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Pavilion - 12:00 - 17:30 Young Reserchers’ Workshop Anti-Influenza Virus Activity of Lanostane Triterpenes from Polypores

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Pavilion - 12:00 - 17:30 Young Reserchers’ Workshop Anti-Influenza Virus Activity of Lanostane Triterpenes from Polypores 351 Monday, 26th August, 2018 - Pavilion - 12:00 - 17:30 Young Reserchers’ Workshop Anti-Influenza Virus Activity of Lanostane Triterpenes from Polypores Julia Zwirchmayr 1, Ulrike Grienke 1, Martina Richter 2, Christina E. Mari 1, Ursula Peintner 3, Michaela Schmidtke 2, Judith M. Rollinger 1 1 Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Vienna, Austria 2 Institute of Medical Microbiology, Section Experimental Virology, Jena University Hospital, Jena, Germany 3 Institute of Microbiology, University of Innsbruck, Innsbruck, Austria The constant increase of viral resistance and the limited number of effective antiviral agents emphasizes that the current portfolio of anti-influenza drugs needs extension[1]. To identify new anti-influenza agents from nature, locally grown European polypores belonging to the polyphyletic group of Agaricomycetes (Basidiomycota) were collected and identified via rDNA ITS phylogenetic analyses[2]. Fruit bodies from ten species were collected and mycochemically investigated, i.e. Fomes fomentarius, Fomitopsis pinicola, Ganoderma lucidum, G. applanatum, Gloeophyllum odoratum, Ischnoderma benzoinum, Laetiporus sulphureus, Phellinus robustus, Piptoporus betulinus, and Trametes gibbosa. The generated ethanol extracts were screened in a cytopathic effect (CPE) inhibition assay against H3N2 influenza virus A/Hong Kong/68 (HK/68) in MDCK cells. Especially the extract of G. odoratum dose-dependently inhibited the CPE with an [3] IC50 of 15.0 μg/mL . A fluorescence-based neuraminidase (NA) inhibition assay excluded that the antiviral activity was based on the inhibition of the surface protein NA. HRESIMS, 1D and 2D NMR spectroscopy were used for the identification of eight isolated lanostane triterpenes with two novel natural compounds and three undescribed so far for G. odoratum. The most potent activity was determined for trametenolic acid B against HK/68 and the 2009 pandemic H1N1 strain A/Jena/8178/09 with IC50s of 14.1 and 11.3 μM, respectively . Additionally, this compound was able to bind to cell-free viruses and to neutralize their infectivity in a plaque reduction assay. [1] U. Grienke, M. Schmidtke, S. von Grafenstein, J. Kirchmair, K. R. Liedl, J. M. Rollinger, Nat Prod Rep 2012, 29, 11-36. [2] P. Dresch, D. A. MN, K. Rosam, U. Grienke, J. M. Rollinger, U. Peintner, AMB Express 2015, 5, 4. [3] U. Grienke, C. E. Mair, J. Kirchmair, M. Schmidtke, J. M. Rollinger, Planta Med 2018. doi 10.1055/a-0590- 5153 A metabolomic approach to investigate metabolization of a medicinal plant extract in the gastrointestinal tract in-vitro Timo Andreas Thumann 1, Eva-Maria Pferschy-Wenzig 1, Christine Moissl-Eichinger 2, Heba Aziz-Kalbhenn 3, Sabine Rabini 3, Rudolf Bauer 1 1 1 University of Graz, Institute of Pharmaceutical Sciences, Department of Pharmacognosy, Graz, Austria 2 Center for Medical Research, Medical University of Graz, Stiftingtalstraße 24, Graz, Austria 3 Steigerwald Arzneimittelwerk GmbH, Bayer Consumer Health, Havelstraße 5, Darmstadt, Germany Introduction Metabolization of medicinal plant extracts in the gastrointestinal tract may lead to the formation of new active compounds and could therefore be highly relevant for the explanation of the mode of action. STW-5 is a well- known liquid fixed 9-herb combination, which is effective in treating functional dyspepsia and irritable bowel syndrome (IBS) [1] . It was pre-digested by a static in-vitro digestion method and thereafter incubated with human gut bacteria to mimic human digestion and microbial fermentation in the gastrointestinal tract. Method Two concentrations of STW-5 were predigested in-vitro according to the InfoGest consensus method [2] . After protein precipitation, all samples were analyzed by UHPLC-HRMS and data were processed with Compound Discoverer 2.1 (Thermo Fisher Scientific). In order to assess metabolization during in-vitro digestion, UHPLC chromatograms of samples taken after simulated digestion were compared to respective STW-5 dilutions. For bacterial fermentation, fecal samples of one donor were anaerobically incubated with InfoGest predigested STW-5 as well as with non-predigested STW-5 (two concentrations). Samples were taken after 30min, 4h and 24h of incubation, and analyzed by UHPLC-HRMS. After data processing, peak areas were compared to respective STW-5 dilutions incubated with PBS-buffer only. Results The majority of STW-5 main constituents were not significantly changed by in-vitro digestion. Microbial fermentation, however, led to fast metabolization of the major compounds detected in STW-5, such as flavonoids, caffeic acid derivatives, and triterpene glycosides. References [1] Kelber O, Bauer R, Kubelka W. Phytotherapy in Functional Gastrointestinal Disorders. Dig Dis 2017; 35 Suppl 1: 36–42 [2] Verhoeckx K, Cotter P, López-Expósito I, Kleiveland C, Lea T, Mackie A, Requena T, Swiatecka D, Wichers H. The Impact of Food Bioactives on Health. Cham: Springer International Publishing; 2015 Discovery of new GPBAR1 agonists by combined in silico - in vitro screening Benjamin Kirchweger 1, Jadel M. Kratz 1, Angela Ladurner 1, Ulrike Grienke 1, Thierry Langer 2, Verena Maria Dirsch 1, Judith Maria Rollinger 1 2 1 Department of Pharmacognosy, Faculty of Life Sciences, University of Vienna, Vienna, Austria 2 Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Vienna, Austria The G protein-coupled bile acid receptor (GPBAR1) is a possible new drug target for the treatment of metabolic and inflammatory diseases, including type 2 diabetes. Previously, it has been shown that a number of herbal remedies and natural small molecule metabolites were able to activate this receptor and thus may exert antidiabetic and anti-inflammatory effects. The fast-forward identification of GPBAR1 agonists is highly relevant, as metabolic diseases like type 2 diabetes have become an epidemic, and novel treatments are urgently needed [1]. The aim of this study was to generate reliable prediction models for the fast-forward assessment of GPBAR1 activating natural compounds. A cheminformatics workflow including ligand-based pharmacophore- and shape-based virtual screening was set up. The workflow was validated theoretically and employed for the prospective virtual screening of open-source and in-house molecular databases. From 34 chemically diverse virtual hits subjected to experimental testing, 14 were confirmed as GPBAR1 activators, including new scaffolds from natural and synthetic origin. Triterpenes previously isolated from the South African tree Burkea africana [2] and coumarins from the middle-eastern spice Ferula assa-foetida [3] showed activities comparable to the endogenous ligands chenodeoxycholic acid and lithocholic acid. [1] Ladurner A, Zehl M, Grienke U, Hofstadler C, Faur N, Pereira FC, Berry D, Dirsch VM, Rollinger JM. Front Pharmacol 2017; 8: 468 [2] Mair CE, Grienke U, Wilhelm A, Urban E, Zehl M, Schmidtke M, Rollinger JM. J Nat Prod 2018; 81(3): 515-523 [3] Rollinger JM, Steindl TM, Schuster D, Kirchmair J, Anrain K, Ellmerer EP, Langer T, Stuppner H, Wutzler P, Schmidtke M. J Med Chem. 2008 Feb 28;51(4):842-51 Bioactive polysaccharides from Codonopsis pilosula Yuan-Feng Zou, Zhong-Qiong Yin, Xing-Fu Chen, Yu-Ping Fu, Zhong-Kai Zhu, Chao Huang Natural Medicine Research Center, College of Veterinary Medicine, Sichuan Agricultural University, Wenjiang 611130, P.R. China, Chengdu, China Radix Codonopsis , the root of Codonopsis pilosula (Franch) Nannf, C. pilosula Nannf. var. modesta (Nannf. ) L. T. Shen, and C. tangshen Oliv, is a traditional herbal medicine in Asian countries, with various pharmacological effects, such as heart protection, lowering blood pressure, anti-ulcer, etc [1]. It was used as the replacement of ginseng because of the similar pharmacological activities. Polysaccharide is one of the major contributors to the biological activity. In our group, we aimed to find out different bioactive polysaccharides from three species of radix Codonopsis. C. pilosula from Gansu province, C. pilosula 3 Nannf. var. modesta (Nannf. ) L. T. Shen from Sichuan and C. tangshen from Guizhou province, were collected and the polysaccharides were hereby obtained. Three crude polysaccharide fractions and more than 20 purified polysaccharide fractions were obtained from those three species using anion exchange chromatography and gel filtration. The structural elucidation of some of the polysaccharide fractions were finished and the results indicated both neutral fractions and acidic fractions are present in all three species. The crude polysaccharides showed activity in regulating intestinal flora and immunity. Complement fixating activity, antioxidant activity, prebiotics activity [2] and immunomodulating activity in intestinal epithelial cells were performed in all purified polysaccharide fractions obtained. The results from biological tests indicated that polysaccharides from different species of Codonopsis showed different activity. The further study aimed structure-activity relationship analysis would be performed. Reference: [1] Zou YF , Chen XF, Malterud KE, et al. Carbohydr Polym 2014; 113: 420-429. [2] Fu YP, Li LX, Zhang BZ, et al. Carbohydr Polym 2018; 193: 212-220 . Nanostructured Lipid Carriers Of Silymarin: Design, Characterization and In Vitro Studies Vieri Piazzini 1, Beatrice Lemmi 1, Giulia Vanti 1, Laura Risaliti 1, Mario D'Ambrosio 2, Lorenzo Cinci 2, Elisabetta Bigagli 2, Cristina Luceri 2, Anna Rita Bilia 1, Maria Camilla Bergonzi 1 1 Department
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