分子修饰对多糖免疫活性影响的研究进展
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摘要
免疫调节活性是多糖最重要的生物活性之一,多糖能够提高机体的免疫功能而对正常细胞没有毒副作用。对多糖进行适当的分子修饰,有利于多糖免疫活性功能的发挥。为了改进多糖的免疫活性,常采用化学修饰、生物修饰、物理修饰等方法对多糖进行结构修饰。本文综述了近年来不同分子修饰方法对多糖免疫活性的影响,并探讨其作用机制,为进一步研究活性多糖的免疫作用机制和构效关系提供参考和依据。
Immunoregulatory activity is one of the most important biological activities of polysaccharides.Polysaccharides can enhance immune activity while offer no side-effects on cells. Appropriate modification on polysaccharide could be good to exert immune function. The common methods for structure modification to improve its immune activity are the chemical method,biological method and physical method. This paper had expounded different methods of polysaccharide modification on the immune activity in recent years and discussed the mechanism of action. It provided reference and basis for further study on the immunologic mechanism and structure-function relationship of polysaccharides.
Immunoregulatory activity is one of the most important biological activities of polysaccharides.Polysaccharides can enhance immune activity while offer no side-effects on cells. Appropriate modification on polysaccharide could be good to exert immune function. The common methods for structure modification to improve its immune activity are the chemical method,biological method and physical method. This paper had expounded different methods of polysaccharide modification on the immune activity in recent years and discussed the mechanism of action. It provided reference and basis for further study on the immunologic mechanism and structure-function relationship of polysaccharides.
引文
[1]尚晓娅,钦传光,曹刚,等.绞股蓝多糖提取分离、化学结构及生物活性的研究进展[J].天然产物研究与开发,2010,22(3):514-518,540.
[2]尚晓娅,张媛,白艳玲,等.绞股蓝多糖体外抗氧化活性研究[J].天然产物研究与开发,2013,25(4):450-454.
[3]江长优,张健,赵江贺.牡蛎多糖增强小鼠免疫功能作用研究[J].中成药,2013,35(5):1062-1065.
[4]Van D,Kee N,Frost C,et al.Extracellular polysaccharide production in bacillus Licheniformis Svd1and its immunomodulatory effect[J].Bio Resources,2012,7(4):4976-4993.
[5]Liu X,Wan Z,Shi L,et al.Preparation and antiherpetic activities of chemically modified polysaccharides from Polygonatum cyrtonema Hua[J].Carbohydr Polym,2011,83(2):737-742.
[6]Bao H,Choi W,You S.Effect of sulfated modification on the molecular characteristics and biological activities of polysaccharides from hypsizigus marmoreus[J].Biosci Biotechnol Biochem,2010,74(7):1408-1414.
[7]Zhang Y,Lu X,Zhang Y,et al.Sulfated modification and immunomodulatory activity of water-soluble polysaccharides derived from fresh Chinese persimmon fruit[J].Int J Biol Macromol,2010,46(1):67-71.
[8]Gamal-Eldeen A,Amer H,Helmy W,et al.Chemicallymodified polysaccharide extract derived from Leucaena leucocephala alters Raw 264.7 murine macrophage functions[J].Int Immunopharmacol,2007,7(6):871-878.
[9]Du X,Zhang J,Yang Y,et al.Purification,chemical modification and immunostimulating activity of polysaccharides from Tremella aurantialba fruit bodies[J].J Zhejiang Univ-sc B,2010,11(6):437-442.
[10]Zhao X,Hu Y,Wang D,et al.The comparison of immuneenhancing activity of sulfated polysaccharidses from Tremella and Condonpsis pilosula[J].Carbohydr Polym,2013,98(1):438-443.
[11]Nguyena T,Wang D,Hu Y,et al.Immuno-enhancing activity of sulfated Auricularia auricula polysaccharides[J].Carbohydr Polym,2012,89(4):1117-1122.
[12]Zhang J,Chen J,Wang D,et al.Immune-enhancing activity comparison of sulfated ophiopogon polysaccharide and sulfated jujube polysaccharide[J].Int J Biol Macromol,2013,52(1):212-217.
[13]Wang J,Hu Y,Wang D,et al.Sulfated modification can enhance the immune-enhancing activity of lyceum barbarum polysaccharides[J].Cell Immunol,2010,263(2):219-223.
[14]陈美珍,余杰,杨拉维,等.龙须菜多糖硫酸化对免疫活性的影响[J].食品多糖,2010,31(15):278-282.
[15]Yang L,Zhao T,Wei H,et al.Carboxymethylation of polysaccharides from Auricularia auricula and their antioxidant activities in vitro[J].Int J Biol Macromol,2011,49(5):1124-1130.
[16]杨文鸽,黄晓春,李花霞,等.葡聚糖与其羧甲基衍生物对养殖大黄鱼非特异免疫作用[J].浙江农业学报,2006,18(1):16-20.
[17]杨小军,王思宇,姚军虎,等.羧甲基化分子修饰制备高效低聚黄芪多糖的方法:中国,103030704A[P].2013-04-10.
[18]Shin J,Lee S,Bae I,et al.Structural and biological study of carboxymethylated Phellinus linteus polysaccharides[J].J Agric Food Chem,2007,55(9):3368-3372.
[19]Dergunova M,Alexeenk T,Zhanaeva S,et al.Characterization of the novel chemically modified fungal polysaccharides as the macrophage stimulators[J].Int Immunopharmacol,2009,9(6):729-733.
[20]吴广枫,王姣斐,李平兰.改性双歧杆菌胞外多糖体外免疫活性研究[J].食品科技,2011,36(2):2-4.
[21]金磊,任敏,严薇,等.羧甲基化海洋真菌多糖的制备及产物对巨噬细胞免疫作用的影响[J].药物生物技术,2009,16(4):369-373.
[22]李全才,李春霞,勾东霞,等.磷酸化多糖的研究进展[J].生命科学,2013,25(3):262-268.
[23]Wei D,Cheng W,Wei Y,et al.Phosphorylated modification and in vitro antioxidant activity of Radix Hedysari polysaccharide[J].Glycoconj J,2012,29(4):167-172.
[24]Suárez E,Kralovec J,Grindley T.Isolation of phosphorylated polysaccharides from algae:the immunostimulatory principle of Chlorella pyrenoidosa[J].Carbohydr Res,2010,345(9):1190-1204.
[25]Nagasawa C,Nishimura U,Tohno M,et al.Oral administration of phosphorylated dextran regulates immune response inovalbumin-immunized mice[J].Asian Austral J Anim,2010,23(1):106-115.
[26]Kitazawa H,Harata T,Uemura J,et al.Phosphate group requirement for mitogenic activation of lymphocytes by an extracellular phosphopolysaccharide from Lactobacillus delbrueckii ssp.Bulgaricus.Int[J].Food Microbiol,1998,40(3):169-175.
[27]Kitazawa H,Ishii H,Uemura J,et al.Augmentation of macrophagefunctions by an extracellular phospho-268polysaccharide from Lactobacillus delbrueckii ssp.Bulgaricus[J].Food Microbiol,2000,17(1):109-118.
[28]Nishimura-Uemura J,Kitazawa H,Kawai Y,et al.Functional alteration of murine macrophages stimulated with extracellular polysaccharides from Lactobacillus delbrueckii ssp.Bulgaricus OLL1073R-1[J].Food Microbiol,2003,20(3):267-273.
[29]魏虎来,贾正平,赵怀顺,等.T-AK细胞和IL-2脂质体联合硒酸酯多糖抗白血病效应的研究[J].中华微生物学和免疫学杂志,1998,18(5):410-413.
[30]Qin T,Chen J,Wang D,et al.Optimization of selenylation conditions for Chinese angelica polysaccharide based on immune-enhancing activity[J].Carbohydr Polym,2013,92(1):645-650.
[31]Qin T,Chen J,Wang D,et al.Selenylation modification can enhance immune-enhancing activity of Chinese angelica polysaccharide[J].Carbohydr Polym,2013,95(1):183-187.
[32]蒋芹,张为民,杨成喜.硒酸酯多糖辅助癌症化疗的临床观察[J].肿瘤防治研究,1997,24(2):110-111.
[33]张哲文,魏虎来,苏海翔.硒酸酯多糖的免疫调节与抗肿瘤作用[J].兰州大学学报,2005,31(2):88-91.
[34]徐兵河,宋雪梅,孙燕,等.硒酸酯多糖Ⅱ期临床结果[J].中国新药杂志,1998,7(4):258-261.
[35]Chauhan D,Ray A,Yiktorsson K,et al.In vitro and in vivo antitumor activity of a novel alkylating agent,MelphalanFlufenamide,against Multiple Myeloma Cells[J].Clin Cancer Res,2013,19(11):3019-3031.
[36]Wang X,Creek D,Schiaffo C,et al.Spiroadamantyl 1,2,4-trioxolane,1,2,4-trioxane,and 1,2,4-trioxepane pairs:relationship between peroxide bond iron(II)reactivity,heme alkylation efficiency,and antimalarial activity[J].Bioorg Med Chem Lett,2009,19(16):4542-4545.
[37]Zhocowski N,Sendra V G,Lorenz V,et al.Catalytic and glycan-binding abilities of ppGalNAc-T2are regulated by acetylation[J].Biochem Biophys Res Commun,2011,410(1):140-145.
[38]Vasconcelosa A,Dekker R,Barbosa A,et al.Sulfonation and anticoagulant activity of fungal exocellular-(1→6)-dglucan(lasiodiplodan)[J].Carbohydr Polym,2013,92(2):1908-1914.
[39]Young M,Davies M J,Bailey D,et al.Characterization of oligosaccharides from an antigenic mannan of Saccharomy cescerevisiae[J].Glycoconjugate J,1998,15(8):815-822.
[40]Liu W,Xu P,Yao W,et al.Preparation of a hydroxypropyl Ganoderma lucidum polysaccharide and its physicochemical properties[J].Food Chem,2010,122(4):965-971.
[41]索金良.4-硒(代)硫酸酯多糖的抗肿瘤免疫调节作用及其机制研究[J].生理科学进展,1996,27(1):43-46.
[42]Chen X,Zhang L,Cheung P,et al.Immunopotentiation and anti-tumor activity of carboxymethylated-sulfatedβ-(1→3)-Dglucan from Poria cocos[J].Int Immunopharmacol,2010,10(4):398-405.
[43]贾俊强,沈健,陈炼,等.蛹虫草多糖的酶法修饰及其抗氧化活性[J].食品科学,2013,34(1):114-120.
[44]刘贺,郭晓飞,李君,等.大豆种皮多糖在甘露聚糖酶修饰下力学行为的演变[J].食品工业科技,2012,33(4):180-183.
[45]Sun Y,Liang H,Cai G,et al.Sulfated modification of the water-soluble polysaccharides from Polyporus albicans mycelia and its potential biological activities[J].Int J Biol Macromol,2009,44(1):14-17.
[46]余志,石玉涛,倪德江,等.酶法修饰绿茶多糖对免疫低下模型小鼠免疫活性的影响[J].茶叶学,2010,30(增刊1):567-572.
[47]刘媛媛,王强,刘红芝.酿酒酵母细胞壁多糖改性研究进展[J].化工进展,2009,28(4):686-691.
[48]王兆梅,李琳,郭祀远,等.多糖结构修饰研究进展[J].中国医药工业杂志,2002,33(12):616-620.
[49]Kasaai M,Charlet G,Paquin P,et al.Fragmentation of chitosan by microfluidization process[J].Innov Food Sci Emerg,2003,4(4):403-413.
[50]高洁,刘红芝,刘丽,等.修饰改性β-葡聚糖溶液构象研究进展[J].食品科学,2013,34(13):323-328.
[51]孔庆彧.低剂量辐射对肿瘤患者外周血NK细胞免疫活性的影响及机制研究[D].长春:吉林大学,2013.
[2]尚晓娅,张媛,白艳玲,等.绞股蓝多糖体外抗氧化活性研究[J].天然产物研究与开发,2013,25(4):450-454.
[3]江长优,张健,赵江贺.牡蛎多糖增强小鼠免疫功能作用研究[J].中成药,2013,35(5):1062-1065.
[4]Van D,Kee N,Frost C,et al.Extracellular polysaccharide production in bacillus Licheniformis Svd1and its immunomodulatory effect[J].Bio Resources,2012,7(4):4976-4993.
[5]Liu X,Wan Z,Shi L,et al.Preparation and antiherpetic activities of chemically modified polysaccharides from Polygonatum cyrtonema Hua[J].Carbohydr Polym,2011,83(2):737-742.
[6]Bao H,Choi W,You S.Effect of sulfated modification on the molecular characteristics and biological activities of polysaccharides from hypsizigus marmoreus[J].Biosci Biotechnol Biochem,2010,74(7):1408-1414.
[7]Zhang Y,Lu X,Zhang Y,et al.Sulfated modification and immunomodulatory activity of water-soluble polysaccharides derived from fresh Chinese persimmon fruit[J].Int J Biol Macromol,2010,46(1):67-71.
[8]Gamal-Eldeen A,Amer H,Helmy W,et al.Chemicallymodified polysaccharide extract derived from Leucaena leucocephala alters Raw 264.7 murine macrophage functions[J].Int Immunopharmacol,2007,7(6):871-878.
[9]Du X,Zhang J,Yang Y,et al.Purification,chemical modification and immunostimulating activity of polysaccharides from Tremella aurantialba fruit bodies[J].J Zhejiang Univ-sc B,2010,11(6):437-442.
[10]Zhao X,Hu Y,Wang D,et al.The comparison of immuneenhancing activity of sulfated polysaccharidses from Tremella and Condonpsis pilosula[J].Carbohydr Polym,2013,98(1):438-443.
[11]Nguyena T,Wang D,Hu Y,et al.Immuno-enhancing activity of sulfated Auricularia auricula polysaccharides[J].Carbohydr Polym,2012,89(4):1117-1122.
[12]Zhang J,Chen J,Wang D,et al.Immune-enhancing activity comparison of sulfated ophiopogon polysaccharide and sulfated jujube polysaccharide[J].Int J Biol Macromol,2013,52(1):212-217.
[13]Wang J,Hu Y,Wang D,et al.Sulfated modification can enhance the immune-enhancing activity of lyceum barbarum polysaccharides[J].Cell Immunol,2010,263(2):219-223.
[14]陈美珍,余杰,杨拉维,等.龙须菜多糖硫酸化对免疫活性的影响[J].食品多糖,2010,31(15):278-282.
[15]Yang L,Zhao T,Wei H,et al.Carboxymethylation of polysaccharides from Auricularia auricula and their antioxidant activities in vitro[J].Int J Biol Macromol,2011,49(5):1124-1130.
[16]杨文鸽,黄晓春,李花霞,等.葡聚糖与其羧甲基衍生物对养殖大黄鱼非特异免疫作用[J].浙江农业学报,2006,18(1):16-20.
[17]杨小军,王思宇,姚军虎,等.羧甲基化分子修饰制备高效低聚黄芪多糖的方法:中国,103030704A[P].2013-04-10.
[18]Shin J,Lee S,Bae I,et al.Structural and biological study of carboxymethylated Phellinus linteus polysaccharides[J].J Agric Food Chem,2007,55(9):3368-3372.
[19]Dergunova M,Alexeenk T,Zhanaeva S,et al.Characterization of the novel chemically modified fungal polysaccharides as the macrophage stimulators[J].Int Immunopharmacol,2009,9(6):729-733.
[20]吴广枫,王姣斐,李平兰.改性双歧杆菌胞外多糖体外免疫活性研究[J].食品科技,2011,36(2):2-4.
[21]金磊,任敏,严薇,等.羧甲基化海洋真菌多糖的制备及产物对巨噬细胞免疫作用的影响[J].药物生物技术,2009,16(4):369-373.
[22]李全才,李春霞,勾东霞,等.磷酸化多糖的研究进展[J].生命科学,2013,25(3):262-268.
[23]Wei D,Cheng W,Wei Y,et al.Phosphorylated modification and in vitro antioxidant activity of Radix Hedysari polysaccharide[J].Glycoconj J,2012,29(4):167-172.
[24]Suárez E,Kralovec J,Grindley T.Isolation of phosphorylated polysaccharides from algae:the immunostimulatory principle of Chlorella pyrenoidosa[J].Carbohydr Res,2010,345(9):1190-1204.
[25]Nagasawa C,Nishimura U,Tohno M,et al.Oral administration of phosphorylated dextran regulates immune response inovalbumin-immunized mice[J].Asian Austral J Anim,2010,23(1):106-115.
[26]Kitazawa H,Harata T,Uemura J,et al.Phosphate group requirement for mitogenic activation of lymphocytes by an extracellular phosphopolysaccharide from Lactobacillus delbrueckii ssp.Bulgaricus.Int[J].Food Microbiol,1998,40(3):169-175.
[27]Kitazawa H,Ishii H,Uemura J,et al.Augmentation of macrophagefunctions by an extracellular phospho-268polysaccharide from Lactobacillus delbrueckii ssp.Bulgaricus[J].Food Microbiol,2000,17(1):109-118.
[28]Nishimura-Uemura J,Kitazawa H,Kawai Y,et al.Functional alteration of murine macrophages stimulated with extracellular polysaccharides from Lactobacillus delbrueckii ssp.Bulgaricus OLL1073R-1[J].Food Microbiol,2003,20(3):267-273.
[29]魏虎来,贾正平,赵怀顺,等.T-AK细胞和IL-2脂质体联合硒酸酯多糖抗白血病效应的研究[J].中华微生物学和免疫学杂志,1998,18(5):410-413.
[30]Qin T,Chen J,Wang D,et al.Optimization of selenylation conditions for Chinese angelica polysaccharide based on immune-enhancing activity[J].Carbohydr Polym,2013,92(1):645-650.
[31]Qin T,Chen J,Wang D,et al.Selenylation modification can enhance immune-enhancing activity of Chinese angelica polysaccharide[J].Carbohydr Polym,2013,95(1):183-187.
[32]蒋芹,张为民,杨成喜.硒酸酯多糖辅助癌症化疗的临床观察[J].肿瘤防治研究,1997,24(2):110-111.
[33]张哲文,魏虎来,苏海翔.硒酸酯多糖的免疫调节与抗肿瘤作用[J].兰州大学学报,2005,31(2):88-91.
[34]徐兵河,宋雪梅,孙燕,等.硒酸酯多糖Ⅱ期临床结果[J].中国新药杂志,1998,7(4):258-261.
[35]Chauhan D,Ray A,Yiktorsson K,et al.In vitro and in vivo antitumor activity of a novel alkylating agent,MelphalanFlufenamide,against Multiple Myeloma Cells[J].Clin Cancer Res,2013,19(11):3019-3031.
[36]Wang X,Creek D,Schiaffo C,et al.Spiroadamantyl 1,2,4-trioxolane,1,2,4-trioxane,and 1,2,4-trioxepane pairs:relationship between peroxide bond iron(II)reactivity,heme alkylation efficiency,and antimalarial activity[J].Bioorg Med Chem Lett,2009,19(16):4542-4545.
[37]Zhocowski N,Sendra V G,Lorenz V,et al.Catalytic and glycan-binding abilities of ppGalNAc-T2are regulated by acetylation[J].Biochem Biophys Res Commun,2011,410(1):140-145.
[38]Vasconcelosa A,Dekker R,Barbosa A,et al.Sulfonation and anticoagulant activity of fungal exocellular-(1→6)-dglucan(lasiodiplodan)[J].Carbohydr Polym,2013,92(2):1908-1914.
[39]Young M,Davies M J,Bailey D,et al.Characterization of oligosaccharides from an antigenic mannan of Saccharomy cescerevisiae[J].Glycoconjugate J,1998,15(8):815-822.
[40]Liu W,Xu P,Yao W,et al.Preparation of a hydroxypropyl Ganoderma lucidum polysaccharide and its physicochemical properties[J].Food Chem,2010,122(4):965-971.
[41]索金良.4-硒(代)硫酸酯多糖的抗肿瘤免疫调节作用及其机制研究[J].生理科学进展,1996,27(1):43-46.
[42]Chen X,Zhang L,Cheung P,et al.Immunopotentiation and anti-tumor activity of carboxymethylated-sulfatedβ-(1→3)-Dglucan from Poria cocos[J].Int Immunopharmacol,2010,10(4):398-405.
[43]贾俊强,沈健,陈炼,等.蛹虫草多糖的酶法修饰及其抗氧化活性[J].食品科学,2013,34(1):114-120.
[44]刘贺,郭晓飞,李君,等.大豆种皮多糖在甘露聚糖酶修饰下力学行为的演变[J].食品工业科技,2012,33(4):180-183.
[45]Sun Y,Liang H,Cai G,et al.Sulfated modification of the water-soluble polysaccharides from Polyporus albicans mycelia and its potential biological activities[J].Int J Biol Macromol,2009,44(1):14-17.
[46]余志,石玉涛,倪德江,等.酶法修饰绿茶多糖对免疫低下模型小鼠免疫活性的影响[J].茶叶学,2010,30(增刊1):567-572.
[47]刘媛媛,王强,刘红芝.酿酒酵母细胞壁多糖改性研究进展[J].化工进展,2009,28(4):686-691.
[48]王兆梅,李琳,郭祀远,等.多糖结构修饰研究进展[J].中国医药工业杂志,2002,33(12):616-620.
[49]Kasaai M,Charlet G,Paquin P,et al.Fragmentation of chitosan by microfluidization process[J].Innov Food Sci Emerg,2003,4(4):403-413.
[50]高洁,刘红芝,刘丽,等.修饰改性β-葡聚糖溶液构象研究进展[J].食品科学,2013,34(13):323-328.
[51]孔庆彧.低剂量辐射对肿瘤患者外周血NK细胞免疫活性的影响及机制研究[D].长春:吉林大学,2013.