Zeranol (BioDeep_00000002605)
Secondary id: BioDeep_00000406064
human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds
代谢物信息卡片
7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
化学式: C18H26O5 (322.1780146)
中文名称: 乙腈中α-玉米赤霉醇溶液标准物质, 折仑诺(玉米赤酶醇)
谱图信息:
最多检出来源 Viridiplantae(plant) 0.68%
分子结构信息
SMILES: CC1CCCC(CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
InChI: InChI=1S/C18H26O5/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/h10-12,14,19-21H,2-9H2,1H3
描述信息
Zeranol is isolated from Fusarium species. It is an anabolic agent and estrogenic agent (mainly veterinary use). Zeranol is used as a growth promoter for food animals. It was banned by the EU in 1989, but is still permitted in the USA and some other countries. It may also arise in livestock by ingestion of Fusarium contaminated pasture or feeds
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
Same as: D06362
同义名列表
22 个代谢物同义名
7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one; 7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-2-benzoxacyclotetradecin-1-one; 6-(6,10-Dihydroxyundecyl)-beta-resorcylic acid, mu-lactone; Dihydroxyundecyl resorcylic acid lactone; Zeranol, ban, inn, usan; alpha-Zearalanol; alpha Zearalanol; alpha-Zeranol; a-Zearalanol; Zearalanol; Taleranol; Frideron; Zearanol; Xeranol; Ralabol; Zeranol; Ralone; Zerano; MK 188; Ralgro; p 1496; alpha-Zearalanol
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:35064
- KEGG: C14752
- PubChem: 22283
- HMDB: HMDB0032702
- Metlin: METLIN70306
- Wikipedia: Zeranol
- MeSH: Zeranol
- KNApSAcK: C00057300
- foodb: FDB010663
- chemspider: 20916
- CAS: 55331-29-8
- CAS: 26538-44-3
- PMhub: MS000004122
- PubChem: 17395750
- PDB-CCD: 27J
- NIKKAJI: J10.434E
- KNApSAcK: 35064
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Honglei Qu, Yunduo Zheng, Ruifen Kang, Yulong Feng, Pengshuai Li, Yantao Wang, Jie Cheng, Cheng Ji, Wenqiong Chai, Qiugang Ma. Toxicokinetics of Zearalenone following Oral Administration in Female Dezhou Donkeys.
Toxins.
2024 Jan; 16(1):. doi:
10.3390/toxins16010051. [PMID: 38251267] - Yanrong Su, Julia Santucci-Pereira, Nhi M Dang, Joice Kanefsky, Vishnuprabha Rahulkannan, Meardey Hillegass, Shalina Joshi, Hafsa Gurdogan, Zhen Chen, Vincent Bessonneau, Ruthann Rudel, Jennifer Ser-Dolansky, Sallie S Schneider, Jose Russo. Effects of Pubertal Exposure to Butyl Benzyl Phthalate, Perfluorooctanoic Acid, and Zeranol on Mammary Gland Development and Tumorigenesis in Rats.
International journal of molecular sciences.
2022 Jan; 23(3):. doi:
10.3390/ijms23031398. [PMID: 35163327] - Carolyn W Kinkade, Zorimar Rivera-Núñez, Ludwik Gorcyzca, Lauren M Aleksunes, Emily S Barrett. Impact of Fusarium-Derived Mycoestrogens on Female Reproduction: A Systematic Review.
Toxins.
2021 05; 13(6):. doi:
10.3390/toxins13060373. [PMID: 34073731] - Jennifer Duringer, Rajarshi Mazumder, Valerie Palmer, A Morrie Craig, Peter Spencer. Case-Control Study of Nodding Syndrome in Acholiland: Urinary Multi-Mycotoxin Screening.
Toxins.
2021 04; 13(5):. doi:
10.3390/toxins13050313. [PMID: 33925470] - Ana Juan-García, Giovanni Caprioli, Gianni Sagratini, Jordi Mañes, Cristina Juan. Coffee Silverskin and Spent Coffee Suitable as Neuroprotectors against Cell Death by Beauvericin and α-Zearalenol: Evaluating Strategies of Treatment.
Toxins.
2021 02; 13(2):. doi:
10.3390/toxins13020132. [PMID: 33579040] - Tim Birr, Tolke Jensen, Nils Preußke, Frank D Sönnichsen, Marthe De Boevre, Sarah De Saeger, Mario Hasler, Joseph-Alexander Verreet, Holger Klink. Occurrence of Fusarium Mycotoxins and Their Modified Forms in Forage Maize Cultivars.
Toxins.
2021 02; 13(2):. doi:
10.3390/toxins13020110. [PMID: 33540691] - Christiane Gruber-Dorninger, Johannes Faas, Barbara Doupovec, Markus Aleschko, Christian Stoiber, Andreas Höbartner-Gußl, Karin Schöndorfer, Manuela Killinger, Qendrim Zebeli, Dian Schatzmayr. Metabolism of Zearalenone in the Rumen of Dairy Cows with and without Application of a Zearalenone-Degrading Enzyme.
Toxins.
2021 01; 13(2):. doi:
10.3390/toxins13020084. [PMID: 33499402] - Yan Qin Tan, Qing Li, Lin Wang, Leo C Chiu-Leung, Lai K Leung. The livestock growth-promoter zeranol facilitates GLUT4 translocation in 3T3 L1 adipocytes.
Chemosphere.
2020 Aug; 253(?):126772. doi:
10.1016/j.chemosphere.2020.126772. [PMID: 32464760] - Shupeng Yang, Yanshen Li, Marthe De Boevre, Sarah De Saeger, Jinhui Zhou, Yi Li, Huiyan Zhang, Feifei Sun. Toxicokinetics of α-zearalenol and its masked form in rats and the comparative biotransformation in liver microsomes from different livestock and humans.
Journal of hazardous materials.
2020 Jul; 393(?):121403. doi:
10.1016/j.jhazmat.2019.121403. [PMID: 32143155] - Ecem Fatma Karaman, Müjdat Zeybel, Sibel Ozden. Evaluation of the epigenetic alterations and gene expression levels of HepG2 cells exposed to zearalenone and α-zearalenol.
Toxicology letters.
2020 Jun; 326(?):52-60. doi:
10.1016/j.toxlet.2020.02.015. [PMID: 32119988] - Silvia W Gratz, Valerie Currie, Gary Duncan, Diane Jackson. Multimycotoxin Exposure Assessment in UK Children Using Urinary Biomarkers-A Pilot Survey.
Journal of agricultural and food chemistry.
2020 Jan; 68(1):351-357. doi:
10.1021/acs.jafc.9b03964. [PMID: 31826612] - Barbara Gzyl-Malcher, Elżbieta Rudolphi-Skórska, Apolonia Sieprawska, Maria Filek. Manganese protects wheat from the mycotoxin zearalenone and its derivatives.
Scientific reports.
2019 10; 9(1):14214. doi:
10.1038/s41598-019-50664-5. [PMID: 31578385] - José L Hidalgo-Ruiz, Roberto Romero-González, José Luis Martínez Vidal, Antonia Garrido Frenich. A rapid method for the determination of mycotoxins in edible vegetable oils by ultra-high performance liquid chromatography-tandem mass spectrometry.
Food chemistry.
2019 Aug; 288(?):22-28. doi:
10.1016/j.foodchem.2019.03.003. [PMID: 30902285] - Iwona Matraszek-Zuchowska, Barbara Wozniak, Andrzej Posyniak. Resorcylic acid lactones in urine samples of slaughtered animals resulting from potential feed contamination with zearalenone.
Food additives & contaminants. Part B, Surveillance.
2019 Jun; 12(2):105-115. doi:
10.1080/19393210.2019.1566933. [PMID: 30727848] - Amelie Catteuw, Nathan Broekaert, Siegrid De Baere, Marianne Lauwers, Elke Gasthuys, Bart Huybrechts, Alfons Callebaut, Lada Ivanova, Silvio Uhlig, Marthe De Boevre, Sarah De Saeger, Ronette Gehring, Mathias Devreese, Siska Croubels. Insights into In Vivo Absolute Oral Bioavailability, Biotransformation, and Toxicokinetics of Zearalenone, α-Zearalenol, β-Zearalenol, Zearalenone-14-glucoside, and Zearalenone-14-sulfate in Pigs.
Journal of agricultural and food chemistry.
2019 Mar; 67(12):3448-3458. doi:
10.1021/acs.jafc.8b05838. [PMID: 30807145] - Zorimar Rivera-Núñez, Emily S Barrett, Elizabeth A Szamreta, Sue A Shapses, Bo Qin, Yong Lin, Helmut Zarbl, Brian Buckley, Elisa V Bandera. Urinary mycoestrogens and age and height at menarche in New Jersey girls.
Environmental health : a global access science source.
2019 03; 18(1):24. doi:
10.1186/s12940-019-0464-8. [PMID: 30902092] - Xiaojing Wang, Chen Wang, Lixin Duan, Liwen Zhang, Hang Liu, Ya-Ming Xu, Qingpei Liu, Tonglin Mao, Wei Zhang, Ming Chen, Min Lin, A A Leslie Gunatilaka, Yuquan Xu, István Molnár. Rational Reprogramming of O-Methylation Regioselectivity for Combinatorial Biosynthetic Tailoring of Benzenediol Lactone Scaffolds.
Journal of the American Chemical Society.
2019 03; 141(10):4355-4364. doi:
10.1021/jacs.8b12967. [PMID: 30767524] - A Vulić, T Lešić, N Kudumija, T Mikuš, J Pleadin. Resorcylic Acid Lactones in Urine Samples of Croatian Farm Animals.
Journal of analytical toxicology.
2019 Mar; 43(2):126-133. doi:
10.1093/jat/bky069. [PMID: 30295910] - Nurshad Ali, Gisela H Degen. Urinary biomarkers of exposure to the mycoestrogen zearalenone and its modified forms in German adults.
Archives of toxicology.
2018 08; 92(8):2691-2700. doi:
10.1007/s00204-018-2261-5. [PMID: 29980802] - Yue Song, Pinggu Wu, Zhengyan Hu, Lijun Yang, Ying Chen. [Determination of zearalenone and α-zearalenol in vegetable oil and grain products by C_(18)-Al_2O_3 solid phase extraction column purification coupled with ultra-performance liquid chromatography tandem mass spectrometry].
Wei sheng yan jiu = Journal of hygiene research.
2018 Jul; 47(4):615-620. doi:
. [PMID: 30081990] - Anna Chiara Nittoli, Susan Costantini, Angela Sorice, Francesca Capone, Roberto Ciarcia, Stefania Marzocco, Alfredo Budillon, Lorella Severino. Effects of α-zearalenol on the metabolome of two breast cancer cell lines by 1H-NMR approach.
Metabolomics : Official journal of the Metabolomic Society.
2018 02; 14(3):33. doi:
10.1007/s11306-018-1330-3. [PMID: 30830360] - M Takagi, S Uno, E Kokushi, F Sato, Mmp Wijayagunawardane, J Fink-Gremmels. Measurement of urinary concentrations of the mycotoxins zearalenone and sterigmatocystin as biomarkers of exposure in mares.
Reproduction in domestic animals = Zuchthygiene.
2018 Feb; 53(1):68-73. doi:
10.1111/rda.13054. [PMID: 28921680] - Silvia W Gratz, Reshma Dinesh, Tomoya Yoshinari, Grietje Holtrop, Anthony J Richardson, Gary Duncan, Susan MacDonald, Antony Lloyd, Jonathan Tarbin. Masked trichothecene and zearalenone mycotoxins withstand digestion and absorption in the upper GI tract but are efficiently hydrolyzed by human gut microbiota in vitro.
Molecular nutrition & food research.
2017 04; 61(4):. doi:
10.1002/mnfr.201600680. [PMID: 27921366] - Sabina B Binder, Heidi E Schwartz-Zimmermann, Elisabeth Varga, Gerlinde Bichl, Herbert Michlmayr, Gerhard Adam, Franz Berthiller. Metabolism of Zearalenone and Its Major Modified Forms in Pigs.
Toxins.
2017 02; 9(2):. doi:
10.3390/toxins9020056. [PMID: 28208710] - Intidhar Ben Salem, Manel Boussabbeh, Alexandre Prola, Arnaud Guilbert, Hassen Bacha, Christophe Lemaire, Salwa Abid-Essefi. Crocin protects human embryonic kidney cells (HEK293) from α- and β-Zearalenol-induced ER stress and apoptosis.
Environmental science and pollution research international.
2016 Aug; 23(15):15504-14. doi:
10.1007/s11356-016-6741-y. [PMID: 27121014] - P Moriel, L F A Artioli, M B Piccolo, R S Marques, M H Poore, R F Cooke. Effects of timing of anabolic implant insertion on growth and immunity of recently weaned beef steers.
Journal of animal science.
2016 Jul; 94(7):3051-60. doi:
10.2527/jas.2016-0470. [PMID: 27482692] - Shaohui Zong, Gaofeng Zeng, Ye Fang, Jinzhen Peng, Bin Zou, Taihang Gao, Jingmin Zhao. The effects of α-zearalanol on the proliferation of bone-marrow-derived mesenchymal stem cells and their differentiation into osteoblasts.
Journal of bone and mineral metabolism.
2016 Mar; 34(2):151-60. doi:
10.1007/s00774-015-0659-1. [PMID: 25944420] - Dudu Demir, Nahit Gencer, Oktay Arslan. An alternative purification method for human serum paraoxonase 1 and its interactions with anabolic compounds.
Journal of enzyme inhibition and medicinal chemistry.
2016; 31(2):247-52. doi:
10.3109/14756366.2015.1018242. [PMID: 25792501] - Sam Bircher, Marcella L Card, Guangshu Zhai, Yu-Ping Chin, Jerald L Schnoor. Sorption, uptake, and biotransformation of 17β-estradiol, 17α-ethinylestradiol, zeranol, and trenbolone acetate by hybrid poplar.
Environmental toxicology and chemistry.
2015 Dec; 34(12):2906-13. doi:
10.1002/etc.3166. [PMID: 26184466] - Urara Nakamura, Hiroya Kadokawa. The nonsteroidal mycoestrogen zearalenone and its five metabolites suppress LH secretion from the bovine anterior pituitary cells via the estradiol receptor GPR30 in vitro.
Theriogenology.
2015 Nov; 84(8):1342-9. doi:
10.1016/j.theriogenology.2015.07.014. [PMID: 26255852] - Fabiola Pizzo, Francesca Caloni, Luis F Schutz, Morgan L Totty, Leon J Spicer. Individual and combined effects of deoxynivalenol and α-zearalenol on cell proliferation and steroidogenesis of granulosa cells in cattle.
Environmental toxicology and pharmacology.
2015 Nov; 40(3):722-8. doi:
10.1016/j.etap.2015.08.025. [PMID: 26425942] - Constanze Pietsch, Susanne Kersten, Hana Valenta, Sven Dänicke, Carsten Schulz, Patricia Burkhardt-Holm, Ranka Junge. Effects of Dietary Exposure to Zearalenone (ZEN) on Carp (Cyprinus carpio L.).
Toxins.
2015 Aug; 7(9):3465-80. doi:
10.3390/toxins7093465. [PMID: 26343724] - Maxim A Yunin, Pavel S Metalnikov, Alexander A Komarov, Alexander N Panin. Development of a rapid method for the analysis of trenbolone, nortestosterone, and zeranol in bovine liver using liquid chromatography tandem mass spectrometry.
Analytical and bioanalytical chemistry.
2015 Jun; 407(15):4363-71. doi:
10.1007/s00216-014-8346-y. [PMID: 25450054] - M Denli, J C Blandon, M E Guynot, S Salado, J F Pérez. Efficacy of activated diatomaceous clay in reducing the toxicity of zearalenone in rats and piglets.
Journal of animal science.
2015 Feb; 93(2):637-45. doi:
10.2527/jas.2014-7356. [PMID: 26020748] - Johannes Gerding, Benedikt Cramer, Hans-Ulrich Humpf. Determination of mycotoxin exposure in Germany using an LC-MS/MS multibiomarker approach.
Molecular nutrition & food research.
2014 Dec; 58(12):2358-68. doi:
10.1002/mnfr.201400406. [PMID: 25243722] - Sven Dänicke, Christina Keese, Ulrich Meyer, Alexander Starke, Asako Kinoshita, Jürgen Rehage. Zearalenone (ZEN) metabolism and residue concentrations in physiological specimens of dairy cows exposed long-term to ZEN-contaminated diets differing in concentrate feed proportions.
Archives of animal nutrition.
2014 Dec; 68(6):492-506. doi:
10.1080/1745039x.2014.973236. [PMID: 25348458] - Matías Regiart, Sirley V Pereira, Viviana G Spotorno, Franco A Bertolino, Julio Raba. Food safety control of zeranol through voltammetric immunosensing on Au-Pt bimetallic nanoparticle surfaces.
The Analyst.
2014 Sep; 139(18):4702-9. doi:
10.1039/c4an00686k. [PMID: 25057514] - Juan M Echarte, Damián C Fernández, Carlos A Chiacchio, Verónica M Torres Leedham. Comparison of a Validated LC/MS/MS Method with a Validated GC/MS Method for the Analysis of Zeranol and its Related Mycotoxin Residues in Bovine Urine Samples Collected During Argentina's Residue Monitoring Control Program (2005-2012).
Journal of AOAC International.
2014 Sep; 97(5):1470-5. doi:
10.5740/jaoacint.13-283. [PMID: 25903002] - H Belhassen, I Jiménez-Díaz, R Ghali, H Ghorbel, J M Molina-Molina, N Olea, A Hedili. Validation of a UHPLC-MS/MS method for quantification of zearalenone, α-zearalenol, β-zearalenol, α-zearalanol, β-zearalanol and zearalanone in human urine.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2014 Jul; 962(?):68-74. doi:
10.1016/j.jchromb.2014.05.019. [PMID: 24907545] - Hui Zhang, Qi Sun, Teng Liu, Lu Ma, Panpan Zhen, Ke Wang, Lingqiao Lu, Xin Liu, Xin Zhang, Dandan Song, Xiaoyun Zuo, Huirong Liu, Wen Wang. Alleviation of plasma homocysteine level by phytoestrogen α-zearalanol might be related to the reduction of cystathionine β-synthase nitration.
BioMed research international.
2014; 2014(?):143192. doi:
10.1155/2014/143192. [PMID: 24783194] - Dwaipayan Mukherjee, Steven G Royce, Jocelyn A Alexander, Brian Buckley, Sastry S Isukapalli, Elisa V Bandera, Helmut Zarbl, Panos G Georgopoulos. Physiologically-based toxicokinetic modeling of zearalenone and its metabolites: application to the Jersey girl study.
PloS one.
2014; 9(12):e113632. doi:
10.1371/journal.pone.0113632. [PMID: 25474635] - Yilong Dong, Aimei Jiang, Hongju Yang, Huicheng Chen, Yanmei Wang. Phytoestrogen α-zearalanol improves memory impairment and hippocampal neurogenesis in ovariectomized mice.
TheScientificWorldJournal.
2014; 2014(?):862019. doi:
10.1155/2014/862019. [PMID: 25143992] - Gordon S Shephard, Hester-Mari Burger, Lucia Gambacorta, Yun Yun Gong, Rudolf Krska, John P Rheeder, Michele Solfrizzo, Chou Srey, Michael Sulyok, Angelo Visconti, Benedikt Warth, Liana van der Westhuizen. Multiple mycotoxin exposure determined by urinary biomarkers in rural subsistence farmers in the former Transkei, South Africa.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2013 Dec; 62(?):217-25. doi:
10.1016/j.fct.2013.08.040. [PMID: 23985452] - Emmanuel Njumbe Ediage, José Diana Di Mavungu, Suquan Song, Isabelle Sioen, Sarah De Saeger. Multimycotoxin analysis in urines to assess infant exposure: a case study in Cameroon.
Environment international.
2013 Jul; 57-58(?):50-9. doi:
10.1016/j.envint.2013.04.002. [PMID: 23669720] - Yanfei Wang, Wenjuan Tan, Lai K Leung. Zeranol upregulates corticotropin releasing hormone expression in the placental cell line JEG-3.
Toxicology letters.
2013 Jun; 219(3):218-22. doi:
10.1016/j.toxlet.2013.03.016. [PMID: 23538034] - Wei-Jun Kong, Hong-Hong Shen, Xiao-Fei Zhang, Xiao-Li Yang, Feng Qiu, Zhen Ou-yang, Mei-Hua Yang. Analysis of zearalenone and α-zearalenol in 100 foods and medicinal plants determined by HPLC-FLD and positive confirmation by LC-MS-MS.
Journal of the science of food and agriculture.
2013 May; 93(7):1584-90. doi:
10.1002/jsfa.5926. [PMID: 23096594] - Rui Feng, Yong Zhang, Haiqin Yu, Dan Wu, Hongmin Ma, Baocun Zhu, Caixia Xu, He Li, Bin Du, Qin Wei. Nanoporous PtCo-based ultrasensitive enzyme-free immunosensor for zeranol detection.
Biosensors & bioelectronics.
2013 Apr; 42(?):367-72. doi:
10.1016/j.bios.2012.10.031. [PMID: 23211452] - Rentsenkhand Sambuu, Mitsuhiro Takagi, Zhao Namula, Masahiro Nii, Masayasu Taniguchi, Seiich Uno, Emiko Kokushi, Chenga Tshering, Regiane Rodrigues dos Santos, Johanna Fink-Gremmels, Takeshige Otoi. Effects of long-term in vitro exposure of ejaculated boar sperm to zearalenone and α-zearalenol in sperm liquid storage medium.
Animal science journal = Nihon chikusan Gakkaiho.
2013 Jan; 84(1):28-34. doi:
10.1111/j.1740-0929.2012.01033.x. [PMID: 23302079] - Marcella L Card, Jerald L Schnoor, Yu-Ping Chin. Uptake of natural and synthetic estrogens by maize seedlings.
Journal of agricultural and food chemistry.
2012 Aug; 60(34):8264-71. doi:
10.1021/jf3014074. [PMID: 22816790] - Yuan Gao, Meihua Yang, Cheng Peng, Xiaohong Li, Runlan Cai, Yun Qi. Preparation of highly specific anti-zearalenone antibodies by using the cationic protein conjugate and development of an indirect competitive enzyme-linked immunosorbent assay.
The Analyst.
2012 Jan; 137(1):229-36. doi:
10.1039/c1an15487g. [PMID: 22049356] - Yilong Dong, Nan Yang, Yanyong Liu, Qing Li, Pingping Zuo. The neuroprotective effects of phytoestrogen α-zearalanol on β-amyloid-induced toxicity in differentiated PC-12 cells.
European journal of pharmacology.
2011 Nov; 670(2-3):392-8. doi:
10.1016/j.ejphar.2011.09.016. [PMID: 21946104] - Elisa V Bandera, Urmila Chandran, Brian Buckley, Yong Lin, Sastry Isukapalli, Ian Marshall, Melony King, Helmut Zarbl. Urinary mycoestrogens, body size and breast development in New Jersey girls.
The Science of the total environment.
2011 Nov; 409(24):5221-7. doi:
10.1016/j.scitotenv.2011.09.029. [PMID: 21975003] - Michele Solfrizzo, Lucia Gambacorta, Veronica M T Lattanzio, Stephen Powers, Angelo Visconti. Simultaneous LC-MS/MS determination of aflatoxin M1, ochratoxin A, deoxynivalenol, de-epoxydeoxynivalenol, α and β-zearalenols and fumonisin B1 in urine as a multi-biomarker method to assess exposure to mycotoxins.
Analytical and bioanalytical chemistry.
2011 Nov; 401(9):2831-41. doi:
10.1007/s00216-011-5354-z. [PMID: 21892639] - Mario Thevis, Gregor Fusshöller, Wilhelm Schänzer. Zeranol: doping offence or mycotoxin? A case-related study.
Drug testing and analysis.
2011 Nov; 3(11-12):777-83. doi:
10.1002/dta.352. [PMID: 22095651] - C Frizzell, D Ndossi, S Verhaegen, E Dahl, G Eriksen, M Sørlie, E Ropstad, M Muller, C T Elliott, L Connolly. Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis.
Toxicology letters.
2011 Oct; 206(2):210-7. doi:
10.1016/j.toxlet.2011.07.015. [PMID: 21803136] - Zhanhui Wang, Pengjie Luo, Linli Cheng, Suxia Zhang, Jianzhong Shen. Hapten-antibody recognition studies in competitive immunoassay of α-zearalanol analogs by computational chemistry and Pearson Correlation analysis.
Journal of molecular recognition : JMR.
2011 Sep; 24(5):815-23. doi:
10.1002/jmr.1121. [PMID: 21812055] - Pan-pan Zhen, Jin-hong Duan, Qian Zhao, Dan-dan Hou, Hong-xia Wang, Ni Hong, Hui-xian Zhen, Wen Wang. Phytoestrogen α-zearalanol improves vascular function in ovariectomized hyperhomocysteinemic rats.
Atherosclerosis.
2011 Apr; 215(2):309-15. doi:
10.1016/j.atherosclerosis.2010.12.029. [PMID: 21292265] - Weiping Ye, Pingping Xu, Saiyi Zhong, Robert Jen, Walter R Threlfall, Christopher V Frasure, Eric Feng, Hong Li, Shu-Hong Lin, Jie-Yu Liu, Young C Lin. In vitro transformation of MCF-10A cells by sera harvested from heifers two months post-Zeranol implantation.
International journal of oncology.
2011 Apr; 38(4):985-92. doi:
10.3892/ijo.2011.941. [PMID: 21318220] - Zheng Han, Yiping Ren, Hailong Zhou, Lianjun Luan, Zengxuan Cai, Yongjiang Wu. A rapid method for simultaneous determination of zearalenone, α-zearalenol, β-zearalenol, zearalanone, α-zearalanol and β-zearalanol in traditional Chinese medicines by ultra-high-performance liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Feb; 879(5-6):411-20. doi:
10.1016/j.jchromb.2010.12.028. [PMID: 21242113] - Saiyi Zhong, Wei-Ping Ye, Eric Feng, Shu-Hong Lin, Jie-Yu Liu, John Leong, Changwei Ma, Young C Lin. Serum derived from zeranol-implanted ACI rats promotes the growth of human breast cancer cells in vitro.
Anticancer research.
2011 Feb; 31(2):481-6. doi:
NULL. [PMID: 21378327] - S Dänicke, M Beyer, G Breves, H Valenta, H-U Humpf. Effects of oral exposure of pigs to deoxynivalenol (DON) sulfonate (DONS) as the non-toxic derivative of DON on tissue residues of DON and de-epoxy-DON and on DONS blood levels.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2010 Nov; 27(11):1558-65. doi:
10.1080/19440049.2010.501036. [PMID: 20677033] - Mei Dong, Phitsanu Tulayakul, Jun-You Li, Ke-Su Dong, Noboru Manabe, Susumu Kumagai. Metabolic conversion of zearalenone to alpha-zearalenol by goat tissues.
The Journal of veterinary medical science.
2010 Mar; 72(3):307-12. doi:
10.1292/jvms.09-0122. [PMID: 19959886] - S Abid-Essefi, C Bouaziz, E El Golli-Bennour, Z Ouanes, Hassen Bacha. Comparative study of toxic effects of zearalenone and its two major metabolites alpha-zearalenol and beta-zearalenol on cultured human Caco-2 cells.
Journal of biochemical and molecular toxicology.
2009 Jul; 23(4):233-43. doi:
10.1002/jbt.20284. [PMID: 19705349] - Guglielmo Dusi, Eros Bozzoni, Walter Assini, Nadia Tognoli, Mara Gasparini, Enrica Ferretti. Confirmatory method for the determination of resorcylic acid lactones in urine sample using immunoaffinity cleanup and liquid chromatography-tandem mass spectrometry.
Analytica chimica acta.
2009 Apr; 637(1-2):47-54. doi:
10.1016/j.aca.2008.11.047. [PMID: 19286011] - Zouhour Ouanes-Ben Othmen, Emna El Golli, Salwa Abid-Essefi, Hassen Bacha. Cytotoxicity effects induced by Zearalenone metabolites, alpha Zearalenol and beta Zearalenol, on cultured Vero cells.
Toxicology.
2008 Oct; 252(1-3):72-7. doi:
10.1016/j.tox.2008.07.065. [PMID: 18755238] - Giovanni Ranzenigo, Francesca Caloni, Fausto Cremonesi, Pauline Y Aad, Leon J Spicer. Effects of Fusarium mycotoxins on steroid production by porcine granulosa cells.
Animal reproduction science.
2008 Aug; 107(1-2):115-30. doi:
10.1016/j.anireprosci.2007.06.023. [PMID: 17656051] - Francesco Massart, Valentina Meucci, Giuseppe Saggese, Giulio Soldani. High growth rate of girls with precocious puberty exposed to estrogenic mycotoxins.
The Journal of pediatrics.
2008 May; 152(5):690-5, 695.e1. doi:
10.1016/j.jpeds.2007.10.020. [PMID: 18410776] - Yuan Liu, Cun-zhen Zhang, Xiang-yang Yu, Zhi-yong Zhang, Xiao Zhang, Rong-rong Liu, Xian-jin Liu, Zhen-ming Gong. Development and evaluation of immunoassay for zeranol in bovine urine.
Journal of Zhejiang University. Science. B.
2007 Dec; 8(12):900-5. doi:
10.1631/jzus.2007.b0900. [PMID: 18257125] - Jian Ying Yang, Guo Xin Wang, Jia Li Liu, Jing Jing Fan, Sheng Cui. Toxic effects of zearalenone and its derivatives alpha-zearalenol on male reproductive system in mice.
Reproductive toxicology (Elmsford, N.Y.).
2007 Nov; 24(3-4):381-7. doi:
10.1016/j.reprotox.2007.05.009. [PMID: 17628394] - William E Trout, Cory T Herr, Brian T Richert, Wayne L Singleton, Stanley A Haglof, Mark A Diekman. Effects of Zeranol upon luteal maintenance and fetal development in peripubertal gilts.
Animal reproduction science.
2007 Jun; 99(3-4):408-12. doi:
10.1016/j.anireprosci.2006.06.018. [PMID: 16889910] - Niccolo Hartmann, Marianne Erbs, Felix E Wettstein, René P Schwarzenbach, Thomas D Bucheli. Quantification of estrogenic mycotoxins at the ng/L level in aqueous environmental samples using deuterated internal standards.
Journal of chromatography. A.
2007 Jan; 1138(1-2):132-40. doi:
10.1016/j.chroma.2006.10.045. [PMID: 17084850] - H Malekinejad, B Colenbrander, J Fink-Gremmels. Hydroxysteroid dehydrogenases in bovine and porcine granulosa cells convert zearalenone into its hydroxylated metabolites alpha-zearalenol and beta-zearalenol.
Veterinary research communications.
2006 May; 30(4):445-53. doi:
10.1007/s11259-006-3325-1. [PMID: 16502112] - M H Blokland, S S Sterk, R W Stephany, F M Launay, D G Kennedy, L A van Ginkel. Determination of resorcylic acid lactones in biological samples by GC-MS. Discrimination between illegal use and contamination with fusarium toxins.
Analytical and bioanalytical chemistry.
2006 Mar; 384(5):1221-7. doi:
10.1007/s00216-005-0274-4. [PMID: 16416095] - S Dänicke, E Swiech, L Buraczewska, K-H Ueberschär. Kinetics and metabolism of zearalenone in young female pigs.
Journal of animal physiology and animal nutrition.
2005 Aug; 89(7-8):268-76. doi:
10.1111/j.1439-0396.2005.00516.x. [PMID: 15972077] - Naoko Takahashi-Ando, Takeshi Tokai, Hiroshi Hamamoto, Isamu Yamaguchi, Makoto Kimura. Efficient decontamination of zearalenone, the mycotoxin of cereal pathogen, by transgenic yeasts through the expression of a synthetic lactonohydrolase gene.
Applied microbiology and biotechnology.
2005 Jun; 67(6):838-44. doi:
10.1007/s00253-004-1816-y. [PMID: 15630583] - Stefanie Weber, Prisca Leuschner, Peter Kämpfer, Wolfgang Dott, Juliane Hollender. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture.
Applied microbiology and biotechnology.
2005 Apr; 67(1):106-12. doi:
10.1007/s00253-004-1693-4. [PMID: 15290133] - W Zwierzchowski, M Przybyłowicz, K Obremski, L Zielonka, E Skorska-Wyszyńska, M Gajecka, M Polak, E Jakimiuk, B Jana, L Rybarczyk, M Gajecki. Level of zearalenone in blood serum and lesions in ovarian follicles of sexually immature gilts in the course of zearalenone micotoxicosis.
Polish journal of veterinary sciences.
2005; 8(3):209-18. doi:
. [PMID: 16180582] - Hai-Shan Xu, Jinhong Duan, Shunling Dai, Yunqing Wu, Renyu Sun, Jun Ren. Phytoestrogen alpha-zearalanol antagonizes oxidized LDL-induced inhibition of nitric oxide production and stimulation of endothelin-1 release in human umbilical vein endothelial cells.
Endocrine.
2004 Dec; 25(3):235-45. doi:
10.1385/endo:25:3:235. [PMID: 15758251] - Shunling Dai, Jinhong Duan, Yuan Lu, Yihua Zhang, Jinxuan Cheng, Jun Ren, Xiaoyuan Zhao, Yunqing Wu, Yue Yu, Pingping Zuo, Yiyong Wu, Qinsheng Ge. Phytoestrogen alpha-zearalanol inhibits atherogenesis and improves lipid profile in ovariectomized cholesterol-fed rabbits.
Endocrine.
2004 Nov; 25(2):121-9. doi:
10.1385/endo:25:2:121. [PMID: 15711025] - Shunling Dai, Jinhong Duan, Yuan Lu, Jinxuan Cheng, Jun Ren, Wenhui Deng, Yiyong Wu. Alpha-Zearalanol, a phytoestrogen for cardiovascular therapy.
Endocrine.
2004 Nov; 25(2):117-9. doi:
10.1385/endo:25:2:117. [PMID: 15711024] - F M Launay, L Ribeiro, P Alves, V Vozikis, S Tsitsamis, G Alfredsson, S S Sterk, M Blokland, A Iitia, T Lövgren, M Tuomola, A Gordon, D G Kennedy. Prevalence of zeranol, taleranol and Fusarium spp. toxins in urine: implications for the control of zeranol abuse in the European Union.
Food additives and contaminants.
2004 Sep; 21(9):833-9. doi:
10.1080/02652030400002121. [PMID: 15666976] - S Abid-Essefi, Z Ouanes, W Hassen, I Baudrimont, E Creppy, H Bacha. Cytotoxicity, inhibition of DNA and protein syntheses and oxidative damage in cultured cells exposed to zearalenone.
Toxicology in vitro : an international journal published in association with BIBRA.
2004 Aug; 18(4):467-74. doi:
10.1016/j.tiv.2003.12.011. [PMID: 15130604] - Wen Wang, Guang-jin Zhu, Shu-Yu Zu. Effects of 17beta-estradiol and phytoestrogen alpha-zearalanol on tissue factor in plasma of ovariectomized rats and HUVECs.
The Chinese journal of physiology.
2004 Jun; 47(2):67-72. doi:
NULL. [PMID: 15481788] - Suling Liu, Yasuro Sugimoto, Claudio Sorio, Cristina Tecchio, Young C Lin. Function analysis of estrogenically regulated protein tyrosine phosphatase gamma (PTPgamma) in human breast cancer cell line MCF-7.
Oncogene.
2004 Feb; 23(6):1256-62. doi:
10.1038/sj.onc.1207235. [PMID: 14676845] - F M Launay, P B Young, S S Sterk, M H Blokland, D G Kennedy. Confirmatory assay for zeranol, taleranol and the Fusarium spp. toxins in bovine urine using liquid chromatography-tandem mass spectrometry.
Food additives and contaminants.
2004 Jan; 21(1):52-62. doi:
10.1080/02652030310001636930. [PMID: 14744680] - K M Cooper, L Ribeiro, P Alves, V Vozikis, S Tsitsamis, G Alfredsson, T Lövgren, M Tuomola, H Takalo, A Iitia, S S Sterk, M Blokland, D G Kennedy. Interlaboratory ring test of time-resolved fluoroimmunoassays for zeranol and alpha-zearalenol and comparison with zeranol test kits.
Food additives and contaminants.
2003 Sep; 20(9):804-12. doi:
10.1080/0265203031000156097. [PMID: 13129775] - Leslie C Dickson, James D MacNeil, JoAnn Reid, Adrian C E Fesser. Validation of screening method for residues of diethylstilbestrol, dienestrol, hexestrol, and zeranol in bovine urine using immunoaffinity chromatography and gas chromatography/mass spectrometry.
Journal of AOAC International.
2003 Jul; 86(4):631-9. doi:
. [PMID: 14509418] - Kazimierz Pasternak, Małgorzata Kiełczykowska, Małgorzata Sztanke, Andrzej Borzecki. The influence of alpha-zearalenol on magnesium concentration in cellular subfractions of certain tissues of female rats and their progeny.
Magnesium research.
2003 Jun; 16(2):106-10. doi:
NULL. [PMID: 12892380] - L A Narro, M G Thomas, G A Silver, K J Rozeboom, D H Keisler. Body composition, leptin, and the leptin receptor and their relationship to the growth hormone (GH) axis in growing wethers treated with zeranol.
Domestic animal endocrinology.
2003 Apr; 24(3):243-55. doi:
10.1016/s0739-7240(02)00239-4. [PMID: 12642164] - S Dänicke, S Matthes, I Halle, K H Ueberschär, S Döll, H Valenta. Effects of graded levels of Fusarium toxin-contaminated wheat and of a detoxifying agent in broiler diets on performance, nutrient digestibility and blood chemical parameters.
British poultry science.
2003 Mar; 44(1):113-26. doi:
10.1080/0007166031000085300. [PMID: 12737233] - S A Whitehead, M Lacey. Phytoestrogens inhibit aromatase but not 17beta-hydroxysteroid dehydrogenase (HSD) type 1 in human granulosa-luteal cells: evidence for FSH induction of 17beta-HSD.
Human reproduction (Oxford, England).
2003 Mar; 18(3):487-94. doi:
10.1093/humrep/deg125. [PMID: 12615812] - B A Reiling, D D Johnson. Effects of implant regimens (trenbolone acetate-estradiol administered alone or in combination with zeranol) and vitamin D3 on fresh beef color and quality.
Journal of animal science.
2003 Jan; 81(1):135-42. doi:
10.2527/2003.811135x. [PMID: 12597383] - K M Cooper, M Tuomola, S Lahdenperä, T Lövgren, C T Elliott, D G Kennedy. Development and validation of dry reagent time-resolved fluoroimmunoassays for zeranol and alpha-zearalenol to assist in distinguishing zeranol abuse from Fusarium spp. toxin contamination in bovine urine.
Food additives and contaminants.
2002 Dec; 19(12):1130-7. doi:
10.1080/0265203021000012411. [PMID: 12623673] - Martina Kleinova, Peter Zöllner, Hermann Kahlbacher, Werner Hochsteiner, Wolfgang Lindner. Metabolic profiles of the mycotoxin zearalenone and of the growth promoter zeranol in urine, liver, and muscle of heifers.
Journal of agricultural and food chemistry.
2002 Aug; 50(17):4769-76. doi:
10.1021/jf020160p. [PMID: 12166958] - I G Lange, A Daxenberger, H H D Meyer, E Rajpert-De Meyts, N E Skakkebaek, D N R Veeramachaneni. Quantitative assessment of foetal exposure to trenbolone acetate, zeranol and melengestrol acetate, following maternal dosing in rabbits.
Xenobiotica; the fate of foreign compounds in biological systems.
2002 Aug; 32(8):641-51. doi:
10.1080/00498250210143010. [PMID: 12296986] - Xiaoming Fang, Jiahua Chen, Dehua Guo, Guoquan Wang. Detection and identification of zeranol in chicken or rabbit liver by liquid chromatography-electrospray tandem mass spectrometry.
Journal of AOAC International.
2002 Jul; 85(4):841-7. doi:
. [PMID: 12180676] - T W Wilson, D A Neuendorff, A W Lewis, R D Randel. Effect of zeranol or melengestrol acetate (MGA) on testicular and antler development and aggression in farmed fallow bucks.
Journal of animal science.
2002 Jun; 80(6):1433-41. doi:
10.2527/2002.8061433x. [PMID: 12078722] - Peter Zöllner, Justus Jodlbauer, Martina Kleinova, Hermann Kahlbacher, Thomas Kuhn, Werner Hochsteiner, Wolfgang Lindner. Concentration levels of zearalenone and its metabolites in urine, muscle tissue, and liver samples of pigs fed with mycotoxin-contaminated oats.
Journal of agricultural and food chemistry.
2002 Apr; 50(9):2494-501. doi:
10.1021/jf0113631. [PMID: 11958611] - Suling Liu, Samuel K Kulp, Yasuro Sugimoto, Jiahua Jiang, Hsiang-Lin Chang, Young C Lin. Involvement of breast epithelial-stromal interactions in the regulation of protein tyrosine phosphatase-gamma (PTPgamma) mRNA expression by estrogenically active agents.
Breast cancer research and treatment.
2002 Jan; 71(1):21-35. doi:
10.1023/a:1013343718942. [PMID: 11859871]