-epimerases from various aerobes[J].Bioscience,Biotechnology&Biochemistry,2013,77(1):189-193.
[13]TAGUCHI H,SENOURA T,HAMADA S,et al.Cloning and sequencing of the gene for cellobiose 2-epimerase from a ruminal strain of Eubacterium cellulosolvens[J].FEMS Microbiology Letters,2008,287(1):34-40.
[14]OJIMA T,SABURI W,SATO H,et al.Biochemical characterization of a thermophilic cellobiose 2-epimerase from a thermohalophilic bacterium,Rhodothermus marinus JCM9785[J].Bioscience,Biotechnology&Biochemistry,2011,75(11):2162-2168.
[15]RENTSCHLER E,SCHUH K,KREWINKEL M,et al.Enzymatic production of lactulose and epilactose in milk[J].Journal of Dairy Science,2015,98(10):6767-6775.
[16]CHEN Q M,ZHANG W L,ZHANG T,et al.Characterization of an epilactose-producing cellobiose 2-epimerase from Thermoanaerobacterium saccharolyticum[J].Journal of Molecular Catalysis B-Enzymatic,2015,116:39-44.
[17]FUJIWARA T,SABURI W,INOUE S,et al.Crystal structure of Ruminococcus albus cellobiose 2-epimerase:Structural insights into epimerization of unmodified sugar[J].FEBS Letters,2013,587(7):840-846.
[18]FUJIWARA T,SABURI W,MATSUI H,et al.Structural insights into the epimerization ofβ-1,4-linked oligosaccharides catalyzed by cellobiose 2-epimerase,the sole enzyme epimerizing non-anomeric hydroxyl groups of unmodified sugars[J].Journal of Biological Chemistry,2014,289(6):3405-3415.
[19]NELOFAR A,LAGHARI A H,YASMIN A.Validated HPLC-RI method for the determination of lactulose and its process related impurities in syrup[J].Indian Journal of Pharmaceutical Sciences,2010,72(2):255-258.
[20]SATO H,SABURI W,OJIMA T,et al.Immobilization of a thermostable cellobiose 2-epimerase from Rhodothermus marinus JCM9785 and continuous production of epilactose[J].Bioscience,Biotechnology,&Biochemistry,2012,76(8):1584-1587.
[21]SABURI W,YAMAMOTO T,TAGUCHI H,et al.Practical preparation of epilactose produced with cellobiose 2-epimerase from Ruminococcus albus NE1[J].Journal of the Agricultural Chemical Society of Japan,2010,74(8):1736-1737.
[22]RENTSCHLER E,KUSCHEL B,KREWINKEL M,et al.Quantification of lactulose and epilactose in the presence of lactose in milk using a dual HPLC analysis[J].Food Analytical Methods,2016,9(8):2210-2222.
[23]MIYASATO M,AJISAKA K.Regioselectivity in beta-galactosidase-catalyzed transglycosylation for the enzymatic assembly of D-galactosyl-D-mannose[J].Bioscience,Biotechnology,&Biochemistry,2004,68(10):2086-2090.
[24]ITO S,TAGUCHI H,HAMADA S,et al.Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme[J].Applied Microbiology and Biotechnology,2008,79(3):433-441.
[25]WATANABE J,NISHIMUKAI M,TAGUCHI H,et al.Prebiotic properties of epilactose[J].Journal of Dairy Science,2008,91(12):4518-4526.
[26]SUZUKI T,NISHIMUKAI M,SHINOKI A,et al.Ingestion of epilactose,a non-digestible disaccharide,improves postgastrectomy osteopenia and anemia in rats through the promotion of intestinal calcium and iron absorption[J].Journal of Agricultural&Food Chemistry,2010,58(19):10787-10792.
[27]SUZUKI T,NISHIMUKAI M,TAKECHI M,et al.The nondigestible disaccharide epilactose increases paracellular Ca absorption via rho-associated kinase-and myosin light chain kinase-dependent mechanisms in rat small intestines[J].Journal of Agricultural&Food Chemistry,2010,58(3):1927-1932.
[28]NISHIMUKAI M,WATANABE J,TAGUCHI H,et al.Effects of epilactose on calcium absorption and serum lipid metabolism in rats[J].Journal of Agricultural&Food Chemistry,2008,56(21):10340-10345.
[29]MURAKAMI Y,OJIMA-KATO T,SABURI W,et al.Supplemental epilactose prevents metabolic disorders through uncoupling protein-1 induction in the skeletal muscle of mice fed high-fat diets[J].British Journal of Nutrition,2015,114(11):1774-1783.
[30]WANG Jiayao,JIANG Rui,LIANG Xiaomei,et al.Efficient synthesis of epilactose[J].Chinese Journal of Organic Chemistry,2017,37(2):375-384.(in Chinese)
[31]SABURI W,YAMAMOTO T,TAGUCHI H,et al.Practical preparation of epilactose produced with cellobiose 2-epimerase from Ruminococcus albus NE1[J].Bioscience,Biotechnology&Biochemistry,2010,74(8):1736-1737.
[32]KUSCHEL B,RIEMER F,PFOST D,et al.Large-scale purification of epilactose using a semi-preparative HPLC system[J].European Food Research and Technology,2016,243(3):391-402.
[33]CHEN Q,HE W,YAN X,et al.Construction of an enzymatic route using a food-grade recombinant Bacillus subtilis for the production and purification of epilactose from lactose[J].Journal of Dairy Science,2018,101(3):1872-1882.
[34]CARDELLE-COBAS A,CORZO N,OLANO A,et al.Galactooligosaccharides derived from lactose and lactulose:Influence of structure on Lactobacillus,Streptococcus and Bifidobacterium growth[J].International Journal of Food Microbiology,2011,149(1):81-87.
[35]SAARELA M,HALLAMAA K,MARRILASANDHOLM T,et al.The effect of lactose derivatives lactulose,lactitol and lactobionic acid on the functional and technological properties of potentially probiotic Lactobacillus strains[J].International Dairy Journal,2003,13(4):291-302.
[36]AIT-AISSA A,AIDER M.Lactulose:production and use in functional food,medical and pharmaceutical applications.Practical and critical review[J].International Journal of Food Science and Technology,2014,49(5):1245-1253.
[37]FINN R D,COGGILL P,EBERHARDT R Y,et al.The Pfam protein families database:towards a more sustainable future[J].Nucleic Acids Research,2016,44(D1):D279-285.
[38]SIDHU S S,GOYAL O,PARKER R A,et al.Rifaximin vs.lactulose in treatment of minimal hepatic encephalopathy[J].Liver International,2016,36(3):378-385.
[39]GLUUD L L,DAM G,BORRE M,et al.Lactulose,rifaximin or branched chain amino acids for hepatic encephalopathy:what is the evidence?[J].Metabolic Brain Disease,2013,28(2):221-225.
[40]PLAYNE M J,CRITTENDEN R G.Galacto-oligosaccharides and other products derived from lactose[J].Advanced Dairy Chemistry,2009,3:121-201.
[41]KIM Y S,OH D K.Lactulose production from lactose as a single substrate by a thermostable cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Bioresource Technology,2012,104:668-672.
[42]KIM Y S,KIM J E,OH D K.Borate enhances the production of lactulose from lactose by cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Bioresource Technology,2013,128(1):809-812.
[43]SHEN Q,ZHANG Y,YANG R,et al.Enhancement of isomerization activity and lactulose production of cellobiose 2-epimerase from Caldicellulosiruptor saccharolyticus[J].Food Chemistry,2016,207:60-67.
[44]KUSCHEL B,SEITL I,GLUCK C,et al.Hidden reaction:mesophilic cellobiose 2-epimerases produce lactulose[J].Journal of Agricultural&Food Chemistry,2017,65(12):2530-2539.
[45]LI Meiling,JIANG Bo,ZHANG Tao,et al.Synthesis of galactooligosaccharides form lactose byβ-galactosidase[J].Journal of Food Science and Biotechnology,2016,35(3):156-158.(in Chinese)
[46]KREWINKEL M,GOSCH M,RENTSCHLER E,et al.Epilactose production by 2 cellobiose 2-epimerases in natural milk[J].Journal of Dairy Science,2014,97(1):155-161.
[47]KREWINKEL M,KAISER J,MERZ M,et al.Novel cellobiose 2-epimerases for the production of epilactose from milk ultrafiltrate containing lactose[J].Journal of Dairy Science,2015,98(6):3665-3678.