Applications of Fungal Laccase in Green Chemistry

doi:10.13560/j.cnki.biotech.bull.1985.2017-0824

Abstract

Abstract: Laccase is a kind of extracellular multi-copper oxidase secreted by fungi. It is widely used in green environmental chemistry because of its multifunctional property. It is proved that the copper-cluster of laccase can catalyze one-electron oxidative of phenolic and non-phenolic substrates via yielding radical intermediates. Then these radical intermediates involved in oxidative coupling or bond rupture,resulting in substrate oxidation,decomposition or polymerization. At present,the methods for immobilization of laccase are primarily divided into four categories including encapsulation in a carrier,adsorption on a carrier,covalent binding,and cross-linking. Compared with the free laccase,the underlying reasons for immobilization of laccase are the need to enhance the activity,stability,and recyclability of fungal laccase. In this paper,we review the molecular composition,structural characteristics,and catalytic oxidation mechanism of fungal laccase. Additionally,the main methods,advantages and disadvantages for immobilization of laccase are comparably evaluated,mainly focusing on the latest advances in the transformation and/or degradation of organic contaminants,the decolorization of synthetic dye,the treatment of paper wastewater,food processing,bio-sensors,and bio-indicators of environmental quality. It is aimed at providing new theoretical evidences and guidance for the multi-functional application of fungal laccase in green chemistry.

Key words: fungal laccase, structural characteristics, immobilization technology, laccase applications, green chemistry

GONG Rui, SUN Kai, XIE Dao-yue. Applications of Fungal Laccase in Green Chemistry[J]. Biotechnology Bulletin, 2018, 34(4): 24-34.

References

[1] 丁惠君, 吴亦潇, 钟家有, 等. 两种介体物质在漆酶降解磺胺类抗生素中的作用[J]. 中国环境科学, 2016, 36(5):1469-1475.
[2] Sun K, Luo Q, Gao Y, et al.Laccase-catalyzed reactions of 17β-
estradiol in the presence of humic acid:Resolved by high-resolution mass spectrometry in combinationwith 13C labeling[J]. Chemos-phere, 2016, 145:394-401.
[3] 张延威, 邱树毅, 韩燕峰, 等. 产漆酶菌株筛选及一株产酶菌株的优化与鉴定[J]. 微生物学通报, 2014, 41(2):251-257.
[4] Dhakar K, Anita P.Phialophora melinii(NFCCI 3617):A newly isolated psychrotolerant fungus that produces enhanced laccase under the influence of organic solvents[J]. Advances in Natural Science, 2015, 8(1):14-20.
[5] Rekadwad B, Khobragade C.Fungi imperfecti laccase:Biotechnological potential and perspectives[M/OL]//Microbial Applications Vol. 2. Springer International Publishing, 2017:203-212.
[6] 刘家扬, 焦国宝, 有小娟, 等. 真菌漆酶的性质, 生产及应用研究进展[J]. 生物技术通报, 2016, 32(4):24-33.
[7] Fernández-Fernández M, Sanromán MÁ, Moldes D.Recent developments and applications of immobilized laccase[J]. Biotechnol Adv, 2013, 31(8):1808-1825.
[8] Piontek K, Antorini M, Choinowski T.Crystal structure of a laccase from the fungus Trametes versicolor at 1. 90-Å resolution containing a full complement of coppers[J]. Journal of Biological Chemistry, 2002, 277(40):37663-37669.
[9] Park JW, Dec J, Kim JE, et al.Effect of humic constituents on the transformation of chlorinated phenols and anilines in the presence of oxidoreductive enzymes or birnessite[J]. Environmental Science & Technology, 1999, 33(12):2028-2034.
[10] 刘欢, 袁兴中, 彭馨, 等. 反胶束体系中漆酶催化愈创木酚的研究[J]. 中国环境科学, 2015, 35(2):493-498.
[11] 罗爽, 谢天, 刘忠川, 等. 漆酶/介体系统研究进展[J]. 应用与环境生物学报, 2015, 21(6):987-995.
[12] Miyazawa N, Tanaka M, Hakamada M, et al.Molecular dynamics study of laccase immobilized on self-assembled monolayer-modified Au[J]. Journal of Materials Science, 2017, 52(21):12848-12853.
[13] 马双新, 刘宁, 贾慧, 等. 玉米大斑病菌漆酶基因Stlac2结构分析及原核表达[J]. 中国农业科学, 2016, 49(21):4130-4139.
[14] Mate DM, Alcalde M.Laccase engineering:From rational design to directed evolution[J]. Biotechnol Adv, 2015, 33(1):25-40.
[15] Couto SR, Herrera JLT.Industrial and biotechnological applications of laccases:A review[J]. Biotechnol Adv, 2006, 24(5):500-513.
[16] Zheng F, An Q, Meng G, et al.A novel laccase from white rot fungus Trametes orientalis:Purification, characterization, and application[J]. Int J Biol Macromol, 2017, 102:758-770.
[17] 李阳, 蒋国翔, 牛军峰, 等. 漆酶催化氧化水中有机污染物[J]. 化学进展, 2009, 21(10):2028-2036.
[18] Polak J, Jarosz-Wilkolazka A.Fungal laccases as green catalysts for dye synthesis[J]. Process Biochemistry, 2012, 47(9):1295-1307.
[19] Subramanian J, Ramesh T, Kalaiselvam M.Fungal laccases-properties and applications:A review[J]. Int J Pharm Biol Arch, 2014, 5(2):8-16.
[20] Yang J, Ng TB, Lin J, et al.A novel laccase from basidiomycete Cerrena sp. :Cloning, heterologous expression, and characterization[J]. Int J Biol Macromol, 2015, 77:344-349.
[21] 罗开昆, 彭红, 龚跃法. 漆酶的固定化及其在废水处理中的应用[J]. 工业水处理, 2005, 25(5):14-17.
[22] 司静, 李伟, 崔宝凯, 等. 真菌漆酶性质, 分子生物学及其应用研究进展[J]. 生物技术通报, 2011(2):48-55.
[23] Giardina P, Faraco V, Pezzella C, et al.Laccases:A never-ending story[J]. Cellular and Molecular Life Sciences, 2010, 67(3):369-385.
[24] 葛宏华, 武赟, 肖亚中. 漆酶空间结构, 反应机理及应用[J]. 生物工程学报, 2011, 27(2):156-163.
[25] Baldrian P.Fungal laccases-occurrence and properties[J]. FEMS Microbiol Rev, 2006, 30(2):215-242.
[26] Riva S.Laccases:Blue enzymes for green chemistry[J]. Trends in Biotechnology, 2006, 24(5):219-226.
[27] 王国栋, 陈晓亚. 漆酶的性质, 功能, 催化机理和应用[J]. 植物学通报, 2003, 20(4):469-475.
[28] Mayer AM, Staples RC.Laccase:New functions for an old enzyme[J]. Phytochemistry, 2002, 60(6):551-565.
[29] 高玉千, 张利明, 张世敏, 等. 真菌漆酶高级结构研究进展[J]. 食品与生物技术学报, 2011, 30(2):166-171.
[30] Palmer AE, Lee SK, Solomon EI.Decay of the peroxide intermed-iate in laccase:Reductive cleavage of the O-O bond[J]. Journal of the American Chemical Society, 2001, 123(27):6591-6599.
[31] Garavaglia S, Cambria MT, Miglio M, et al.The structure of Rigidoporus lignosus laccase containing a full complement of copper ions, reveals an asymmetrical arrangement for the T3 copper pair[J]. Journal of Molecular Biology, 2004, 342(5):1519-1531.
[32] Su J, Fu J, Wang Q, et al.Laccase:a green catalyst for the biosyn-thesis of poly-phenols[J]. Critical Reviews in Biotechnology, 2018, 38(2):294-307.
[33] Christopher LP, Yao B, Ji Y.Lignin biodegradation with laccase-mediator systems[J]. Frontiers in Energy Research, 2014, 2:12.
[34] Peng X, Yuan X, Liu H, et al.Degradation of polycyclic aromatic hydrocarbons(PAHs)by laccase in rhamnolipid reversed micellar system[J]. Applied Biochemistry and Biotechnology, 2015, 176(1):45-55.
[35] Sun K, Huang Q, Li S.Transformation and toxicity evaluation of tetracycline in humic acid solution by laccase coupled with 1-hydroxybenzotriazole[J]. Journal of Hazardous Materials, 2017, 331:182-188.
[36] 赖超凤, 李爽, 彭丽丽, 等. 漆酶及其在有机合成中应用的研究进展[J]. 化工进展, 2010(7):1300-1308.
[37] 靳蓉, 张飞龙. 漆酶的结构与催化反应机理[J]. 中国生漆, 2012, 31(4):6-16.
[38] Dodor DE, Hwang HM, Ekunwe SIN.Oxidation of anthracene and benzo[a]pyrene by immobilized laccase from Trametes versicolor[J]. Enzyme and Microbial Technology, 2004, 35(2):210-217.
[39] Han MJ, Choi HT, Song HG.Degradation of phenanthrene by Trametes versicolor and its laccase[J]. The Journal of Microbiology, 2004, 42(2):94-98.
[40] 邓寒梅, 邵可, 梁家豪, 等. 漆酶的来源及固定化漆酶载体研究进展[J]. 生物技术通报, 2017, 33(6):10-15.
[41] 王新, 刘丽, 陆佳靓, 等. 固定化漆酶载体研究进展[J]. 生态学杂志, 2013(10):2823-2829.
[42] 潘洪艳, 张安龙, 张佳. 漆酶的固定化及其在造纸废水处理中的应用[J]. 黑龙江造纸, 2011, 39(1):43-45.
[43] 游金坤, 余旭亚, 赵鹏. 吸附法固定化酶的研究进展[J]. 化学工程, 2012(4):1-5.
[44] 王美银, 张新颖, 汤真平. 固定化漆酶处理染料废水的研究进展[J]. 能源与环境, 2017(3):85-86.
[45] 乔德亮, 胡冰, 曾晓雄. 酶固定化及其在食品工业中应用新进展[J]. 食品工业科技, 2008(1):304-308.
[46] 代云容, 袁钰, 于彩虹, 等. 静电纺丝纤维膜固定化漆酶对水中双酚A的降解性能[J]. 环境科学学报, 2015, 35(7):2107-2113.
[47] Xu Y, Zhou G, Wu C, et al.Improving adsorption and activation of the lipase immobilized in amino-functionalized ordered mesoporous SBA-15[J]. Solid State Sciences, 2011, 13(5):867-874.
[48] Tan Y, Deng W, Ge B, et al.Biofuel cell and phenolic biosensor based on acid-resistant laccase-glutaraldehyde functionalized chitosan-multiwalled carbon nanotubes nanocomposite film[J]. Biosensors and Bioelectronics, 2009, 24(7):2225-2231.
[49] 王颖, 张笛, 茹加, 等. 壳聚糖固定化漆酶酶学性质及其催化氧化水中2, 4-二氯酚的效能与途径[J]. 环境化学, 2013, 32(10):1901-1908.
[50] 杜东霞, 王宜磊. 固定化漆酶对刚果红染料脱色降解的研究[J]. 安徽农业科学, 2013, 41(11):4985-4987.
[51] 罗贵民. 酶工程[M]. 北京:化学工业出版社, 2003:251-253.
[52] 陈冬梅. 固定化酶及其在食品工业中的应用[J]. 现代农业科技, 2010(19):330-332.
[53] 傅婉秋, 谢星光, 戴传超, 等. 植物-微生物联合对环境有机污染物降解的研究进展[J]. 微生物学通报, 2017, 44(4):929-939.
[54] 冯秋园, 吴桐, 万祎, 等. 持久性有机污染物(POPs)在水生生态系统中的环境行为[J]. 北京大学学报:自然科学版, 2017, 53(3):588-596.
[55] Dai Y, Yin L, Niu J.Laccase-carrying electrospun fibrous membranes for adsorption and degradation of PAHs in shoal soils[J]. Environmental Science & Technology, 2011, 45(24):10611-10618.
[56] Kudanga T, Nyanhongo GS, Guebitz GM, et al.Potential applications of laccase-mediated coupling and grafting reactions:A review[J]. Enzyme and Microbial Technology, 2011, 48(3):195-208.
[57] Farnet AM, Gil G, Ferre E.Effects of pollutants on laccase activities of Marasmius quercophilus, a white-rot fungus isolated from a Mediterranean schlerophyllous litter[J]. Chemosphere, 2008, 70(5):895-900.
[58] 孙凯, 李舜尧. 漆酶催化氧化水溶液中三氯生转化的作用机理[J]. 中国环境科学, 2017, 37(8):2947-2954.
[59] 夏青, 谢卫平, 刘国强, 等. 漆酶催化氧化水中雌激素的研究[J]. 环境科学, 2013, 34(8):3119-3124.
[60] 陈辉, 张剑波, 刘小鹏, 等. 漆酶催化降解氯酚类有机污染物[J]. 北京大学学报:自然科学版, 2005, 41(4):605-611.
[61] Singh R, Cabrera ML, Radcliffe DE, et al.Laccase mediated transformation of 17β-estradiol in soil[J]. Environmental Pollution, 2015, 197:28-35.
[62] 赵月春, 付蓉, 莫测辉, 易筱筠. 固定化反胶团漆酶及其在修复土壤DDT污染中的应用[J]. 生态环境, 2008(2):606-610.
[63] Li X, Lin X, Yin R, et al.Optimization of laccase-mediated benzo[a]pyrene oxidation and the bioremedial application in aged polycyclic aromatic hydrocarbons-contaminated soil[J]. Journal of Health Science, 2010, 56(5):534-540.
[64] 林先贵, 吴宇澄, 曾军, 等. 多环芳烃的真菌漆酶转化及污染土壤修复技术[J]. 微生物学通报, 2017, 44(7):1720-1727.
[65] 葛世杰. 固定化阿特拉津降解酶制备及其土壤修复效果研究[D]. 哈尔滨:东北农业大学, 2013.
[66] Sukor MZ, Yin CY, Savory RM, et al.Biodegradation kinetics of naphthalene in soil medium using Pleurotus ostreatus in batch mode with addition of fibrous biomass as a nutrient[J]. Bioremediation Journal, 2012, 16(3):177-184.
[67] 任大军, 许琴, 张元元, 等. 漆酶/ABTS介体系统对蒽的降解研究[J]. 工业安全与环保, 2013(12):1-3.
[68] Bautista LF, Morales G, Sanz R.Biodegradation of polycyclic aromatic hydrocarbons(PAHs)by laccase from Trametes versicolor covalently immobilized on amino-functionalized SBA-15[J]. Chemosphere, 2015, 136:273-280.
[69] Li X, Wang Y, Wu S, et al.Peculiarities of metabolism of anthracene and pyrene by laccase-producing fungus Pycnoporus sanguineus H1[J]. Biotechnology and Applied Biochemistry, 2014, 61(5):549-554.
[70] Hu X, Zhang Y, Zhao X, et al.Biodegradation of benzo[a]pyrene with immobilized laccase:Genotoxicity of the products in HaCat and A3 cells[J]. Environmental and Molecular Mutagenesis, 2007, 48(2):106-113.
[71] Lloret L, Hollmann F, Eibes G, et al.Immobilisation of laccase on Eupergit supports and its application for the removal of endocrine disrupting chemicals in a packed-bed reactor[J]. Biodegradation, 2012, 23(3):373-386.
[72] Blánquez P, Guieysse B.Continuous biodegradation of 17β-estradiol and 17α-ethynylestradiol by Trametes versicolor[J]. Journal of Hazardous Materials, 2008, 150(2):459-462.
[73] Arca-Ramos A, Eibes G, Feijoo G, et al.Potentiality of a ceramic membrane reactor for the laccase-catalyzed removal of bisphenol A from secondary effluents[J]. Appl Microbiol Biotechnol, 2015, 99(21):9299-9308.
[74] Liang S, Luo Q, Huang Q.Degradation of sulfadimethoxine catalyzed by laccase with soybean meal extract as natural mediator:Mechanism and reaction pathway[J]. Chemosphere, 2017, 181:320-327.
[75] Peralta-Zamora P, Pereira CM, Tiburtius ERL, et al.Decolorization of reactive dyes by immobilized laccase[J]. Applied Catalysis B:Environmental, 2003, 42(2):131-144.
[76] 袁海生, 戴玉成, 曹云, 等. 白腐真菌染料脱色菌株的筛选及一色齿毛菌脱色条件的研究[J]. 菌物学报, 2010(3):429-436.
[77] 赵林果, 季永新, 李强, 等. 固定化漆酶对染料酸性紫43的脱色和降解[J]. 工业微生物, 2007, 37(6):35-40.
[78] Manu B, Chaudhari S.Anaerobic decolorisation of simulated textile wastewater containing azo dyes[J]. Bioresource Technology, 2002, 82(3):225-231.
[79] 付时雨, 詹怀宇. 漆酶/介体系统漂白尾叶桉硫酸盐浆的初步研究[J]. 中国造纸, 2000(2):8-12.
[80] Rich JO, Anderson AM, Berhow MA.Laccase-mediator catalyzed conversion of model lignin compounds[J]. Biocatalysis and Agricultural Biotechnology, 2016, 5:111-115.
[81] Wang Q, Liu S, Yang G, et al.Modeling laccase-induced lignin removal in prehydrolysis liquor from kraft-based dissolving pulp production[J]. Bioresource Technology, 2015, 175:638-641.
[82] 刘娜娜. 固定化漆酶在SBR处理造纸废水中的应用[J]. 天津造纸, 2015, 37(2):7-10.
[83] 刘帅, 张安龙, 罗清. 固定漆酶与游离漆酶对造纸废水深度处理的研究[J]. 纸和造纸, 2012, 31(3):63-65.
[84] 张昱, 赵倩, 李冠华. 漆酶在食品领域的应用研究进展[J]. 食品工业科技, 2016, 17:77.
[85] Minussi RC, Pastore GM, Durán N.Potential applications of laccase in the food industry[J]. Trends in Food Science & Technology, 2002, 13(6):205-216.
[86] Alberts JF, Gelderblom WCA, Botha A, et al.Degradation of aflatoxin B 1 by fungal laccase enzymes[J]. International Journal of Food Microbiology, 2009, 135(1):47-52.
[87] Brinch DS, Pedersen PB.Toxicological studies on laccase from Myceliophthora thermophila expressed in Aspergillus oryzae[J]. Regulatory Toxicology and Pharmacology, 2002, 35(3):296-307.
[88] 王岁楼, 王琼波. 漆酶在食品工业中的应用及其产生菌的研究[J]. 食品科学, 2005(2):260-263.
[89] 刘佳, 殷立峰, 代云容, 等. 电化学酶传感器在环境污染监测中的应用[J]. 化学进展, 2011, 24(01):131-143.
[90] García-Arellano H, Fink D, Hernández GM, et al.Nuclear track-based biosensors with the enzyme laccase[J]. Applied Surface Science, 2014, 310:66-76.
[91] Casero E, Petit-Domínguez MD, Vázquez L, et al.Laccase biosensors based on different enzyme immobilization strategies for phenolic compounds determination[J]. Talanta, 2013, 115:401-408.
[92] 陈玲. 生物传感器的研究进展综述[J]. 传感器与微系统, 2006, 25(9):4-7.
[93] Liu J, Niu J, Yin L, et al.In situ encapsulation of laccase in nanofibers by electrospinning for development of enzyme biosensors for chlorophenol monitoring[J]. Analyst, 2011, 136(22):4802-4808.
[94] 曹治云, 郑腾, 谢必峰, 等. 漆酶在生物检测中的应用进展[J]. 传感器技术, 2004, 23(8):1-3.
[95] Riffaldi R, Levi-Minzi R, Cardelli R, et al.Soil biological activities in monitoring the bioremediation of diesel oil-contaminated soil[J]. Water, Air, & Soil Pollution, 2006, 170(1):3-15.
[96] 宁娜, 谭慧军, 孙新新, 等. 真核生物来源漆酶的异源表达研究进展[J]. 生物工程学报, 2017, 33(4):565-577.