Cited by 112

The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.

Recent advances in fungal xenobiotic metabolism: enzymes and applications

Khan, Mohd Faheem, Hof, Carina, Niemcová, Patricie, Murphy, Cormac D.·2023·World Journal of Microbiology and Biotechnology

Abstract

Fungi have been extensively studied for their capacity to biotransform a wide range of natural and xenobiotic compounds. This versatility is a reflection of the broad substrate specificity of fungal enzymes such as laccases, peroxidases and cytochromes P450, which are involved in these reactions. This review gives an account of recent advances in the understanding of fungal metabolism of drugs and pollutants such as dyes, agrochemicals and per- and poly-fluorinated alkyl substances (PFAS), and describes the key enzymes involved in xenobiotic biotransformation. The potential of fungi and their enzymes in the bioremediation of polluted environments and in the biocatalytic production of important compounds is also discussed.

Overview

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Integrity signals

Registry

Crossref · 10.1007/s11274-023-03737-7

Cites

2 of 2 references verified0 citation errors · 0 not checkable

Statistics

Figures

Fig. 1 Structures of the synthetic cannabinoids EG-018 and EG-2201
Fig. 1 Structures of the synthetic cannabinoids EG-018 and EG-2201CC BY · PubMed Central
Fig. 2 Biotransformation of drostanolone ethanate by F. lini and C. aphidicola generates nine metabolites: The compounds in blue were previously known and the remainder were newly discovered (Choudhary et al. 2017)
Fig. 2 Biotransformation of drostanolone ethanate by F. lini and C. aphidicola generates nine metabolites: The compounds in blue were previously known and the remainder were newly discovered (Choudhary et al. 2017)CC BY · PubMed Central
Fig. 3 Degradation of PBA-PU by Cladosporium sp. P7. The initial products of esterase and urethanase activity were further degraded by the fungus (Liu et al. 2023)
Fig. 3 Degradation of PBA-PU by Cladosporium sp. P7. The initial products of esterase and urethanase activity were further degraded by the fungus (Liu et al. 2023)CC BY · PubMed Central
Fig. 4 Catalytic mechanism of CYP system involved interaction between CPR, Cyt b5 and CYP monooxygenase in the hydroxylation of substrate X-H
Fig. 4 Catalytic mechanism of CYP system involved interaction between CPR, Cyt b5 and CYP monooxygenase in the hydroxylation of substrate X-HCC BY · PubMed Central
Fig. 5 General mechanism of peroxidases (LiP lignin peroxidase, MnP manganese peroxidase, VP versatile peroxidase, X-H substrate). The free radical product X• non-specifically reacts with other phenolic compounds
Fig. 5 General mechanism of peroxidases (LiP lignin peroxidase, MnP manganese peroxidase, VP versatile peroxidase, X-H substrate). The free radical product X• non-specifically reacts with other phenolic compoundsCC BY · PubMed Central
Fig. 6 Mechanism of UPO
Fig. 6 Mechanism of UPOCC BY · PubMed Central
Fig. 7 Mechanism of laccase. For each O2 molecule, four phenolic substrates are oxidised
Fig. 7 Mechanism of laccase. For each O2 molecule, four phenolic substrates are oxidisedCC BY · PubMed Central
Fig. 8 Catalytic mechanism of tyrosinase showing both cresolase and catecholase cycles. Eoxy/Emet/Edeoxy forms of oxidation state of tyrosinase. EoxyM monophenolase Eoxy complex, EoxyD diphenolase Eoxy complex, EmetM monophenolase Emet complex, and EmetD diphenolase Emet complex. A description of the mechanism is in the main text
Fig. 8 Catalytic mechanism of tyrosinase showing both cresolase and catecholase cycles. Eoxy/Emet/Edeoxy forms of oxidation state of tyrosinase. EoxyM monophenolase Eoxy complex, EoxyD diphenolase Eoxy complex, EmetM monophenolase Emet complex, and EmetD diphenolase Emet complex. A description of the mechanism is in the main textCC BY · PubMed Central

Verification

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

A few free checks a day · papers already verified open instantly · results are public

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

Citations

Cites

Show all 2 references

Research works printed but not linked: 136

  1. Agrawal K, Chaturvedi V, Verma P (2018) Fungal laccase discovered but yet undiscovered. Bioresour Bioprocess 5(1):4. https://doi.org/10.1186/s40643-018-0190-z · DOI
  2. Ahmaditabatabaei S, Kyazze G, Iqbal HMN, Keshavarz T (2021) Fungal enzymes as catalytic tools for polyethylene terephthalate (PET) degradation. J Fungi. https://doi.org/10.3390/jof7110931 · DOI
  3. Alvarenga N, Birolli WG, Seleghim MHR, Porto ALM (2014) Biodegradation of methyl parathion by whole cells of marine-derived fungi Aspergillus sydowii and Penicillium decaturense. Chemosphere 117:47–52. https://doi.org/10.1016/j.chemosphere.2014.05.069 · DOI
  4. Amadio J, Casey E, Murphy CD (2013) Filamentous fungal biofilm for production of human drug metabolites. Appl Microbiol Biotechnol 97(13):5955–5963. https://doi.org/10.1007/s00253-013-4833-x · DOI
  5. Aranda C, Carro J, González-Benjumea A, Babot ED, Olmedo A, Linde D, Martínez AT, Gutiérrez A (2021) Advances in enzymatic oxyfunctionalization of aliphatic compounds. Biotechnol Adv 51:107703. https://doi.org/10.1016/j.biotechadv.2021.107703 · DOI
  6. Asha S, Vidyavathi M (2009) Cunninghamella—a microbial model for drug metabolism studies—a review. Biotechnol Adv 27(1):16–29. https://doi.org/10.1016/j.biotechadv.2008.07.005 · DOI
  7. Ayilara MS, Babalola OO (2023) Bioremediation of environmental wastes: the role of microorganisms. Front Agron. https://doi.org/10.3389/fagro.2023.1183691 · DOI · Paper page
  8. Balcázar-López E, Méndez-Lorenzo LH, Batista-García RA, Esquivel-Naranjo U, Ayala M, Kumar VV, Savary O, Cabana H, Herrera-Estrella A, Folch-Mallol JL (2016) Xenobiotic compounds degradation by heterologous expression of a Trametes sanguineus laccase in Trichoderma atroviride. PLoS ONE 11(2):e0147997. https://doi.org/10.1371/journal.pone.0147997 · DOI
  9. Baldantoni D, Morelli R, Bellino A, Prati MV, Alfani A, De Nicola F (2017) Anthracene and benzo(a)pyrene degradation in soil is favoured by compost amendment: perspectives for a bioremediation approach. J Hazard Mater 339:395–400. https://doi.org/10.1016/j.jhazmat.2017.06.043 · DOI
  10. Bansal N, Kanwar SS (2013) Peroxidase(s) in environment protection. Sci World J 2013:714639. https://doi.org/10.1155/2013/714639 · DOI · Paper page
  11. Bhatt P, Zhang WP, Lin ZQ, Pang SM, Huang YH, Chen SH (2020) Biodegradation of allethrin by a novel fungus Fusarium proliferatum strain CF2, isolated from contaminated soils. Microorganisms. https://doi.org/10.3390/microorganisms8040593 · DOI
  12. Bhavsar P, Bhave M, Webb HK (2023) Solving the plastic dilemma: the fungal and bacterial biodegradability of polyurethanes. World J Microbiol Biotechnol. https://doi.org/10.1007/s11274-023-03558-8 · DOI
  13. Bianchini LF, Ramos R, de Oliveira NS, de Paula RC, Rosa RT, Glassey J, Rosa EAR (2021) Drug biotransformation process favored by fungal biofilms formed on a proposed fixed bed-airlift hybrid reactor. J Chem Technol Biotechnol 96(4):999–1006. https://doi.org/10.1002/jctb.6610 · DOI
  14. Cha CJ, Doerge DR, Cerniglia CE (2001) Biotransformation of malachite green by the fungus Cunninghamella elegans. Appl Environ Microbiol 67(9):4358–4360. https://doi.org/10.1128/aem.67.9.4358-4360.2001 · DOI
  15. Chang T-S (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440–2475 · DOI
  16. Chen W, Lee M-K, Jefcoate C, Kim S-C, Chen F, Yu J-H (2014) Fungal cytochrome P450 monooxygenases: their distribution, structure, functions, family expansion, and evolutionary origin. Genome Biol Evol 6(7):1620–1634. https://doi.org/10.1093/gbe/evu132 · DOI
  17. Chen L, Zhang X, Zhang M, Zhu Y, Zhuo R (2022) Removal of heavy-metal pollutants by white rot fungi: mechanisms, achievements, and perspectives. J Clean Prod 354:131681. https://doi.org/10.1016/j.jclepro.2022.131681 · DOI
  18. Chen S, Zhu M, Guo X, Yang B, Zhuo R (2023) Coupling of Fenton reaction and white rot fungi for the degradation of organic pollutants. Ecotoxicol Environ Saf 254:114697. https://doi.org/10.1016/j.ecoenv.2023.114697 · DOI
  19. Choudhary MI, Siddiqui M, Atia tul W, Yousuf S, Fatima N, Ahmad MS, Choudhry H (2017) Bio-catalytic structural transformation of anti-cancer steroid, drostanolone enanthate with Cephalosporium aphidicola and Fusarium lini, and cytotoxic potential evaluation of its metabolites against certain cancer cell lines. Front Pharmacol. https://doi.org/10.3389/fphar.2017.00900 · DOI
  20. Chun SC, Muthu M, Hasan N, Tasneem S, Gopal J (2019) Mycoremediation of PCBs by Pleurotus ostreatus: possibilities and prospects. Appl Sci 9(19):4185 · DOI
  21. Cong LTN, Mai CTN, Thanh VT, Nga LP, Minh NN (2014) Application of a biofilm formed by a mixture of yeasts isolated in Vietnam to degrade aromatic hydrocarbon polluted wastewater collected from petroleum storage. Water Sci Technol 70(2):329–336. https://doi.org/10.2166/wst.2014.233 · DOI
  22. Črešnar B, Petrič Å (2011) Cytochrome P450 enzymes in the fungal kingdom. Biochimica et Biophysica Acta (BBA)—Proteins Proteomics 1814(1):29–35. https://doi.org/10.1016/j.bbapap.2010.06.020 · DOI
  23. Čvančarová M, Křesinová Z, Filipová A, Covino S, Cajthaml T (2012) Biodegradation of PCBs by ligninolytic fungi and characterization of the degradation products. Chemosphere 88(11):1317–1323. https://doi.org/10.1016/j.chemosphere.2012.03.107 · DOI
  24. da Silva LV, Tavares AP, Kameda E, Macedo EA, Coelho MA, Amaral PF (2013) Factors affecting water colour removal by tyrosinase. Int J Environ Stud 70(2):316–326 · DOI
  25. Di Napoli M, Silvestri B, Castagliuolo G, Carpentieri A, Luciani G, Di Maro A, Sorbo S, Pezzella A, Zanfardino A, Varcamonti M (2023) High density polyethylene (HDPE) biodegradation by the fungus Cladosporium halotolerans. FEMS Microbiol Ecol. https://doi.org/10.1093/femsec/fiac148 · DOI
  26. Dong S, Yan PF, Liu C, Manz KE, Mezzari MP, Abriola LM, Pennell KD, Capiro NL (2023) Assessing aerobic biotransformation of 8:2 fluorotelomer alcohol in aqueous film-forming foam (AFFF)-impacted soils: pathways and microbial community dynamics. J Hazard Mater. https://doi.org/10.1016/j.jhazmat.2022.130629 · DOI
  27. Durairaj P, Hur J-S, Yun H (2016) Versatile biocatalysis of fungal cytochrome P450 monooxygenases. Microb Cell Fact 15(1):125. https://doi.org/10.1186/s12934-016-0523-6 · DOI
  28. Elyamine AM, Kan J, Meng S, Tao P, Wang H, Hu Z (2021) Aerobic and anaerobic bacterial and fungal degradation of pyrene: mechanism pathway including biochemical reaction and catabolic genes. Int J Mol Sci 22(15):8202 · DOI
  29. Faiza M, Huang S, Lan D, Wang Y (2019) New insights on unspecific peroxygenases: superfamily reclassification and evolution. BMC Evol Biol 19(1):76. https://doi.org/10.1186/s12862-019-1394-3 · DOI
  30. Falade AO, Nwodo UU, Iweriebor BC, Green E, Mabinya LV, Okoh AI (2017) Lignin peroxidase functionalities and prospective applications. MicrobiologyOpen 6(1):e00394. https://doi.org/10.1002/mbo3.394 · DOI
  31. Freakley SJ, Kochius S, van Marwijk J, Fenner C, Lewis RJ, Baldenius K, Marais SS, Opperman DJ, Harrison STL, Alcalde M, Smit MS, Hutchings GJ (2019) A chemo-enzymatic oxidation cascade to activate C–H bonds with in situ generated H2O2. Nat Commun 10(1):4178. https://doi.org/10.1038/s41467-019-12120-w · DOI
  32. Fu W-Q, Xu M, Zhang A-Y, Sun K, Dai C-C, Jia Y (2022) Remediation of phenanthrene phytotoxicity by the interaction of rice and endophytic fungus P. liquidambaris in practice. Ecotoxicol Environ Saf 235:113415. https://doi.org/10.1016/j.ecoenv.2022.113415 · DOI
  33. Gangola S, Joshi S, Kumar S, Pandey SC (2019) Comparative analysis of fungal and bacterial enzymes in biodegradation of xenobiotic compounds. In: Bhatt P (ed) Smart Bioremediation technologies. Academic Press, Cambridge, pp 169–189 · DOI
  34. Gao YF, Shah KT, Kwok I, Wang M, Rome LH, Mahendra S (2022) Immobilized fungal enzymes: innovations and potential applications in biodegradation and biosynthesis. Biotechnol Adv. https://doi.org/10.1016/j.biotechadv.2022.107936 · DOI
  35. Gaunitz F, Dahm P, Mogler L, Thomas A, Thevis M, Mercer-Chalmers-Bender K (2019) In vitro metabolic profiling of synthetic cannabinoids by pooled human liver microsomes, cytochrome P450 isoenzymes, and Cunninghamella elegans and their detection in urine samples. Anal Bioanal Chem 411(16):3561–3579. https://doi.org/10.1007/s00216-019-01837-8 · DOI
  36. Gayosso-Canales M, Rodriguez-Vazquez R, Esparza-Garcia FJ, Bermudez-Cruz RM (2012) PCBs stimulate laccase production and activity in Pleurotus ostreatus thus promoting their removal. Folia Microbiol 57(2):149–158. https://doi.org/10.1007/s12223-012-0106-9 · DOI
  37. Germain J, Raveton M, Binet MN, Mouhamadou B (2021) Screening and metabolic potential of fungal strains isolated from contaminated soil and sediment in the polychlorinated biphenyl degradation. Ecotoxicol Environ Saf. https://doi.org/10.1016/j.ecoenv.2020.111703 · DOI
  38. Geyer R, Jambeck JR, Law KL (2017) Production, use, and fate of all plastics ever made. Sci Adv 3(7):e1700782. https://doi.org/10.1126/sciadv.1700782 · DOI · Paper page
  39. Gomez de Santos P, Cañellas M, Tieves F, Younes SHH, Molina-Espeja P, Hofrichter M, Hollmann F, Guallar V, Alcalde M (2018) Selective synthesis of the human drug metabolite 5′-hydroxypropranolol by an evolved self-sufficient peroxygenase. ACS Catal 8(6):4789–4799. https://doi.org/10.1021/acscatal.8b01004 · DOI
  40. Goncalves MD, Tomiotto-Pellissier F, de Matos RLN, Assolini JP, Bortoleti BTD, Concato VM, Silva TF, Rafael JA, Pavanelli WR, Conchon-Costa I, Arakawa NS (2021) Recent advances in biotransformation by Cunninghamella species. Curr Drug Metab 22(13):1035–1064. https://doi.org/10.2174/1389200222666211126100023 · DOI
  41. Govindwar SP, Kurade MB, Tamboli DP, Kabra AN, Kim PJ, Waghmode TR (2014) Decolorization and degradation of xenobiotic azo dye reactive yellow-84A and textile effluent by Galactomyces geotrichum. Chemosphere 109:234–238. https://doi.org/10.1016/j.chemosphere.2014.02.009 · DOI
  42. Gupta S, Pathak B (2020) Mycoremediation of polycyclic aromatic hydrocarbons. In: Singh P, Kumar A, Borthakur A (eds) Abatement of environmental pollutants. Elsevier, Amsterdam, pp 127–149 · DOI
  43. Halaouli S, Asther M, Sigoillot JC, Hamdi M, Lomascolo A (2006) Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J Appl Microbiol 100(2):219–232. https://doi.org/10.1111/j.1365-2672.2006.02866.x · DOI
  44. Harding MW, Marques LLR, Howard RJ, Olson ME (2009) Can filamentous fungi form biofilms? Trends Microbiol 17(11):475–480. https://doi.org/10.1016/j.tim.2009.08.007 · DOI
  45. Hofrichter M, Kellner H, Pecyna MJ, Ullrich R (2015) Fungal unspecific peroxygenases: heme-thiolate proteins that combine peroxidase and cytochrome P450 properties. In: Hrycay EG, Bandiera SM (eds) Monooxygenase, peroxidase and peroxygenase properties and mechanisms of cytochrome P450. Springer, Cham, pp 341–368 · DOI
  46. Hofrichter M, Kellner H, Herzog R, Karich A, Kiebist J, Scheibner K, Ullrich R (2022) Peroxide-mediated oxygenation of organic compounds by fungal peroxygenases. Antioxidants 11(1):163 · DOI
  47. Hu KD, Toran J, Lopez-Garcia E, Barbieri MV, Postigo C, de Alda ML, Caminal G, Sarra M, Blanquez P (2020) Fungal bioremediation of diuron-contaminated waters: evaluation of its degradation and the effect of amendable factors on its removal in a trickle-bed reactor under non-sterile conditions. Sci Total Environ. https://doi.org/10.1016/j.scitotenv.2020.140628 · DOI
  48. Hussain S, Quinn L, Li JJ, Casey E, Murphy CD (2017) Simultaneous removal of malachite green and hexavalent chromium by Cunninghamella elegans biofilm in a semi-continuous system. Int Biodeterior Biodegrad 125:142–149. https://doi.org/10.1016/j.ibiod.2017.09.003 · DOI
  49. Ide M, Ichinose H, Wariishi H (2012) Molecular identification and functional characterization of cytochrome P450 monooxygenases from the brown-rot basidiomycete Postia placenta. Arch Microbiol 194(4):243–253. https://doi.org/10.1007/s00203-011-0753-2 · DOI
  50. Ismaya WT, Rozeboom HJ, Weijn A, Mes JJ, Fusetti F, Wichers HJ, Dijkstra BW (2011) Crystal structure of Agaricus bisporus mushroom tyrosinase: identity of the tetramer subunits and interaction with tropolone. Biochemistry 50(24):5477–5486. https://doi.org/10.1021/bi200395t · DOI · Paper page
  51. Jiang L, Huang L, Cai J, Xu Z, Lian J (2021) Functional expression of eukaryotic cytochrome P450s in yeast. Biotechnol Bioeng 118(3):1050–1065. https://doi.org/10.1002/bit.27630 · DOI
  52. Kadri T, Rouissi T, Brar SK, Cledon M, Sarma S, Verma M (2017) Biodegradation of polycyclic aromatic hydrocarbons (PAHs) by fungal enzymes: a review. J Environ Sci 51:52–74. https://doi.org/10.1016/j.jes.2016.08.023 · DOI
  53. Kalsoom U, Ahsan Z, Bhatti HN, Amin F, Nadeem R, Aftab K, Bilal M (2022) Iron oxide nanoparticles immobilized Aspergillus flavus manganese peroxidase with improved biocatalytic, kinetic, thermodynamic, and dye degradation potentialities. Process Biochem 117:117–133. https://doi.org/10.1016/j.procbio.2022.04.002 · DOI
  54. Kameda E, Langone MAP, Coelho MAZ (2006) Tyrosinase extract from Agaricus bisporus mushroom and its in natura tissue for specific phenol removal. Environ Technol 27(11):1209–1215. https://doi.org/10.1080/09593332708618736 · DOI
  55. Karich A, Ullrich R, Scheibner K, Hofrichter M (2017) Fungal unspecific peroxygenases oxidize the majority of organic EPA priority pollutants. Front Microbiol. https://doi.org/10.3389/fmicb.2017.01463 · DOI
  56. Khan MF, Murphy CD (2021) Cunninghamella spp. produce mammalian-equivalent metabolites from fluorinated pyrethroid pesticides. Amb Express. https://doi.org/10.1186/s13568-021-01262-0 · DOI
  57. Khan MF, Murphy CD (2022) Cytochrome P450 5208A3 is a promiscuous xenobiotic biotransforming enzyme in Cunninghamella elegans. Enzym Microb Technol 161:110102. https://doi.org/10.1016/j.enzmictec.2022.110102 · DOI · Paper page
  58. Khan MF, Murphy CD (2023a) Environmental remediation by novel nanomaterials and fungi with high-degradation capacity of hazardous contaminants. In: Fernández-Luqueño F (ed) Bio and nanoremediation of hazardous environmental pollutants. CRC Press, London, pp 283–310 · DOI
  59. Khan MF, Murphy CD (2023b) Fluorotelomer alcohols are efficiently biotransformed by Cunninghamella elegans. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-022-23901-0 · DOI · Paper page
  60. Khan MF, Paul Guin J, Thampi RK, Sullivan JA, Murphy CD (2023) Enhanced removal of perfluorooctanoic acid with sequential photocatalysis and fungal treatment. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-023-28588-5 · DOI
  61. Kim Y, Li C-J (2020) Perspectives on green synthesis and catalysis. Green Synth Catal 1(1):1–11. https://doi.org/10.1016/j.gresc.2020.06.002 · DOI
  62. Kinner A, Rosenthal K, Lutz S (2021) Identification and expression of new unspecific peroxygenases-recent advances, challenges and opportunities. Front Bioeng Biotechnol. https://doi.org/10.3389/fbioe.2021.705630 · DOI
  63. Klenk JM, Kontny LH, Kontny, Escobedo-Hinojosa W, Nebel BA, Hauer B (2019) Oxyfunctionalization of nonsteroidal anti-inflammatory drugs by filamentous-fungi. J Appl Microbiol 127(3):724–738. https://doi.org/10.1111/jam.14342 · DOI
  64. Kordon K, Mikolasch A, Schauer F (2010) Oxidative dehalogenation of chlorinated hydroxybiphenyls by laccases of white-rot fungi. Int Biodeterior Biodegrad 64(3):203–209. https://doi.org/10.1016/j.ibiod.2009.10.010 · DOI
  65. Korošec B, Sova M, Turk S, Kraševec N, Novak M, Lah L, Stojan J, Podobnik B, Berne S, Zupanec N, Bunc M, Gobec S, Komel R (2014) Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53). J Appl Microbiol 116(4):955–966. https://doi.org/10.1111/jam.12417 · DOI
  66. Kumar A, Chandra R (2020) Ligninolytic enzymes and its mechanisms for degradation of lignocellulosic waste in environment. Heliyon 6(2):e03170. https://doi.org/10.1016/j.heliyon.2020.e03170 · DOI · Paper page
  67. Kurniati A, Puspaningsih NNT, Putri KDA, Damayanti M, Purwani NN, Rahmah SA, Fujiyama K, Sakka M, Sakka K, Kimura T, Rohman A, Baktir A, Sanjaya RE, Sanjaya RE (2022) Heterologous fusion gene expression and characterization of a novel carbohydrate binding module (Cbm36) to laccase (Lcc2). Biocatal Agric Biotechnol. https://doi.org/10.1016/j.bcab.2022.102377 · DOI
  68. Lin S, Wei J, Yang B, Zhang M, Zhuo R (2022) Bioremediation of organic pollutants by white rot fungal cytochrome P450: the role and mechanism of CYP450 in biodegradation. Chemosphere 301:134776. https://doi.org/10.1016/j.chemosphere.2022.134776 · DOI
  69. Liu JW, Zeng QY, Lei HR, Xin KY, Xu AM, Wei R, Li D, Zhou J, Dong WL, Jiang M (2023) Biodegradation of polyester polyurethane by Cladosporium sp. P7: evaluating its degradation capacity and metabolic pathways. J Hazard Mater. https://doi.org/10.1016/j.jhazmat.2023.130776 · DOI
  70. Lu XF, Feng CY, Li SF, Liu GH, Yang Z (2021) Tyrosinase@HKUST-1: a super stable biocatalyst efficient for catecholic product synthesis. Bioresour Bioprocess. https://doi.org/10.1186/s40643-021-00462-7 · DOI
  71. Lucio J, Gonzalez-Jimenez I, Rivero-Menendez O, Alastruey-Izquierdo A, Pelaez T, Alcazar-Fuoli L, Mellado E (2020) Point mutations in the 14-α sterol demethylase Cyp51A or Cyp51C could contribute to azole resistance in Aspergillus flavus. Genes. https://doi.org/10.3390/genes11101217 · DOI
  72. Malafatti-Picca L, Bucioli EC, de Barros Chaves MR, de Castro AM, Valoni É, de Oliveira VM, Marsaioli AJ, Govone JS, de Franceschi de Angelis D, Brienzo M, Attili-Angelis D (2023) Fungal screening for potential PET depolymerization. Polymers 15(6):1581 · DOI
  73. Maqbool Z, Hussain S, Imran M, Mahmood F, Shahzad T, Ahmed Z, Azeem F, Muzammil S (2016) Perspectives of using fungi as bioresource for bioremediation of pesticides in the environment: a critical review. Environ Sci Pollut Res 23(17):16904–16925. https://doi.org/10.1007/s11356-016-7003-8 · DOI
  74. Mayolo-Deloisa K, González-González M, Rito-Palomares M (2020) Laccases in food industry: bioprocessing, potential industrial and biotechnological applications. Front Bioeng Biotechnol. https://doi.org/10.3389/fbioe.2020.00222 · DOI
  75. Merino N, Wang M, Ambrocio R, Mak K, O’Connor E, Gao A, Hawley EL, Deeb RA, Tseng LY, Mahendra S (2018) Fungal biotransformation of 6:2 fluorotelomer alcohol. Remediat J Environ Cleanup Costs Technol Tech 28(2):59–70. https://doi.org/10.1002/rem.21550 · DOI
  76. Merino N, Wang N, Gao YF, Wang M, Mahendra S (2023) Roles of various enzymes in the biotransformation of 6:2 fluorotelomer alcohol (6:2 FTOH) by a white-rot fungus. J Hazard Mater. https://doi.org/10.1016/j.jhazmat.2023.131007 · DOI · Paper page
  77. Mitra S, Pramanik A, Banerjee S, Haldar S, Gachhui R, Mukherjee J (2013) Enhanced biotransformation of fluoranthene by intertidally derived Cunninghamella elegans under biofilm-based and niche-mimicking conditions. Appl Environ Microbiol 79(24):7922–7930. https://doi.org/10.1128/aem.02129-13 · DOI
  78. Mori T, Ohno H, Ichinose H, Kawagishi H, Hirai H (2021) White-rot fungus Phanerochaete chrysosporium metabolizes chloropyridinyl-type neonicotinoid insecticides by an N-dealkylation reaction catalyzed by two cytochrome P450s. J Hazard Mater 402:123831. https://doi.org/10.1016/j.jhazmat.2020.123831 · DOI
  79. Munck C, Thierry E, Grassle S, Chen SH, Ting ASY (2018) Biofilm formation of filamentous fungi Coriolopsis sp on simple muslin cloth to enhance removal of triphenylmethane dyes. J Environ Manage 214:261–266. https://doi.org/10.1016/j.jenvman.2018.03.025 · DOI
  80. Muniraj I, Shameer S, Uthandi S (2021) Tyrosinase and laccase-producing Bacillus aryabhattai TFG5 and its role in the polymerization of phenols. BMC Microbiol 21(1):187. https://doi.org/10.1186/s12866-021-02258-3 · DOI
  81. Murphy CD (2015) Drug metabolism in microorganisms. Biotechnol Lett 37(1):19–28. https://doi.org/10.1007/s10529-014-1653-8 · DOI
  82. Nauen R, Zimmer CT, Vontas J (2021) Heterologous expression of insect P450 enzymes that metabolize xenobiotics. Curr Opin Insect Sci 43:78–84. https://doi.org/10.1016/j.cois.2020.10.011 · DOI
  83. Nykiel-Szymanska J, Bernat P, Slaba M (2020) Biotransformation and detoxification of chloroacetanilide herbicides by Trichoderma spp. with plant growth-promoting activities. Pestic Biochem Physiol 163:216–226. https://doi.org/10.1016/j.pestbp.2019.11.018 · DOI
  84. Ostrem Loss Erin M, Lee M-K, Wu M-Y, Martien J, Chen W, Amador-Noguez D, Jefcoate C, Remucal C, Jung S, Kim S-C, Yu J-H (2019) Cytochrome P450 monooxygenase-mediated metabolic utilization of benzo[a]pyrene by Aspergillus species. mBio. https://doi.org/10.1128/mbio.00558-19 · DOI
  85. Palmer-Brown W, Souza PLD, Murphy CD (2019) Cyhalothrin biodegradation in Cunninghamella elegans. Environ Sci Pollut Res 26(2):1414–1421. https://doi.org/10.1007/s11356-018-3689-0 · DOI
  86. Park H, Min B, Jang Y, Kim J, Lipzen A, Sharma A, Andreopoulos B, Johnson J, Riley R, Spatafora JW, Henrissat B, Kim KH, Grigoriev IV, Kim JJ, Choi IG (2019) Comprehensive genomic and transcriptomic analysis of polycyclic aromatic hydrocarbon degradation by a mycoremediation fungus, Dentipellis sp. Appl Microbiol Biotechnol KUC8613(19):8145–8155. https://doi.org/10.1007/s00253-019-10089-6 · DOI
  87. Passatore L, Rossetti S, Juwarkar AA, Massacci A (2014) Phytoremediation and bioremediation of polychlorinated biphenyls (PCBs): state of knowledge and research perspectives. J Hazard Mater 278:189–202. https://doi.org/10.1016/j.jhazmat.2014.05.051 · DOI
  88. Patil PD, Singh AA, Yadav GD (2021) Biodegradation of organophosphorus insecticide chlorpyrifos into a major fuel additive 2,4-bis(1,1 dimethylethyl) phenol using white-rot fungal strain Trametes hirsuta MTCC-1171. J Indian Chem Soc. https://doi.org/10.1016/j.jics.2021.100120 · DOI
  89. Pereira ARB, Pereira PM, de Franca AD, da Silva M, Ferreira-Leitao VS (2016) Propazine degradation by intra- and extracellular enzymes from Pleurotus ostreatus INCQS 40310. Biocatal Biotransform 34(2):66–75. https://doi.org/10.1080/10242422.2016.1227795 · DOI
  90. Perigon S, Massier M, Germain J, Binet MN, Legay N, Mouhamadou B (2019) Metabolic adaptation of fungal strains in response to contamination by polychlorinated biphenyls. Environ Sci Pollut Res 26(15):14943–14950. https://doi.org/10.1007/s11356-019-04701-5 · DOI
  91. Permana D, Niesel K, Ford MJ, Ichinose H (2022) Latent functions and applications of cytochrome P450 monooxygenases from Thamnidium elegans: a novel biocatalyst for 14 alpha-hydroxylation of testosterone. ACS Omega 7(16):13932–13941. https://doi.org/10.1021/acsomega.2c00430 · DOI
  92. Plackova M, Svobodova K, Cajthaml T (2012) Laccase activity profiling and gene expression in PCB-degrading cultures of Trametes versicolor. Int Biodeterior Biodegrad 71:22–28. https://doi.org/10.1016/j.ibiod.2012.03.005 · DOI
  93. Poraj-Kobielska M, Kinne M, Ullrich R, Scheibner K, Kayser G, Hammel KE, Hofrichter M (2011) Preparation of human drug metabolites using fungal peroxygenases. Biochem Pharmacol 82(7):789–796. https://doi.org/10.1016/j.bcp.2011.06.020 · DOI
  94. Poraj-Kobielska M, Peter S, Leonhardt S, Ullrich R, Scheibner K, Hofrichter M (2015) Immobilization of unspecific peroxygenases (EC 1.11.2.1) in PVA/PEG gel and hollow fiber modules. Biochem Eng J 98:144–150. https://doi.org/10.1016/j.bej.2015.02.037 · DOI
  95. Quinn L, Dempsey R, Casey E, Kane A, Murphy CD (2015) Production of drug metabolites by immobilised Cunninghamella elegans: from screening to scale up. J Ind Microbiol Biotechnol 42(5):799–806. https://doi.org/10.1007/s10295-015-1594-9 · DOI
  96. Rodrigues AD, Montanholi AD, Shimabukuro AA, Yonekawa MKA, Cassemiro NS, Silva DB, Marchetti CR, Weirich CE, Beatriz A, Zanoelo FF, Marques MR, Giannesi GC, das Neves SC, Oliveira RJ, Ruller R, de Limad DP, dos Santos ED (2023) N-acetylation of toxic aromatic amines by fungi: strain screening, cytotoxicity and genotoxicity evaluation, and application in bioremediation of 3,4-dichloroaniline. J Hazard Mater. https://doi.org/10.1016/j.jhazmat.2022.129887 · DOI
  97. Rodríguez-Delgado MM, Alemán-Nava GS, Rodríguez-Delgado JM, Dieck-Assad G, Martínez-Chapa SO, Barceló D, Parra R (2015) Laccase-based biosensors for detection of phenolic compounds. TRAC Trends Anal Chem 74:21–45. https://doi.org/10.1016/j.trac.2015.05.008 · DOI · Paper page
  98. Rotilio L, Swoboda A, Ebner K, Rinnofner C, Glieder A, Kroutil W, Mattevi A (2021) Structural and biochemical studies enlighten the unspecific peroxygenase from Hypoxylon sp. ec38 as an efficient oxidative biocatalyst. ACS Catal 11(18):11511–11525. https://doi.org/10.1021/acscatal.1c03065 · DOI
  99. Sadanoski MA, Benitez SF, Fonseca MI, Velazquez JE, Zapata PD, Levin LN, Villalba LL (2019) Mycoremediation of high concentrations of polychlorinated biphenyls with Pleurotus sajor-caju LBM 105 as an effective and cheap treatment. J Environ Chem Eng. https://doi.org/10.1016/j.jece.2019.103453 · DOI
  100. Sadanoski MA, Benitez SF, Velazquez JE, Fonseca MI, Zapata PD, Levin LN, Villalba LL (2020) Bioprocess conditions for treating mineral transformer oils contaminated with polychlorinated biphenyls (PCBs). J Environ Chem Eng. https://doi.org/10.1016/j.jece.2020.104068 · DOI
  101. Schadt S, Bister B, Chowdhury SK, Funk C, Hop CECA, Humphreys WG, Igarashi F, James AD, Kagan M, Khojasteh SC, Nedderman ANR, Prakash C, Runge F, Scheible H, Spracklin DK, Swart P, Tse S, Yuan J, Obach RS (2018) A decade in the MIST: Learnings from investigations of drug metabolites in drug development under the metabolites in safety testing regulatory guidance. Drug Metab Dispos 46(6):865–878. https://doi.org/10.1124/dmd.117.079848 · DOI
  102. Sharma J, Sharma D, Sharma A, Bansal S (2021) Thermo stable tyrosinase purified from Pleurotus djamor grown in biomimetic calcium carbonate: a biological strategy to industrial waste remediation. Environ Technol Innov. https://doi.org/10.1016/j.eti.2020.101294 · DOI
  103. Sharma M, Agarwal S, Agarwal Malik R, Kumar G, Pal DB, Mandal M, Sarkar A, Bantun F, Haque S, Singh P, Srivastava N, Gupta VK (2023) Recent advances in microbial engineering approaches for wastewater treatment: a review. Bioengineered 14(1):2184518. https://doi.org/10.1080/21655979.2023.2184518 · DOI
  104. Siddeeg SM, Tahoon MA, Mnif W, Ben Rebah F (2020) Iron oxide/chitosan magnetic nanocomposite immobilized manganese peroxidase for decolorization of textile wastewater. Processes 8(1):5 · DOI
  105. Smith RV, Rosazza JP (1974) Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch Biochem Biophys 161(2):551–558. https://doi.org/10.1016/0003-9861(74)90338-5 · DOI
  106. Solanki S, Sinha S, Singh R (2022) Myco-degradation of microplastics: an account of identified pathways and analytical methods for their determination. Biodegradation 33(6):529–556. https://doi.org/10.1007/s10532-022-10001-6 · DOI
  107. Son H, Seo H, Han S, Kim SM, Pham LTM, Khan MF, Sung HJ, Kang S-h, Kim K-J, Kim YH (2021) Extra disulfide and ionic salt bridge improves the thermostability of lignin peroxidase H8 under acidic condition. Enzym Microb Technol 148:109803. https://doi.org/10.1016/j.enzmictec.2021.109803 · DOI
  108. Song J, Zhang S, Lu L (2018) Fungal cytochrome P450 protein Cyp51: what we can learn from its evolution, regulons and Cyp51-based azole resistance. Fungal Biology Rev 32(3):131–142. https://doi.org/10.1016/j.fbr.2018.05.001 · DOI
  109. Sredlova K, Sirova K, Stella T, Cajthaml T (2021) Degradation products of polychlorinated biphenyls and their in vitro transformation by ligninolytic fungi. Toxics. https://doi.org/10.3390/toxics9040081 · DOI
  110. Štefanac T, Grgas D, Landeka Dragičević T (2021) Xenobiotics-division and methods of detection: a review. J Xenobiot 11(4):130–141. https://doi.org/10.3390/jox11040009 · DOI
  111. Stella T, Covino S, Čvančarová M, Filipová A, Petruccioli M, D’Annibale A, Cajthaml T (2017) Bioremediation of long-term PCB-contaminated soil by white-rot fungi. J Hazard Mater 324:701–710. https://doi.org/10.1016/j.jhazmat.2016.11.044 · DOI
  112. Sunderland EM, Hu XC, Dassuncao C, Tokranov AK, Wagner CC, Allen JG (2019) A review of the pathways of human exposure to poly- and perfluoroalkyl substances (PFASs) and present understanding of health effects. J Expo Sci Environ Epidemiol 29(2):131–147. https://doi.org/10.1038/s41370-018-0094-1 · DOI · Paper page
  113. Syed K, Yadav JS (2012) P450 monooxygenases (P450ome) of the model white rot fungus Phanerochaete chrysosporium. Crit Rev Microbiol 38(4):339–363. https://doi.org/10.3109/1040841x.2012.682050 · DOI
  114. Syed K, Porollo A, Lam YW, Yadav JS (2011) A fungal P450 (CYP5136A3) capable of oxidizing polycyclic aromatic hydrocarbons and endocrine disrupting alkylphenols: role of Trp129 and Leu324. PLoS ONE 6(12):e28286. https://doi.org/10.1371/journal.pone.0028286 · DOI
  115. Taxeidis G, Nikolaivits E, Siaperas R, Gkountela C, Vouyiouka S, Pantelic B, Nikodinovic-Runic J, Topakas E (2023) Triggering and identifying the polyurethane and polyethylene-degrading machinery of filamentous fungi secretomes. Environ Pollut. https://doi.org/10.1016/j.envpol.2023.121460 · DOI
  116. Theron CW, Labuschagné M, Gudiminchi R, Albertyn J, Smit MS (2014) A broad-range yeast expression system reveals Arxula adeninivorans expressing a fungal self-sufficient cytochrome P450 monooxygenase as an excellent whole-cell biocatalyst. FEMS Yeast Res 14(4):556–566. https://doi.org/10.1111/1567-1364.12142 · DOI
  117. Thoa LTK, Thao TTP, Nguyen-Thi M-L, Chung ND, Ooi CW, Park S-M, Lan TT, Quang HT, Khoo KS, Show PL, Huy ND (2023) Microbial biodegradation of recalcitrant synthetic dyes from textile-enriched wastewater by Fusarium oxysporum. Chemosphere 325:138392. https://doi.org/10.1016/j.chemosphere.2023.138392 · DOI
  118. Tromp SA, Matijošytė I, Sheldon RA, Arends IWCE, Mul G, Kreutzer MT, Moulijn JA, de Vries S (2010) Mechanism of laccase–TEMPO-catalyzed oxidation of benzyl alcohol. ChemCatChem 2(7):827–833. https://doi.org/10.1002/cctc.201000068 · DOI
  119. Tseng N, Wang N, Szostek B, Mahendra S (2014) Biotransformation of 6:2 fluorotelomer alcohol (6:2 FTOH) by a wood-rotting fungus. Environ Sci Technol 48(7):4012–4020. https://doi.org/10.1021/es4057483 · DOI · Paper page
  120. Ullrich R, Nüske J, Scheibner K, Spantzel J, Hofrichter M (2004) Novel haloperoxidase from the agaric basidiomycete Agrocybe aegerita oxidizes aryl alcohols and aldehydes. Appl Environ Microbiol 70(8):4575–4581. https://doi.org/10.1128/aem.70.8.4575-4581.2004 · DOI
  121. Vipotnik Z, Michelin M, Tavares T (2021) Ligninolytic enzymes production during polycyclic aromatic hydrocarbons degradation: effect of soil pH, soil amendments and fungal co-cultivation. Biodegradation 32(2):193–215. https://doi.org/10.1007/s10532-021-09933-2 · DOI
  122. Wang J, Ohno H, Ide Y, Ichinose H, Mori T, Kawagishi H, Hirai H (2019a) Identification of the cytochrome P450 involved in the degradation of neonicotinoid insecticide acetamiprid in Phanerochaete chrysosporium. J Hazard Mater 371:494–498. https://doi.org/10.1016/j.jhazmat.2019.03.042 · DOI
  123. Wang JQ, Tanaka Y, Ohno H, Jia JB, Mori T, Xiao TF, Yan B, Kawagishi H, Hirai H (2019b) Biotransformation and detoxification of the neonicotinoid insecticides nitenpyram and dinotefuran by Phanerochaete sordida YK-624. Environ Pollut 252:856–862. https://doi.org/10.1016/j.envpol.2019.06.022 · DOI
  124. Wang J, Bao H, Pan G, Zhang H, Li J, Li J, Cai J, Wu F (2021) Combined application of rhamnolipid and agricultural wastes enhances PAHs degradation via increasing their bioavailability and changing microbial community in contaminated soil. J Environ Manage 294:112998. https://doi.org/10.1016/j.jenvman.2021.112998 · DOI
  125. Xiao PF, Kondo R (2020) Biodegradation and biotransformation of pentachlorophenol by wood-decaying white rot fungus Phlebia acanthocystis TMIC34875. J Wood Sci. https://doi.org/10.1186/s10086-020-1849-6 · DOI
  126. Xiao PF, Mori T, Kondo R (2011) Biotransformation of the organochlorine pesticide trans-chlordane by wood-rot fungi. New Biotechnol 29(1):107–115. https://doi.org/10.1016/j.nbt.2011.06.013 · DOI
  127. Xu D-Y, Yang Y, Yang Z (2011) Activity and stability of cross-linked tyrosinase aggregates in aqueous and nonaqueous media. J Biotechnol 152(1–2):30–36 · DOI
  128. Yang WB, Li QY, Guo SQ, Sun SJ, Tang AX, Liu HB, Liu YY (2022) Rational design of aspergillus flavus A5p1-immobilized cell system to enhance the decolorization of reactive blue 4 (RB4). Chin J Chem Eng 52:37–44. https://doi.org/10.1016/j.cjche.2021.11.028 · DOI
  129. Yu X, Mao C, Zong S, Khan A, Wang W, Yun H, Zhang P, Shigaki T, Fang Y, Han H, Li X (2023) Transcriptome analysis reveals self-redox mineralization mechanism of azo dyes and novel decolorizing hydrolases in Aspergillus tabacinus LZ-M. Environ Pollut 325:121459. https://doi.org/10.1016/j.envpol.2023.121459 · DOI
  130. Zhang X, Guo J, Cheng F, Li S (2021) Cytochrome P450 enzymes in fungal natural product biosynthesis. Nat Prod Rep 38(6):1072–1099. https://doi.org/10.1039/d1np00004g · DOI
  131. Zhang K, Hu JG, Yang S, Xu W, Wang ZC, Zhuang PW, Grossart HP, Luo ZH (2022) Biodegradation of polyester polyurethane by the marine fungus Cladosporium halotolerans 6UPA1. J Hazard Mater. https://doi.org/10.1016/j.jhazmat.2022.129406 · DOI
  132. Zhao MA, Gu H, Zhang CJ, Jeong H, Kim EOH, Zhu YZ (2020) Metabolism of insecticide diazinon by Cunninghamella elegans ATCC36112. RSC Adv 10(33):19659–19668. https://doi.org/10.1039/d0ra02253e · DOI
  133. Zhao H, Wang LT, Bai YH, Li Y, Tang T, Liang H, Gao DW (2023) Immobilized enzyme with sustainable chestnut biochar to remediate polycyclic aromatic hydrocarbons contaminated soils. Environ Technol. https://doi.org/10.1080/09593330.2022.2164221 · DOI
  134. Zheng B, Yan L, Liang W, Yang Q (2019) Paralogous Cyp51s mediate the differential sensitivity of Fusarium oxysporum to sterol demethylation inhibitors. Pest Manag Sci 75(2):396–404. https://doi.org/10.1002/ps.5127 · DOI
  135. Zhu Y-Z, Fu M, Jeong I-H, Kim J-H, Zhang C-J (2017) Metabolism of an insecticide fenitrothion by Cunninghamella elegans ATCC36112. J Agric Food Chem 65(49):10711–10718. https://doi.org/10.1021/acs.jafc.7b04273 · DOI
  136. Zhuo R, Fan F (2021) A comprehensive insight into the application of white rot fungi and their lignocellulolytic enzymes in the removal of organic pollutants. Sci Total Environ 778:146132. https://doi.org/10.1016/j.scitotenv.2021.146132 · DOI

Cited by

Sorted by citations

See all 112

Metadata

Authors
Khan, M. F., Hof, C., Niemcová, P., & Murphy, C. D.
Venue
World Journal of Microbiology and Biotechnology
Published
2023-09-02
Volume
39
Issue
11
ISSN
  • 0959-3993
  • 1573-0972
Cited by
112
References
2
Language
en
Funders
  • Science Foundation Ireland (18/EPSRC-CDT/3582, 22/NCF/HE/11280)
  • University College Dublin

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

How to cite

Cite CoChat for the checks on this page, and the paper for its own findings.

This page
CoChat. (2026). Citation check: Recent advances in fungal xenobiotic metabolism: enzymes and applications. https://app.cochat.ai/papers/10.1007/s11274-023-03737-7
The paper
Khan, M. F., Hof, C., Niemcová, P., & Murphy, C. D. (2023). Recent advances in fungal xenobiotic metabolism: enzymes and applications. World Journal of Microbiology and Biotechnology. https://doi.org/10.1007/s11274-023-03737-7