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Archives of Pharmacal Research

, Volume 41, Issue 2, pp 208–218 | Cite as

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

  • Marcela Šafratová
  • Anna Hošťálková
  • Daniela Hulcová
  • Kateřina Breiterová
  • Veronika Hrabcová
  • Marta Machado
  • Diana Fontinha
  • Miguel Prudêncio
  • Jiří Kuneš
  • Jakub Chlebek
  • Daniel Jun
  • Martina Hrabinová
  • Lucie Nováková
  • Radim Havelek
  • Martina Seifrtová
  • Lubomír Opletal
  • Lucie Cahlíková
Research Article

Abstract

Fifteen Amaryllidaceae alkaloids (115) 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).

Keywords

Narcissus poeticus cv. Pink Parasol Amaryllidaceae Alzheimer’s disease Cytotoxicity Antiplasmodial activity 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

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Copyright information

© The Pharmaceutical Society of Korea 2017

Authors and Affiliations

  • Marcela Šafratová
    • 1
  • Anna Hošťálková
    • 1
  • Daniela Hulcová
    • 1
  • Kateřina Breiterová
    • 1
  • Veronika Hrabcová
    • 2
    • 6
  • Marta Machado
    • 7
  • Diana Fontinha
    • 7
  • Miguel Prudêncio
    • 7
  • Jiří Kuneš
    • 3
  • Jakub Chlebek
    • 1
  • Daniel Jun
    • 2
  • Martina Hrabinová
    • 2
  • Lucie Nováková
    • 4
  • Radim Havelek
    • 5
  • Martina Seifrtová
    • 5
  • Lubomír Opletal
    • 1
  • Lucie Cahlíková
    • 1
  1. 1.ADINACO Research Group, Department of Pharmaceutical Botany and Ecology, Faculty of PharmacyCharles UniversityHradec KraloveCzech Republic
  2. 2.Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health SciencesUniversity of DefenceHradec KraloveCzech Republic
  3. 3.Department of Inorganic and Organic Chemistry, Faculty of PharmacyCharles UniversityHradec KraloveCzech Republic
  4. 4.Department of Analytical Chemistry, Faculty of PharmacyCharles UniversityHradec KrálovéCzech Republic
  5. 5.Department of Medical Biochemistry, Faculty of Medicine in Hradec KrálovéCharles UniversityHradec KrálovéCzech Republic
  6. 6.Department of Biology, Faculty of ScienceUniversity of Hradec KraloveHradec KraloveCzech Republic
  7. 7.Instituto de Medicina Molecular, Faculdade de MedicinaUniversidade de LisboaLisbonPortugal

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