Discovery of a new sesquiterpenoid from Phellinus ignarius with antiviral activity against influenza virus (original) (raw)

Abstract

Seven natural products, including one new sesquiterpenoid (eudesm-1β, 6α, 11-triol, compound 1), one ergosta -4, 6, 8(14), 22-tetraen-3-one (compound 2), four polyphenols (compounds 3, 4, 5, 6), and one pyrone (3-hydroxy-2-methyl-4-pyrone, compound 7) were isolated from cultures of Phellinus ignarius by column chromatography. The detailed structure of compound 1 was determined using a combination of one- and two-dimensional nuclear magnetic resonance, mass spectrometry and infrared spectroscopy. The antiviral activity of these compounds against H5N1 influenza A virus was investigated using an MTT colorimetric assay system in Madin-Darby canine kidney cells. The results indicate that compound 1 possesses significant ability to inhibit influenza virus. The 50 % effective concentration was 0.14 ± 0.04 μM. Molecular modeling further suggested that the anti-influenza virus activity of this compound was partially attributed to the interactions of hydroxyl groups with an amino acid residue (Asn 170) of neuraminidase (NA) at the binding site. Moreover, the results of enzyme inhibition assays indicated that 50 % inhibition of NA was achieved by compound 1 at a concentration of 0.657 ± 0.325 mg/mL, which suggested that compound 1 is likely to interact with the NA enzyme.

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Acknowledgments

This project was financially supported by Science and Technology Development Plan of Shandong Province (No. 2010GNC10956). We are grateful for the help of Professor Ji-Kai Liu. We thank Dr. Martin Sadilek and Loren Kruse (Department of Chemistry, University of Washington, USA) for English editing. We also thank BioBioPha Co., Ltd. and National Reference Laboratory for Newcastle Disease, China Animal Health and Epidemiology Center for their contributions.

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Authors and Affiliations

  1. Shandong Province Key Laboratory of Applied Mycology, School of Life Sciences, Qingdao Agricultural University, Changcheng Road 700, Chengyang, Qingdao, 266109, People’s Republic of China
    Ai-Rong Song, Xiao-Le Sun, Chao Kong, Chen Zhao, Dan Qin, Fang Huang & Song Yang
  2. Key Laboratory of Systems Bioengineering, Ministry of Education, Tianjin University, Tianjin, 300072, People’s Republic of China
    Song Yang

Authors

  1. Ai-Rong Song
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  2. Xiao-Le Sun
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  3. Chao Kong
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  4. Chen Zhao
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  5. Dan Qin
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  6. Fang Huang
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  7. Song Yang
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Corresponding author

Correspondence toSong Yang.

Additional information

A.-R. Song, X.-L. Sun, and C. Kong equally contributed to this work.

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Song, AR., Sun, XL., Kong, C. et al. Discovery of a new sesquiterpenoid from Phellinus ignarius with antiviral activity against influenza virus.Arch Virol 159, 753–760 (2014). https://doi.org/10.1007/s00705-013-1857-6

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