Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer's disease. (September 2019)

• Record Type: Journal Article
• Authors: Hulcová, Daniela; Maříková, Jana; Korábečný, Jan; Hošťálková, Anna; Jun, Daniel; Kuneš, Jiří; Chlebek, Jakub; Opletal, Lubomír; De Simone, Angela; Nováková, Lucie; Andrisano, Vincenza; Růžička, Aleš; Cahlíková, Lucie
• Is Part Of: Phytochemistry. Volume 165(2019)
• Publication Date: 2019-09
• Subjects: Narcissus pseudonarcissus L. cv. Dutch master -- Amaryllidaceae -- Alkaloids -- Narcimatuline -- Alzheimer's disease -- Cholinesterase inhibition -- Glycogen synthase kinase-3β inhibition -- Prolyl oligopeptidase; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.112055
• Languages: English
• ISSNs: 0031-9422

Abstract

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. Graphical abstract: Image 1 Highlights: Twenty-one Amaryllidaceae alkaloids were isolated. Structure of undescribed alkaloid narcimatuline was determined. Absolute configuration of tetrahydromasonine was determined. Biological activities with potential treatment of Alzheimer's disease were studied. Narcimatuline revealed multipotent profile.