Mycobiology

The Korean Society of Mycology (한국균학회)
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Neuraminidase Inhibitors from the Fruiting Body of Glaziella splendens

  • Kim, Ji-Yul (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University) ;
  • Woo, E-Eum (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University) ;
  • Ha, Lee Su (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University) ;
  • Ki, Dae-Won (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University) ;
  • Lee, In-Kyoung (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University) ;
  • Yun, Bong-Sik (Division of Biotechnology and Advanced Institute of Environment and Bioscience, College of Environmental and Bioresource Sciences, Chonbuk National University)
  • Received : 2019.03.06
  • Accepted : 2019.05.05
  • Published : 2019.06.01
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Abstract

Neuraminidase (NA) cleaves the glycosidic bond linkages of sialic acids to release the mature virions from infected cells and has been an attractive therapeutic target for anti-influenza agents. In our ongoing investigation of NA inhibitors in mushroom extracts, we found that the extract the fruiting body of Glaziella splendens potently inhibited neuraminidase. The fruiting bodies of G. splendens were extracted and partitioned successively with hexane, ethyl acetate, and butanol. The ethyl acetate soluble-layer was subjected to silica gel and Sephadex LH-20 column chromatographies, and MPLC to obtain five compounds (1-5). Their structures were determined by spectroscopic methods. NA inhibitory activity of these compounds was evaluated using NAs from recombinant rvH1N1, H3N2, and H5N1 influenza A viruses. One compound (1) was elucidated as a new azaphilone derivative, and four compounds (2-5) were identified as entonaemin A, comazaphilone D, rubiginosin A, and entonaemin B, respectively. Compounds 3 and 4 showed considerable inhibitory activity against three types of neuraminidases with the $IC_{50}$ values of 30.9, 41.8, and $35.7{\mu}M$ for 3 and 46.5, 50.4, and $29.9{\mu}M$ for 4, respectively. This study reveals that the fruiting bodies of G. splendens possess azaphilone derivatives with the NA inhibitory activity. This is the first report on the isolation of neuraminidase inhibitors from the fruiting bodies of G. splendens.

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References

  1. Hong BT, Chen CL, Fang JM, et al. Oseltamivir hydroxamate and acyl sulfonamide derivatives as influenza neuraminidase inhibitors. Bioorg Med Chem. 2014;22:6647-6654. https://doi.org/10.1016/j.bmc.2014.10.005
  2. Sakado A, Baba K, Tsukamoto M, et al. Anionic polymer, poly(methyl vinyl ether-maleic anhydride)-coated beads-based capture of human influenza A and B virus. Bioorg Med Chem. 2009;17:752-757. https://doi.org/10.1016/j.bmc.2008.11.046
  3. Pielak RM, Schnell JR, Chou JJ. Mechanism of drug inhibition and drug resistance of influenza A M2 channel. Proc Natl Acad Sci USA. 2009;106:7379-7384. https://doi.org/10.1073/pnas.0902548106
  4. Hwang BS, Lee IK, Choi HJ, et al. Anti-influenza activities of polyphenols from the medicinal mushroom Phellinus baumii. Bioorg Med Chem Lett. 2015;25:3256-3260. https://doi.org/10.1016/j.bmcl.2015.05.081
  5. Nguyen-Van-Tam JS, Venkatesan S, Muthuri SG, et al. Neuraminidase inhibitors: who, when, where? Clin Microbiol Infect. 2015;21:222-225. https://doi.org/10.1016/j.cmi.2014.11.020
  6. Regoes RR, Bonhoeffer S. Emergence of drugresistant influenza virus: population dynamical considerations. Science. 2006;312:389-391. https://doi.org/10.1126/science.1122947
  7. Stadler M, Ju YM, Rogers JD. Chemotaxonomy of Entonaema, Rhopalostroma and other Xylariaceae. Mycol Res. 2004;108:239-256. https://doi.org/10.1017/S0953756204009347
  8. Quang DN, Hashimoto T, Radulovic N, et al. Antimicrobial Azaphilones from the Xylariaceous inedible mushrooms. Int J Med Mushr. 2005;7:452-455.
  9. Li LQ, Yang YG, Zeng Y, et al. A new azaphilone, kasanosin C, from an endophytic Talaromyces sp. T1BF. Molecules. 2010;15:3993-3997. https://doi.org/10.3390/molecules15063993
  10. Gao SS, Li XM, Zhang Y, et al. Comazaphilones A-F, azaphilone derivatives from the marine sediment-derived fungus Penicillium commune QSD-17. J Nat Prod. 2011;74:256-261. https://doi.org/10.1021/np100788h
  11. Quang DN, Hashimoto T, Stadler M, et al. New azaphilones from the inedible mushroom Hypoxylon rubiginosum. J Nat Prod. 2004;67:1152-1155. https://doi.org/10.1021/np040063l
  12. Asakawa Y, Hashimoto T. Biologically active substances of Japanese inedible mushrooms. Heterocycles. 1998;47:1067-1110. https://doi.org/10.3987/REV-97-SR(N)6

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