151
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Comparative analysis of the white rot fungus Trametes hirsuta 072 laccases ability to modify 17β-oestradiol in the aqueous medium

, , , &
Pages 475-485 | Received 19 Apr 2022, Accepted 29 May 2022, Published online: 13 Jun 2022

References

  • Adeel M, Song X, Wang Y, Francis D, Yang Y. 2017. Environmental impact of estrogens on human, animal and plant life: a critical review. Environ Int. 99:107–119.
  • Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY. 2006. Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem. 41(3):525–539.
  • Auriol M, Filali-Meknassi Y, Adams CD, Tyagi RD, Noguerol T-N, Pina B. 2008. Removal of estrogenic activity of natural and synthetic hormones from a municipal wastewater: efficiency of horseradish peroxidase and laccase from Trametes versicolor. Chemosphere. 70(3):445–452.
  • Avar P, Zrínyi Z, Maász G, Takátsy A, Lovas S, Tóth LG, Pirger Z. 2016. β-Estradiol and ethinyl-estradiol contamination in the rivers of the Carpathian Basin. Environ Sci Pollut Res Int. 23(12):11630–11638.
  • Baldanta S, Navarro Llorens JM, Guevara G. 2021. Further studies on the 3-ketosteroid 9α-hydroxylase of Rhodococcus ruber Chol-4, a Rieske oxygenase of the steroid degradation pathway. Microorganisms. 9(6):1171.
  • Bolton JL, Thatcher GRJ. 2008. Potential mechanisms of estrogen quinone carcinogenesis. Chem Res Toxicol. 21(1):93–101.
  • Cargouet M, Perdiz D, Mouatassim-Souali A, Tamisier-Karolak S, Levi Y. 2004. Assessment of river contamination by estrogenic compounds in Paris area (France). Sci Total Environ. 324(1–3):55–66.
  • Claus H. 2004. Laccases: structure, reactions, distribution. Micron. 35(1–2):93–96.
  • Coates JM, Gurnell M, Sarnyai Z. 2010. From molecule to market: steroid hormones and financial risk-taking. Philos Trans R Soc Lond B Biol Sci. 365(1538):331–343.
  • Directive. 2013. Directive 2013/39/EU of the European Parliament and of the Council of 12 August 2013 amending Directives 2000/60/EC and 2008/105/EC as regards priority substances in the field of water policy. Official Journal of the European Union. L 226/1. Article 8b.
  • Fernández-Cabezón L, Galán B, García JL. 2018. New insights on steroid biotechnology. Front Microbiol. 9:958.
  • Haroune L, Saibi S, Bellenger J-P, Cabana H. 2014. Evaluation of the efficiency of Trametes hirsuta for the removal of multiple pharmaceutical compounds under low concentrations relevant to the environment. Bioresour Technol. 171:199–202.
  • Ius A, Meroni G, Ferrara L. 1977. Two dimers, 4:4′- and 2:2′-di[estradiol], obtained by chemical oxidative coupling of estradiol. J Steroid Biochem. 8(12):1259–1261.
  • Kilaru S, Hoegger PJ, Kües U. 2006. The laccase multi-gene family in Coprinopsis cinerea has seventeen different members that divide into two distinct subfamilies. Curr Genet. 50(1):45–60.
  • Koschorreck K, Richter SM, Swierczek A, Beifuss U, Schmid RD, Urlacher VB. 2008. Comparative characterization of four laccases from Trametes versicolor concerning phenolic C–C coupling and oxidation of PAHs. Arch Biochem Biophys. 474(1):213–219.
  • Kuch HM, Ballschmiter KH. 2001. Determination of endocrine-disrupting phenolic compounds and estrogens in surface and drinking water by HRGC-(NCI)-MS in the picogram per liter range. Environ Sci Technol. 35(15):3201–3206.
  • Lorenzo M, Moldes D, Sanromán MÁ. 2006. Effect of heavy metals on the production of several laccase isoenzymes by Trametes versicolor and on their ability to decolourise dyes. Chemosphere. 63(6):912–917.
  • Lloret L, Eibes G, Feijoo G, Moreira MT, Lema JM. 2012. Degradation of estrogens by laccase from Myceliophthora thermophila in fed-batch and enzymatic membrane reactors. J Hazard Mater. 213–214:175–183.
  • Lloret L, Eibes G, Feijoo G, Moreira MT, Feijoo G, Lema JM. 2013. Removal of estrogenic compounds from filtered secondary wastewater effluent in a continuous enzymatic membrane reactor. Identification of biotransformation products. Environ Sci Technol. 47(9):4536–4543.
  • Lugaro G, Carrea G, Cremonesi P, Casellato MM, Antonini E. 1973. The oxidation of steroid hormones by fungal laccase in emulsion of water and organic solvents. Arch Biochem Biophys. 159(1):1–6.
  • Morozova OV, Shumakovich GP, Shleev SV, Yaropolov YI. 2007. Laccase-mediator systems and their applications: a review. Appl Biochem Microbiol. 43(5):523–535.
  • Nicotra S, Intra A, Ottolina G, Riva S, Danieli B. 2004. Laccase-mediated oxidation of the steroid hormone 17b-estradiol in organic solvents. Tetrahedron Asymmetry. 15(18):2927–2931.
  • Ojoghoro JO, Scrimshaw MD, Sumpter JP. 2021. Steroid hormones in the aquatic environment. Sci Total Environ. 792:148306.
  • Olicón-Hernández DR, González-López J, Aranda E. 2017. Overview on the biochemical potential of filamentous fungi to degrade pharmaceutical compounds. Front Microbiol. 8:1792.
  • Petrovic M, Sole M, Lopez de Alda MJ, Barcelo D. 2002. Endocrine disruptors in sewage treatment plants, receiving river waters, and sediments: integration of chemical analysis and biological effects on feral carp. Environ Toxicol Chem. 21(10):2146–2156.
  • Pezzella A, Lista L, Napolitano A, D'Ischia M. 2004. Oxidative coupling of 17beta-estradiol: inventory of oligomer products and configuration assignment of atropoisomeric C4-linked biphenyl-type dimers and trimers. J Org Chem. 69(17):5652–5659.
  • Rebrikov DV, Stepanova EV, Koroleva OV, Budarina Z, Zakharova MV, Yurkova TV, Solonin AS, Belova OV, Pozhidaeva ZA, Leont’evsky AA. 2006. Laccase of the lignolytic fungus Trametes hirsuta: purification and characterization of the enzyme, and cloning and primary structure of the gene. Appl Biochem Microbiol. 42(6):564–572.
  • Savinova OS, Moiseenko KV, Vavilova EA, Tyazhelova TV, Vasina DV. 2017. Properties of two laccases from the Trametes hirsuta 072 multigene family: twins with different faces. Biochimie. 142:183–190.
  • Savinova OS, Moiseenko KV, Vavilova EA, Chulkin AM, Fedorova TV, Tyazhelova TV, Vasina DV. 2019a. Evolutionary relationships between the laccase genes of Polyporales: orthology-based classification of laccase isozymes and functional insight from Trametes hirsuta. Front Microbiol. 10:152.
  • Savinova OS, Zorov IN, Vasina DV, Sinitsyn AP, Fedorova TV. 2019b. The minor recombinant laccase isozymes of Trametes hirsuta 072: preparation and properties. Moscow Univ Chem Bull. 74(4):173–179.
  • Szentirrnai A. 1990. Microbial physiology of sidechain degradation of sterols. J Ind Microbiol. 6:101–116.
  • Sun K, Liang S, Kang F, Gao Y, Huang Q. 2016. Transformation of 17β-estradiol in humic acid solution by ε-MnO2 nanorods as probed by high-resolution mass spectrometry combined with (13)C labeling. Environ Pollut. 214:211–218.
  • Sun K, Cheng X, Yu J, Chen L, Wei J, Chen W, Wang J, Li S, Liu Q, Si Y. 2020. Isolation of Trametes hirsuta La-7 with high laccase-productivity and its application in metabolism of 17β-estradiol. Environ Pollut. 263(Pt B):114381.
  • Temp U, Zierold U, Eggert C. 1999. Cloning and characterization of a second laccase gene from the lignin-degrading basidiomycete Pycnoporus cinnabarinus. Gene. 236(1):169–177.
  • Ting YF, Praveena SM. 2017. Sources, mechanisms, and fate of steroid estrogens in wastewater treatment plants: a mini review. Environ Monit Assess. 189(4):178.
  • Touahar IE, Haroune L, Ba S, Bellenger JP, Cabana H. 2014. Characterization of combined cross-linked enzyme aggregates from laccase, versatile peroxidase and glucose oxidase, and their utilization for the elimination of pharmaceuticals. Sci Total Environ. 481:90–99.
  • Vasina DV, Mustafaev ON, Moiseenko KV, Sadovskaya NS, Glazunova OA, Tyurin АА, Fedorova TV, Pavlov AR, Tyazhelova TV, Goldenkova-Pavlova IV, et al. 2015. The Trametes hirsuta 072 laccase multigene family: genes identification and transcriptional analysis under copper ions induction. Biochimie. 116:154–164.
  • Wang X, Liu J, Qu R, Wang Z, Huang Q. 2017. The laccase-like reactivity of manganese oxide nanomaterials for pollutant conversion: rate analysis and cyclic voltammetry. Sci Rep. 7(1):7756.
  • Woerdenbag HJ, Pras N, Frijlink HW, Lerk CF, Malingre TM. 1990. Cyclodextrin-facilitated bioconversion of 17 beta-estradiol by a phenoloxidase from Mucuna pruriens cell cultures. Phytochemistry. 29(5):1551–1554.
  • Xia Q, Kong D, Liu G, Huang Q, Alalewi A, Lu J. 2014. Removal of 17β-estradiol in laccase catalyzed treatment processes. Front Environ Sci Eng. 8(3):372–378.
  • Xiao YZ, Chen Q, Hang J, Shi YY, Xiao YZ, Wu J, Hong YZ, Wang YP. 2004. Selective induction, purification and characterization of a laccase isozyme from the basidiomycete Trametes sp. AH28-2. Mycologia. 96(1):26–35.
  • Yaver DS, Xu F, Golightly EJ, Brown KM, Brown SH, Rey MW, Schneider P, Halkier T, Mondorf K, Dalboge H. 1996. Purification, characterization, molecular cloning, and expression of two laccase genes from the white rot basidiomycete Trametes villosa. Appl Environ Microbiol. 62(3):834–841.
  • Zdarta J, Nguen LN, Jankovska K, Jesionowski T, Nghiem LD. 2021. A contemporary review of enzymatic applications in the remediation of emerging estrogenic compounds. Crit Rev Environ Sci Technol;
  • Zhang F, Chen Y, Pisha E, Shen L, Xiong Y, van Breemen RB, Bolton JL. 1999. The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem Res Toxicol. 12(2):204–213.
  • Zhou L, Luo Q, Lu J, Huang Q. 2015. Transformation of 17β-estradiol by Phanerochaete chrysosporium in different culture media. Bull Environ Contam Toxicol. 95(2):265–271.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.