Zearalenone
Zearalenone was first discovered in 1962 in extracts from moldy maize and is produced by several species of Fusarium. ZEN is also detected in other grains including oats and barley. Zenis a non-steroidal estrogen mimic capable of binding to the mammalian estrogen receptor. Zen can lead to significant reproductive defects, including enlargement and swelling of the ovaries and uterus along with reduced litter sizes and increased stillbirths in swine. Zearalenone can be hydrolyzed and inactivated by the lactonase ZHD. The term 'macrolide' encompasses a diverse family of unrelated compounds with large macrolactam rings. Zearalenone differs from other quorum-sensing lactones. These are organic compounds containing a lactone ring of at least twelve members. The term 'macrolide' encompasses a diverse family of unrelated compounds with large macrolactam rings.
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
Target
Structures : 5XO8, 5Z97, 5C7Y, 5C81, 5C8Z, 5C8X, 3WZM, 6JQZ, 6JR9
Families : Carbon-carbon_bond_hydrolase, Zearalenone-hydrolase, Zearalenone-hydrolase-fam2, 6_AlphaBeta_hydrolase
References (29)
| 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 : 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 : Enzymatic Hydrolysis of Resorcylic Acid Lactones by an Aeromicrobium sp - Hoogstra_2024_Toxins.(Basel)_16_404 |
| Author(s) : Hoogstra SJ , Hendricks KN , McMullin DR , Renaud JB , Bora J , Sumarah MW , Garnham CP |
| Ref : Toxins (Basel) , 16 :404 , 2024 |
| Abstract : |
| PubMedSearch : Hoogstra_2024_Toxins.(Basel)_16_404 |
| PubMedID: 39330862 |
| Gene_locus related to this paper: 9actn-RALH |
| Title : New Hydrolase from Aeromicrobium sp. HA for the Biodegradation of Zearalenone: Identification, Mechanism, and Application - Hu_2023_J.Agric.Food.Chem_71_2411 |
| Author(s) : Hu J , Wang G , Hou M , Du S , Han J , Yu Y , Gao H , He D , Shi J , Lee YW , Mohamed SR , Dawood DH , Hong Q , Liu X , Xu J |
| Ref : Journal of Agricultural and Food Chemistry , 71 :2411 , 2023 |
| Abstract : |
| PubMedSearch : Hu_2023_J.Agric.Food.Chem_71_2411 |
| PubMedID: 36701132 |
| Gene_locus related to this paper: 9actn-RALH , 9actn-ZENH , 9euro-a0a0d2e8j6 |
| 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 : 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 |
| Title : Isolation of an Anabolic, Uterotrophic Compound from Corn infected with Gibberella zeae - Stob_1962_Nature_196_1318 |
| Author(s) : Stob M , Baldwin RS , Tuite J , Andrews FN , Gillette KG |
| Ref : Nature , 196 :1318 , 1962 |
| Abstract : |
| PubMedSearch : Stob_1962_Nature_196_1318 |
| PubMedID: 13984207 |