Enniatin B (BioDeep_00000003923)

   

natural product


代谢物信息卡片


Enniatin B

化学式: C33H57N3O9 (639.4094592)
中文名称: 恩镰孢菌素B
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 97.87%

分子结构信息

SMILES: CC(C)C1C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
InChI: InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25+,26+,27+/m0/s1

描述信息

An enniatin obtained from formal cyclocondensation of three N-[(2R)-2-hydroxy-3-methylbutanoyl]-N-methyl-L-valine units.
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
CONFIDENCE Reference Standard (Level 1)

同义名列表

2 个代谢物同义名

Enniatin B; NSC692895



数据库引用编号

22 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)

14 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

  • Hongping Shen, Yili Cai, Keqi Zhu, Dong Wang, Rui Yu, Xueqin Chen. Enniatin B1 induces damage to Leydig cells via inhibition of the Nrf2/HO-1 and JAK/STAT3 signaling pathways. Ecotoxicology and environmental safety. 2024 Mar; 273(?):116116. doi: 10.1016/j.ecoenv.2024.116116. [PMID: 38387140]
  • Milos Sevarika, Giovanni Beccari, Francesco Tini, Luisa Ederli, Ilaria Bellezza, Lorenzo Covarelli, Roberto Romani. Effect of the mycotoxins enniatin B and deoxynivalenol on the wheat aphid Sitobion avenae and on the predatory lacewing Chrysoperla carnea. Pest management science. 2024 Feb; ?(?):. doi: 10.1002/ps.8005. [PMID: 38312069]
  • Irene Valenti, Francesco Tini, Milos Sevarika, Alessandro Agazzi, Giovanni Beccari, Ilaria Bellezza, Luisa Ederli, Silvia Grottelli, Matias Pasquali, Roberto Romani, Marco Saracchi, Lorenzo Covarelli. Impact of Enniatin and Deoxynivalenol Co-Occurrence on Plant, Microbial, Insect, Animal and Human Systems: Current Knowledge and Future Perspectives. Toxins. 2023 04; 15(4):. doi: 10.3390/toxins15040271. [PMID: 37104209]
  • Yasmine Chakroun, Youssef Snoussi, Mohamed M Chehimi, Manef Abderrabba, Jean-Michel Savoie, Souheib Oueslati. Encapsulation of Ammoides pusila Essential Oil into Mesoporous Silica Particles for the Enhancement of Their Activity against Fusarium avenaceum and Its Enniatins Production. Molecules (Basel, Switzerland). 2023 Apr; 28(7):. doi: 10.3390/molecules28073194. [PMID: 37049956]
  • M H G Berntssen, P G Fjeldal, P J Gavaia, V Laizé, K Hamre, C E Donald, J V Jakobsen, Å Omdal, S Søderstrøm, K K Lie. Dietary beauvericin and enniatin B exposure cause different adverse health effects in farmed Atlantic salmon. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Feb; 174(?):113648. doi: 10.1016/j.fct.2023.113648. [PMID: 36736876]
  • Sofie Søderstrøm, Liv Søfteland, Veronika Sele, Anne-Katrine Lundebye, Marc Hg Berntssen, Kai K Lie. Enniatin B and beauvericin affect intestinal cell function and hematological processes in Atlantic salmon (Salmo salar) after acute exposure. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Feb; 172(?):113557. doi: 10.1016/j.fct.2022.113557. [PMID: 36526092]
  • Manisha Bhateria, Kajal Karsauliya, Ashish Kumar Sonker, C Yahavi, Sheelendra Pratap Singh. Cytochrome P450 isoforms contribution, plasma protein binding, toxicokinetics of enniatin A in rats and in vivo clearance prediction in humans. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Jun; 164(?):112988. doi: 10.1016/j.fct.2022.112988. [PMID: 35398446]
  • Sofie Søderstrøm, Kai K Lie, Anne-Katrine Lundebye, Liv Søfteland. Beauvericin (BEA) and enniatin B (ENNB)-induced impairment of mitochondria and lysosomes - Potential sources of intracellular reactive iron triggering ferroptosis in Atlantic salmon primary hepatocytes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Mar; 161(?):112819. doi: 10.1016/j.fct.2022.112819. [PMID: 35038498]
  • Barbara Novak, Amanda Lopes Hasuda, Mahdi Ghanbari, Viviane Mayumi Maruo, Ana Paula F R L Bracarense, Manon Neves, Caroline Emsenhuber, Silvia Wein, Isabelle P Oswald, Philippe Pinton, Dian Schatzmayr. Effects of Fusarium metabolites beauvericin and enniatins alone or in mixture with deoxynivalenol on weaning piglets. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Dec; 158(?):112719. doi: 10.1016/j.fct.2021.112719. [PMID: 34843867]
  • Luisa Ederli, Giovanni Beccari, Francesco Tini, Irene Bergamini, Ilaria Bellezza, Roberto Romani, Lorenzo Covarelli. Enniatin B and Deoxynivalenol Activity on Bread Wheat and on Fusarium Species Development. Toxins. 2021 10; 13(10):. doi: 10.3390/toxins13100728. [PMID: 34679021]
  • M Alonso-Garrido, M Frangiamone, G Font, A Cimbalo, L Manyes. In vitro blood brain barrier exposure to mycotoxins and carotenoids pumpkin extract alters mitochondrial gene expression and oxidative stress. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Jul; 153(?):112261. doi: 10.1016/j.fct.2021.112261. [PMID: 34015425]
  • Charlotte Gautier, Laetitia Pinson-Gadais, Marie-Noelle Verdal-Bonnin, Christine Ducos, Judith Tremblay, Sylvain Chéreau, Vessela Atanasova, Florence Richard-Forget. Investigating the Efficiency of Hydroxycinnamic Acids to Inhibit the Production of Enniatins by Fusarium avenaceum and Modulate the Expression of Enniatins Biosynthetic Genes. Toxins. 2020 11; 12(12):. doi: 10.3390/toxins12120735. [PMID: 33255199]
  • Yelko Rodríguez-Carrasco, Alfonso Narváez, Luana Izzo, Anna Gaspari, Giulia Graziani, Alberto Ritieni. Biomonitoring of Enniatin B1 and Its Phase I Metabolites in Human Urine: First Large-Scale Study. Toxins. 2020 06; 12(6):. doi: 10.3390/toxins12060415. [PMID: 32580411]
  • Noelia Pallarés, Laura Righetti, Silvia Generotti, Daniele Cavanna, Emilia Ferrer, Chiara Dall'Asta, Michele Suman. Investigating the in vitro catabolic fate of Enniatin B in a human gastrointestinal and colonic model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Mar; 137(?):111166. doi: 10.1016/j.fct.2020.111166. [PMID: 32001315]
  • Natalia Arroyo-Manzanares, Ahmed M Hamed, Ana M García-Campaña, Laura Gámiz-Gracia. Plant-based milks: unexplored source of emerging mycotoxins. A proposal for the control of enniatins and beauvericin using UHPLC-MS/MS. Food additives & contaminants. Part B, Surveillance. 2019 Dec; 12(4):296-302. doi: 10.1080/19393210.2019.1663276. [PMID: 31791225]
  • Ł Stępień, K Gromadzka, J Chełkowski, A Basińska-Barczak, J Lalak-Kańczugowska. Diversity and mycotoxin production by Fusarium temperatum and Fusarium subglutinans as causal agents of pre-harvest Fusarium maize ear rot in Poland. Journal of applied genetics. 2019 Feb; 60(1):113-121. doi: 10.1007/s13353-018-0478-x. [PMID: 30430379]
  • Yelko Rodríguez-Carrasco, Luana Izzo, Anna Gaspari, Giulia Graziani, Jordi Mañes, Alberto Ritieni. Urinary levels of enniatin B and its phase I metabolites: First human pilot biomonitoring study. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Aug; 118(?):454-459. doi: 10.1016/j.fct.2018.05.052. [PMID: 29802944]
  • Minely Cerón-Bustamante, Todd J Ward, Amy Kelly, Martha M Vaughan, Susan P McCormick, Christina Cowger, Santos G Leyva-Mir, Héctor E Villaseñor-Mir, Victoria Ayala-Escobar, Cristian Nava-Díaz. Regional differences in the composition of Fusarium Head Blight pathogens and mycotoxins associated with wheat in Mexico. International journal of food microbiology. 2018 May; 273(?):11-19. doi: 10.1016/j.ijfoodmicro.2018.03.003. [PMID: 29554557]
  • Susana Viegas, Bernd Osteresch, Ana Almeida, Benedikt Cramer, Hans-Ulrich Humpf, Carla Viegas. Enniatin B and ochratoxin A in the blood serum of workers from the waste management setting. Mycotoxin research. 2018 May; 34(2):85-90. doi: 10.1007/s12550-017-0302-1. [PMID: 29185179]
  • Sophie Fraeyman, Siska Croubels, Mathias Devreese, Richard Ducatelle, Michael Rychlik, Gunther Antonissen. Chronic Dietary Intake of Enniatin B in Broiler Chickens Has Low Impact on Intestinal Morphometry and Hepatic Histology, and Shows Limited Transfer to Liver Tissue. Toxins. 2018 01; 10(1):. doi: 10.3390/toxins10010045. [PMID: 29346316]
  • Lada Ivanova, Silvio Uhlig, Mathias Devreese, Siska Croubels, Christiane Kruse Fæste. Biotransformation of the mycotoxin enniatin B1 in pigs: A comparative in vitro and in vivo approach. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Jul; 105(?):506-517. doi: 10.1016/j.fct.2017.04.041. [PMID: 28472676]
  • Lien Taevernier, Nathalie Bracke, Lieselotte Veryser, Evelien Wynendaele, Bert Gevaert, Kathelijne Peremans, Bart De Spiegeleer. Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins. Toxicology letters. 2016 Sep; 258(?):175-184. doi: 10.1016/j.toxlet.2016.06.1741. [PMID: 27349679]
  • Martina Jonsson, Marika Jestoi, Minna Anthoni, Annikki Welling, Iida Loivamaa, Ville Hallikainen, Matti Kankainen, Erik Lysøe, Pertti Koivisto, Kimmo Peltonen. Fusarium mycotoxin enniatin B: Cytotoxic effects and changes in gene expression profile. Toxicology in vitro : an international journal published in association with BIBRA. 2016 Aug; 34(?):309-320. doi: 10.1016/j.tiv.2016.04.017. [PMID: 27163883]
  • Pierre Hellin, Géraldine Dedeurwaerder, Maxime Duvivier, Jonathan Scauflaire, Bart Huybrechts, Alfons Callebaut, Françoise Munaut, Anne Legrève. Relationship between Fusarium spp. diversity and mycotoxin contents of mature grains in southern Belgium. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2016 Jul; 33(7):1228-40. doi: 10.1080/19440049.2016.1185900. [PMID: 27181458]
  • Veli Hietaniemi, Sari Rämö, Tapani Yli-Mattila, Marika Jestoi, Sari Peltonen, Mirja Kartio, Elina Sieviläinen, Tauno Koivisto, Päivi Parikka. Updated survey of Fusarium species and toxins in Finnish cereal grains. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2016 May; 33(5):831-48. doi: 10.1080/19440049.2016.1162112. [PMID: 27002810]
  • Yelko Rodríguez-Carrasco, Daniela Heilos, Lennart Richter, Roderich D Süssmuth, Petra Heffeter, Michael Sulyok, Lukas Kenner, Walter Berger, Rita Dornetshuber-Fleiss. Mouse tissue distribution and persistence of the food-born fusariotoxins Enniatin B and Beauvericin. Toxicology letters. 2016 Apr; 247(?):35-44. doi: 10.1016/j.toxlet.2016.02.008. [PMID: 26892719]
  • Ana Belén Serrano, Anna Laura Capriotti, Chiara Cavaliere, Susy Piovesana, Roberto Samperi, Salvatore Ventura, Aldo Laganà. Development of a Rapid LC-MS/MS Method for the Determination of Emerging Fusarium mycotoxins Enniatins and Beauvericin in Human Biological Fluids. Toxins. 2015 Sep; 7(9):3554-71. doi: 10.3390/toxins7093554. [PMID: 26371043]
  • Zdenka Veprikova, Milena Zachariasova, Zbynek Dzuman, Alena Zachariasova, Marie Fenclova, Petra Slavikova, Marta Vaclavikova, Katerina Mastovska, Daniel Hengst, Jana Hajslova. Mycotoxins in Plant-Based Dietary Supplements: Hidden Health Risk for Consumers. Journal of agricultural and food chemistry. 2015 Jul; 63(29):6633-43. doi: 10.1021/acs.jafc.5b02105. [PMID: 26168136]
  • Laura Escrivá, Guillermina Font, Lara Manyes. Quantitation of enniatins in biological samples of Wistar rats after oral administration by LC-MS/MS. Toxicology mechanisms and methods. 2015; 25(7):552-8. doi: NULL. [PMID: 26228087]
  • Cormac McElhinney, Pádraig O'Kiely, Chris Elliott, Martin Danaher. Development and validation of an UHPLC-MS/MS method for the determination of mycotoxins in grass silages. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(12):2101-12. doi: 10.1080/19440049.2015.1094830. [PMID: 26374621]
  • Cristina Juan, Lara Manyes, Guillermina Font, Ana Juan-García. Evaluation of immunologic effect of Enniatin A and quantitative determination in feces, urine and serum on treated Wistar rats. Toxicon : official journal of the International Society on Toxinology. 2014 Sep; 87(?):45-53. doi: 10.1016/j.toxicon.2014.05.005. [PMID: 24857789]
  • Lara Manyes, Laura Escrivá, Ana Belén Serrano, Yelko Rodríguez-Carrasco, Josefa Tolosa, Giuseppe Meca, Guillermina Font. A preliminary study in Wistar rats with enniatin A contaminated feed. Toxicology mechanisms and methods. 2014 Mar; 24(3):179-90. doi: 10.3109/15376516.2013.876135. [PMID: 24329503]
  • Ling Hu, Michael Rychlik. Occurrence of enniatins and beauvericin in 60 Chinese medicinal herbs. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2014; 31(7):1240-5. doi: 10.1080/19440049.2014.913813. [PMID: 24720681]
  • A Prosperini, A Juan-García, G Font, M J Ruiz. Reactive oxygen species involvement in apoptosis and mitochondrial damage in Caco-2 cells induced by enniatins A, A₁, B and B₁. Toxicology letters. 2013 Sep; 222(1):36-44. doi: 10.1016/j.toxlet.2013.07.009. [PMID: 23867914]
  • Mathias Devreese, Siegrid De Baere, Patrick De Backer, Siska Croubels. Quantitative determination of the Fusarium mycotoxins beauvericin, enniatin A, A1, B and B1 in pig plasma using high performance liquid chromatography-tandem mass spectrometry. Talanta. 2013 Mar; 106(?):212-9. doi: 10.1016/j.talanta.2012.11.068. [PMID: 23598119]
  • Lukasz Stępień, Agnieszka Waśkiewicz. Sequence divergence of the enniatin synthase gene in relation to production of beauvericin and enniatins in Fusarium species. Toxins. 2013 Mar; 5(3):537-55. doi: 10.3390/toxins5030537. [PMID: 23486233]
  • A Gammelsrud, A Solhaug, B Dendelé, W J Sandberg, L Ivanova, A Kocbach Bølling, D Lagadic-Gossmann, M Refsnes, R Becher, G Eriksen, J A Holme. Enniatin B-induced cell death and inflammatory responses in RAW 267.4 murine macrophages. Toxicology and applied pharmacology. 2012 May; 261(1):74-87. doi: 10.1016/j.taap.2012.03.014. [PMID: 22483798]
  • Diana C Tan, Gavin R Flematti, Emilio L Ghisalberti, Krishnapillai Sivasithamparam, Sukumar Chakraborty, Friday Obanor, Kithsiri Jayasena, Martin J Barbetti. Mycotoxins produced by Fusarium spp. associated with Fusarium head blight of wheat in Western Australia. Mycotoxin research. 2012 May; 28(2):89-96. doi: 10.1007/s12550-011-0122-7. [PMID: 23606046]
  • Łukasz Stępień, Karolina Gromadzka, Jerzy Chełkowski. Polymorphism of mycotoxin biosynthetic genes among Fusarium equiseti isolates from Italy and Poland. Journal of applied genetics. 2012 May; 53(2):227-36. doi: 10.1007/s13353-012-0085-1. [PMID: 22354659]
  • Daniela S Christ, Ruben Gödecke, Andreas von Tiedemann, Mark Varrelmann. Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet. Phytopathology. 2011 Nov; 101(11):1338-45. doi: 10.1094/phyto-01-11-0003. [PMID: 21635142]
  • Daniela S Christ, Bernward Märländer, Mark Varrelmann. Characterization and mycotoxigenic potential of Fusarium species in freshly harvested and stored sugar beet in Europe. Phytopathology. 2011 Nov; 101(11):1330-7. doi: 10.1094/phyto-01-11-0002. [PMID: 21770776]
  • Diana C Tan, Gavin R Flematti, Emilio L Ghisalberti, Krishnapillai Sivasithamparam, Martin J Barbetti. Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana). Toxicon : official journal of the International Society on Toxinology. 2011 Apr; 57(5):817-25. doi: 10.1016/j.toxicon.2011.02.019. [PMID: 21352844]
  • Anton A Tonshin, Vera V Teplova, Maria A Andersson, Mirja S Salkinoja-Salonen. The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis. Toxicology. 2010 Sep; 276(1):49-57. doi: 10.1016/j.tox.2010.07.001. [PMID: 20621153]
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  • Irena Ivnitski-Steele, Ann R Holmes, Erwin Lamping, Brian C Monk, Richard D Cannon, Larry A Sklar. Identification of Nile red as a fluorescent substrate of the Candida albicans ATP-binding cassette transporters Cdr1p and Cdr2p and the major facilitator superfamily transporter Mdr1p. Analytical biochemistry. 2009 Nov; 394(1):87-91. doi: 10.1016/j.ab.2009.07.001. [PMID: 19577533]
  • T Kulik, M Jestoi. Quantification of Fusarium poae DNA and associated mycotoxins in asymptomatically contaminated wheat. International journal of food microbiology. 2009 Apr; 130(3):233-7. doi: 10.1016/j.ijfoodmicro.2009.01.036. [PMID: 19237220]
  • Jens Laurids Sørensen, Richard Kerry Phipps, Kristian Fog Nielsen, Hans-Josef Schroers, Jana Frank, Ulf Thrane. Analysis of Fusarium avenaceum metabolites produced during wet apple core rot. Journal of agricultural and food chemistry. 2009 Feb; 57(4):1632-9. doi: 10.1021/jf802926u. [PMID: 19170495]
  • A Moretti, G Mulè, A Ritieni, A Logrieco. Further data on the production of beauvericin, enniatins and fusaproliferin and toxicity to Artemia salina by Fusarium species of Gibberella fujikuroi species complex. International journal of food microbiology. 2007 Sep; 118(2):158-63. doi: 10.1016/j.ijfoodmicro.2007.07.004. [PMID: 17706820]
  • Tomasz Kulik, Agnieszka Pszczółkowska, Gabriel Fordoński, Jacek Olszewski. PCR approach based on the esyn1 gene for the detection of potential enniatin-producing Fusarium species. International journal of food microbiology. 2007 May; 116(3):319-24. doi: 10.1016/j.ijfoodmicro.2007.02.003. [PMID: 17391792]
  • Silvio Uhlig, Arno C Gutleb, Ulf Thrane, Arne Flåøyen. Identification of cytotoxic principles from Fusarium avenaceum using bioassay-guided fractionation. Toxicon : official journal of the International Society on Toxinology. 2005 Aug; 46(2):150-9. doi: 10.1016/j.toxicon.2005.03.005. [PMID: 15946720]
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  • A Logrieco, A Rizzo, R Ferracane, A Ritieni. Occurrence of beauvericin and enniatins in wheat affected by Fusarium avenaceum head blight. Applied and environmental microbiology. 2002 Jan; 68(1):82-5. doi: 10.1128/aem.68.1.82-85.2002. [PMID: 11772612]
  • M Herrmann, R Zocher, A Haese. Effect of disruption of the enniatin synthetase gene on the virulence of Fusarium avenaceum. Molecular plant-microbe interactions : MPMI. 1996 May; 9(4):226-32. doi: 10.1094/mpmi-9-0226. [PMID: 8634475]