茶多酚与多糖的相互作用:作用机理及功能特性变化研究进展
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摘要
茶多酚具有抗氧化、抗肿瘤、抗辐射等多种生物活性,与环糊精、黑木耳多糖或壳聚糖等多种多糖作用后,功能活性增强,但相互作用的过程与机理尚不明确。因此,对茶多酚与多糖的结构及其相互作用的研究显得尤为重要。近几年,关于茶多酚与多糖之间相互作用的研究日益增多,本文介绍了茶多酚和多糖的分类及结构,概括了多糖与茶多酚之间的相互作用类型、影响因素及研究方法,针对二者之间的相互作用对茶多酚功能特性的影响进行了综述,为后续研究二者与其他活性物质相互作用以及功能特性变化等方面提供参考。
Tea polyphenols(TP) have various biological activities including anti-oxidation, anti-tumor, anti-cancer,anti-virus and the enhancement of non-specific immunity of human body. After combining with various polysaccharides such as cyclodextrin, black fungus polysaccharide or chitosan, some biological activities of TP can be strengthened.However, the mechanism of the interaction between TP and polysaccharides still remains unclear. Therefore, it is of great importance to explore the structure and interaction between TP and polysaccharides. Recently, an increasing number of researches were reported on the interaction between TP and polysaccharides. Generally, this review introduced the classification and structure of TP and polysaccharides, then summarized the types, influencing factors,research methods and function of interactions between TP and polysaccharides, which provided a reference for the subsequent study of the interaction between TP and polysaccharides with other active substances and changes in functional properties.
Tea polyphenols(TP) have various biological activities including anti-oxidation, anti-tumor, anti-cancer,anti-virus and the enhancement of non-specific immunity of human body. After combining with various polysaccharides such as cyclodextrin, black fungus polysaccharide or chitosan, some biological activities of TP can be strengthened.However, the mechanism of the interaction between TP and polysaccharides still remains unclear. Therefore, it is of great importance to explore the structure and interaction between TP and polysaccharides. Recently, an increasing number of researches were reported on the interaction between TP and polysaccharides. Generally, this review introduced the classification and structure of TP and polysaccharides, then summarized the types, influencing factors,research methods and function of interactions between TP and polysaccharides, which provided a reference for the subsequent study of the interaction between TP and polysaccharides with other active substances and changes in functional properties.
引文
[1]陈小雷,胡王,周蓓蓓,等.天然抗氧化剂茶多酚对水产品的抗氧化研究[J].安徽农业科学,2016,44(1):112-114.
[2]Bansal S,Syan N,Mathur P,et al.Pharmacological profile of green tea and its polyphenols:a review[J].Medicinal Chemistry Research,2012,21(11):3347-3360.
[3]Frei B,Higdon J V.Antioxidant activity of tea polyphenols in vivo:evidence from animal studies[J].Journal of Nutrition,2003,133(10):3275S-3284S.
[4]Severino J F,Goodman B A,Kay C W M,et al.Free radicals generated during oxidation of green tea polyphenols:electron paramagnetic resonance spectroscopy combined with density functional theory calculations[J].Free Radic Biol Med,2009,46(8):1076-1088.
[5]Nakamura K,Ishiyama K,Hong S,et al.Bactericidal activity and mechanism of photoirradiated polyphenols against gram-positive and-negative bacteria[J].J Agric Food Chem,2015,63(35):7707-7713.
[6]Yang C S,Li G,Yang Z,et al.Cancer prevention by tocopherols and tea polyphenols[J].Cancer Letters,2013,334(1):79-85.
[7]宛晓春.茶叶生物化学[M].3版.北京:中国农业出版社,2003:15-18.
[8]高海荣,黄振旭,李华敏.16种中国茶叶中茶多酚含量对比研究[J].食品研究与开发,2016,37(7):33-36.
[9]Li X,Sun C,Luo L,et al.Determination of tea polyphenols content by infrared spectroscopy coupled with iPLS and random frog techniques[J].Computers&Electronics in Agriculture,2015,112:28-35.
[10]王媛,殷红,陈小波,等.茶多酚抗氧化作用的研究[J].安徽农业科学,2013,41(3):1232-1235.
[11]Min Z,Guo Z,Wang K,et al.Antioxidant effects of grape vine cane extracts from different Chinese grape varieties on edible oils[J].Molecules,2014,19(9):15213-15223.
[12]冯丽琴.富硒茶中茶多酚和茶多糖的分离纯化及抗氧化性研究[D].西安:陕西科技大学,2017.
[13]高媛圆,毛立民,徐平,等.茶多酚防治2型糖尿病的分子机理研究进展[J].茶叶科学,2015,35(3):239-247.
[14]范红艳,王艳春,顾饶胜,等.茶多酚抗衰老的研究进展[J].中国老年学杂志,2011,31(5):893-895.
[15]Koirala N,Pandey R P,Thang D V,et al.Glycosylation and subsequent malonylation of isoflavonoids in E.coli:strain development,production and insights into future metabolic perspectives[J].Journal of Industrial Microbiology&Biotechnology,2014,41(11):1647-1658.
[16]林杰,段玲靓,吴春燕,等.茶叶中的黄酮醇类物质及对感官品质的影响[J].茶叶,2010,36(1):14-18.
[17]Chen Z M,Lin Z.Tea and human health:biomedical functions of tea active components and current issues[J].Journal of Zhejiang University-SCIENCE B,2015,16(2):87-102.
[18]Lv H P,Zhu Y,Tan J F,et al.Bioactive compounds from Pu-erh tea with therapy for hyperlipidaemia[J].Journal of Functional Foods,2015,19:194-203.
[19]Bian M,Skidmore A K,Schlerf M,et al.Predicting foliar biochemistry of tea(Camellia sinensis)using reflectance spectra measured at powder,leaf and canopy levels[J].Isprs Journal of Photogrammetry&Remote Sensing,2013,78(4):148-156.
[20]Gjini E,Valente C,Sá-Le?o R,et al.How direct competition shapes coexistence and vaccine effects in multi-strain pathogen systems[J].Journal of Theoretical Biology,2016,388(7):50-60.
[21]于美汇,赵鑫,尹红力,等.碱提醇沉黑木耳多糖体外和体内降血脂功能[J].食品科学,2017,38(1):232-237.
[22]关倩倩,张文龙,杜方岭,等.山药多糖生物活性及作用机理研究进展[J].中国食物与营养,2018,24(3):11-14.
[23]陈小强.不同方法提制的绿茶多糖理化特性及生物学活性研究[D].杭州:浙江工商大学,2015.
[24]Venkatpurwar V,Pokharkar V.Green synthesis of silver nanoparticles using marine polysaccharide:study of in-vitro,antibacterial activity[J].Materials Letters,2011,65(6):999-1002.
[25]Lu L,Chai L,Wang W,et al.A selenium-enriched Ziyang green tea polysaccharide induces bax-dependent mitochondrial apoptosis and inhibits TGF-β1-stimulated collagen expression in human keloid fibroblasts via NG2inactivation[J].Biological Trace Element Research,2017,176(2):270-277.
[26]Le B C,Renard C M.Interactions between polyphenols and macromolecules:quantification methods and mechanisms[J].Critical Reviews in Food Science&Nutrition,2012,52(3):213-248.
[27]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(4):42-46.
[28]魏子淏.乳蛋白-EGCG和壳聚糖-绿原酸复合物的制备、结构表征及功能评价[D].北京:中国农业大学,2015.
[29]Soldati R,Cervellati R,Martelli G,et al.Unprotected Polyphenols in substitution reactions with4-acetoxy-azetidinones[J].ChemistrySelect,2016,1(12):3232-3238.
[30]Zhu F.Interactions between cell wall polysaccharides and polyphenols[J].Crit Rev Food Sci Nutr,2018,58(11):1-24.
[31]Renard C M G C,Baron A,Guyot S,et al.Interactions between apple cell walls and native apple polyphenols:quantification and some consequences[J].International Journal of Biological Macromolecules,2001,29(2):115-125.
[32]Prochowicz D,Kornowicz A,Janusz L.Interactions of native cyclodextrins with metal ions and inorganic nanoparticles fertile landscape for chemistry and materials science[J].Chemical Reviews,2017,11(7):13461-13501.
[33]任旭东.几种手性药物色谱保留行为的预测和一种儿茶素与生物大分子及β-环糊精相互作用的研究[D].西安:西北大学,2012.
[34]Riou V,Vernhet A,Doco T,et al.Aggregation of grape seed tannins in model wine-effect of wine polysaccharides[J].Food Hydrocolloids,2002,16(1):17-23.
[35]Piroonpan T,Katemake P,Panritdam E,et al.Alternative chitosan-based EPR dosimeter applicable for a relatively wide range of gamma radiation doses[J].Radiation Physics&Chemistry,2017,141:57-65.
[36]Wang Y,Liu J,Chen F,et al.Effects of molecular structure of polyphenols on their noncovalent interactions with oatβ-glucan[J].Journal of Agricultural&Food Chemistry,2013,61(19):4533-4538.
[37]Bo?i?M,Gorgieva S,Kokol V.Homogeneous and heterogeneous methods for laccase-mediated functionalization of chitosan by tannic acid and quercetin[J].Carbohydrate Polymers,2012,89(3):854-864.
[38]Bo?i?M,Gorgieva S,Kokol V.Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties[J].Carbohydrate Polymers,2012,87(4):2388-2398.
[39]Chen T,Kumar G,Harris M T,et al.Enzymatic grafting of hexyloxyphenol onto chitosan to alter surface and rheological properties[J].Biotechnology&Bioengineering,2015,70(5):564-573.
[40]Sousa F,Guebitz G M,Kokol V.Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids[J].Process Biochemistry,2009,44(7):749-756.
[41]Le B C,Guyot S,Renard C M.Non-covalent interaction between procyanidins and apple cell wall material:part i.effect of some environmental parameters[J].Biochimica Et Biophysica Acta,2004,1672(3):192-202.
[42]Watrelot A A,Le B C,Imberty A,et al.Interactions between pectic compounds and procyanidins are influenced by methylation degree and chain length[J].Biomacromolecules,2013,14(3):709-718.
[43]Mcmanus J P,Davis K G,Beart J E,et al.Polyphenol interactions:part i.introduction.Some observation on the reversible complexation of polyphenols with proteins and polysaccharides[J].Journal of the Chemical Society Perkin Transactions,1985,9(9):1429-1438.
[44]许勇泉,尹军峰.茶汤沉淀形成及其调控方法研究进展[J].茶叶科学,2016,36(4):337-346.
[45]Cai Y,Gaffney S H,Lilley T H,et al.Polyphenol interactions.Part 4.Model studies with caffeine and cyclodextrins[J].Journal of the Chemical Society,Perkin Transactions 2,1990(12):2197-2209.
[46]魏子淏.乳蛋白-EGCG和壳聚糖-绿原酸复合物的制备、结构表征及功能评价[D].北京:中国农业大学,2015.
[47]白海娜,王振宇,张华,等.多酚类化合物与黑木耳多糖协同抗氧化作用研究[J].食品工业科技,2013,34(22):124-127.
[48]Coma V,Freire C S R,Silvestre A J D.Recent advances on the development of antibacterial,polysaccharide-based materials[J].Polysaccharides,DOI:10.1007/978-3-319-03751-6_12-1.
[49]Kosza?ka P,Go?uńska M,Stanis?awowski M,et al.CD73 on B16F10 melanoma cells in CD73-deficient mice promotes tumor growth,angiogenesis,neovascularization,macrophage infiltration and metastasis[J].International Journal of Biochemistry&Cell Biology,2015,69:1-10.
[50]Aytekin A O,Morimura S,Kida K.Synthesis of chitosan-caffeic acid derivatives and evaluation of their antioxidant activities[J].Journal of Bioscience&Bioengineering,2011,111(2):212-216.
[51]Charernsriwilaiwat N,Opanasopit P,Rojanarata T,et al.Preparation and characterization of chitosanhydroxybenzotriazole/polyvinyl alcohol blend nanofibers by the electrospinning technique[J].Carbohydrate Polymers,2010,81(3):675-680.
[52]Sousa F,Guebitz G M,Kokol V.Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids[J].Process Biochemistry,2009,44(7):749-756.
[53]Chen T,Kumar G,Harris M T,et al.Enzymatic grafting of hexyloxyphenol onto chitosan to alter surface and rheological properties[J].Biotechnology and bioengineering,2000,70(5):564-573.
[54]Imming P,Sinning C,Meyer A.Drugs,their targets and the nature and number of drug targets[J].Nature Reviews Drug Discovery,2006,5(10):821-834.
[55]白海娜.黑木耳多糖AAP-4与原花青素对辐射诱导氧化损伤协同防护作用[D].哈尔滨:哈尔滨工业大学,2016.
[56]王静,张斌,管昶.褐藻寡糖茶多酚抗辐射复合制剂:2015100624438[P].2015-02-06.
[57]李赟,邹伟,孙威,等.槲皮素与环糊精衍生物包合物的理化性质和分子对接研究[J].食品科学,2017,38(23):45-50.
[2]Bansal S,Syan N,Mathur P,et al.Pharmacological profile of green tea and its polyphenols:a review[J].Medicinal Chemistry Research,2012,21(11):3347-3360.
[3]Frei B,Higdon J V.Antioxidant activity of tea polyphenols in vivo:evidence from animal studies[J].Journal of Nutrition,2003,133(10):3275S-3284S.
[4]Severino J F,Goodman B A,Kay C W M,et al.Free radicals generated during oxidation of green tea polyphenols:electron paramagnetic resonance spectroscopy combined with density functional theory calculations[J].Free Radic Biol Med,2009,46(8):1076-1088.
[5]Nakamura K,Ishiyama K,Hong S,et al.Bactericidal activity and mechanism of photoirradiated polyphenols against gram-positive and-negative bacteria[J].J Agric Food Chem,2015,63(35):7707-7713.
[6]Yang C S,Li G,Yang Z,et al.Cancer prevention by tocopherols and tea polyphenols[J].Cancer Letters,2013,334(1):79-85.
[7]宛晓春.茶叶生物化学[M].3版.北京:中国农业出版社,2003:15-18.
[8]高海荣,黄振旭,李华敏.16种中国茶叶中茶多酚含量对比研究[J].食品研究与开发,2016,37(7):33-36.
[9]Li X,Sun C,Luo L,et al.Determination of tea polyphenols content by infrared spectroscopy coupled with iPLS and random frog techniques[J].Computers&Electronics in Agriculture,2015,112:28-35.
[10]王媛,殷红,陈小波,等.茶多酚抗氧化作用的研究[J].安徽农业科学,2013,41(3):1232-1235.
[11]Min Z,Guo Z,Wang K,et al.Antioxidant effects of grape vine cane extracts from different Chinese grape varieties on edible oils[J].Molecules,2014,19(9):15213-15223.
[12]冯丽琴.富硒茶中茶多酚和茶多糖的分离纯化及抗氧化性研究[D].西安:陕西科技大学,2017.
[13]高媛圆,毛立民,徐平,等.茶多酚防治2型糖尿病的分子机理研究进展[J].茶叶科学,2015,35(3):239-247.
[14]范红艳,王艳春,顾饶胜,等.茶多酚抗衰老的研究进展[J].中国老年学杂志,2011,31(5):893-895.
[15]Koirala N,Pandey R P,Thang D V,et al.Glycosylation and subsequent malonylation of isoflavonoids in E.coli:strain development,production and insights into future metabolic perspectives[J].Journal of Industrial Microbiology&Biotechnology,2014,41(11):1647-1658.
[16]林杰,段玲靓,吴春燕,等.茶叶中的黄酮醇类物质及对感官品质的影响[J].茶叶,2010,36(1):14-18.
[17]Chen Z M,Lin Z.Tea and human health:biomedical functions of tea active components and current issues[J].Journal of Zhejiang University-SCIENCE B,2015,16(2):87-102.
[18]Lv H P,Zhu Y,Tan J F,et al.Bioactive compounds from Pu-erh tea with therapy for hyperlipidaemia[J].Journal of Functional Foods,2015,19:194-203.
[19]Bian M,Skidmore A K,Schlerf M,et al.Predicting foliar biochemistry of tea(Camellia sinensis)using reflectance spectra measured at powder,leaf and canopy levels[J].Isprs Journal of Photogrammetry&Remote Sensing,2013,78(4):148-156.
[20]Gjini E,Valente C,Sá-Le?o R,et al.How direct competition shapes coexistence and vaccine effects in multi-strain pathogen systems[J].Journal of Theoretical Biology,2016,388(7):50-60.
[21]于美汇,赵鑫,尹红力,等.碱提醇沉黑木耳多糖体外和体内降血脂功能[J].食品科学,2017,38(1):232-237.
[22]关倩倩,张文龙,杜方岭,等.山药多糖生物活性及作用机理研究进展[J].中国食物与营养,2018,24(3):11-14.
[23]陈小强.不同方法提制的绿茶多糖理化特性及生物学活性研究[D].杭州:浙江工商大学,2015.
[24]Venkatpurwar V,Pokharkar V.Green synthesis of silver nanoparticles using marine polysaccharide:study of in-vitro,antibacterial activity[J].Materials Letters,2011,65(6):999-1002.
[25]Lu L,Chai L,Wang W,et al.A selenium-enriched Ziyang green tea polysaccharide induces bax-dependent mitochondrial apoptosis and inhibits TGF-β1-stimulated collagen expression in human keloid fibroblasts via NG2inactivation[J].Biological Trace Element Research,2017,176(2):270-277.
[26]Le B C,Renard C M.Interactions between polyphenols and macromolecules:quantification methods and mechanisms[J].Critical Reviews in Food Science&Nutrition,2012,52(3):213-248.
[27]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(4):42-46.
[28]魏子淏.乳蛋白-EGCG和壳聚糖-绿原酸复合物的制备、结构表征及功能评价[D].北京:中国农业大学,2015.
[29]Soldati R,Cervellati R,Martelli G,et al.Unprotected Polyphenols in substitution reactions with4-acetoxy-azetidinones[J].ChemistrySelect,2016,1(12):3232-3238.
[30]Zhu F.Interactions between cell wall polysaccharides and polyphenols[J].Crit Rev Food Sci Nutr,2018,58(11):1-24.
[31]Renard C M G C,Baron A,Guyot S,et al.Interactions between apple cell walls and native apple polyphenols:quantification and some consequences[J].International Journal of Biological Macromolecules,2001,29(2):115-125.
[32]Prochowicz D,Kornowicz A,Janusz L.Interactions of native cyclodextrins with metal ions and inorganic nanoparticles fertile landscape for chemistry and materials science[J].Chemical Reviews,2017,11(7):13461-13501.
[33]任旭东.几种手性药物色谱保留行为的预测和一种儿茶素与生物大分子及β-环糊精相互作用的研究[D].西安:西北大学,2012.
[34]Riou V,Vernhet A,Doco T,et al.Aggregation of grape seed tannins in model wine-effect of wine polysaccharides[J].Food Hydrocolloids,2002,16(1):17-23.
[35]Piroonpan T,Katemake P,Panritdam E,et al.Alternative chitosan-based EPR dosimeter applicable for a relatively wide range of gamma radiation doses[J].Radiation Physics&Chemistry,2017,141:57-65.
[36]Wang Y,Liu J,Chen F,et al.Effects of molecular structure of polyphenols on their noncovalent interactions with oatβ-glucan[J].Journal of Agricultural&Food Chemistry,2013,61(19):4533-4538.
[37]Bo?i?M,Gorgieva S,Kokol V.Homogeneous and heterogeneous methods for laccase-mediated functionalization of chitosan by tannic acid and quercetin[J].Carbohydrate Polymers,2012,89(3):854-864.
[38]Bo?i?M,Gorgieva S,Kokol V.Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties[J].Carbohydrate Polymers,2012,87(4):2388-2398.
[39]Chen T,Kumar G,Harris M T,et al.Enzymatic grafting of hexyloxyphenol onto chitosan to alter surface and rheological properties[J].Biotechnology&Bioengineering,2015,70(5):564-573.
[40]Sousa F,Guebitz G M,Kokol V.Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids[J].Process Biochemistry,2009,44(7):749-756.
[41]Le B C,Guyot S,Renard C M.Non-covalent interaction between procyanidins and apple cell wall material:part i.effect of some environmental parameters[J].Biochimica Et Biophysica Acta,2004,1672(3):192-202.
[42]Watrelot A A,Le B C,Imberty A,et al.Interactions between pectic compounds and procyanidins are influenced by methylation degree and chain length[J].Biomacromolecules,2013,14(3):709-718.
[43]Mcmanus J P,Davis K G,Beart J E,et al.Polyphenol interactions:part i.introduction.Some observation on the reversible complexation of polyphenols with proteins and polysaccharides[J].Journal of the Chemical Society Perkin Transactions,1985,9(9):1429-1438.
[44]许勇泉,尹军峰.茶汤沉淀形成及其调控方法研究进展[J].茶叶科学,2016,36(4):337-346.
[45]Cai Y,Gaffney S H,Lilley T H,et al.Polyphenol interactions.Part 4.Model studies with caffeine and cyclodextrins[J].Journal of the Chemical Society,Perkin Transactions 2,1990(12):2197-2209.
[46]魏子淏.乳蛋白-EGCG和壳聚糖-绿原酸复合物的制备、结构表征及功能评价[D].北京:中国农业大学,2015.
[47]白海娜,王振宇,张华,等.多酚类化合物与黑木耳多糖协同抗氧化作用研究[J].食品工业科技,2013,34(22):124-127.
[48]Coma V,Freire C S R,Silvestre A J D.Recent advances on the development of antibacterial,polysaccharide-based materials[J].Polysaccharides,DOI:10.1007/978-3-319-03751-6_12-1.
[49]Kosza?ka P,Go?uńska M,Stanis?awowski M,et al.CD73 on B16F10 melanoma cells in CD73-deficient mice promotes tumor growth,angiogenesis,neovascularization,macrophage infiltration and metastasis[J].International Journal of Biochemistry&Cell Biology,2015,69:1-10.
[50]Aytekin A O,Morimura S,Kida K.Synthesis of chitosan-caffeic acid derivatives and evaluation of their antioxidant activities[J].Journal of Bioscience&Bioengineering,2011,111(2):212-216.
[51]Charernsriwilaiwat N,Opanasopit P,Rojanarata T,et al.Preparation and characterization of chitosanhydroxybenzotriazole/polyvinyl alcohol blend nanofibers by the electrospinning technique[J].Carbohydrate Polymers,2010,81(3):675-680.
[52]Sousa F,Guebitz G M,Kokol V.Antimicrobial and antioxidant properties of chitosan enzymatically functionalized with flavonoids[J].Process Biochemistry,2009,44(7):749-756.
[53]Chen T,Kumar G,Harris M T,et al.Enzymatic grafting of hexyloxyphenol onto chitosan to alter surface and rheological properties[J].Biotechnology and bioengineering,2000,70(5):564-573.
[54]Imming P,Sinning C,Meyer A.Drugs,their targets and the nature and number of drug targets[J].Nature Reviews Drug Discovery,2006,5(10):821-834.
[55]白海娜.黑木耳多糖AAP-4与原花青素对辐射诱导氧化损伤协同防护作用[D].哈尔滨:哈尔滨工业大学,2016.
[56]王静,张斌,管昶.褐藻寡糖茶多酚抗辐射复合制剂:2015100624438[P].2015-02-06.
[57]李赟,邹伟,孙威,等.槲皮素与环糊精衍生物包合物的理化性质和分子对接研究[J].食品科学,2017,38(23):45-50.
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