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Planta Med 2019; 85(03): 195-202
DOI: 10.1055/a-0690-9236
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Lanostane Triterpenes from Gloeophyllum odoratum and Their Anti-Influenza Effects

Ulrike Grienke
1   Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Austria
,
Julia Zwirchmayr
1   Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Austria
,
Ursula Peintner
2   Institute of Microbiology, University of Innsbruck, Austria
,
Ernst Urban
3   Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Austria
,
Martin Zehl
4   Department of Analytical Chemistry, Faculty of Chemistry, University of Vienna, Austria
,
Michaela Schmidtke
5   Institute of Medical Microbiology, Section Experimental Virology, Jena University Hospital, Germany
,
Judith M. Rollinger
1   Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Austria
› Author Affiliations
Further Information

Publication History

received 05 July 2018
revised 08 August 2018

accepted 14 August 2018

Publication Date:
21 August 2018 (online)

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Abstract

In an in vitro screening for anti-influenza agents from European polypores, the fruit body extract of Gloeophyllum odoratum dose-dependently inhibited the cytopathic effect of the H3N2 influenza virus A/Hong Kong/68 (HK/68) in Madin Darby canine kidney cells with a 50% inhibitory concentration (IC50) of 15 µg/mL, a noncytotoxic concentration. After a chromatographic work-up, eight lanostane triterpenes (1–8) were isolated and their structures were elucidated based on high-resolution electrospray ionization mass spectrometry analyses, and one- and two-dimensional nuclear magnetic resonance experiments. Constituents 1 (gloeophyllin K) and 2 (gloeophyllin L) are reported here for the first time, and compounds 5, 7, and 8 have not been described for the investigated fungal material so far. The highest activity was determined for trametenolic acid B (3) against HK/68 and the 2009 pandemic H1N1 strain A/Jena/8178/09 with IC50 values of 14 and 11 µM, respectively. In a plaque reduction assay, this compound was able to bind to cell-free viruses and to neutralize their infectivity.

Key words

Gloeophyllum odoratum - Gloeophyllales - polypores - lanostane triterpenes - anti-influenza

Supporting Information

    The NMR, HRESIMS, and IR spectra of compounds 1 and 2 and graphs showing dose-dependencies for the investigated compounds (Fig. 24S) are provided as Supporting Information (Fig. 1S–23S).

  • Supporting Information
 

  • References

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