Zearalenone

General

Type : Natural, Toxin, Macrolide, Polyketide, Mycotoxin-metabolite

Chemical_Nomenclature : (2E,11S)-15,17-dihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraene-7,13-dione

Canonical SMILES : CC1CCCC(=O)CCCC=CC2=CC(=CC(=C2C(=O)O1)O)O

InChI : InChI=1S\/C18H22O5\/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12\/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3\/b7-3+\/t12-\/m0\/s1

InChIKey : MBMQEIFVQACCCH-QBODLPLBSA-N

Other name(s) : ZHD-substrate  ||  Trans-Zearalenone  ||  (-)-Zearalenone  ||  F-2 toxin  ||  Mycotoxin F2  ||  ZER  ||  ZEN


MW : 318.36

Formula : C18H22O5

CAS_number : 17924-92-4

PubChem : 5281576

UniChem : MBMQEIFVQACCCH-QBODLPLBSA-N

References (26)

Title : Bacterial Lactonases ZenA with Noncanonical Structural Features Hydrolyse the Mycotoxin Zearalenone - Fruhauf_2024_ACS.Catal_14_3392
Author(s) : Fruhauf S , Puhringer D , Thamhesl M , Fajtl P , Kunz-Vekiru E , Hobartner-Gussl A , Schatzmayr G , Adam G , Damborsky J , Djinovic-Carugo K , Prokop Z , Moll WD
Ref : ACS Catal , 14 :3392 , 2024
Abstract :
PubMedSearch : Fruhauf_2024_ACS.Catal_14_3392
PubMedID: 38449531
Gene_locus related to this paper: 9actn-ZenA , 9noca-a0aa46n777

Title : Characterization, Structural Analysis, and Thermal Stability Mutation of a New Zearalenone-Degrading Enzyme Mined from Bacillus subtilis - Shi_2024_J.Agric.Food.Chem__
Author(s) : Shi J , Mwabulili F , Xie Y , Yang Y , Sun S , Li Q , Ma W , Jia H
Ref : Journal of Agricultural and Food Chemistry , : , 2024
Abstract :
PubMedSearch : Shi_2024_J.Agric.Food.Chem__
PubMedID: 38300990
Gene_locus related to this paper: bacsu-YRAK

Title : Metabolism of Zearalenone in the Rumen of Dairy Cows with and without Application of a Zearalenone-Degrading Enzyme - Gruber-Dorninger_2021_Toxins.(Basel)_13_
Author(s) : Gruber-Dorninger C , Faas J , Doupovec B , Aleschko M , Stoiber C , Hobartner-Gussl A , Schondorfer K , Killinger M , Zebeli Q , Schatzmayr D
Ref : Toxins (Basel) , 13 : , 2021
Abstract :
PubMedSearch : Gruber-Dorninger_2021_Toxins.(Basel)_13_
PubMedID: 33499402
Gene_locus related to this paper: biooc-ZHD101

Title : Degradation mechanism for Zearalenone ring-cleavage by Zearalenone hydrolase RmZHD: A QM\/MM study - Zhou_2020_Sci.Total.Environ_709_135897
Author(s) : Zhou J , Zhu L , Chen J , Wang W , Zhang R , Li Y , Zhang Q
Ref : Sci Total Environ , 709 :135897 , 2020
Abstract :
PubMedSearch : Zhou_2020_Sci.Total.Environ_709_135897
PubMedID: 31887512
Gene_locus related to this paper: 9euro-a0a0d2ilk1

Title : Characterization and Genome Analysis of a Zearalenone-Degrading Bacillus velezensis Strain ANSB01E - Guo_2020_Curr.Microbiol_77_273
Author(s) : Guo Y , Zhou J , Tang Y , Ma Q , Zhang J , Ji C , Zhao L
Ref : Curr Microbiol , 77 :273 , 2020
Abstract :
PubMedSearch : Guo_2020_Curr.Microbiol_77_273
PubMedID: 31748861
Gene_locus related to this paper: 9baci-QBK11187

Title : The Trp183 is essential in lactonohydrolase ZHD detoxifying zearalenone and zearalenols - Zhou_2020_Biochem.Biophys.Res.Commun_522_986
Author(s) : Zhou H , Li L , Zhan B , Wang S , Li J , Hu XJ
Ref : Biochemical & Biophysical Research Communications , 522 :986 , 2020
Abstract :
PubMedSearch : Zhou_2020_Biochem.Biophys.Res.Commun_522_986
PubMedID: 31810602
Gene_locus related to this paper: biooc-ZHD101

Title : Crystal Structure of a Mycoestrogen-Detoxifying Lactonase from Rhinocladiella mackenziei: Molecular Insight into ZHD Substrate Selectivity - Zheng_2018_ACS.Catal_8_4294
Author(s) : Zheng YY , Liu WT , Chen CC , Hu XY , Liu WD , Ko TP , Tang XK , Wei HL , Huang JW , Guo RT
Ref : ACS Catal , 8 :4294 , 2018
Abstract :
PubMedSearch : Zheng_2018_ACS.Catal_8_4294
PubMedID:
Gene_locus related to this paper: 9euro-a0a0d2ilk1

Title : Characterization, expression and application of a zearalenone degrading enzyme from Neurospora crassa - Bi_2018_AMB.Express_8_194
Author(s) : Bi K , Zhang W , Xiao Z , Zhang D
Ref : AMB Express , 8 :194 , 2018
Abstract :
PubMedSearch : Bi_2018_AMB.Express_8_194
PubMedID: 30570697
Gene_locus related to this paper: neucr-B15B24.080

Title : Theoretical Study on Zearalenol Compounds Binding with Wild Type Zearalenone Hydrolase and V153H Mutant - Liu_2018_Int.J.Mol.Sci_19_
Author(s) : Liu Y , Wan Y , Zhu J , Yu Z , Tian X , Han J , Zhang Z , Han W
Ref : Int J Mol Sci , 19 : , 2018
Abstract :
PubMedSearch : Liu_2018_Int.J.Mol.Sci_19_
PubMedID: 30231501
Gene_locus related to this paper: biooc-ZHD101

Title : Zearalenone induced embryo and neurotoxicity in zebrafish model (Danio rerio): Role of oxidative stress revealed by a multi biomarker study - Muthulakshmi_2018_Chemosphere_198_111
Author(s) : Muthulakshmi S , Maharajan K , Habibi HR , Kadirvelu K , Venkataramana M
Ref : Chemosphere , 198 :111 , 2018
Abstract :
PubMedSearch : Muthulakshmi_2018_Chemosphere_198_111
PubMedID: 29421719

Title : Esterase activity inspired selection and characterization of zearalenone degrading bacteria Bacillus pumilus ES-21 - Wang_2017_Food.Control_77_57
Author(s) : Wang G , Yu M , Dong F , Shi J , Xu J
Ref : Food Control , 77 :57 , 2017
Abstract :
PubMedSearch : Wang_2017_Food.Control_77_57
PubMedID:

Title : Characterization and crystal structure of a novel zearalenone hydrolase from Cladophialophora bantiana - Hui_2017_Acta.Crystallogr.F.Struct.Biol.Commun_73_515
Author(s) : Hui R , Hu X , Liu W , Zheng Y , Chen Y , Guo RT , Jin J , Chen CC
Ref : Acta Crystallographica F Struct Biol Commun , 73 :515 , 2017
Abstract :
PubMedSearch : Hui_2017_Acta.Crystallogr.F.Struct.Biol.Commun_73_515
PubMedID: 28876230
Gene_locus related to this paper: xylba-a0a0d2h023

Title : The structure of a complex of the lactonohydrolase zearalenone hydrolase with the hydrolysis product of zearalenone at 1.60 A resolution - Qi_2017_Acta.Crystallogr.F.Struct.Biol.Commun_73_376
Author(s) : Qi Q , Yang WJ , Zhou HJ , Ming DM , Sun KL , Xu TY , Hu XJ , Lv H
Ref : Acta Crystallographica F Struct Biol Commun , 73 :376 , 2017
Abstract :
PubMedSearch : Qi_2017_Acta.Crystallogr.F.Struct.Biol.Commun_73_376
PubMedID: 28695844
Gene_locus related to this paper: biooc-ZHD101

Title : Isolation and characterisation of enzymatic zearalenone hydrolysis reaction products - Vekiru_2016_World.Mycotoxin.J_9_353
Author(s) : Vekiru E , Fruhauf S , Hametner C , Schatzmayr G , Krska R , Moll WD , Schuhmacher R
Ref : World Mycotoxin Journal , 9 :353 , 2016
Abstract :
PubMedSearch : Vekiru_2016_World.Mycotoxin.J_9_353
PubMedID:
Gene_locus related to this paper: biooc-ZHD101

Title : Enhanced alpha-Zearalenol Hydrolyzing Activity of a Mycoestrogen-Detoxifying Lactonase by Structure-Based Engineering - Xu_2016_ACS.Catal_6_7657
Author(s) : Xu Z , Liu W , Chen CC , Li Q , Huang JW , Ko TP , Liu G , Peng W , Cheng YS , Chen Y , Jin J , Li H , Zheng Y , Guo RT
Ref : ACS Catal , 6 :7657 , 2016
Abstract :
PubMedSearch : Xu_2016_ACS.Catal_6_7657
PubMedID:
Gene_locus related to this paper: biooc-ZHD101

Title : Zearalenone detoxification by zearalenone hydrolase is important for the antagonistic ability of Clonostachys rosea against mycotoxigenic Fusarium graminearum - Kosawang_2014_Fungal.Biol_118_364
Author(s) : Kosawang C , Karlsson M , Velez H , Rasmussen PH , Collinge DB , Jensen B , Jensen DF
Ref : Fungal Biol , 118 :364 , 2014
Abstract :
PubMedSearch : Kosawang_2014_Fungal.Biol_118_364
PubMedID: 24742831
Gene_locus related to this paper: biooc-ZHD101

Title : Individual in vitro effects of ochratoxin A, deoxynivalenol and zearalenone on oxidative stress and acetylcholinesterase in lymphocytes of broiler chickens - Lautert_2014_Springerplus_3_506
Author(s) : Lautert C , Ferreiro L , Wolkmer P , Paim FC , da Silva CB , Jaques JA , Lopes ST , Santurio JM
Ref : Springerplus , 3 :506 , 2014
Abstract :
PubMedSearch : Lautert_2014_Springerplus_3_506
PubMedID: 25279298

Title : Crystal structure and substrate-binding mode of the mycoestrogen-detoxifying lactonase ZHD from Clonostachys rosea - Peng_2014_RSC.Adv_4_62321
Author(s) : Peng W , Ko TP , Yang YY , Zheng YY , Chen CC , Zhu Z , Huang CH , Zeng YF , Huang JW , Wang AHJ , Liu JR , Guo RT
Ref : RSC Advances , 4 :62321 , 2014
Abstract :
PubMedSearch : Peng_2014_RSC.Adv_4_62321
PubMedID:
Gene_locus related to this paper: biooc-ZHD101

Title : Zearalenone lactonohydrolase activity in Hypocreales and its evolutionary relationships within the epoxide hydrolase subset of a\/b-hydrolases - Popiel_2014_BMC.Microbiol_14_82
Author(s) : Popiel D , Koczyk G , Dawidziuk A , Gromadzka K , Blaszczyk L , Chelkowski J
Ref : BMC Microbiol , 14 :82 , 2014
Abstract :
PubMedSearch : Popiel_2014_BMC.Microbiol_14_82
PubMedID: 24708405
Gene_locus related to this paper: biooc-ZHD101

Title : Effect on hepatonephric organs, serum metabolites and oxidative stress in post-weaning piglets fed purified zearalenone-contaminated diets with or without Calibrin-Z - Jiang_2012_J.Anim.Physiol.Anim.Nutr.(Berl)_96_1147
Author(s) : Jiang SZ , Yang ZB , Yang WR , Wang SJ , Wang Y , Broomhead J , Johnston SL , Chi F
Ref : J Anim Physiol Anim Nutr (Berl) , 96 :1147 , 2012
Abstract :
PubMedSearch : Jiang_2012_J.Anim.Physiol.Anim.Nutr.(Berl)_96_1147
PubMedID: 21967683

Title : Reduced contamination by the Fusarium mycotoxin zearalenone in maize kernels through genetic modification with a detoxification gene - Igawa_2007_Appl.Environ.Microbiol_73_1622
Author(s) : Igawa T , Takahashi-Ando N , Ochiai N , Ohsato S , Shimizu T , Kudo T , Yamaguchi I , Kimura M
Ref : Applied Environmental Microbiology , 73 :1622 , 2007
Abstract :
PubMedSearch : Igawa_2007_Appl.Environ.Microbiol_73_1622
PubMedID: 17209063
Gene_locus related to this paper: biooc-ZHD101

Title : Efficient decontamination of zearalenone, the mycotoxin of cereal pathogen, by transgenic yeasts through the expression of a synthetic lactonohydrolase gene - Takahashi-Ando_2005_Appl.Microbiol.Biotechnol_67_838
Author(s) : Takahashi-Ando N , Tokai T , Hamamoto H , Yamaguchi I , Kimura M
Ref : Applied Microbiology & Biotechnology , 67 :838 , 2005
Abstract :
PubMedSearch : Takahashi-Ando_2005_Appl.Microbiol.Biotechnol_67_838
PubMedID: 15630583
Gene_locus related to this paper: biooc-ZHD101

Title : Two different polyketide synthase genes are required for synthesis of zearalenone in Gibberella zeae - Kim_2005_Mol.Microbiol_58_1102
Author(s) : Kim YT , Lee YR , Jin J , Han KH , Kim H , Kim JC , Lee T , Yun SH , Lee YW
Ref : Molecular Microbiology , 58 :1102 , 2005
Abstract :
PubMedSearch : Kim_2005_Mol.Microbiol_58_1102
PubMedID: 16262793
Gene_locus related to this paper: gibze-q2vlj3

Title : A model transgenic cereal plant with detoxification activity for the estrogenic mycotoxin zearalenone - Higa-Nishiyama_2005_Transgenic.Res_14_713
Author(s) : Higa-Nishiyama A , Takahashi-Ando N , Shimizu T , Kudo T , Yamaguchi I , Kimura M
Ref : Transgenic Res , 14 :713 , 2005
Abstract :
PubMedSearch : Higa-Nishiyama_2005_Transgenic.Res_14_713
PubMedID: 16245162
Gene_locus related to this paper: biooc-ZHD101

Title : Metabolism of zearalenone by genetically modified organisms expressing the detoxification gene from Clonostachys rosea - Takahashi-Ando_2004_Appl.Environ.Microbiol_70_3239
Author(s) : Takahashi-Ando N , Ohsato S , Shibata T , Hamamoto H , Yamaguchi I , Kimura M
Ref : Applied Environmental Microbiology , 70 :3239 , 2004
Abstract :
PubMedSearch : Takahashi-Ando_2004_Appl.Environ.Microbiol_70_3239
PubMedID: 15184117
Gene_locus related to this paper: biooc-ZHD101

Title : A novel lactonohydrolase responsible for the detoxification of zearalenone: enzyme purification and gene cloning - Takahashi-Ando_2002_Biochem.J_365_1
Author(s) : Takahashi-Ando N , Kimura M , Kakeya H , Osada H , Yamaguchi I
Ref : Biochemical Journal , 365 :1 , 2002
Abstract :
PubMedSearch : Takahashi-Ando_2002_Biochem.J_365_1
PubMedID: 11978180
Gene_locus related to this paper: biooc-ZHD101