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Structure Activity Relationship for Fumonisin Phytotoxicity

  • Justin B. Renaud
    Justin B. Renaud
    London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada
  • Natasha DesRochers
    Natasha DesRochers
    London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada
  • Shawn Hoogstra
    Shawn Hoogstra
    London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada
  • Christopher P. Garnham*
    Christopher P. Garnham
    London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada
    *Tel.: 519 953 6643. E-mail: [email protected] (C.G.).
  • , and 
  • Mark W. Sumarah*
    Mark W. Sumarah
    London Research and Development Centre, Agriculture and Agri-Food Canada, 1391 Sandford Street, London, Ontario N5V 4T3, Canada
    *Tel.: 519 953 6723. E-mail: [email protected] (M.S.).
Cite this: Chem. Res. Toxicol. 2021, 34, 6, 1604–1611
Publication Date (Web):April 23, 2021
https://doi.org/10.1021/acs.chemrestox.1c00057
Copyright Crown © 2021. Published by American Chemical Society

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    Abstract

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    Fumonisins are mycotoxins produced by a number of species of Fusarium and Aspergillus. They are polyketides that possess a linear polyol structure with two tricarballylic acid side chains and an amine moiety. Toxicity results from their inhibition of Ceramide Synthase (CerS), which perturbs sphingolipid concentrations. The tricarballylic side chains and amine group of fumonisins are key molecular features responsible for inhibiting CerS, however their individual contributions toward overall toxicity are not fully understood. We have recently reported novel, deaminated fumonisins produced by A. niger and have identified an enzyme (AnFAO) responsible for their synthesis. Here we performed a structure/function activity assay to investigate the individual contributions of the tricarballylic acid and amine toward overall fumonisin toxicity. Lemna minor was treated at 40 μM against FB1, hydrolyzed FB1 (hFB1), deaminated FB1 (FPy1), or hydrolyzed/deaminated (hFPy1). Four end points were monitored: plant dry weight, frond surface area, lipidomics, and metabolomics. Overall, hFB1 was less toxic than FB1 and FPy1 was less toxic than hFB1. hFPy1 which lacks both the amine group and tricarballylic side chains was also less toxic than FB1 and hFB1, however it was not significantly less toxic than FPy1. Lipidomic analysis showed that FB1 treatment significantly increased levels of phosphotidylcholines, ceramides, and pheophorbide A, while significantly decreasing the levels of diacylglycerides, sulfoquinovosyl diacylglycerides, and chlorophyll. Metabolomic profiling revealed a number of significantly increased compounds that were unique to FB1 treatment including phenylalanine, asymmetric dimethylarginine (ADMA), S-methylmethionine, saccharopine, and tyrosine. Conversely, citrulline, N-acetylornithine and ornithine were significantly elevated in the presence of hFB1 but not any of the other fumonisin analogues. These data provide evidence that although removal of the tricarballylic side chains significantly reduces toxicity of fumonisins, the amine functional group is a key contributor to fumonisin toxicity in L. minor and justify future toxicity studies in mammalian systems.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.chemrestox.1c00057.

    • Table S1, identified lipid classes in Lemna minor and Table S2, identified polar compounds in Lemna minor (PDF)

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    Cited By

    This article is cited by 9 publications.

    1. Song Yu, Lianpeng Zou, Jiawei Zhao, Yiping Zhu. Individual and Combined Cytotoxic Effects of Co-Occurring Fumonisin Family Mycotoxins on Porcine Intestinal Epithelial Cell. Foods 2023, 12 (13) , 2555. https://doi.org/10.3390/foods12132555
    2. Carlos Humberto Corassin, Carlos Augusto Fernandes de Oliveira. Mycotoxins in the Dairy Industry. Dairy 2023, 4 (2) , 392-394. https://doi.org/10.3390/dairy4020025
    3. A. O. Berestetskiy. Prospects for the development of new herbicides based on natural compounds. PLANT PROTECTION NEWS 2023, 106 (1) , 5-25. https://doi.org/10.31993/2308-6459-2023-106-1-15502
    4. Zhicheng Gao, Kangxin Luo, Qiuxiang Zhu, Jinghui Peng, Chang Liu, Xiaoyue Wang, Shoujun Li, Haiyang Zhang. The natural occurrence, toxicity mechanisms and management strategies of Fumonisin B1:A review. Environmental Pollution 2023, 320 , 121065. https://doi.org/10.1016/j.envpol.2023.121065
    5. Alexander Berestetskiy. Modern Approaches for the Development of New Herbicides Based on Natural Compounds. Plants 2023, 12 (2) , 234. https://doi.org/10.3390/plants12020234
    6. Alessandra Lanubile, Roberto De Michele, Martina Loi, Safieh Fakhari, Adriano Marocco, Costantino Paciolla. Cell death induced by mycotoxin fumonisin B1 is accompanied by oxidative stress and transcriptional modulation in Arabidopsis cell culture. Plant Cell Reports 2022, 41 (8) , 1733-1750. https://doi.org/10.1007/s00299-022-02888-5
    7. Patrick G. Telmer, Megan J. Kelman, Justin B. Renaud, Mark W. Sumarah, Christopher P. Garnham. Application of Aspergillus niger Fumonisin Amine Oxidase (AnFAO) to Detoxify Fumonisin-Contaminated Maize. Toxins 2022, 14 (8) , 544. https://doi.org/10.3390/toxins14080544
    8. Jacob P. Walsh, David R. McMullin, Ken K.-C. Yeung, Mark W. Sumarah. Resorcylic acid lactones from the ginseng pathogen Ilyonectria mors-panacis. Phytochemistry Letters 2022, 48 , 94-99. https://doi.org/10.1016/j.phytol.2022.02.008
    9. Anna Dalinova, Anatoly Fedorov, Vsevolod Dubovik, Olga Voitsekhovskaja, Elena Tyutereva, Sergey Smirnov, Dmitry Kochura, Leonid Chisty, Igor Senderskiy, Alexander Berestetskiy. Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives. Journal of Fungi 2021, 7 (10) , 829. https://doi.org/10.3390/jof7100829

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