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Alkaloids of Amaryllidaceae family: isolation, structural identification, biological activity. III
Hanusová, Petra ; Cahlíková, Lucie (advisor) ; Chlebek, Jakub (referee)
Hanusová P.: Alkaloids of Amaryllidaceae family: isolation, structural identification, biological activity. III. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové, 2017. For phytochemical study was selected plant cultivar Narcissus cv. PROFESSOR EINSTEIN. The aim of the work was to isolate Amaryllidaceae alkaloids in pure form and screening of their biological activities. Summary alkaloidal extract was prepared from 34 kg of fresh bulbs and separated by column chromatography. Preparative TLC and crystallization were used for the isolation of substances from subfraction 6/1. Two pure alkaloids of galanthamine structural type were obtained. The alkaloids were identified based on their MS, NMR analysis and optical rotation as narwedine and lycoraminone. Lycoraminone has been isolated for the first time from natural source. Both substances were tested for their acetylcholinesterase, butyrylcholinestease and prolyl oligopeptidase inhibition activity. Anticancer activity against two gastrointestinal cancer cell lines Caco-2 and HT-29 (colorectal adenocarcinoma) and antimalarial activity has been also measured. Unfortunately, none of isolated alkaloids showed some significant activity in biological assays. Keywords:...
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Alkaloids of Narcissus 'Dutch Master '(Amaryllidaceae) and their biological activity. I.
Vacková, Lucie ; Chlebek, Jakub (advisor) ; Hošťálková, Anna (referee)
Vacková, L.: Alkaloids Narcissus 'Dutch Master' (Amaryllidaceae) and their biological activity. I. Diploma thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2016. From a selected fraction ND-6, which was obtained by column chromatography of an alkaloid extract of Narcissus 'Dutch Master' (preparation of the alkaloid extract and column chromatography was performed by Mgr. Daniela Hulcová within her doctoral thesis), lycorine alakloid O-acetylpluviin was isolated using preparative TLC. Its structure was determined on the basis of MS, NMR analysis, and optical rotation, the obtained data were compared with the literature. The isolated alkaloid was tested on its possibility to inhibit human acetylcholinesterase and butyrylcholinesterase. The activity was expressed as IC 50 values (IC50 AChE = 648.03 ± 53.95 μM, IC50 BChE = 602.50 ± 48.50 μM) and compared with IC50 values of galanthamine, huperzine A and physostigmine. O-acetylpluviine showed a very low inhibitory cholinesterase activity, and so, the alkaloid does not seem to be a suitable cholinesterase inhibitor for potential use in the treatment of Alzheimer's disease. Keywords: Narcissus 'Dutch Master', Amaryllidaceae, lycorine alkaloids, Alzheimer's disease,...
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Alkaloids of Narcissus'Dutch Master ' (Amaryllidaceae) and their biological activity. II.
Dvořáková, Zdeňka ; Chlebek, Jakub (advisor) ; Ločárek, Miroslav (referee)
Dvořáková Zdeňka: Alkaloids of Narcissus 'Dutch Master' (Amaryllidaceae) and their biological activity II. Diploma thesis 2016, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology. The content of this work was isolation of compounds from the selected fraction ND-6 obtained by column chromatography of Narcissus 'Dutch Master' alkaloid extract. Preparation of extract and its column chromatography was performed by Mrg. Daniela Hulcová as part of her doctoral studies. By the means preparative TLC was from fraction ND- 6 homolycorine type alkaloid (+)-O-methyllycorenine gained. Its structure was determined on the basis NMR, GC-MS analysis and optical rotation. The obtained data were compared with facts in known literature. By the isolated alkaloid was determined its cholinesterase inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Its inhibitory activity was expressed as IC50 (M) and compared with known standards galanthamine, physostigmine, and Huperzine A. This alkaloid is inactive against cholinesterase (IC50 AChE > 1000 M, IC50 BChE > 1000 M). On the basis of gained results, we can evaluate this alkaloid from the point of view of cholinesterase inhibition as potentially unusable in the treatment of AD. Key...
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Alkaloids of family Amaryllidaceae and their biological activity.
Gábrlová, Lucie ; Cahlíková, Lucie (advisor) ; Opletal, Lubomír (referee)
Charles University in Prague, Faculty of Pharmacy in Hradci Králové Department of Pharmaceutical Botany and Ecology Lucie Gábrlová Diploma thesis: Alkaloids of family Amaryllidaceae and their biological activity The aim of this diploma thesis was to compile assigned fraction of alkaloidal extract obtained from Chlidanthus fragrans and isolation of at least two alkaloids for testing their biological aktivity. For the processing of the extract and isolation of the alkaloids contained in it was used preparative TLC. The obtained substances were then undegone structure analysis, specifically, there were used EI-MS and NMR methods. Based on the results obtained were isolated substances identified and prepared for screening of their biological activity, which was not part of this diploma thesis anymore. The isolated alkaloids were identified as 6α-hydroxybuphanidrine, crinamidine and crinine. 6α-Hydroxybuphanidrine failed to get enough for biological testing. Inhibitory activity of crinamidine and crinine against erythrocyte AChE and serum BuChE was quite weak. Equally, neither of alkaloids showed stronger ability to inhibit the POP, where for crinamidine was determined IC50 = 0,790 ± 0,062 mM and for crinine IC50 = 1,473 ± 0,122 mM. The measurment of cytotoxic activity has been carried out only with...
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Alkaloids of family Amaryllidaceae and their analogues as potential drugs
Kavková, Zuzana ; Cahlíková, Lucie (advisor) ; Němeček, Jan (referee)
Charles University in Prague Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Zuzana Kavková Supervisor: doc. Ing. Lucie Cahlíková, Ph.D. Title of diploma thesis: Alkaloids of family Amaryllidaceae and their analogues as potential drugs The object of this diploma thesis was to prepare derivatives of alkaloids of Amaryllidaceae family and to deal with their biological activity. These alkaloids are famous for their antibacterial, antiinfectives, antifungal, antimalarial and inhibitory activity against AChE, BuChE and POP and also for cytotoxic effect against cell lines. In the current studies about anticancer activity it was found that the most active alkaloids are Amaryllidaceae alkaloids of these types: lycorine, crinane and pancratistatine. Their biological activity relates closely with their structure. The changes of different parts of the structure can explain the relationship between structure and activity, and also the importance of their organization which is necessary for starting the activity. Based on this finding were for the experiments chosen alkaloids like haemanthamine, haemanthidine and lycorine. An eleven derivatives were prepared and identified mostly by GC-MS and NMR. These derivatives were tested on a wide spectrum of tumor lines....
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Alkaloids of family Amaryllidaceae: genus Lycoris.
Nekolná, Petra ; Cahlíková, Lucie (advisor) ; Macáková, Kateřina (referee)
Author: Petra Nekolná Title: Alkaloids of family Amaryllidaceae: genus Lycoris Diploma thesis Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology 2015, 79 p. The aim of this diploma thesis was to summarize the findings about alkaloids which were isolated from Lycoris plants of Amaryllidaceae family. It contains a botanical characteristics of species of genus Lycoris which were studied phytochemically, a file of alkaloids which were isolated from these plants and findings about the biological activity of these compounds. Within the genus Lycoris 11 species were studied phytochemically and 118 alkaloids were isolated from these plants. Alkaloids which were isolated from Lycoris plants are divided in several structural groups. The lycorine-, homolycorine-, crinine-, galanthamine- and pancratistatine-type alkaloids occur the most numerously. Anticancer, acetylcholinesterase-inhibitory and antimalarial activity of the alkaloids were described. The biological activity of alkaloids is connected with their structure. The most significant anticancer activity was observed in alkaloids from lycorine-, crinine- and pancratistatine-type. Acetylcholinesterase-inhibitory activity was pronounced the most in galanthamine-type alkaloids. The most...
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Neurotropic and antioxidative activity of some selected species of monocotyledonous alkaloidal plants in vitro. VIII.
Breiterová, Kateřina ; Cahlíková, Lucie (advisor) ; Ločárek, Miroslav (referee)
Author: Kateřina Breiterová Title: Neurotropic and antioxidative activity of some selected species of monocotyledonous alkaloidal plants in vitro. VIII. Diploma thesis Charles Univerzity in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology 2015, 101 p. More than 50 % cases of dementia are nowadays caused byAlzheimer's disease (AD). AD is a progressive neurodegenerative disease and it causes gradual memory loss, disorientation and behavioral disorders which affect patient's social and occupational life. AD is characteristic by loss of neurons in some regions of brain - for example hippocampus and cortex. Ethiopathogenesis of this disease is not completely known - that is why the treatment is still just symptomatic. Formation of β-amyloid deposits in brain tissue plays an important role - it is a protein which creates extracellular plagues around neurites and causes their degeneration and death. Intracellular tangles are made up of the changed τ-protein. These tangles also cause death of the neuronal cell. The degeneration of neurons is supported by reactive oxygen radicals too. The another problem is a glutamatergic system disorder. This set of excitatory amino acids is important for correct long-term memory formation. Patients with AD suffer from...
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Biological aktivity of secondary plants metabolites III. Alkaloids of Narcissus tazetta L.
Panchartková, Markéta ; Ločárek, Miroslav (advisor) ; Opletal, Lubomír (referee)
Panchartková, M.: Biological aktivity of secondary plants metabolites III. Alkaloids of Narcissus tazetta L., Diploma thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové, 2015, 67s. Plants from the Amaryllidaceae family contain alkaloids that have multiple biological effects. There is described antiviral, antitumor, antibacterial, antimalarial and anti-fungal effect. Activity against human cholinesterases is important too. The aim of this thesis was to prepare seven alkaloid extracts of individual cultivars of the plants Narcissus and then to realize their GC/MS analysis. Thanks to this analysis, several different structural types of alkaloids from the Amaryllidaceae family were identified. The most frequently identified alkaloids were homolycorine, lycorine, tazettine and galanthamine type. This was followed by the measuring of biological activity against human acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE). The highest inhibitory activity IC50 identified the alkaloidal extract of the Narcissus jonquilla cv. New baby with the values in relation to HuAChE 13,78 ± 1,48 and in relation to HuBuChE 96,12 ± 9,55. The main reason was probably the highest content of galanthamine of all cultivars,...
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Biological aktivity of secondary plants metabolites I. Alkaloids of Narcissus jonquilla L.
Nováková, Dana ; Ločárek, Miroslav (advisor) ; Chlebek, Jakub (referee)
Nováková D.: Biological activity of secondary plants metabolites I. Alkaloids of Narcissus jonquilla L. Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2015, pp. 70. The aim of the diploma thesis was a preparation of alkaloid extracts to identification of alkaloid patterns and measure cholinesterase inhibitory activity. This activity is useful for treating Alzheimer's disease. Alkaloid extracts of seven Narcissus jonquilla L. (Amaryllidaceae) varieties (Sundial, Sundisc, Sweetness, Waterperry, Simplex, Twinkling Yellow, Yazz) were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Twenty-three alkaloids were determined by GC/MS, and ten of them identified from their mass spectra and retention times. All samples exhibited content of galanthamine, most samples contained lycorine and tazettine. Promising HuAChE inhibition activity was demonstrated by Narcissus jonquilla L. cv. Waterperry with IC50 values of 6.53 ± 0.88 μg/mL. The strongest inhibitory activity against HuBuChE was detected in extract from Narcissus jonquilla L. cv. Sundisc with IC50 value of 5.09 ± 0.64 μg/mL. Keywords: Alzheimer's disease, Amaryllidaceae, Narcissus,...
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In vitro anti-proliferation activity alkaloids the Amaryllidaceae
Panenková, Kristýna ; Havlík, Jaroslav (advisor) ; Jarošová, Veronika (referee)
Summary
Natural phytochemicals are currently used in the treatment of many diseases. Cancers are just ones of them and they are ranked among the most common and the most serious. Phytochemicals in the form of cytostatics are used in chemotherapeutic treatment of cancer. In future there could be included among cytostatics also some alkaloids from the family
of Amaryllidaceae, whose testing for a selective cytostatic effect on tumor cell lines
of colorectal carcinoma Caco-2 and HT-29 and on normal cell lines of human intestinal epithelial FHs 74 Int is a subject of this thesis.
There were tested 17 alkaloids isolated from plants of Chlidanthusfragrans, Zephyranthes robusta and Nerine bowdenii. Particularly alkaloids from plant Zephyranthes robusta namely haemanthamine with this values: IC50 = 0.99 plus/minus 0.14 microM for tumor cells, Caco-2, 0.59 plus/minus 0.01 microM for tumor cells HT-29 and 19.47 plus/minus 8.86 microM for normal cells
FHs 74 Int, Lycorine with values IC50 = 0.99 plus/minus 0.08 microM for tumor cells Caco-2, 1.2 plus/minus 0.01 microM for tumor cells HT-29 and 22.68 plus/minus 0.09 microM for normal cells FHs 74 Int and Haemanthidin with values IC50 = 3.29 plus/minus 0.91 microM to tumor cells Caco-2, 1.72 plus/minus 0.11 microM to tumor cells HT-29, and 11.63 plus/minus 0.86 microM for normal cells FHs 74 Int proved a significant
anti-proliferative activity.
From these results there is evident the selectivity against colorectal cancer cell lines. For this reason, those tested alkaloids are suitable for further testing and for study of their biological activity against tumor cells in the terms of in vitro and in vivo.
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