Biodegradation and Biotransformation of Indole: Advances and Perspectives
Tóm tắt
Từ khóa
Tài liệu tham khảo
Alemayehu, 2004, Cloning and functional analysis by gene disruption of a novel gene involved in indigo production and fluoranthene metabolism in Pseudomonas alcaligenes PA-10, FEMS Microbiol. Lett., 239, 285, 10.1016/j.femsle.2004.08.046
America, 2015, Characterization of a flavin-containing monooxygenase from Corynebacterium glutamicum and its application to production of indigo and indirubin, Biotechnol. Lett., 37, 1637, 10.1007/s10529-015-1824-2
Arora, 2015, Bacterial degradation of monocyclic aromatic amines, Front. Microbiol., 6, 820, 10.3389/fmicb.2015.00820
Arora, 2014, Identification of new metabolites of bacterial transformation of indole by gas chromatography-mass spectrometry and high performance liquid chromatography, Int. J. Anal. Chem., 2014, 239641, 10.1155/2014/239641
Arora, 2015, Microbial degradation of indole and its derivatives, J. Chem., 2015, 129159, 10.1155/2015/129159
Baeyer, 1866, Ueber die reduction aromatischer verbindungen mittelst zinkstaub, Eur. J. Inorg. Chem., 140, 295, 10.1002/jlac.18661400306
Bak, 1986, Anaerobic degradation of indolic compounds by sulfate-reducing enrichment cultures, and description of Desulfobacterium indolicum gen. nov., sp. nov, Arch. Microbiol., 146, 170, 10.1007/BF00402346
Balba, 1980, Methanogenic fermentation of the naturally occurring aromatic amino acids by a microbial consortium, Biochem. Soc. Trans., 8, 625, 10.1042/bst0080625
Bansal, 2010, The bacterial signal indole increases epithelial-cell tight-junction resistance and attenuates indicators of inflammation, Proc. Natl. Acad. Sci. U.S.A., 107, 228, 10.1073/pnas.0906112107
Barden, 2010, Indoles: industrial, agricultural and over-the-counter uses, Heterocyclic Scaffolds II:. Topics in Heterocyclic Chemistry, 31, 10.1007/7081_2010_48
Berry, 2002, Application of metabolic engineering to improve both the production and use of biotech indigo, J. Ind. Microbiol. Biotechnol., 28, 127, 10.1038/sj/jim/7000228
Berry, 1987, Conversion of indole to oxindole under methanogenic conditions, Appl. Environ. Microbiol, 53, 180, 10.1128/AEM.53.1.180-182.1987
Bhushan, 2000, Indigo production by naphthalene-degrading bacteria, Lett. Appl. Microbiol., 31, 5, 10.1046/j.1472-765x.2000.00754.x
Bialy, 1997, Biotechnology, bioremediation, and blue genes, Nat. Biotechnol., 15, 110, 10.1038/nbt0297-110
Bjerregaard-Andersen, 2014, A proton wire and water channel revealed in the crystal structure of isatin hydrolase, J. Biol. Chem., 289, 21351, 10.1074/jbc.M114.568824
Boyd, 1997, Metabolism of naphthalene, 1-naphthol, indene, and indole by Rhodococcus sp. strain NCIMB 12038, Appl. Environ. Microbiol., 63, 151, 10.1128/AEM.63.1.151-155.1997
Cheng, 2016, Enhancing indigo production by over-expression of the styrene monooxygenase in Pseudomonas putida, Curr. Microbiol., 73, 248, 10.1007/s00284-016-1055-3
Chimerel, 2014, Bacterial metabolite indole modulates incretin secretion from intestinal enteroendocrine L cells, Cell Rep., 9, 1202, 10.1016/j.celrep.2014.10.032
Chimerel, 2012, Indole prevents Escherichia coli cell division by modulating membrane potential, Biochim. Biophys. Acta, 1818, 1590, 10.1016/j.bbamem.2012.02.022
Choi, 2003, A novel flavin-containing monooxygenase from Methylophaga sp. strain SK1 and its indigo synthesis in Escherichia coli, Biochem. Biophys. Res. Commun., 306, 930, 10.1016/S0006-291X(03)01087-8
Claus, 1983, Degradation of indole by Alcaligenes spec, Syst. Appl. Microbial., 4, 169, 10.1016/S0723-2020(83)80046-0
Collin, 2000, Ullmann's Encyclopedia of Industrial Chemistry, 75
de Sá Alves, 2009, From nature to drug discovery: the indole scaffold as a ‘privileged structure’, Mini. Rev. Med. Chem., 9, 782, 10.2174/138955709788452649
Deslandes, 2001, Review of microbiological and biochemical effects of skatole on animal production, Livest. Prod. Sci, 71, 193, 10.1016/S0301-6226(01)00189-0
Doukyu, 1997, Biodegradation of indole at high concentration by persolvent fermentation with Pseudomonas sp. ST-200, Extremophiles, 1, 100, 10.1007/s007920050021
Doukyu, 1998, Effects of organic solvents on indigo formation by Pseudomonas sp. strain ST-200 grown with high levels of indole, Biosci. Biotechnol. Biochem, 62, 1075, 10.1271/bbb.62.1075
Doukyu, 2002, Isolation of an Acinetobacter sp. ST-550 which produces a high level of indigo in a water-organic solvent two-phase system containing high levels of indole, Appl. Microbiol. Biotechnol., 58, 543, 10.1007/s00253-001-0919-y
Doukyu, 2003, Indigo production by Escherichia coli carrying the phenol hydroxylase gene from Acinetobacter sp. strain ST-550 in a water-organic solvent two-phase system, Appl. Microbiol. Biotechnol., 60, 720, 10.1007/s00253-002-1187-1
Drewlo, 2001, Cloning and expression of a Ralstonia eutropha HF39 gene mediating indigo formation in Escherichia coli, Appl. Environ. Microbiol, 67, 1964, 10.1128/AEM.67.4.1964-1969.2001
Ensley, 1983, Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo, Science, 222, 167, 10.1126/science.6353574
Erb, 2015, Indole is an essential herbivoreinduced volatile priming signal in maize, Nat. Commun., 6, 6273, 10.1038/ncomms7273
Feng, 2013, Quorum sensing in water and wastewater treatment biofilms, J. Environ. Biol., 34, 437
Fischer, 1883, Ueber die hydrazine der brenztraubensäure, Eur. J. Inorg. Chem., 16, 2241, 10.1002/cber.188301602141
Frey, 1997, Analysis of a chemical plant defense mechanism in grasses, Science, 277, 696, 10.1126/science.277.5326.696
Frey, 2000, An herbivore elicitor activates the gene for indole emission in maize, Proc. Natl. Acad. Sci. U. S. A., 97, 14801, 10.1073/pnas.260499897
Fujioka, 1968, The bacterial oxidation of indole, Biochim. Biophys. Acta, 158, 70, 10.1016/0304-4165(68)90073-1
Fukuoka, 2015, Biotransformation of indole by Cupriavidus sp. strain KK10 proceeds through N-heterocyclic-and carbocyclic-aromatic ring cleavage and production of indigoids, Int. Biodeter. Biodegr, 97, 13, 10.1016/j.ibiod.2014.11.007
Garbe, 2000, Indole-inducible proteins in bacteria suggest membrane and oxidant toxicity, Arch. Microbiol., 173, 78, 10.1007/s002030050012
Gillam, 1999, Formation of indigo by recombinant mammalian cytochrome P450, Biochem. Biophys. Res. Commun., 265, 469, 10.1006/bbrc.1999.1702
Gillam, 2000, Oxidation of indole by cytochrome P450 enzymes, Biochemistry, 39, 13817, 10.1021/bi001229u
Gray, 1928, The formation of indigotin from indol by soil bacteria, Proc. R. Soc. Lond. B, 102, 263, 10.1098/rspb.1928.0003
Gribble, 2010, Heterocyclic Scaffolds II: Reactions and Applications of Indoles., 10.1007/978-3-642-15733-2
Gu, 1991, Degradation of substituted indoles by an indole-degrading methanogenic consortium, Appl. Environ. Microbiol., 57, 2622, 10.1128/AEM.57.9.2622-2627.1991
Guan, 2007, Signal mimics derived from a metagenomic analysis of the gypsy moth gut microbiota, Appl. Environ. Microbiol., 73, 3669, 10.1128/AEM.02617-06
Guengerich, 2004, Generation of new protein kinase inhibitors utilizing cytochrome P450 mutant enzymes for indigoid synthesis, J. Med. Chem., 47, 3236, 10.1021/jm030561b
Hales, 2012, Potential odorous volatile organic compound emissions from feces and urine from cattle fed corn-based diets with wet distillers grains and solubles, Atmos. Environ., 60, 292, 10.1016/j.atmosenv.2012.06.080
Han, 2013, Enhanced indirubin production in recombinant Escherichia coli harboring a flavin-containing monooxygenase gene by cysteine supplementation, J. Biotechnol., 164, 179, 10.1016/j.jbiotec.2012.08.015
Han, 2008, Optimization of bio-indigo production by recombinant E. coli harboring fmo gene, Enzyme Microb. Technol., 42, 617, 10.1016/j.enzmictec.2008.02.004
Han, 2011, Environmental factors affecting indole production in Escherichia coli, Res. Microbiol, 162, 108, 10.1016/j.resmic.2010.11.005
Hong, 2010, Structural differentiation of bacterial communities in indole-degrading bioreactors under denitrifying and sulfate-reducing conditions, Res. Microbiol, 161, 687, 10.1016/j.resmic.2010.06.010
Hsu, 2018, Employing a biochemical protecting group for a sustainable indigo dyeing strategy, Nat. Chem. Biol., 14, 256, 10.1038/nchembio.2552
Hu, 2010, Altering the regioselectivity of cytochrome P450 BM-3 by saturation mutagenesis for the biosynthesis of indirubin, J. Mol. Catal. B Enzym., 67, 29, 10.1016/j.molcatb.2010.07.001
Huxtable, 2001, The mutability of blue, Mol. Interv, 1, 141
Ishikawa, 2014, Application of the adhesive bacterionanofiber AtaA to a novel microbial immobilization method for the production of indigo as a model chemical, Biotechnol. Bioeng, 111, 16, 10.1002/bit.25012
Kamath, 1990, “New pathway for the biodegradation of indole,” in Aspergillus niger, Appl. Environ. Microbiol, 56, 275, 10.1128/AEM.56.1.275-280.1990
Kim, 2013, Accelerated degradation of exogenous indole by Burkholderia unamae strain CK43B exposed to pyrogallol-type polyphenols, Biosci. Biotechnol. Biochem., 77, 1722, 10.1271/bbb.130282
Kim, 2013, Indole toxicity involves the inhibition of adenosine triphosphate production and protein folding in Pseudomonas putida, FEMS Microbiol. Lett, 343, 89, 10.1111/1574-6968.12135
Kim, 2005, Multicomponent phenol hydroxylase-catalysed formation of hydroxyindoles and dyestuffs from indole and its derivatives, Lett. Appl. Microbiol., 41, 163, 10.1111/j.1472-765X.2005.01734.x
Kim, 2003, Production of dyestuffs from indole derivatives by naphthalene dioxygenase and toluene dioxygenase, Lett. Appl. Microbiol., 36, 343, 10.1046/j.1472-765X.2003.01279.x
Kim, 2016, Isolation of indole utilizing bacteria Arthrobacter sp. and Alcaligenes sp. from livestock waste, Indian J. Microbiol, 56, 158, 10.1007/s12088-016-0570-z
Kinney, 2006, Survey of organic wastewater contaminants in biosolids destined for land application, Environ. Sci. Technol., 40, 7207, 10.1021/es0603406
Kobayashi, 2006, Growth phase-dependent expression of drug exporters in Escherichia coli and its contribution to drug tolerance, J. Bacteriol., 188, 5693, 10.1128/JB.00217-06
Kwon, 2008, Identification of functionally important amino acids in a novel indigo-producing oxygenase from Rhodococcus sp. strain T104, Appl. Microbiol. Biotechnol., 79, 417, 10.1007/s00253-008-1445-y
Langkau, 1995, 2-Aminobenzoyl-CoA monooxygenase/reductase: evidence for two distinct loci catalyzing substrate monooxygenation and hydrogenation, Eur. J. Biochem., 230, 676, 10.1111/j.1432-1033.1995.tb20609.x
Lee, 2009, Indole and 7-hydroxyindole diminish Pseudomonas aeruginosa virulence, Microb. Biotechnol., 2, 75, 10.1111/j.1751-7915.2008.00061.x
Lee, , The multifaceted roles of the interspecies signaling molecule indole in Agrobacterium tumefaciens, Environ. Microbiol., 17, 1234, 10.1111/1462-2920.12560
Lee, 2010, Indole as an intercellular signal in microbial communities, FEMS Microbiol. Rev, 34, 426, 10.1111/j.1574-6976.2009.00204.x
Lee, , Roles of indole as an interspecies and interkingdom signaling molecule, Trends Microbiol., 23, 707, 10.1016/j.tim.2015.08.001
Li, 2013, Indole production by the tryptophanase TnaA in Escherichia coli is determined by the amount of exogenous tryptophan, Microbiology, 159, 402, 10.1099/mic.0.064139-0
Li, 2009, Indole degrading of ammonia oxidizing bacteria isolated from swine wastewater treatment system, Water Sci. Technol, 59, 2405, 10.2166/wst.2009.312
Lim, 2005, Characterization of a forest soil metagenome clone that confers indirubin and indigo production on Escherichia coli, Appl. Environ. Microbiol., 71, 7768, 10.1128/AEM.71.12.7768-7777.2005
Lin, 2012, Identification and characterization of an indigo-producing oxygenase involved in indole 3-acetic acid utilization by Acinetobacter baumannii, Antonie Van Leeuwenhoek, 101, 881, 10.1007/s10482-012-9704-4
Lin, 2015, Detoxification of indole by an indole-induced flavoprotein oxygenase from Acinetobacter baumannii, PLoS ONE, 10, e0138798, 10.1371/journal.pone.0138798
Lu, 2007, Co-expression of P450 BM3 and glucose dehydrogenase by recombinant Escherichia coli and its application in an NADPH-dependent indigo production system, J. Ind. Microbiol. Biotechnol., 34, 247, 10.1007/s10295-006-0193-1
Luo, 2010, Electricity generation from indole and microbial community analysis in the microbial fuel cell, J. Hazard. Mater., 176, 759, 10.1016/j.jhazmat.2009.11.100
Ma, 2012, Genome sequence of a novel indigo-producing strain, Pseudomonas monteilii QM, J. Bacteriol., 194, 4459, 10.1128/JB.00867-12
Ma, , Systematic investigation and microbial community profile of indole degradation processes in two aerobic activated sludge systems, Sci. Rep., 5, 17674, 10.1038/srep17674
Ma, , Genome sequence of an efficient indole-degrading bacterium, Cupriavidus sp. strain IDO, with potential polyhydroxyalkanoate production applications, Genome. Announc., 3, e00102, 10.1128/genomeA.00102-15
Mackie, 1998, Biochemical identification and biological origin of key odor components in livestock waste, J. Anim. Sci., 76, 1331, 10.2527/1998.7651331x
Madsen, 1989, Pathway of indole metabolism by a denitrifying microbial community, Arch. Microbiol., 151, 71, 10.1007/BF00444672
Madsen, 1988, Environmental factors affecting indole metabolism under anaerobic conditions, Appl. Environ. Microbiol., 54, 74, 10.1128/AEM.54.1.74-78.1988
Mao, 2010, Versatile aromatic compound-degrading capacity and microdiversity of Thauera strains isolated from a coking wastewater treatment bioreactor, J. Ind. Microbiol. Biotechnol., 37, 927, 10.1007/s10295-010-0740-7
McClay, 2005, Mutations of toluene-4-monooxygenase that alter regiospecificity of indole oxidation and lead to production of novel indigoid pigments, Appl. Environ. Microbiol., 71, 5476, 10.1128/AEM.71.9.5476-5483.2005
Mercadal, 2010, Indigo production by Pseudomonas sp. J26, a marine naphthalene-degrading strain, J. Basic. Microbiol., 50, 290, 10.1002/jobm.200900276
Mermod, 1986, New route to bacterial production of indigo, Nat. Biotechnol., 4, 321, 10.1038/nbt0486-321
Meyer, 2002, Hydroxylation of indole by laboratory-evolved 2-hydroxybiphenyl 3-monooxygenase, J. Biol. Chem., 277, 34161, 10.1074/jbc.M205621200
Moreno-Ruiz, 2003, Identification and functional characterization of Sphingomonas macrogolitabida strain TFA genes involved in the first two steps of the tetralin catabolic pathway, J. Bacteriol., 185, 2026, 10.1128/JB.185.6.2026-2030.2003
Mueller, 2009, Indole acts as an extracellular cue regulating gene expression in Vibrio cholerae, J. Bacteriol., 191, 3504, 10.1128/JB.01240-08
Müller, 1986, Production and degradation of indole by gram-negative bacteria, Zbl. Bakt. Hyg. A, 261, 1, 10.1016/S0176-6724(86)80058-X
Murdock, 1993, Construction of metabolic operons catalyzing the de novo biosynthesis of indigo in Escherichia coli, Nat. Biotechnol., 11, 381, 10.1038/nbt0393-381
Nakamura, 2001, Random mutagenesis of human cytochrome P450 2A6 and screening with indole oxidation products, Arch. Biochem. Biophys., 395, 25, 10.1006/abbi.2001.2569
Nordlund, 1990, Complete nucleotide sequence and polypeptide analysis of multi component phenol hydroxylase from Pseudomonas sp. strain CF600, J. Bacteriol., 172, 6826, 10.1128/jb.172.12.6826-6833.1990
O'Connor, 1997, Indigo formation by microorganisms expressing styrene monooxygenase activity, Appl. Environ. Microbiol, 63, 4287, 10.1128/AEM.63.11.4287-4291.1997
O'Connor, 1998, Indigo formation by aromatic hydrocarbon-degrading bacteria, Biotechnol. Lett, 20, 219, 10.1023/A:1005361415496
Osawa, 1983, Mutagen formation by intestinal bacteria, Mutat. Res., 122, 299, 10.1016/0165-7992(83)90010-6
Oshima, 1965, Oxidation of indole to indigotin by Pseudomonas indoloxidans, J. Biochem, 58, 259, 10.1093/oxfordjournals.jbchem.a128196
Pathak, 2010, Biosynthesis of indigo dye by newly isolated naphthalene-degrading strain Pseudomonas sp. HOB1 and its application in dyeing cotton fabric, Appl. Biochem. Biotechnol., 160, 1616, 10.1007/s12010-009-8638-4
Philp, 2013, Biobased chemicals, the convergence of green chemistry with industrial biotechnology, Trends Biotechnol., 31, 219, 10.1016/j.tibtech.2012.12.007
Qu, 2017, Unveiling the biotransformation mechanism of indole in a Cupriavidus sp. strain, Mol. Microbiol., 106, 905, 10.1111/mmi.13852
Qu, 2010, Influence and optimization of growth substrates on indigo formation by a novel isolate Acinetobacter sp. PP-2, Bioresour. Technol., 101, 4527, 10.1016/j.biortech.2010.01.033
Qu, 2015, Biodegradation of indole by a newly isolated Cupriavidus sp, SHE. J. Environ. Sci., 34, 126, 10.1016/j.jes.2015.01.023
Qu, , Characterization of a novel phenol hydroxylase in indoles biotranformation from a strain Arthrobacter sp. W1, PLoS ONE, 7, e44313, 10.1371/journal.pone.0044313
Qu, 2013, Biotransformation of indole by whole cells of recombinant biphenyl dioxygenase and biphenyl-2, 3-dihydrodiol-2, 3-dehydrogenase, Biochem. Eng. J., 72, 54, 10.1016/j.bej.2012.12.021
Qu, , Indigo biosynthesis by Comamonas sp. MQ, Biotechnol. Lett., 34, 353, 10.1007/s10529-011-0778-2
Radwanski, 1995, Tryptophan biosynthesis and metabolism, biochemical and molecular genetics, Plant Cell, 7, 921, 10.1105/tpc.7.7.921
Raistrick, 1921, Studies on the cycloclastic power of bacteria, Part II. A quantitative study of the aerobic decomposition of tryptophan and tyrosine by bacteria, Biochem. J., 15, 76, 10.1042/bj0150076
Regar, 2016, Draft genome sequence of Alcaligenes faecalis strain IITR89, an indole-oxidizing bacterium, Genome. Announc., 4, e00067, 10.1128/genomeA.00067-16
Rui, 2005, Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds, Appl. Microbiol Biotechnol, 66, 422, 10.1007/s00253-004-1698-z
Sadauskas, 2017, Indole biodegradation in Acinetobacter sp. strain O153, genetic and biochemical characterization, Appl. Environ. Microbiol., 83, e01453, 10.1128/AEM.01453-17
Sakamoto, 1953, The bacterial decomposition of indole. I. Studies on its metabolic pathway by successive adaptation, Med. J. Osaka Univ., 3, 477
Shanker, 1990, Transformation of indole by methanogenic and sulfate-reducing microorganisms isolated from digested sludge, Microb. Ecol., 20, 171, 10.1007/BF02543875
Sharma, 2010, Biological importance of the indole nucleus in recent years: a comprehensive review, J. Heterocyclic Chem., 47, 491, 10.1002/jhet.349
Singh, 2010, Identification of two flavin monooxygenases from an effluent treatment plant sludge metagenomic library, Bioresour. Technol, 101, 8481, 10.1016/j.biortech.2010.06.025
Smith, 1897, A modification of the method for determining the production of indol by bacteria, J. Exp. Med, 2, 543, 10.1084/jem.2.5.543
Sonowal, 2017, Indoles from commensal bacteria extend healthspan, Proc. Natl. Acad. Sci. U.S.A., 114, E7506, 10.1073/pnas.1706464114
Supniewski, 1923, Transformation of carbon compounds by Bacillus pyocyaneus, Compt. Rend. Soc. Biol., 89, 1377
Takao, 1994, A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish, Biosci. Biotechnol. Biochem., 5, 1780, 10.1271/bbb.58.1780
Urlacher, 2012, Cytochrome P450 monooxygenases, an update on perspectives for synthetic application, Trends Biotechnol., 30, 26, 10.1016/j.tibtech.2011.06.012
Van Hellemond, 2007, Discovery of a novel styrene monooxygenase originating from the metagenome, Appl. Environ. Microbiol, 73, 5832, 10.1128/AEM.02708-06
Wang, 2015, Indigoids biosynthesis from indole by two phenol-degrading strains, Pseudomonas sp. PI1 and Acinetobacter sp. PI2, Appl. Biochem. Biotechnol, 176, 1263, 10.1007/s12010-015-1644-9
Wang, 1984, Anaerobic biodegradation of indole to methane, Appl. Environ. Microbiol, 48, 1058, 10.1128/AEM.48.5.1058-1060.1984
Watanabe, 1972, Reversibility of the tryptophanase reaction, synthesis of tryptophan from indole, pyruvate, and ammonia, Proc. Natl. Acad. Sci. U.S.A., 69, 1086, 10.1073/pnas.69.5.1086
Yamamoto, 1991, Separation of high purity indole from coal tar by high pressure crystallization, Fuel, 70, 565, 10.1016/0016-2361(91)90039-D
Yang, 2017, Analysis of the metabolites of indole degraded by an isolated Acinetobacter pittii L1, Biomed. Res. Int., 2017, 2564363, 10.1155/2017/2564363
Yeon, 2008, Quorum sensing, a new biofouling control paradigm in a membrane bioreactor for advanced wastewater treatment, Environ. Sci. Technol., 43, 380, 10.1021/es8019275
Yin, 2005, Degradation of indole by enrichment culture and Pseudomonas aeruginosa Gs isolated from mangrove sediment, Int. Biodeterior. Biodegrad., 56, 243, 10.1016/j.ibiod.2005.10.001
Zhang, 2015, Illumina MiSeq sequencing reveals diverse microbial communities of activated sludge systems stimulated by different aromatics for indigo biosynthesis from indole, PLoS ONE, 10, e0125732, 10.1371/journal.pone.0125732
Zhang, 2013, Cloning and expression of naphthalene dioxygenase genes from Comamonas sp. MQ for indigoids production, Process Biochem., 48, 581, 10.1016/j.procbio.2013.02.008