Silvestrol Explained

Silvestrol is a natural product from the flavagline family, with a cyclopenta[b] benzofuran core structure and an unusual dioxane ether side chain, which is found in the bark of trees from the genus Aglaia, especially Aglaia silvestris and Aglaia foveolata.[1]

Bioactivity

It acts as a potent and selective inhibitor of the RNA helicase enzyme eIF4A, and has both broad-spectrum antiviral activity against diseases such as Ebola and coronaviruses, [2] [3] [4] [5] [6] and anti-cancer properties,[7] [8] which makes it of considerable interest in medical research. However, as it cannot be extracted from tree bark in commercial amounts and is prohibitively complex to produce synthetically,[9] practical applications have focused more on structurally simplified analogues such as CR-31-B.[10]

See also

Notes and References

  1. Pan L, Woodard JL, Lucas DM, Fuchs JR, Kinghorn AD . Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species . Natural Product Reports . 31 . 7 . 924–39 . July 2014 . 24788392 . 4091845 . 10.1039/c4np00006d .
  2. Biedenkopf N, Lange-Grünweller K, Schulte FW, Weißer A, Müller C, Becker D, Becker S, Hartmann RK, Grünweller A . 6 . The natural compound silvestrol is a potent inhibitor of Ebola virus replication . Antiviral Research . 137 . 76–81 . January 2017 . 27864075 . 10.1016/j.antiviral.2016.11.011 . 205577158 .
  3. Elgner F, Sabino C, Basic M, Ploen D, Grünweller A, Hildt E . Inhibition of Zika Virus Replication by Silvestrol . Viruses . 10 . 4 . 149 . March 2018 . 29584632 . 5923443 . 10.3390/v10040149 . free .
  4. Müller C, Schulte FW, Lange-Grünweller K, Obermann W, Madhugiri R, Pleschka S, Ziebuhr J, Hartmann RK, Grünweller A . 6 . Broad-spectrum antiviral activity of the eIF4A inhibitor silvestrol against corona- and picornaviruses . Antiviral Research . 150 . 123–129 . February 2018 . 29258862 . 10.1016/j.antiviral.2017.12.010 . 7113723 .
  5. Henss L, Scholz T, Grünweller A, Schnierle BS . Silvestrol Inhibits Chikungunya Virus Replication . Viruses . 10 . 11 . 592 . October 2018 . 30380742 . 6266838 . 10.3390/v10110592 . free .
  6. Pillaiyar T, Meenakshisundaram S, Manickam M . Recent discovery and development of inhibitors targeting coronaviruses . Drug Discovery Today . 25 . 4 . 668–688 . April 2020 . 32006468 . 7102522 . 10.1016/j.drudis.2020.01.015 .
  7. Kogure T, Kinghorn AD, Yan I, Bolon B, Lucas DM, Grever MR, Patel T . Therapeutic potential of the translation inhibitor silvestrol in hepatocellular cancer . PLOS ONE . 8 . 9 . e76136 . 24086701 . 3784426 . 10.1371/journal.pone.0076136 . 2013 . 2013PLoSO...876136K . free .
  8. Pelletier J, Graff J, Ruggero D, Sonenberg N . Targeting the eIF4F translation initiation complex: a critical nexus for cancer development . Cancer Research . 75 . 2 . 250–63 . January 2015 . 25593033 . 4299928 . 10.1158/0008-5472.CAN-14-2789 .
  9. El Sous M, Khoo ML, Holloway G, Owen D, Scammells PJ, Rizzacasa MA . Total synthesis of (-)-episilvestrol and (-)-silvestrol . Angewandte Chemie . 46 . 41 . 7835–8 . 17823902 . 10.1002/anie.200702700 . 2007 . free .
  10. Müller C, Obermann W, Schulte FW, Lange-Grünweller K, Oestereich L, Elgner F, Glitscher M, Hildt E, Singh K, Wendel HG, Hartmann RK, Ziebuhr J, Grünweller A . 6 . Comparison of broad-spectrum antiviral activities of the synthetic rocaglate CR-31-B (-) and the eIF4A-inhibitor Silvestrol . Antiviral Research . 175 . 104706 . January 2020 . 31931103 . 10.1016/j.antiviral.2020.104706 . 7114339 . free .

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