果蔬中木质素提取及其生物活性应用研究进展
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摘要
木质素作为一类具有众多生物活性的天然多酚类化合物,广泛存在于植物细胞中,果蔬中的小分子量木质素作为一种绿色、安全、健康的活性物质具有广阔的应用前景和开发价值。参考近年来国内外对木质素的大量研究,主要对果蔬中木质素的提取方法、结构表征、生物活性及应用等方面进行阐述,分析木质素研究现状及存在的问题,并结合实际展望木质素的未来发展趋势。
Lignin,as a kind of natural polyphenol compounds with many biological activities,is widely found in plant cells,which has a wide range of application prospect and development value because they are regarded as the green,safe and healthy bioactive substances. Reference to a large number of researches of lignins in China and aboard,the studies of the extraction methods,structural characterization,bioactivities,and application of lignins are reviewed,the existing problems of its application was analyzed,and the future development trend of further application of lignins on the food industry was also discussed.
Lignin,as a kind of natural polyphenol compounds with many biological activities,is widely found in plant cells,which has a wide range of application prospect and development value because they are regarded as the green,safe and healthy bioactive substances. Reference to a large number of researches of lignins in China and aboard,the studies of the extraction methods,structural characterization,bioactivities,and application of lignins are reviewed,the existing problems of its application was analyzed,and the future development trend of further application of lignins on the food industry was also discussed.
引文
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[3]龚卫华,马玥,吕霞,等.葵花籽壳木质素的结构分析及抗氧化活性[J].食品科学,2017,38(7):23-28
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[6]隋鑫金.工业木质素催化液化制备酚类化学品的研究[D].广州:华南理工大学,2011
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[8]Ghaffa SH,Fan M.Lignin in straw and its applications as an adhesive[J].International Journal of Adhesion&Adhesives,2014,48:92-101
[9]Lapierre C,Jouin D,Monties B.On the molecular origin of the alkali solubility of Gramineae lignins[J].Phytochemistry,1989,28(5):1401-1403
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[17]李维英.蔗渣及其纤维素在离子液体中的溶解、改性及分离的研究[D].广州:华南理工大学,2011
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[21]龚卫华,马玥,吕霞,等.葵花籽壳木质素的结构分析及抗氧化活性[J].食品科学,2017,38(7):23-28
[22]Li MF,Sun SN,Xu F,et al.Mild acetosolv process to fractionatebamboo for the biorefinery:structural and antioxidant properties of thedissolved lignin[J].Journal of Agricultural&Food Chemistry,2012,60(7):1703-1712
[23]Villaverde JJ,Li J,Ek M,et al.Native lignin structure of Miscanthus X giganteus and its changes during acetic and formic acid fractionation[J].Journal of Agricultural and Food Chemistry,2009,57(14):6262-6270
[24]Li B,Wang C,Chen X,et al.Highly specific separation for antitumor Spiropreussione A from endophytic fungal fermentation broth by one-step macroporous resins AB-8 treatment[J].Journal of Chromatography B,2013,938(5):1-7
[25]Pasquini D,Pimenta MTB,Ferreira LH,et al.Sugar cane bagasse pulping using supercritical CO2asso-ciated with co-solvent 1-butanol/water[J].Journal of Supercritical Fluids,2005,34(2):125-131
[26]任苗苗,吕惠生,张敏华.玉米秸秆木质素的超临界提取及结构表征[J].化学工业与工程,2012,29(5):53-57
[27]Wen JL,Sun SL,Xue BL,et al.Structural elucidation of inhomogeneous lignins from bamboo[J].International Journal of Biological Macromolecules,2015,77:250-259
[28]杨东杰,杜艳刚,付尽国,等.蔗渣木质素磺酸镁的结构特征及表面物化性能[J].化工学报,2010,61(7):1859-1865
[29]彭锋.农林生物质半纤维素分离纯化、结构表征及化学改性的研究[D].广州:华南理工大学,2010
[30]Yin HS,Liu HM,Liu YL.Structural Characterization of Lignin in Fruits and Stalks of Chinese Quince[J].Molecules,2017,22(6):1-14
[31]Fracassetti D,Costa C,Moulay L,et al.Ellagic acid derivatives,ellagitannins,proanthocyanidins and other phenolics,vitamin C and antioxidant capacity of two powder products fromcamu-camu fruit(Myrciaria dubia)[J].Food Chemistry,2013,139(1/4):578-583
[32]Li MF,Sun,SN Xu F,et al.Microwave-assisted organic acid extraction of lignin from bamboo:structure and antioxidant activity investigation[J].Food Chemistry,2012,134(3):1392-1398
[33]杨玲,何亚之,周钰珊,等.胡萝卜木质素的提取及其抗氧化性研究[J].化学工程与装备,2014(8):29-31
[34]Zhou S,Liu L,Wang B,et al.Microwave-enhanced extraction of lignin from birch in formic acid:structural characterization and antioxidant activity study[J].Process Biochemistry,2012,47(12):1799-1806
[35]Zacherl C,Eisner P,Engel KH.In vitro model tocorrelate viscosity and bile acid-binding capacity of digested water-soluble and insoluble dietary fibres[J].Food Chemstry,2011,126(2):423-428
[36]Kim HJ,White PJ.In vitro bile-acid binding and fermentation of high,medium and low molecular weightβ-glucan[J].Journal ofA-gricultural&Food Chemistry,2010,58(1):628-634
[37]Rodríguez-Gutiérrez G,Rubio-Senent F,Lama-Mu觡oz A,et al.Properties of lignin,cellulose,and hemicelluloses isolated from olive cake and olive stones:binding of water,oil,bile acids,and glucose[J].Journal of Agricultural&Food Chemistry,2014,62(36):8973-8981
[38]Norikura T,Mukai Y,Fujita S,et al.Lignophenols decrease oleateinduced apolipoprotein-B secretion in HepG2 cells[J].Basic&Clinical Pharmacology&Toxicology,2010,107(4):813-817
[39]Ana María Quesille-Villalobos,Jorge Saavedra Torrico,Lena Gálvez Ranilla.Phenolic compounds,antioxidant capacity,and in vitroα-amylase inhibitory potential of tea infusions(Camellia sinensis)commercialized in Chile[J].CyTA-Journal of Food,2013,11(1):60-67
[40]Hasegawa Y,Kadota Y,Hasegawa C,et al.Lignosulfonic Acid-Induced Inhibition of Intestinal Glucose Absorption[J].Journal of Nutritional Science&Vitaminology,2015,61(6):449-454
[41]Qiu M,Wang Q,Chu Y,et al.Lignosulfonic Acid Exhibits Broadly Anti-HIV-1 Activity-Potential as a Microbicide Candidate for the Prevention of HIV-1 Sexual Transmission[J].Plos One,2012,7(4):1-12
[42]Mitsuhashi S,Kishimoto T,Uraki Y,et al.Low molecular weight lignin suppresses activation of NF-κB and HIV-1 promoter[J].Bioorganic&Medicinal Chemistry,2008,16(5):2645-2650
[43]Gordts SC,Geoffrey Férir,Thomas D’huys,et al.The Low-Cost Compound Lignosulfonic Acid(LA)Exhibits Broad-Spectrum AntiHIV and Anti-HSV Activity and Has Potential for Microbicidal Applications[J].Plos One,2015,10(7):e0131219
[44]Cerrutti BM,Moraes ML,Pulcinelli SH,et al.Lignin as immobilization matrix for HIV p17 peptide used in immunosensing[J].Biosensors&Bioelectronics,2015,71:420-426
[45]Wang Q,Mu H,Zhang L,et al.Characterization of two water-soluble ligninmetabolites with antiproliferative activities from Inonotus obliquus[J].International Journal of Biological Macromolecules,2015,74:507-514
[46]Barapatre A,Meena AS,Mekala S.In vitro evaluation of antioxidant and cytotoxic activities of lignin fractions extracted from Acacia nilotica[J].International Journal of Biological Macromolecules,2016,86:443-453
[47]Figueiredo P,Lintinen K,Kiriazis A,et al.In vitro evaluation of biodegradable lignin-based nanoparticles for drug delivery and enhanced antiproliferation effect in cancer cells[J].Biomaterials,2017,121:97-108
[48]Henry BL,Desai UR.Sulfated Low Molecular Weight Lignins,Allosteric Inhibitors of Coagulation Proteinases via the Heparin Binding Site,Significantly Alter the Active Site of Thrombin and Factor Xa Compared to Heparin[J].Thrombosis Research,2014,134(5):1123-1129
[49]Mehta AY,Mohammed BM,Martin EJ,et al.Allosterism-based simultaneous,dual anticoagulant and antiplatelet action:allosteric inhibitor targeting the glycoprotein Ibα-binding and heparin-binding site of thrombin[J].Journal of Thrombosis&Haemostasis,2016,14(4):828-838
[50]邸明伟,王森,姚子巍.木质素基非甲醛木材胶黏剂的研究进展[J].林业工程学报,2017,2(1):8-14
[51]Luo J,Luo J L,Yuan C,et al.An eco-friendly wood adhesivefrom soy protein and lignin:performance properties[J].Rsc Advances,2015,122(5):100849-100855
[52]艾青,方桂珍,赵银凤,等.二乙醇胺基木质素非离子表面活性剂的制备及表征[J].林产化学与工业,2009,29(6):52-56
[53]Doherty W O S,Mousavioun P,Fellows C M.Value-adding to cellulosic ethanol:lignin polymers[J].Industrial Crops and Products,2011,33(2):259-276
[54]王芳,蒯君涛,胡高铨,等.酚化酶解木质素-环氧树脂/环氧树脂复合材料的合成及性能[J].复合材料学报,2017,34(12):2681-2688
[55]Cedo L,Castell AA,Pallares V,et al.Grape seedprocyanidin extract modulates proliferation and apoptosis of pancreaticbeta-cells[J].Food Chemistry,2013,138(1):524-530
[56]Connor CA,Adriaens M,Pierini R,et al.Procyanidin inducesapoptosis of esophageal adenocarcinoma cells via JNK activation ofcJun[J].Nutrition and Cancer,2014,66(2):335-341
[2]Gong W,Xiang Z,Ye F,et al.Composition and structure of an antioxidant acetic acid lignin isolated from shoot shell of bamboo(Dendrocalamus Latiforus)[J].Industrial Crops&Products,2016,91(30):340-349
[3]龚卫华,马玥,吕霞,等.葵花籽壳木质素的结构分析及抗氧化活性[J].食品科学,2017,38(7):23-28
[4]路瑶,魏贤勇,宗志敏,等.木质素的结构研究与应用[J].化学进展,2013,25(5):838-858
[5]Li MF,Sun SN,Xu F,et al.Microwave-assisted organic acid extraction of lignin from bamboo:structure and antioxidant activity investigation[J].Food Chemistry,2012,134(3):1392-1398
[6]隋鑫金.工业木质素催化液化制备酚类化学品的研究[D].广州:华南理工大学,2011
[7]Zhou M,Kong Q,Pan B,et al.Evaluation of treated black liquor used as dispersant of concentrated coal-water slurry[J].Fuel,2010,89(3):716-723
[8]Ghaffa SH,Fan M.Lignin in straw and its applications as an adhesive[J].International Journal of Adhesion&Adhesives,2014,48:92-101
[9]Lapierre C,Jouin D,Monties B.On the molecular origin of the alkali solubility of Gramineae lignins[J].Phytochemistry,1989,28(5):1401-1403
[10]孙文鹏,宋燕西,王栋纬,等.水葫芦木质素的提取及其苯胺吸附性能[J].分析测试学报,2017,36(6):788-793
[11]庞庭才,熊拯,胡上英,等.银叶树果壳木质素提取及抗氧化性[J].江苏农业科学,2016,44(6):385-388
[12]张保平,杨芳,马钟琛,等.稻草木质素的硫酸法提取与表征[J].河北大学学报(自然科学版),2016,36(5):474-486
[13]龚卫华,向卓亚,叶发银,等.麻竹笋笋壳中木质素的理化特性[J].食品科学,2017,38(9):59-65
[14]张朝波,柳燕,李林燕,等.南五味子总木质素有效部位镇静、催眠作用研究[J].中药药理与临床,2011,27(1):29-30
[15]Xie F,Gong S,Zhang W,et al.Potential of lignin from Canna edulis ker residue in the inhibition ofα-d-glucosidase:Kinetics and interaction mechanism merging with docking simulation[J].International Journal of Biological Macromolecules,2017,95:592-602
[16]Li MF,Sun SN,Xu F,et al.Microwave-assisted organic acid extraction of lignin from bamboo:Structure and antioxidant activity investigation[J].Food Chemistry,2012,134(3):1392-1398
[17]李维英.蔗渣及其纤维素在离子液体中的溶解、改性及分离的研究[D].广州:华南理工大学,2011
[18]唐婷范,刘雄民,郭占京,等.蒜头果木质素提取及成分分析[J].精细化工,2013,30(5):591-594
[19]缪正调,杨海艳,史正军,等.水热环境下的核桃壳木质素提取及结构表征[J].林业工程学报,2016,1(6):108-113
[20]孟仙,李那.木质素提取的研究进展[J].杭州化工,2015,45(4):7-10
[21]龚卫华,马玥,吕霞,等.葵花籽壳木质素的结构分析及抗氧化活性[J].食品科学,2017,38(7):23-28
[22]Li MF,Sun SN,Xu F,et al.Mild acetosolv process to fractionatebamboo for the biorefinery:structural and antioxidant properties of thedissolved lignin[J].Journal of Agricultural&Food Chemistry,2012,60(7):1703-1712
[23]Villaverde JJ,Li J,Ek M,et al.Native lignin structure of Miscanthus X giganteus and its changes during acetic and formic acid fractionation[J].Journal of Agricultural and Food Chemistry,2009,57(14):6262-6270
[24]Li B,Wang C,Chen X,et al.Highly specific separation for antitumor Spiropreussione A from endophytic fungal fermentation broth by one-step macroporous resins AB-8 treatment[J].Journal of Chromatography B,2013,938(5):1-7
[25]Pasquini D,Pimenta MTB,Ferreira LH,et al.Sugar cane bagasse pulping using supercritical CO2asso-ciated with co-solvent 1-butanol/water[J].Journal of Supercritical Fluids,2005,34(2):125-131
[26]任苗苗,吕惠生,张敏华.玉米秸秆木质素的超临界提取及结构表征[J].化学工业与工程,2012,29(5):53-57
[27]Wen JL,Sun SL,Xue BL,et al.Structural elucidation of inhomogeneous lignins from bamboo[J].International Journal of Biological Macromolecules,2015,77:250-259
[28]杨东杰,杜艳刚,付尽国,等.蔗渣木质素磺酸镁的结构特征及表面物化性能[J].化工学报,2010,61(7):1859-1865
[29]彭锋.农林生物质半纤维素分离纯化、结构表征及化学改性的研究[D].广州:华南理工大学,2010
[30]Yin HS,Liu HM,Liu YL.Structural Characterization of Lignin in Fruits and Stalks of Chinese Quince[J].Molecules,2017,22(6):1-14
[31]Fracassetti D,Costa C,Moulay L,et al.Ellagic acid derivatives,ellagitannins,proanthocyanidins and other phenolics,vitamin C and antioxidant capacity of two powder products fromcamu-camu fruit(Myrciaria dubia)[J].Food Chemistry,2013,139(1/4):578-583
[32]Li MF,Sun,SN Xu F,et al.Microwave-assisted organic acid extraction of lignin from bamboo:structure and antioxidant activity investigation[J].Food Chemistry,2012,134(3):1392-1398
[33]杨玲,何亚之,周钰珊,等.胡萝卜木质素的提取及其抗氧化性研究[J].化学工程与装备,2014(8):29-31
[34]Zhou S,Liu L,Wang B,et al.Microwave-enhanced extraction of lignin from birch in formic acid:structural characterization and antioxidant activity study[J].Process Biochemistry,2012,47(12):1799-1806
[35]Zacherl C,Eisner P,Engel KH.In vitro model tocorrelate viscosity and bile acid-binding capacity of digested water-soluble and insoluble dietary fibres[J].Food Chemstry,2011,126(2):423-428
[36]Kim HJ,White PJ.In vitro bile-acid binding and fermentation of high,medium and low molecular weightβ-glucan[J].Journal ofA-gricultural&Food Chemistry,2010,58(1):628-634
[37]Rodríguez-Gutiérrez G,Rubio-Senent F,Lama-Mu觡oz A,et al.Properties of lignin,cellulose,and hemicelluloses isolated from olive cake and olive stones:binding of water,oil,bile acids,and glucose[J].Journal of Agricultural&Food Chemistry,2014,62(36):8973-8981
[38]Norikura T,Mukai Y,Fujita S,et al.Lignophenols decrease oleateinduced apolipoprotein-B secretion in HepG2 cells[J].Basic&Clinical Pharmacology&Toxicology,2010,107(4):813-817
[39]Ana María Quesille-Villalobos,Jorge Saavedra Torrico,Lena Gálvez Ranilla.Phenolic compounds,antioxidant capacity,and in vitroα-amylase inhibitory potential of tea infusions(Camellia sinensis)commercialized in Chile[J].CyTA-Journal of Food,2013,11(1):60-67
[40]Hasegawa Y,Kadota Y,Hasegawa C,et al.Lignosulfonic Acid-Induced Inhibition of Intestinal Glucose Absorption[J].Journal of Nutritional Science&Vitaminology,2015,61(6):449-454
[41]Qiu M,Wang Q,Chu Y,et al.Lignosulfonic Acid Exhibits Broadly Anti-HIV-1 Activity-Potential as a Microbicide Candidate for the Prevention of HIV-1 Sexual Transmission[J].Plos One,2012,7(4):1-12
[42]Mitsuhashi S,Kishimoto T,Uraki Y,et al.Low molecular weight lignin suppresses activation of NF-κB and HIV-1 promoter[J].Bioorganic&Medicinal Chemistry,2008,16(5):2645-2650
[43]Gordts SC,Geoffrey Férir,Thomas D’huys,et al.The Low-Cost Compound Lignosulfonic Acid(LA)Exhibits Broad-Spectrum AntiHIV and Anti-HSV Activity and Has Potential for Microbicidal Applications[J].Plos One,2015,10(7):e0131219
[44]Cerrutti BM,Moraes ML,Pulcinelli SH,et al.Lignin as immobilization matrix for HIV p17 peptide used in immunosensing[J].Biosensors&Bioelectronics,2015,71:420-426
[45]Wang Q,Mu H,Zhang L,et al.Characterization of two water-soluble ligninmetabolites with antiproliferative activities from Inonotus obliquus[J].International Journal of Biological Macromolecules,2015,74:507-514
[46]Barapatre A,Meena AS,Mekala S.In vitro evaluation of antioxidant and cytotoxic activities of lignin fractions extracted from Acacia nilotica[J].International Journal of Biological Macromolecules,2016,86:443-453
[47]Figueiredo P,Lintinen K,Kiriazis A,et al.In vitro evaluation of biodegradable lignin-based nanoparticles for drug delivery and enhanced antiproliferation effect in cancer cells[J].Biomaterials,2017,121:97-108
[48]Henry BL,Desai UR.Sulfated Low Molecular Weight Lignins,Allosteric Inhibitors of Coagulation Proteinases via the Heparin Binding Site,Significantly Alter the Active Site of Thrombin and Factor Xa Compared to Heparin[J].Thrombosis Research,2014,134(5):1123-1129
[49]Mehta AY,Mohammed BM,Martin EJ,et al.Allosterism-based simultaneous,dual anticoagulant and antiplatelet action:allosteric inhibitor targeting the glycoprotein Ibα-binding and heparin-binding site of thrombin[J].Journal of Thrombosis&Haemostasis,2016,14(4):828-838
[50]邸明伟,王森,姚子巍.木质素基非甲醛木材胶黏剂的研究进展[J].林业工程学报,2017,2(1):8-14
[51]Luo J,Luo J L,Yuan C,et al.An eco-friendly wood adhesivefrom soy protein and lignin:performance properties[J].Rsc Advances,2015,122(5):100849-100855
[52]艾青,方桂珍,赵银凤,等.二乙醇胺基木质素非离子表面活性剂的制备及表征[J].林产化学与工业,2009,29(6):52-56
[53]Doherty W O S,Mousavioun P,Fellows C M.Value-adding to cellulosic ethanol:lignin polymers[J].Industrial Crops and Products,2011,33(2):259-276
[54]王芳,蒯君涛,胡高铨,等.酚化酶解木质素-环氧树脂/环氧树脂复合材料的合成及性能[J].复合材料学报,2017,34(12):2681-2688
[55]Cedo L,Castell AA,Pallares V,et al.Grape seedprocyanidin extract modulates proliferation and apoptosis of pancreaticbeta-cells[J].Food Chemistry,2013,138(1):524-530
[56]Connor CA,Adriaens M,Pierini R,et al.Procyanidin inducesapoptosis of esophageal adenocarcinoma cells via JNK activation ofcJun[J].Nutrition and Cancer,2014,66(2):335-341