Alternariol (BioDeep_00000399713)

Main id: BioDeep_00000014694

 

natural product


代谢物信息卡片


Alternariol 3,4,5-Trihydroxy-6-methyl-dibenzo[a]pyrone

化学式: C14H10O5 (258.052821)
中文名称: 交链孢酚
谱图信息: 最多检出来源 Homo sapiens(natural_products) 13.95%

分子结构信息

SMILES: c1c(cc2c(c1C)c1c(c(=O)o2)c(cc(c1)O)O)O
InChI: InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

描述信息

A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide.
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002800 - Cholinesterase Inhibitors
D004791 - Enzyme Inhibitors
CONFIDENCE Reference Standard (Level 1)

同义名列表

4 个代谢物同义名

Alternariol 3,4,5-Trihydroxy-6-methyl-dibenzo[a]pyrone; 3,4,5-Trihydroxy-6-methyl-dibenzo[a]pyrone; Alternariol; Alternariol_120108



数据库引用编号

14 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)

9 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

  • Ruiqi Yang, Liping Zhao, Fengchao Wang, Jin Chen, Xiao Ma, Yunxia Luan, Weijun Kong. High-throughput extraction and automatic purification of alternariol from edible and medicinal herbs based on aptamer-functionalized magnetic nanoparticles. Journal of separation science. 2024 Mar; 47(5):e2300870. doi: 10.1002/jssc.202300870. [PMID: 38471979]
  • Luis G Addante-Moya, Antonio Abad-Fuentes, Consuelo Agulló, Antonio Abad-Somovilla, Josep V Mercader. Sensitive and selective alternariol analysis by a newly developed monoclonal antibody-based immunoassay. Talanta. 2024 Jan; 267(?):125263. doi: 10.1016/j.talanta.2023.125263. [PMID: 37816292]
  • Octavian Augustin Mihalache, Laura Carbonell-Rozas, Sara Cutroneo, Chiara Dall'Asta. Multi-mycotoxin determination in plant-based meat alternatives and exposure assessment. Food research international (Ottawa, Ont.). 2023 06; 168(?):112766. doi: 10.1016/j.foodres.2023.112766. [PMID: 37120216]
  • Asmaa Mahana, Hala M Hammoda, Mona M G Saad, Mohamed M Radwan, Mahmoud A ElSohly, Doaa A Ghareeb, Fathallah M Harraz, Eman Shawky. Bio-guided isolation of potential anti-inflammatory constituents of some endophytes isolated from the leaves of ground cherry (Physalis pruinosa L.) via ex-vivo and in-silico studies. BMC complementary medicine and therapies. 2023 Apr; 23(1):103. doi: 10.1186/s12906-023-03934-9. [PMID: 37013553]
  • Aleksandra Steglińska, Michael Sulyok, Regina Janas, Mieczysław Grzesik, Wiktoria Liszkowska, Dorota Kręgiel, Beata Gutarowska. Metabolite Formation by Fungal Pathogens of Potatoes (Solanum tuberosum L.) in the Presence of Bioprotective Agents. International journal of environmental research and public health. 2023 Mar; 20(6):. doi: 10.3390/ijerph20065221. [PMID: 36982130]
  • Yi Lv, Ying Wang. Chemical constituents from Oldenlandia diffusa and their cytotoxic effects on human cancer cell lines. Natural product research. 2023 Feb; 37(3):397-403. doi: 10.1080/14786419.2021.1974434. [PMID: 34933627]
  • Z A Chalyy, M G Kiseleva, I B Sedova, V A Tutelyan. [Mycotoxins in spices consumed in Russia]. Voprosy pitaniia. 2023; 92(2):26-34. doi: 10.33029/0042-8833-2023-92-2-26-34. [PMID: 37346017]
  • Nikola Puvača, Giuseppina Avantaggiato, Jordan Merkuri, Gorica Vuković, Vojislava Bursić, Magdalena Cara. Occurrence and Determination of Alternaria Mycotoxins Alternariol, Alternariol Monomethyl Ether, and Tentoxin in Wheat Grains by QuEChERS Method. Toxins. 2022 11; 14(11):. doi: 10.3390/toxins14110791. [PMID: 36422965]
  • Valerie Isabella Charlotte Rebhahn, Endre Kiss, Doris Marko, Giorgia Del Favero. Foodborne compounds that alter plasma membrane architecture can modify the response of intestinal cells to shear stress in vitro. Toxicology and applied pharmacology. 2022 07; 446(?):116034. doi: 10.1016/j.taap.2022.116034. [PMID: 35461954]
  • Jiahe Fan, Shiwei Sun, Chaoyi Lv, Zhizhou Li, Mengru Guo, Yichen Yin, Hui Wang, Wei Wang. Discovery of mycotoxin alternariol as a potential lead compound targeting xanthine oxidase. Chemico-biological interactions. 2022 Jun; 360(?):109948. doi: 10.1016/j.cbi.2022.109948. [PMID: 35430257]
  • I B Sedova, M G Kiseleva, Z A Chalyy, N R Efimochkina, V A Tutelyan. [Mycotoxins contamination of cocoa products and carob marketed in the Russian Federation]. Voprosy pitaniia. 2022; 91(5):65-77. doi: 10.33029/0042-8833-2022-91-5-65-77. [PMID: 36394930]
  • Husam Ibrahem Aroud, Bianca May, Helmut Dietrich, Ralf Schweiggert, Sabine Kemmlein. Influence of processing steps on the fate of ochratoxin A, patulin, and alternariol during production of cloudy and clear apple juices. Mycotoxin research. 2021 Nov; 37(4):341-354. doi: 10.1007/s12550-021-00443-x. [PMID: 34693499]
  • Agnieszka Tkaczyk, Piotr Jedziniak. Development of a multi-mycotoxin LC-MS/MS method for the determination of biomarkers in pig urine. Mycotoxin research. 2021 May; 37(2):169-181. doi: 10.1007/s12550-021-00428-w. [PMID: 33772455]
  • Dongmei Jiang, Dizhe Wei, Hongtao Li, Liuqing Wang, Nan Jiang, Yunchao Li, Meng Wang. Natural occurrence of Alternaria mycotoxins in wheat and potential of reducing associated risks using magnolol. Journal of the science of food and agriculture. 2021 May; 101(7):3071-3077. doi: 10.1002/jsfa.10901. [PMID: 33124688]
  • Megha Bansal, Ishrat Jahan Saifi, Indra Dev, Aashish Kumar Sonkar, Sumita Dixit, Sheelendra Pratap Singh, Kausar Mahmood Ansari. Occurrence of Alternariol and Alternariolmonomethyl ether in edible oils: Their thermal stability and intake assessment in state of Uttar Pradesh, India. Journal of food science. 2021 Mar; 86(3):1124-1131. doi: 10.1111/1750-3841.15629. [PMID: 33580502]
  • Francesco Crudo, Georg Aichinger, Jovana Mihajlovic, Luca Dellafiora, Elisabeth Varga, Hannes Puntscher, Benedikt Warth, Chiara Dall'Asta, David Berry, Doris Marko. Gut microbiota and undigested food constituents modify toxin composition and suppress the genotoxicity of a naturally occurring mixture of Alternaria toxins in vitro. Archives of toxicology. 2020 10; 94(10):3541-3552. doi: 10.1007/s00204-020-02831-1. [PMID: 32623606]
  • Xiaoting Qiao, Jing Zhang, Yunjia Yang, Jie Yin, Hong Li, Yang Xing, Bing Shao. Development of a simple and rapid LC-MS/MS method for the simultaneous quantification of five Alternaria mycotoxins in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 May; 1144(?):122096. doi: 10.1016/j.jchromb.2020.122096. [PMID: 32251989]
  • Sophie Scheibenzuber, Thomas Hoffmann, Isabelle Effenberger, Wilfried Schwab, Stefan Asam, Michael Rychlik. Enzymatic Synthesis of Modified Alternaria Mycotoxins Using a Whole-Cell Biotransformation System. Toxins. 2020 04; 12(4):. doi: 10.3390/toxins12040264. [PMID: 32326012]
  • Jieshi Tang, Ling Huang, Yu Liu, Zokir Toshmatov, Chi Zhang, Hua Shao. Two Phytotoxins Isolated from the Pathogenic Fungus of the Invasive Weed Xanthium italicum. Chemistry & biodiversity. 2020 Apr; 17(4):e2000043. doi: 10.1002/cbdv.202000043. [PMID: 32112467]
  • P Palanichamy, S Kannan, D Murugan, P Alagusundaram, M Marudhamuthu. Purification, crystallization and anticancer activity evaluation of the compound alternariol methyl ether from endophytic fungi Alternaria alternata. Journal of applied microbiology. 2019 Nov; 127(5):1468-1478. doi: 10.1111/jam.14410. [PMID: 31403229]
  • Maximilian Wenderoth, Francesca Garganese, Markus Schmidt-Heydt, Sebastian Tobias Soukup, Antonio Ippolito, Simona Marianna Sanzani, Reinhard Fischer. Alternariol as virulence and colonization factor of Alternaria alternata during plant infection. Molecular microbiology. 2019 07; 112(1):131-146. doi: 10.1111/mmi.14258. [PMID: 30947377]
  • Eszter Fliszár-Nyúl, Beáta Lemli, Sándor Kunsági-Máté, Luca Dellafiora, Chiara Dall'Asta, Gabriele Cruciani, Gábor Pethő, Miklós Poór. Interaction of Mycotoxin Alternariol with Serum Albumin. International journal of molecular sciences. 2019 May; 20(9):. doi: 10.3390/ijms20092352. [PMID: 31083629]
  • Hannes Puntscher, Svenja Hankele, Katharina Tillmann, Eva Attakpah, Dominik Braun, Mary-Liis Kütt, Giorgia Del Favero, Georg Aichinger, Gudrun Pahlke, Harald Höger, Doris Marko, Benedikt Warth. First insights into Alternaria multi-toxin in vivo metabolism. Toxicology letters. 2019 Feb; 301(?):168-178. doi: 10.1016/j.toxlet.2018.10.006. [PMID: 30321595]
  • Bita Zaferanloo, Stephanie A Pepper, Sally A Coulthard, Christopher P F Redfern, Enzo A Palombo. Metabolites of endophytic fungi from Australian native plants as potential anticancer agents. FEMS microbiology letters. 2018 05; 365(9):. doi: 10.1093/femsle/fny078. [PMID: 29590360]
  • Maximilian Wenderoth, Christoph Pinecker, Benjamin Voß, Reinhard Fischer. Establishment of CRISPR/Cas9 in Alternaria alternata. Fungal genetics and biology : FG & B. 2017 04; 101(?):55-60. doi: 10.1016/j.fgb.2017.03.001. [PMID: 28286319]
  • Jin Tian, Linyun Fu, Zihao Zhang, Xuejiao Dong, Dan Xu, Ziling Mao, Yang Liu, Daowan Lai, Ligang Zhou. Dibenzo-α-pyrones from the endophytic fungus Alternaria sp. Samif01: isolation, structure elucidation, and their antibacterial and antioxidant activities. Natural product research. 2017 Feb; 31(4):387-396. doi: 10.1080/14786419.2016.1205052. [PMID: 27388053]
  • N Estiarte, C B Lawrence, V Sanchis, A J Ramos, A Crespo-Sempere. LaeA and VeA are involved in growth morphology, asexual development, and mycotoxin production in Alternaria alternata. International journal of food microbiology. 2016 Dec; 238(?):153-164. doi: 10.1016/j.ijfoodmicro.2016.09.003. [PMID: 27642688]
  • N Estiarte, A Crespo-Sempere, S Marín, V Sanchis, A J Ramos. Effect of 1-methylcyclopropene on the development of black mold disease and its potential effect on alternariol and alternariol monomethyl ether biosynthesis on tomatoes infected with Alternaria alternata. International journal of food microbiology. 2016 Nov; 236(?):74-82. doi: 10.1016/j.ijfoodmicro.2016.07.001. [PMID: 27454782]
  • Daowan Lai, Ali Wang, Yuheng Cao, Kaiyi Zhou, Ziling Mao, Xuejiao Dong, Jin Tian, Dan Xu, Jungui Dai, Yu Peng, Ligang Zhou, Yang Liu. Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22. Journal of natural products. 2016 08; 79(8):2022-31. doi: 10.1021/acs.jnatprod.6b00327. [PMID: 27441892]
  • Hannah Simon, Grete Hoffmann, Florian Hübner, Hans-Ulrich Humpf, Uwe Karst. Electrochemical simulation of metabolic reactions of the secondary fungal metabolites alternariol and alternariol methyl ether. Analytical and bioanalytical chemistry. 2016 Apr; 408(10):2471-83. doi: 10.1007/s00216-016-9344-z. [PMID: 26869346]
  • Yit-Heng Chooi, Mariano Jordi Muria-Gonzalez, Oliver L Mead, Peter S Solomon. SnPKS19 Encodes the Polyketide Synthase for Alternariol Mycotoxin Biosynthesis in the Wheat Pathogen Parastagonospora nodorum. Applied and environmental microbiology. 2015 Aug; 81(16):5309-17. doi: 10.1128/aem.00278-15. [PMID: 26025896]
  • Andreas A Hildebrand, Beate N Kohn, Erika Pfeiffer, Daniel Wefers, Manfred Metzler, Mirko Bunzel. Conjugation of the mycotoxins alternariol and alternariol monomethyl ether in tobacco suspension cells. Journal of agricultural and food chemistry. 2015 May; 63(19):4728-36. doi: 10.1021/acs.jafc.5b00806. [PMID: 25912034]
  • Panagiota Ntasiou, Charalampos Myresiotis, Sotiris Konstantinou, Euphemia Papadopoulou-Mourkidou, George S Karaoglanidis. Identification, characterization and mycotoxigenic ability of Alternaria spp. causing core rot of apple fruit in Greece. International journal of food microbiology. 2015 Mar; 197(?):22-9. doi: 10.1016/j.ijfoodmicro.2014.12.008. [PMID: 25560914]
  • Ilenia Siciliano, Giuseppe Ortu, Giovanna Gilardi, Maria Lodovica Gullino, Angelo Garibaldi. Mycotoxin production in liquid culture and on plants infected with Alternaria spp. isolated from rocket and cabbage. Toxins. 2015 Mar; 7(3):743-54. doi: 10.3390/toxins7030743. [PMID: 25751147]
  • Pilar Vila-Donat, Celia Fernández-Blanco, Gianni Sagratini, Guillermina Font, María-José Ruiz. Effects of soyasaponin I and soyasaponins-rich extract on the alternariol-induced cytotoxicity on Caco-2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Mar; 77(?):44-9. doi: 10.1016/j.fct.2014.12.016. [PMID: 25542527]
  • C Chiesi, C Fernandez-Blanco, L Cossignani, G Font, M J Ruiz. Alternariol-induced cytotoxicity in Caco-2 cells. Protective effect of the phenolic fraction from virgin olive oil. Toxicon : official journal of the International Society on Toxinology. 2015 Jan; 93(?):103-11. doi: 10.1016/j.toxicon.2014.11.230. [PMID: 25451539]
  • Celia Fernández-Blanco, Guillermina Font, Maria-Jose Ruiz. Oxidative stress of alternariol in Caco-2 cells. Toxicology letters. 2014 Sep; 229(3):458-64. doi: 10.1016/j.toxlet.2014.07.024. [PMID: 25072143]
  • Vanessa Mara Chapla, Maria Luiza Zeraik, Valdecir F Ximenes, Lisinéia Maria Zanardi, Márcia N Lopes, Alberto José Cavalheiro, Dulce Helena S Silva, Maria Cláudia M Young, Luiz Marcos da Fonseca, Vanderlan S Bolzani, Angela Regina Araújo. Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis. Molecules (Basel, Switzerland). 2014 May; 19(5):6597-608. doi: 10.3390/molecules19056597. [PMID: 24858094]
  • Lauren A Du Fall, Peter S Solomon. The necrotrophic effector SnToxA induces the synthesis of a novel phytoalexin in wheat. The New phytologist. 2013 Oct; 200(1):185-200. doi: 10.1111/nph.12356. [PMID: 23782173]
  • Jovana Vučković, Marija Bodroža-Solarov, Đura Vujić, Aleksandra Bočarov-Stančić, Ferenc Bagi. The protective effect of hulls on the occurrence of Alternaria mycotoxins in spelt wheat. Journal of the science of food and agriculture. 2013 Jun; 93(8):1996-2001. doi: 10.1002/jsfa.6005. [PMID: 23255302]
  • Christine Tiessen, Markus Fehr, Christoph Schwarz, Simone Baechler, Katharina Domnanich, Ute Böttler, Gudrun Pahlke, Doris Marko. Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether. Toxicology letters. 2013 Jan; 216(1):23-30. doi: 10.1016/j.toxlet.2012.11.005. [PMID: 23154127]
  • Jieyin Sun, Takayoshi Awakawa, Hiroshi Noguchi, Ikuro Abe. Induced production of mycotoxins in an endophytic fungus from the medicinal plant Datura stramonium L. Bioorganic & medicinal chemistry letters. 2012 Oct; 22(20):6397-400. doi: 10.1016/j.bmcl.2012.08.063. [PMID: 22967766]
  • Jun-Wei He, Guo-Dong Chen, Hao Gao, Fan Yang, Xiao-Xia Li, Tao Peng, Liang-Dong Guo, Xin-Sheng Yao. Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp. Fitoterapia. 2012 Sep; 83(6):1087-91. doi: 10.1016/j.fitote.2012.05.002. [PMID: 22613072]
  • Lucas M Abreu, Sarah S Costa, Ludwig H Pfenning, Jacqueline A Takahashi, Thomas O Larsen, Birgitte Andersen. Chemical and molecular characterization of Phomopsis and Cytospora-like endophytes from different host plants in Brazil. Fungal biology. 2012 Feb; 116(2):249-60. doi: 10.1016/j.funbio.2011.11.008. [PMID: 22289771]
  • Stefania Somma, Graciela Pose, Alejandro Pardo, Giuseppina Mulè, Virginia Fernandez Pinto, Antonio Moretti, Antonio Francesco Logrieco. AFLP variability, toxin production, and pathogenicity of Alternaria species from Argentinean tomato fruits and puree. International journal of food microbiology. 2011 Feb; 145(2-3):414-9. doi: 10.1016/j.ijfoodmicro.2011.01.006. [PMID: 21303723]
  • A A Burkin, G P Kononenko. [Enzyme immunassay of alternariol for the assessment of risk of agricultural products contamination]. Prikladnaia biokhimiia i mikrobiologiia. 2011 Jan; 47(1):79-83. doi: NULL. [PMID: 21442923]
  • Sofie Monbaliu, Kris Van Poucke, Kurt Heungens, Carlos Van Peteghem, Sarah De Saeger. Production and migration of mycotoxins in sweet pepper analyzed by Multimycotoxin LC-MS/MS. Journal of agricultural and food chemistry. 2010 Oct; 58(19):10475-9. doi: 10.1021/jf102722k. [PMID: 20825158]
  • Simon V S IpCho, Kar-Chun Tan, Geraldine Koh, Joel Gummer, Richard P Oliver, Robert D Trengove, Peter S Solomon. The transcription factor StuA regulates central carbon metabolism, mycotoxin production, and effector gene expression in the wheat pathogen Stagonospora nodorum. Eukaryotic cell. 2010 Jul; 9(7):1100-8. doi: 10.1128/ec.00064-10. [PMID: 20495056]
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  • Julia Kjer, Victor Wray, RuAngelie Edrada-Ebel, Rainer Ebel, Alexander Pretsch, Wenhan Lin, Peter Proksch. Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba. Journal of natural products. 2009 Nov; 72(11):2053-7. doi: 10.1021/np900417g. [PMID: 19835393]
  • Sofie Monbaliu, Christof Van Poucke, Carlos Van Peteghem, Kris Van Poucke, Kurt Heungens, Sarah De Saeger. Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. Rapid communications in mass spectrometry : RCM. 2009 Jan; 23(1):3-11. doi: 10.1002/rcm.3833. [PMID: 19051227]
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  • Birgitte Andersen, Jørn Smedsgaard, Ida Jørring, Pernille Skouboe, Lars Hagsholm Pedersen. Real-time PCR quantification of the AM-toxin gene and HPLC qualification of toxigenic metabolites from Alternaria species from apples. International journal of food microbiology. 2006 Sep; 111(2):105-11. doi: 10.1016/j.ijfoodmicro.2006.04.021. [PMID: 16890318]
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