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

Hulcová, Daniela; Maříková, Jana; Korábečný, Jan; Hošťálková, Anna; Jun, Daniel; Kuneš, Jiřı́; Chlebek, Jakub; Opletal, Lubomı́r; Simone, Angela De; Nováková, Lucie; Andrisano, Vincenza; Růžička, Aleš; Cahlíková, Lucie

doi:10.1016/j.phytochem.2019.112055

Cited by 48 publications

(45 citation statements)

References 52 publications

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“…The compounds were analyzed by various spectroscopic methods (GC-MS, LC-MS, and 1D and 2D NMR spectroscopy) and identified by comparison with literature data as masonine (1) [22], homolycorine (2) [23], ismine (3) [24], caranine (4) [25], galanthamine (5) [26], narwedine (6) [27], lycoraminone (7) [28], pluviine (8) [25], incartine (9) [29], galanthine (10) [30], lycoramine (11) [26], epinorgalanthamine (12) [31], norlycoramine (13) [32], haemanthamine (14) [32], hippeastrine (15) [33], epimaritidine (16) [34], lycorine (17) [35], tazettine (18) [36], eugenine (19) [37], norpluviine (20) [38], 9-O-demethylmaritidine (21) [39], pancracine (22) [40], and 9-O-demethylhomolycorine (23) [23] (Figure 1). The alkaloids that were isolated were representatives of the homolycorine (1,2,15,19,23), galanthamine (5,6,7,11,12,<...>…”

Section: Isolation and Identification Of Amaryllidaceae Alkaloids Fromentioning

confidence: 99%

“…Plants from this family contain a distinct and still not fully explored group of alkaloids called Amaryllidaceae alkaloids (AA). They are most well known for their broad spectrum of biological properties such as antitumor [2,3], antimalarial [4], anti-inflammatory [5], antimicrobial [6], and AChE-inhibiting activities [7,8]. The AA are classified into 9 main structural types (crinine, galanthamine, haemanthamine, homolycorine, lycorine, montanine, narciclasine, norbelladine, and tazettine) alongside more than 10 others (plicamine, galanthindole, augustamine, graciline, etc.).…”

Section: Introductionmentioning

confidence: 99%

“…For commercial production of AAs, the cultivars are preferred over native species because of their availability. Some Narcissus cultivars have been already studied in detail, and a number of AAs have been isolated throughout the years [7,10,21]. From previous phytochemical studies of 40 differing Narcissus cultivars, 14 AAs were identified in the alkaloid extract of Narcissus cv.…”

Section: Introductionmentioning

confidence: 99%

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Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity

Breiterová

Koutová

Maříková

et al. 2020

Plants

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In this detailed phytochemical study of Narcissus cv. Professor Einstein, we isolated 23 previously known Amaryllidaceae alkaloids (1–23) of several structural types and one previously undescribed alkaloid, 7-oxonorpluviine. The chemical structures were identified by various spectroscopic methods (GC-MS, LC-MS, 1D, and 2D NMR spectroscopy) and were compared with literature data. Alkaloids which had not previously been isolated and studied for cytotoxicity before and which were obtained in sufficient amounts were assayed for their cytotoxic activity on a panel of human cancer cell lines of different histotype. Above that, MRC-5 human fibroblasts were used as a control noncancerous cell line to determine the general toxicity of the tested compounds. The cytotoxicity of the tested alkaloids was evaluated using the WST-1 metabolic activity assay. The growth of all studied cancer cell lines was inhibited by pancracine (montanine-type alkaloid), with IC50 values which were in the range of 2.20 to 5.15 µM.

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Section: Isolation and Identification Of Amaryllidaceae Alkaloids Fromentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity

Breiterová

Koutová

Maříková

et al. 2020

Plants

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“…The pharmaceutical potential of Amaryllidaceae alkaloids including galanthamine, lycorine, haemanthamine, and pancratistatin, is well recognized, primarily as anticancer drugs [ 1 ]. Recently, 21 known Amaryllidaceae alkaloids with various structural types and one previously undescribed alkaloid named narcimatuline were isolated from the fresh bulbs of Narcissus pseudonarcissus L. and identified as potential drugs for use in the treatment of Alzheimer’s disease [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Optimization of Plant Production by Seed Treatment in Two Wild Subspecies of Narcissus pseudonarcissus Rich in Alkaloids

et al. 2020

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The daffodil Narcissus pseudonarcissus L. contains alkaloids of pharmaceutical interest. Wild daffodil populations have diverse genetic backgrounds and various genetic traits of possible importance. Developing protocols for plant production from seeds may ensure the availability of a large reservoir of individuals as well as being important for species with bulbs that are difficult to acquire. The closely related Narcissus pseudonarcissus subsp. munozii-garmendiae and subsp. nevadensis were investigated in this study because the alkaloids isolated from both are of high pharmacological interest. At the dispersal time, the seeds of both were dormant with underdeveloped embryos, i.e., morphophysiological dormancy (MPD). Experiments were conducted outdoors and under controlled laboratory conditions. Embryo growth and the percentages of radicle and seedling emergence were calculated under different temperature–light stratifications. In N. munozii-garmendiae, embryo growth occurred during warm stratification (28/14 °C or 25/10 °C) and the radicle then emerged when the temperature decreased, but the shoot was dormant. In N. nevadensis, the seeds germinated when cold stratified (5 °C) and then incubated at cool temperatures. Thus, N. munozii-garmendiae and N. nevadensis exhibit different levels of MPD, i.e., deep simple epicotyl and intermediate complex, respectively. Plant production protocols from seeds were established for both taxa in this study.

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“…The haemanthamineand crinine-type alkaloids differ only in the position of the 5,10b-ethano bridge, but it appears that the configuration of this bridge has no effect on the AChE inhibition activity [59]. Contrary to these conclusions, AChE/BuChE inhibition activity of some crinine-type AA isolated in the last decade is also interesting [15,17,60,61]. Two crinine-type alkaloids, undulatine (26) and powelline (25), were the most active compounds in the AChE assay of the alkaloids isolated from N. bowdenii, with IC 50 values of 23.5 ± 1.2 µM and 29.1 ± 1.6 µM, respectively [58].…”

Section: Biological Activity Connected With Potential Treatment Of Almentioning

confidence: 99%

The Genus Nerine Herb. (Amaryllidaceae): Ethnobotany, Phytochemistry, and Biological Activity

et al. 2019

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Nerine Herbert, family Amaryllidaceae, is a genus of about 30 species that are native to South Africa, Botswana, Lesotho, Namibia, and Swatini (formerly known as Swaziland). Species of Nerine are autumn-flowering, perennial, bulbous plants, which inhabit areas with summer rainfall and cool, dry winters. Most Nerine species have been cultivated for their elegant flowers, presenting a source of innumerable horticultural hybrids. For many years, species of Nerine have been subjected to extensive phytochemical and pharmacological investigations, which resulted in either the isolation or identification of more than fifty Amaryllidaceae alkaloids belonging to different structural types. Amaryllidaceae alkaloids are frequently studied for their interesting biological properties, including antiviral, antibacterial, antitumor, antifungal, antimalarial, analgesic, cytotoxic, and cholinesterase inhibition activities. The present review aims to summarize comprehensively the research that has been reported on the phytochemistry and pharmacology of the genus Nerine.

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

Cited by 48 publications

References 52 publications

Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity

Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity

Optimization of Plant Production by Seed Treatment in Two Wild Subspecies of Narcissus pseudonarcissus Rich in Alkaloids

The Genus Nerine Herb. (Amaryllidaceae): Ethnobotany, Phytochemistry, and Biological Activity

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