Isoquinoline Alkaloids from <i>Fumaria officinalis</i> L. and Their Biological Activities Related to <i>Alzheimer</i>'s Disease

Chlebek, Jakub; Novák, Zdeněk; Kassemová, Dominika; Šafratová, Marcela; Kostelník, Jan; Malý, Lukáš; Ločárek, Miroslav; Opletal, Lubomı́r; Hošťálková, Anna; Hrabinová, Martina; Kuneš, Jiřı́; Novotná, Pavlína; Urbanová, Marie; Nováková, Lucie; Macáková, Kateřina; Hulcová, Daniela; Solich, Petr; Martı́n, Concepción Pérez; Jun, Daniel; Cahlíková, Lucie

doi:10.1002/cbdv.201500033

Cited by 35 publications

(25 citation statements)

References 37 publications

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“…Other biological activities reported for this species are anticholinesterasic and analgesic activities [ 15 , 16 ]. An important number of biological activities are associated and assessed to the Fumaria officinalis L. ( Figure 1 ) [ 17 , 18 ], a species that is also spontaneous in the Western part of Europe [ 2 ]. The antibacterial [ 7 ] and the antioxidant [ 19 ] activities are the most frequently cited by scientific literature.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Polyphenolic Content, Antioxidant and Diuretic Activities of Six Fumaria Species

et al. 2017

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Romanian traditional medicine describes the use of aerial parts of Fumaria species to treat hepatobiliary diseases as well as diuretic agents. The present study aims to investigate the chemical composition, antioxidant properties, and diuretic effects of several Fumaria species. LC/MS analysis revealed that Fumaria species contain phenolic acids and high amounts of flavonoids with rutin and isoquercitrin as main compounds. Concerning antioxidant capacity, the most significant results were obtained for F. capreolata and F. vailantii. Both species showed a good correlation between the antioxidant capacity and a high amount of flavonoids. Furthermore, the extracts of F. officinalis and F. schleicheri produced a strong increase in urinary volumetric excretion of saline-loaded rats, 24 h after the oral administration of a single dose of 250 mg/kg bw. Moreover, both extracts of F. officinalis and F. schleicheri increased the urinary excretion of Na+ and K+. Results from the present study offer a new perspective concerning the chemical composition and bioactivities of traditionally used fumitory species.

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Section: Introductionmentioning

confidence: 99%

Evaluation of Polyphenolic Content, Antioxidant and Diuretic Activities of Six Fumaria Species

et al. 2017

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“…Column chromatography (CC) and subsequent preparative thin-layer chromatography (TLC) led to the isolation of seven compounds ( 1 – 7 ) belonging to pavine, protopine and benzylisoquinoline structural types. The chemical structures of the isolated alkaloids were elucidated by means of optical rotation, spectroscopic ( 1 H- and 13 C-NMR) and spectrometric (GC-MS, ESI) analyses and by comparison of the obtained data with those in the literature [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 38 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 ]. The compounds were determined as (+)-laudanosine ( 1 ), protopine ( 2 ), (–)-argemonine ( 3 ), allocryptopine ( 4 ), (–)-platycerine ( 5 ), (–)-munitagine ( 6 ) and (–)-norargemonine ( 7 ) ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Thus, POP-inhibiting compounds appear as a promising therapeutic approach to the treatment of AD. POP inhibitors were also found among natural products of different structural types (e.g., phenolics, benzofurans, terpenes, peptides, and alkaloids) [ 13 , 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

et al. 2017

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Alzheimer’s disease is an age-related, neurodegenerative disorder, characterized by cognitive impairment and restrictions in activities of daily living. This disease is the most common form of dementia with complex multifactorial pathological mechanisms. Many therapeutic approaches have been proposed. Among them, inhibition of acetylcholinesterase, butyrylcholinesterase, and prolyl oligopeptidase can be beneficial targets in the treatment of Alzheimer’s disease. Roots, along with aerial parts of Argemone platyceras, were extracted with ethanol and fractionated on an alumina column using light petrol, chloroform and ethanol. Subsequently, repeated preparative thin-layer chromatography led to the isolation of (+)-laudanosine, protopine, (–)-argemonine, allocryptopine, (–)-platycerine, (–)-munitagine, and (–)-norargemonine belonging to pavine, protopine and benzyltetrahydroisoquinoline structural types. Chemical structures of the isolated alkaloids were elucidated by optical rotation, spectroscopic and spectrometric analysis (NMR, MS), and comparison with literature data. (+)-Laudanosine was isolated from A. platyceras for the first time. Isolated compounds were tested for human blood acetylcholinesterase, human plasma butyrylcholinesterase and recombinant prolyl oligopeptidase inhibitory activity. The alkaloids inhibited the enzymes in a dose-dependent manner. The most active compound (–)-munitagine, a pavine alkaloid, inhibited both acetylcholinesterase and prolyl oligopeptidase with IC50 values of 62.3 ± 5.8 µM and 277.0 ± 31.3 µM, respectively.

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“…Compounds isolated in sufficient amounts have been screened for h AChE, h BuCh, POP and GSK-3β inhibition activity. Of the studied alkaloids, only parfumidine and sinactine exhibited interesting inhibition potency against POP (IC 50 = 99 ± 5 and 53 ± 2 μM, respectively) [ 120 ]. The other isolated IAs have been considered inactive.…”

Section: Further Isoquinoline Alkaloidsmentioning

confidence: 99%

Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’s Disease

et al. 2021

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Alzheimer’s disease (AD) is a progressive age-related neurodegenerative disease recognized as the most common form of dementia among elderly people. Due to the fact that the exact pathogenesis of AD still remains to be fully elucidated, the treatment is only symptomatic and available drugs are not able to modify AD progression. Considering the increase in life expectancy worldwide, AD rates are predicted to increase enormously, and thus the search for new AD drugs is urgently needed. Due to their complex nitrogen-containing structures, alkaloids are considered to be promising candidates for use in the treatment of AD. Since the introduction of galanthamine as an antidementia drug in 2001, Amaryllidaceae alkaloids (AAs) and further isoquinoline alkaloids (IAs) have been one of the most studied groups of alkaloids. In the last few years, several compounds of new structure types have been isolated and evaluated for their biological activity connected with AD. The present review aims to comprehensively summarize recent progress on AAs and IAs since 2010 up to June 2021 as potential drugs for the treatment of AD.

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Isoquinoline Alkaloids from Fumaria officinalis L. and Their Biological Activities Related to Alzheimer's Disease

Cited by 35 publications

References 37 publications

Evaluation of Polyphenolic Content, Antioxidant and Diuretic Activities of Six Fumaria Species

Evaluation of Polyphenolic Content, Antioxidant and Diuretic Activities of Six Fumaria Species

Cholinesterase and Prolyl Oligopeptidase Inhibitory Activities of Alkaloids from Argemone platyceras (Papaveraceae)

Recent Progress on Biological Activity of Amaryllidaceae and Further Isoquinoline Alkaloids in Connection with Alzheimer’s Disease

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