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Vinca minor L. alkaloids and their biological activity (inhibition of human cholinesterases) V.
Vašíčková, Alžběta ; Chlebek, Jakub (advisor) ; Hošťálková, Anna (referee)
Vašíčková A.: Alkaloids of Vinca minor L. and their biological activity (inhibition of human cholinesterases) V. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové 2020. From the selected fraction VM 215-258 were isolated 3 alkaloids by flash chromatography followed, preparative thin layer chromatography and crystallization. Their structure was determined by mass spectroscopy, NMR and optical rotation, and the obtained data were compared with those in literature. Strictamine and minovincinine belong to alkaloids previously isolated, the alkaloid AV-3 has not been isolated yet. These alkaloids were tested for their ability to inhibit human cholinesterases and their inhibitory activity was compared to standards galanthamine and physostigmine. Compound AV-3 showed mild inhibitory activity against BChE (IC50 μM > 86.3 ± 2.3), other alkaloids were considered inactive, their IC50 values against cholinesterases were > 100 μM. Key words: Vinca minor L. (Apocynaceae), vinca alkaloids, minovincinine, strictamine, Alzheimer's disease, acetylcholinesterase, butyrylcholinesterase.
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Vinca minor L. alkaloids and their biological activity III.
Valová, Dominika ; Chlebek, Jakub (advisor) ; Hradiská Breiterová, Kateřina (referee)
Valová D.: Vinca minor L. alkaloids and their biological activity III. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2020, 75 p. Alzheimer's disease (AD) is a progressive, neurodegenerative disorder and it's the most common form of dementia. Because we're still not able to treat the cause of disease, searching for a new substance is relevant. This thesis is focused on isolation of alkaloids from a Vinca minor L. alkaloidal extract as a potential drug. The preparation and column chromatography of the summary extract were performed by Ing. Miroslav Ločárek as a part of his doctoral studies. Subsequent preparative TLC led to the isolation of three compounds. The chemical structures of the isolated alkaloids were elucidated by means of optical rotation, NMR and MS analyses and by comparison of the obtained data with those in the literature. One of the compounds was determined as(-)-vincine, other two compounds have not been isolated yet. Isolated compounds were also tested for their biological activity. Vincine, DV-1 a DV-3 were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Additionally, vincine and DV-3 were also tested for their inhibitory activity on prolyl...
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Secondary metabolites of familly Apocynaceae as a souce of cytotoxic substances
Měšťanová, Kristýna ; Šafratová, Marcela (advisor) ; Hradiská Breiterová, Kateřina (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy and Pharmaceutical Botany Student: Kristýna Měšťanová Thesis supervisor: PharmDr. Marcela Šafratová, Ph.D. Thesis title: Secondary metabolites of the Apocynaceae family as a source of cytotoxically active substances The diploma thesis is focused on elaborating a comprehensive overview of secondary metabolites of the Apocynaceae family with a focus on their application in practice and the importance of Vinca alkaloids in the treatment of Hodgkin's and non- Hodgkin's disease. First, the major representatives of the Apocynaceae family, their constituents and mechanisms of action are mentioned. The uses and the desired and side effects are described and the effects of cardenolides are also stated. The work also deals with Hodgkin's and non-Hodgkin's disease, their incidence, symptomatology and classification of these diseases. Risk factors, including biological and genetic characteristics, are listed. Furthermore, the topic of staging and the treatment of these diseases according to the individual stages of the disease and differences in therapy of specific groups of patients are elaborated. The individual types of lymphomas, their diagnosis and subsequent treatment, including side effects, are described in detail. The...
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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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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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Biological aktivity of secondary plants metabolites X. Alkaloids of Vinca minor L.
Šípková, Pavla ; Hošťálková, Anna (advisor) ; Chlebek, Jakub (referee)
Šípková, P.: Biological activity of secondary plants metabolites X. Alkaloids of Vinca minor L. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2019, 66 s. Key words: Apocynaceae, Vinca minor, alkaloids, isolation, biological activity, screening Alzheimer's disease is a progressive neurodegenerative disease. The number of affected patients is constantly increasing. This disease cannot be treated casually, therefore discovering and testing new substances that could potentially be used in a treatment is very important. The Vinca minor L. fraction after column chromatography was separated by flash chromatography. Isolation of the individual alkaloids was performed by preparative TLC. Based on NMR and MS analyses and comparison with literature, alkaloids were identified as vincarubine and (-)-vinoxine. Modified Ellman's method was used to test cholinesterase inhibitory activity of isolated alkaloids. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) are enzymes, that play a very important role in the pathofysiology of Alzheimer's diasease. (-)-Vinoxine showed relatively high activity against BuChE (IC50 = 24,61 ± 1,71 µM), inhibitory activity against AChE was insignificant (IC50 > 1000µM). Vincarubin did not...
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Vinca minor L. alkaloids and their biological activity (inhibition of human cholinesterases) V.
Vašíčková, Alžběta ; Chlebek, Jakub (advisor) ; Hošťálková, Anna (referee)
Vašíčková A.: Alkaloids of Vinca minor L. and their biological activity (inhibition of human cholinesterases) V. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové 2020. From the selected fraction VM 215-258 were isolated 3 alkaloids by flash chromatography followed, preparative thin layer chromatography and crystallization. Their structure was determined by mass spectroscopy, NMR and optical rotation, and the obtained data were compared with those in literature. Strictamine and minovincinine belong to alkaloids previously isolated, the alkaloid AV-3 has not been isolated yet. These alkaloids were tested for their ability to inhibit human cholinesterases and their inhibitory activity was compared to standards galanthamine and physostigmine. Compound AV-3 showed mild inhibitory activity against BChE (IC50 μM > 86.3 ± 2.3), other alkaloids were considered inactive, their IC50 values against cholinesterases were > 100 μM. Key words: Vinca minor L. (Apocynaceae), vinca alkaloids, minovincinine, strictamine, Alzheimer's disease, acetylcholinesterase, butyrylcholinesterase.
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Vinca minor L. alkaloids and their biological activity III.
Valová, Dominika ; Chlebek, Jakub (advisor) ; Breiterová, Kateřina (referee)
Valová D.: Vinca minor L. alkaloids and their biological activity III. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2020, 75 p. Alzheimer's disease (AD) is a progressive, neurodegenerative disorder and it's the most common form of dementia. Because we're still not able to treat the cause of disease, searching for a new substance is relevant. This thesis is focused on isolation of alkaloids from a Vinca minor L. alkaloidal extract as a potential drug. The preparation and column chromatography of the summary extract were performed by Ing. Miroslav Ločárek as a part of his doctoral studies. Subsequent preparative TLC led to the isolation of three compounds. The chemical structures of the isolated alkaloids were elucidated by means of optical rotation, NMR and MS analyses and by comparison of the obtained data with those in the literature. One of the compounds was determined as(-)-vincine, other two compounds have not been isolated yet. Isolated compounds were also tested for their biological activity. Vincine, DV-1 a DV-3 were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Additionally, vincine and DV-3 were also tested for their inhibitory activity on prolyl...
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Biological aktivity of secondary plants metabolites X. Alkaloids of Vinca minor L.
Šípková, Pavla ; Hošťálková, Anna (advisor) ; Chlebek, Jakub (referee)
Šípková, P.: Biological activity of secondary plants metabolites X. Alkaloids of Vinca minor L. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2019, 66 s. Key words: Apocynaceae, Vinca minor, alkaloids, isolation, biological activity, screening Alzheimer's disease is a progressive neurodegenerative disease. The number of affected patients is constantly increasing. This disease cannot be treated casually, therefore discovering and testing new substances that could potentially be used in a treatment is very important. The Vinca minor L. fraction after column chromatography was separated by flash chromatography. Isolation of the individual alkaloids was performed by preparative TLC. Based on NMR and MS analyses and comparison with literature, alkaloids were identified as vincarubine and (-)-vinoxine. Modified Ellman's method was used to test cholinesterase inhibitory activity of isolated alkaloids. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) are enzymes, that play a very important role in the pathofysiology of Alzheimer's diasease. (-)-Vinoxine showed relatively high activity against BuChE (IC50 = 24,61 ± 1,71 µM), inhibitory activity against AChE was insignificant (IC50 > 1000µM). Vincarubin did not...
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Alkaloids of Vinca minor (Apocynaceae) and their biological activities
Klátilová, Anežka ; Cahlíková, Lucie (advisor) ; Chlebek, Jakub (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical botany Candidate: Anežka Klátilová Supervisor: doc. Ing. Lucie Cahlíková Ph. D. Title of diploma thesis: Alcaloids of Vinca minor (Apocynaceae) and their biological activities The aim of this diploma thesis was to process the assigned fraction isolated from the Vinca minor L. plant and to isolate at least one alkaloid to test its biological activity. Using preparative TLC, the alkaloid was sequentially isolated from the fraction, which was then subjected to a structural analysis. NMR and EI-MS methods were used herein. Thanks to these analyzes, the alkaloid was identified as venoterpine. Furthermore, the alkaloid was prepared to test for biological activity. Thus, the isolated alkaloid was identified as venoterpine and tested for biological activity. The observed inhibitory concentration (IC50) to HuAChE and HuBuChe was more than 500 μM, indicating that venoterpine does not rank as a significant inhibitor of cholinesterase. Likewise, the value of cytotoxic activity, when this activity was found to be greater than 10 μM to colorectal cancer cells as well as to healthy cells, is not significant. Key words: Vinca minor, Apocynaceae, alkaloids, biological activities
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