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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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Study of biological activity of alkaloids isolated from Fumaria officinalis L. (Fumariaceae) II.
Malý, Lukáš ; Chlebek, Jakub (advisor) ; Opletal, Lubomír (referee)
Malý, L.: Study of biological activity of alkaloids isolated from Fumaria officinalis L. (Fumariaceae) II. Diploma Thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2014, 49 pp. Obtained diethylether extract of Fumaria officinalis L. was separated to fractions in column chromatography with petrol, chloroform and ethanol. Preparative TLC and crystalisation led to isolation of five alkaloids from fraction. Alkaloids were identified by GC-MS and NMR specters, optical rotation and melting point as protopine, cryptopine, (-)-fumaricine, (+)-fumariline and (+)-parfumidine. Isolated alkaloids were tested for their inhibition activity towards acetyl- and butyrylcholinesterase and towards prolyloligopeptidase. Activities were compared with standards. Natural inhibitor galanthamine showed IC50 AChE 1.710 ± 0.065 µM, IC50 BuChE 42.30 ± 1.30 µM. Best inhibition activity showed protopine (IC50 AChE 345.4 ± 24 µM, IC50 BuChE 239.6 ± 22.3 µM) and cryptopine (IC50 AChE 477.71 ± 47.33 µM, IC50 BuChE 270.82 ± 39.12 µM). The highest prolyloligopeptidase inhibition activity showed (+)-parfumidine with IC50 POP 99.2 µM, which was more active than used natural inhibitor baicaline (IC50 POP 605.9 ± 0.021 µM). Synthetic POP...
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Biological aktivity of secondary plants metabolites IV. Alkaloids of Vinca minor L.
Vítovcová, Aneta ; Ločárek, Miroslav (advisor) ; Chlebek, Jakub (referee)
Vítovcová, A.: Biological activity of secondary plants metabolites IV. Alkaloids of Vinca minor L. Diploma thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2016. Extract of Vinca minor L. was separated to fractions in column chromatography. Flash chromatography, preparative TLC and crystalisation led to isolation of two alkaloids from fraction number two and number five. Alkaloids were identified by GC/MS as (+)-vincaminorine and vincorine. These alkaloids were tested for their inhibition activity towards cholinesterase (AChE and BuChe). Obtained activities IC50 were compared with standards (galanthamine, huperzine A). The most interesting activity against galanthamine (AChE 1,710 ± 0,065 µM, BuChE 42,30 ± 1,30 µM) and huperzine A (AChE 0,033 ± 0,001 µM, BuChE > 1000 µM) showed vincorine (AChE > 1000 µM, BuChE 9,75 ± 0,45 µM). His activity toward BuChE is higher than the activity of both standards. Inhibition activities of (+)-vincaminorine (AChE 746,5 ± 84,13 µM, BuChE 684,32 ± 70,66 µM) are negligible. Key words: Alzheimerʼs disease, cholinesterase, Apocynaceae, Vinca minor L., indole alkaloids
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Pharmacognostic study of Alnus spp.
Chlebek, Jakub ; Jahodář, Luděk (advisor) ; Karlíčková, Jana (referee)
Charles Univerzity in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Degree work term: Pharrnacognostic study of Alnus spp. Student: Jakub Chlebek Abstract The degree work Pharmacognostic study of radix Alnus spp. consists of theoretical and experimental part. Theoretical part contains botanical characteristic of the three home species of Czech Republic (Alnus glutinosa, Alnus incana, Alnus rugosa), phytochemical review of the compounds of the genus Alnus and their biological acivities. Experimental part deals with phytochemical and biological study of the roots of Alnus glutinosa. Dried roots of the black alder (Alnus glutinosa) were extracted with Me2CO-H2O (7:3). Final extract was chromatographed over test silica gel colum using a MeOH- CHCl3 gradient (0, 1, 2, 4, 8, 16, 32, 100 %). Elution gave 36 fractions. All the separations were analysed by TLC (hexane-EtOAc MeOH, 2:2:1). The sterols were detected in the fraction No. 7 by TLC, melting point and GC-MS. Major present sterols were β-sitosterol, β-sitostanol, minor sterols campestanol, campesterol. Fractions No. 10 and 19 were analysed by HPLC. Antioxidant activity of the fraction No. 19 was measured with DPPH radical and was low (EC50 0.32 mg/mL). Test silica gel colum experience were used in analysis on...
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In Vitro Study of Anticancer Effect of Amaryllidaceae Montanine Alkaloids
Koutová, Darja ; Havelek, Radim (advisor) ; Tichý, Aleš (referee) ; Chlebek, Jakub (referee)
The possibilities of current therapy of cancer diseases are wide, yet these diseases are still among the most common causes of death. The current findings of biomedical research are increasingly being applied in the treatment strategy of cancer. Understanding the molecular pathways associated with cancer cell formation, progression, and metastasis has led to the discovery of new anticancer drugs and the development of targeted therapies. Simultaneously, knowledge of the molecular mechanism of action of anticancer drugs derived from plants or their semisynthetic derivatives makes it possible to expand the portfolio of cytostatics used so far. The aim of the dissertation was to study the cytotoxic effect of hitherto unexplored montanine-type isoquinoline alkaloids in vitro using a panel of cancer cell lines and a non- cancer cell line of human lung fibroblasts. In the initial phase of the study, the basic types of montanine alkaloids, montanine and pancracine, were isolated, further subjected to cytotoxicity screening using a panel of 9 cancer cell lines of different histotype and one non-cancerous cell line formed by lung fibroblasts. Mean inhibitory concentrations IC50 values were determined. Pancracine, the parent alkaloid of the Amaryllidaceae family, has been comprehensively studied in order to...
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The use of separation techniques in phytochemical analysis
Víchová, Simona ; Jenčo, Jaroslav (advisor) ; Chlebek, Jakub (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Botany Candidate: Simona Víchová Supervisor: RNDr. Jaroslav Jenčo, Ph.D. Title of dissertation thesis: The use of separation techniques in phytochemical analysis The alkaloid extract obtained from stems with immature capsules from Papaver rhoeas L. was subjected to a phytochemical study. The summary extract was separated into individual fractions by Flash chromatography. After performing biological tests for inhibitory activities of acetylcholinesterase and butyrylcholinesterase, the fraction PPR-11 and PPR-12 was selected. The fraction showed the highest activity against butyrylcholinesterase (95.55 ± 0.96 and 97.03 ± 0.79% inhibition of butyrylcholinesterase at 50 /g / ml). The combined PPR 11-12 fractions were purified by preparative chromatography to individual subfractions, which were purified by preparative thin layer chromatography. A monocomponent crystalline substance of alkaloid origin was obtained from the subfraction named PPR 11-12Fr # 8-A. Based on instrumental analysis, the analyte was identified as an alkaloid of the aporphine type (+)-caaverine. The inhibitory activities against acetylcholinesterase and butyrylcholinesterase for (+)-caaverine, were determined and compared with...
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Cytotoxic and cholinesterase inhibitory activity of extracts from selected species of the Centaurea L. genus
Faschingbauer, Jakub ; Chlebek, Jakub (advisor) ; Šafratová, Marcela (referee)
Faschingbauer J.: Cytotoxic and cholinesterase inhibitory activity of extracts from selected species of the Centaurea L. genus. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2019. During the screening of biologically active secondary metabolites of plants carried out at the Department of Pharmaceutical Botany FAF UK, selected taxa of the genus Centaurea (Asteraceae) were investigated. This study is focused on a basic phytohemical research of extracts prepared from Centaurea cyanus, Centaurea jacea, Centaurea scabiosa, Centaurea pseudophrygia, Centuarea stoebe, Centaurea solstitialis a Centaurea benedicta. Extracts were prepared for evidence of the proof reactions of TLC and MS analysis (EI, ESI) to clarify a potential presence of alkaloids. EtOAc and ethanol extracts were evaluated for potential inhibitory activity against human erythrocyte acetylcholinesterase (AChE) and plasma butyrylcholinesterase (BChE) and cytotoxicity against selected 9 tumor lines. C. cyanus alkaloid extract had interesting cholinesterase activity which selectively inhibited BChE (IC50 BChE = 22.62 ± 3.62 μg / ml, IC50 AChE = 221.50 ± 44.56 g / ml). Other EtOAc extracts of selected Centaurea species were considered inactive (IC50 > 100 μg/ml)....
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Vinca minor L. alkaloids and their biological activity VIII.
Hojgrová, Veronika ; Chlebek, Jakub (advisor) ; Šafratová, Marcela (referee)
V. Hojgrová: Alkaloids of Vinca minor L. and their biological activity VIII. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany. Number of pages 69. This diploma thesis deals with the isolation of alkaloids from Vinca minor L. from the family Apocynaceae. Separation of alkaloids from the selected fraction (VM 215-258) or from their subfractions (VM 34-41, VM 86, VM 87-113) was performed by preparative TLC. Two pure alkaloids were isolated from the subfraction (VH 34-41). The first VH-1 alkaloid not yet isolated and the second VH 2 alkaloid: (-)-raucubainin. Alkaloids were identified by EI-MS, LC-MS, NMR and optical rotation and were compared with data in the literature. Isolated alkaloids were tested for acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and prolyloligopeptidase (POP) inhibitory activity and for cytotoxicity. Both substances did not show significant cholinesterase inhibitory activity IC50 against AChE after measurement, only (-)-raucubainin showed a slight activity against BuChE (IC50 = 94 ± 7 μM), VH-1 was found to be inactive (IC50 > 100 μM). POP inhibitory activity has so far only been tested for (-)-raucubainin; was found to be inactive (IC50 > 1000 µM). The results of the cytotoxic activity of the alkaloids...
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Vinca minor L. alkaloids and their biological activity II.
Pavuková, Simona ; Chlebek, Jakub (advisor) ; Hradiská Breiterová, Kateřina (referee)
Pavuková, S.:Vinca minor L. alkaloids and their biological activity II. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové 2020. Vinca minor L. is a species of species of flowering plant, native mainly to central and southern Europe, which containst more than 50 indole alkaloids. During screening of potential plant inhibitors against human acetylcholinesterase (hAChE) and butyrylcholinesterase (HBChE) at our department, an alkaloidal extract from dried aerial parts of Vinca minor demonstrated strong and selective hBChE inhibitory activity with an IC50 value of 13.60 ± 0.83 μg/mL, however, against hAChE was inactive (IC50 value >100 μg/mL). The fraction VM 323 - 327 (4,72 g) was separated by column chromatography on silica gel again with stepwise elution by using chloroform and ethanol and overall 7 joined fractions were obtained.Subsequently, repeated preparative TLC on silica gel led to isolation of three compounds; the newly isolated substance SP-1, (-)-picrinine (SP-2) and deacetylakuammiline (SP-3). Their structures were elucidated with mass spectrometry (ESI), NMR and optical rotation. Isolated alkaloids were tested on ability to inhibit AChE, BuChE, POP a GSK-3β, which are enzymes playing an important role in...
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Study of biological activity of alkaloids isolated from Fumaria officinalis L. (Fumariaceae) II.
Malý, Lukáš ; Chlebek, Jakub (advisor) ; Opletal, Lubomír (referee)
Malý, L.: Study of biological activity of alkaloids isolated from Fumaria officinalis L. (Fumariaceae) II. Diploma Thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2014, 49 pp. Obtained diethylether extract of Fumaria officinalis L. was separated to fractions in column chromatography with petrol, chloroform and ethanol. Preparative TLC and crystalisation led to isolation of five alkaloids from fraction. Alkaloids were identified by GC-MS and NMR specters, optical rotation and melting point as protopine, cryptopine, (-)-fumaricine, (+)-fumariline and (+)-parfumidine. Isolated alkaloids were tested for their inhibition activity towards acetyl- and butyrylcholinesterase and towards prolyloligopeptidase. Activities were compared with standards. Natural inhibitor galanthamine showed IC50 AChE 1.710 ± 0.065 µM, IC50 BuChE 42.30 ± 1.30 µM. Best inhibition activity showed protopine (IC50 AChE 345.4 ± 24 µM, IC50 BuChE 239.6 ± 22.3 µM) and cryptopine (IC50 AChE 477.71 ± 47.33 µM, IC50 BuChE 270.82 ± 39.12 µM). The highest prolyloligopeptidase inhibition activity showed (+)-parfumidine with IC50 POP 99.2 µM, which was more active than used natural inhibitor baicaline (IC50 POP 605.9 ± 0.021 µM). Synthetic POP...
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