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Alkaloids from Narcissus poeticus cv. Pink Parasol of various structural types and their biological activity

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Abstract

Fifteen Amaryllidaceae alkaloids (1–15) of various structural types were isolated by standard chromatographic methods from fresh bulbs of Narcissus poeticus cv. Pink Parasol. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analyses, and by comparison with literature data. Narcipavline (5) and narcikachnine (6) are reported here for the first time. In their structure are combined two basic structural types of Amaryllidaceae alkaloids (galanthamine- and galanthindole-structural types), which represent a new structural type of these compounds. Alkaloids isolated in sufficient amounts were evaluated for their human erythrocytic acetylcholinesterase, and human serum butyrylcholinesterase (HuBuChE) inhibition activity using Ellman’s method. Z-Gly-Pro-p-nitroanilide was used as substrate in the prolyl oligopeptidase (POP) assay. Untested alkaloids were also screened for their cytotoxic activity against a small panel of human cancer cells, which spanned cell lines from different tissue types. In parallel, MRC-5 human fibroblasts were employed to determine overall toxicity against noncancerous cells. Some compounds were evaluated for their antiprotozoal activity. The newly isolated alkaloid narcipavline (5) showed interesting HuBuChE inhibition activity (IC50 = 24.4 ± 1.2 µM), and norlycoramine (11) demonstrated promising POP inhibition (IC50 = 0.21 ± 0.01 mM).

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Acknowledgements

This project was supported by Charles University Grants (SVV UK 260 412, 17/2012/UNCE), by the Czech Ministry of Education, Youth and Sports (SV/FVZ201506) and by the Ministry of Defence of the Czech Republic.

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Authors and Affiliations

  1. ADINACO Research Group, Department of Pharmaceutical Botany and Ecology, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Kralove, Czech Republic

    Marcela Šafratová, Anna Hošťálková, Daniela Hulcová, Kateřina Breiterová, Jakub Chlebek, Lubomír Opletal & Lucie Cahlíková

  2. Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 05, Hradec Kralove, Czech Republic

    Veronika Hrabcová, Daniel Jun & Martina Hrabinová

  3. Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Kralove, Czech Republic

    Jiří Kuneš

  4. Department of Analytical Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic

    Lucie Nováková

  5. Department of Medical Biochemistry, Faculty of Medicine in Hradec Králové, Charles University, Šimkova 870, 500 03, Hradec Králové, Czech Republic

    Radim Havelek & Martina Seifrtová

  6. Department of Biology, Faculty of Science, University of Hradec Kralove, Rokitanskeho 62, 50003, Hradec Kralove, Czech Republic

    Veronika Hrabcová

  7. Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Av. Professor Egas Moniz, 1649-028, Lisbon, Portugal

    Marta Machado, Diana Fontinha & Miguel Prudêncio

Authors
  1. Marcela Šafratová
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  2. Anna Hošťálková
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  3. Daniela Hulcová
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  4. Kateřina Breiterová
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  5. Veronika Hrabcová
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  6. Marta Machado
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  7. Diana Fontinha
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  8. Miguel Prudêncio
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  9. Jiří Kuneš
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  10. Jakub Chlebek
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  11. Daniel Jun
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  12. Martina Hrabinová
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  13. Lucie Nováková
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  14. Radim Havelek
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  15. Martina Seifrtová
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  16. Lubomír Opletal
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  17. Lucie Cahlíková
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Correspondence to Lucie Cahlíková.

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Šafratová, M., Hošťálková, A., Hulcová, D. et al. Alkaloids from Narcissus poeticus cv. Pink Parasol of various structural types and their biological activity. Arch. Pharm. Res. 41, 208–218 (2018). https://doi.org/10.1007/s12272-017-1000-4

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  • DOI: https://doi.org/10.1007/s12272-017-1000-4

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