alpha-Zearalenol (BioDeep_00000003886)

 

Secondary id: BioDeep_00000418824

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one

化学式: C18H24O5 (320.1624)
中文名称: ALPHA-玉米赤霉烯醇, α-玉米赤霉烯醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 29.97%

分子结构信息

SMILES: CC1CCCC(CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1)O
InChI: InChI=1S/C18H24O5/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/h3,7,10-12,14,19-21H,2,4-6,8-9H2,1H3

描述信息

Alpha-zearlenol is a nonsteroidal estrogen or mycoestrogen found in fungi belonging to the Fusarium genus including F. graminearum, F. culmorum, F. crookwellense, etc (PMID: 22095651), As a mycotoxin, alpha-zearalenol is a widely distributed compound that contaminates many crops, grains, and other commodities (PMID: 30830360). Alpha-zearalenol, is also a major hepatic metabolite of zearalenone (another mycotoxin). Zearalenone has two metabolites, alpha and beta zearalenol which are produced in the liver by 3α-hydroxisteroid dehydrogenase and 3β-hydroxisteroid dehydrogenase (PMID: 30830360). Like Alpha-zearlenol, zearalenone or F-2 mycotoxin is produced by certain Fusarium species. It causes infertility, abortion and other breeding problems in swine. Alpha-zearlenol is also produced synthetically and sold as Zeranol, which is used as an anabolic agent for cattle. Alpha-zearlenol exhibits strong growth-promoting properties, but its sale is restricted in Europe (PMID: 22095651). Alpha-zearalenol has three to four times the biological activity of zearalenone. Alpha-zearlenol contains a lactone ring in its structure and is structurally analogous to estrogen, thus it can bind to estrogen receptors, and causes hepatotoxic, hematotoxic, immunotoxic, genotoxic, teratogenic and carcinogenic effects on different animal species (PMID: 17045381).

同义名列表

15 个代谢物同义名

(3R,7R,11E)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one; (3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one; 3,4,5,6,7,8,9,10-Octahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one; alpha-Zearalenol, (cis)-isomer; beta-trans-Zearalenol; (-)-beta-Zearalenol; alpha-Zearalenol; trans-Zearalenol; alfa-Zearalenol; beta-zearalenol; a-Zearalenol; α-Zearalenol; Zearalenol; Zeranol; alpha-Zearalenol



数据库引用编号

20 个数据库交叉引用编号

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)

7 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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 AKT1, ALB, BCL2, CASP3, CAT, ESR1, FABP1, GPER1, NOS3, TFPT
Peripheral membrane protein 3 CYP11A1, CYP1B1, ESR1
Endoplasmic reticulum membrane 5 BCL2, CYP19A1, CYP1B1, DHRS9, GPER1
Mitochondrion membrane 2 CYP11A1, GPER1
Nucleus 10 AKT1, ALB, BCL2, CASP3, ESR1, FABP1, GPER1, NOS3, PCNA, TFPT
cytosol 9 AKT1, ALB, BCL2, CASP3, CAT, ESR1, FABP1, GPER1, NOS3
dendrite 1 GPER1
mitochondrial membrane 1 GPER1
nuclear body 1 PCNA
trans-Golgi network 1 GPER1
centrosome 2 ALB, PCNA
nucleoplasm 9 AKT1, ATP2B1, CASP3, ESR1, FABP1, GPER1, NOS3, PCNA, TFPT
Cell membrane 4 AKT1, ATP2B1, ESR1, TNF
Cytoplasmic side 1 ESR1
lamellipodium 1 AKT1
Cell projection, axon 1 GPER1
Multi-pass membrane protein 3 ATP2B1, CYP19A1, GPER1
Golgi apparatus membrane 1 GPER1
Synapse 1 ATP2B1
cell cortex 1 AKT1
cell surface 1 TNF
dendritic shaft 1 GPER1
glutamatergic synapse 3 AKT1, ATP2B1, CASP3
Golgi apparatus 4 ALB, ESR1, GPER1, NOS3
Golgi membrane 2 GPER1, NOS3
mitochondrial inner membrane 1 CYP11A1
neuronal cell body 2 CASP3, TNF
postsynapse 1 AKT1
presynaptic membrane 2 ATP2B1, GPER1
plasma membrane 6 AKT1, ATP2B1, ESR1, GPER1, NOS3, TNF
presynaptic active zone 1 GPER1
synaptic vesicle membrane 1 ATP2B1
Membrane 9 AKT1, ATP2B1, BCL2, CAT, CYP11A1, CYP19A1, CYP1B1, ESR1, GPER1
axon 1 GPER1
basolateral plasma membrane 1 ATP2B1
caveola 1 NOS3
extracellular exosome 5 ALB, ATP2B1, CAT, FABP1, PCNA
endoplasmic reticulum 4 ALB, BCL2, CYP19A1, GPER1
extracellular space 5 ALB, CXCL8, IGF1, IL2, TNF
perinuclear region of cytoplasm 2 GPER1, NOS3
mitochondrion 4 BCL2, CAT, CYP11A1, CYP1B1
protein-containing complex 6 AKT1, ALB, BCL2, CAT, ESR1, FABP1
intracellular membrane-bounded organelle 5 ATP2B1, CAT, CYP1B1, DHRS9, GPER1
Microsome membrane 3 CYP19A1, CYP1B1, DHRS9
postsynaptic density 2 CASP3, GPER1
Secreted 4 ALB, CXCL8, IGF1, IL2
extracellular region 6 ALB, CAT, CXCL8, IGF1, IL2, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
hippocampal mossy fiber to CA3 synapse 1 GPER1
mitochondrial matrix 2 CAT, CYP11A1
anchoring junction 1 ALB
transcription regulator complex 1 ESR1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
microtubule cytoskeleton 1 AKT1
nucleolus 1 GPER1
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 GPER1
cell-cell junction 1 AKT1
recycling endosome 2 GPER1, TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Mitochondrion inner membrane 1 CYP11A1
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
spindle 1 AKT1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, FABP1
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
lateral plasma membrane 1 ATP2B1
ciliary basal body 2 AKT1, ALB
chromatin 2 ESR1, PCNA
cell projection 1 ATP2B1
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
centriole 1 ALB
spindle pole 1 ALB
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
actin filament 1 TFPT
blood microparticle 1 ALB
Basolateral cell membrane 1 ATP2B1
nuclear envelope 1 GPER1
Cytoplasmic vesicle membrane 1 GPER1
Cell projection, dendrite 1 GPER1
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
euchromatin 1 ESR1
Presynaptic cell membrane 1 ATP2B1
replication fork 1 PCNA
myelin sheath 1 BCL2
exocytic vesicle 1 IGF1
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 ALB
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 2 ALB, IGF1
axon terminus 1 GPER1
endocytic vesicle membrane 1 NOS3
immunological synapse 1 ATP2B1
nuclear lamina 1 PCNA
[Isoform 1]: Nucleus 1 ESR1
death-inducing signaling complex 1 CASP3
keratin filament 1 GPER1
dendritic spine head 1 GPER1
Cell projection, dendritic spine membrane 1 GPER1
dendritic spine membrane 1 GPER1
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
Ino80 complex 1 TFPT
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
alphav-beta3 integrin-IGF-1-IGF1R complex 1 IGF1
insulin-like growth factor binding protein complex 1 IGF1
insulin-like growth factor ternary complex 1 IGF1
apical cortex 1 FABP1
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • Jiao Tian, Jiaoyang Luo, Jiaan Qin, Yudan Wang, Xinqi Sun, Jing Zhang, Tongwei Ke, Mengyue Guo, Haonan Ruan, Fang An, Meihua Yang. Preparation of a broad-specificity antibody against zearalenone and its primary analogues and development of immunoassay of Coicis Semen and related products. Journal of food science. 2023 May; ?(?):. doi: 10.1111/1750-3841.16600. [PMID: 37195191]
  • Neda Alvarez-Ortega, Karina Caballero-Gallardo, Cristina Juan, Ana Juan-Garcia, Jesus Olivero-Verbel. Cytoprotective, Antiproliferative, and Anti-Oxidant Potential of the Hydroethanolic Extract of Fridericia chica Leaves on Human Cancer Cell Lines Exposed to α- and β-Zearalenol. Toxins. 2023 Jan; 15(1):. doi: 10.3390/toxins15010036. [PMID: 36668856]
  • Qian Lu, Ming Sui, Ya-Wen Luo, Jiao-Yang Luo, Mei-Hua Yang. Further insight into the potential toxicity of zearalenone-14-glucoside based on toxicokinetics, tissue distribution, transformation, and excretion in rats. Ecotoxicology and environmental safety. 2022 Nov; 246(?):114184. doi: 10.1016/j.ecoenv.2022.114184. [PMID: 36244169]
  • 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]
  • 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]
  • 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]
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  • 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]
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  • 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]
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