Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer's disease

  • Phytochemistry. 2019 Sep:165:112055. doi: 10.1016/j.phytochem.2019.112055.
Daniela Hulcová  1 ,  Jana Maříková  2 ,  Jan Korábečný  3 ,  Anna Hošťálková  4 ,  Daniel Jun  5 ,  Jiří Kuneš  2 ,  Jakub Chlebek  4 ,  Lubomír Opletal  4 ,  Angela De Simone  6 ,  Lucie Nováková  7 ,  Vincenza Andrisano  6 ,  Aleš Růžička  8 ,  Lucie Cahlíková  9
Affiliations
  • 1. ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic; Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.
  • 2. Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.
  • 3. Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 05, Hradec Králové, Czech Republic; Department Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05, Hradec Králové, Czech Republic.
  • 4. ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.
  • 5. Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 05, Hradec Králové, Czech Republic.
  • 6. Department for Life Quality Studies, University of Bologna, Corso D'Augusto 237, 47921, Rimini, Italy.
  • 7. Department of Analytical Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.
  • 8. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 95, 532 10, Pardubice, Czech Republic.
  • 9. ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic. Electronic address: [email protected].
PMID: 31261031 DOI: 10.1016/j.phytochem.2019.112055
Abstract

Twenty-one known Amaryllidaceae alkaloids of various structural types and one undescribed alkaloid, named narcimatuline, have been isolated from fresh bulbs of Narcissus pseudonarcissus L. cv. Dutch Master. The chemical structures were elucidated by combination of MS, HRMS, 1D and 2D NMR spectroscopic techniques, and by comparison with literature data. Narcimatuline amalgamates two basic scaffolds of Amaryllidaceae alkaloids in its core, namely galanthamine and galanthindole. All isolated compounds were evaluated for their in vitro acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), prolyl oligopeptidase (POP), and glycogen synthase kinase-3β (GSK-3β) inhibitory activities. The most interesting biological profile was demonstrated by newly isolated alkaloid narcimatuline.

Keywords
Alkaloids; Alzheimer's disease; Amaryllidaceae; Cholinesterase inhibition; Glycogen synthase kinase-3β inhibition; Narcimatuline; Narcissus pseudonarcissus L. cv. Dutch master; Prolyl oligopeptidase.
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