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Isolation of biologically active alkaloids from Papaver rhoeas with the use of separation methods
Češpivová, Barbora ; Jenčo, Jaroslav (advisor) ; Šafratová, Marcela (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of pharmacognosy and pharmaceutical botany Candidate: Barbora Češpivová Supervisor: RNDr. Jaroslav Jenčo, Ph.D. Title of diploma thesis: Isolation of biologically active alkaloids from Papaver rhoeas with the use of separation methods Alzheimer's disease is a neurodegenerative disorder characterized by progressive cognitive decline. This thesis focuses on the isolation of alkaloids from Papaver rhoeas L. as potential drugs for this disease. Isolating new substances in this area is significant due to the current inability to fully cure the patient through therapy, but rather only to positively influence the disease by delaying its severe stages. A phytochemical study was conducted on an alkaloid extract obtained from the aerial parts and immature capsules of Papaver rhoeas L. Based on biological testing of inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), the fraction exhibiting the highest activity against BuChE, which had not been previously explored, was selected for the isolation of active compounds. This fraction was identified as PPR Fr-B and contained compounds PPR-9 and PPR-10. From the PPR Fr-B fraction, two aporphine-type alkaloids were isolated using separation...
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Alkaloids of Papaver rhoeas L. (Papaveraceae) and their biological activity related to Alzheimerʼs disease VI.
Ludvik, Matěj ; Chlebek, Jakub (advisor) ; Šafratová, Marcela (referee)
Ludvik M., Papaver rhoeas L. (Papaveraceae) alkaloids and their activity related to Alzheimer disease VI., diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové 2023, number of pages 69. This diploma thesis was focused on alkaloids from combined fractions 13-15 of diethylether extract from Papaver rhoeas L. The methods used for extraction of the alcaloids include flash chromatography and preparative thin-layer chromatography. The structures of isolated compounds were determined by using mass spectrometric and spectrophotometric methods (GC-MS, NMR and optical rotation). Alkaloids were identified as galanthamine and N,N-dimethyltryptamine. Subsequently, N,N-dimethyltryptamine was tested for its biological activity against human cholinesterases, specifically acetylcholinesterase and butyrylcholinesterase. Galanthamine was not tested on ability to inhibit cholinesterase, since the compound has been already tested on this activity at the Department of Pharmacognosy and Pharmaceutical Botany. N,N-dimethyltryptamine showed mild inhibitory activity against butyrylcholinesterase (IC50 = 44,14 ± 1,76) and no activity against acetylcholinesterase (IC50 = >100). Despite its mild activity towards butyrylcholinesterase, N,N-dimethyltryptamine can't be used in therapy of Alzheimer's disease,...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity IV.
Emrichová, Eliška ; Šafratová, Marcela (advisor) ; Hradiská Breiterová, Kateřina (referee)
Eliška Emrichová: Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity IV. Diploma thesis 2020. Charles University, faculty of Pharmacy in Hradec Králové, Department of Pharmacognosy. Key words: Geissospermum vellosii, bark, alkaloidal extracts, isolation of alkaloids, GC/MS analysis, biological aktivity, acetylcholinesterase, butyrylcholinesterase. The aim of this study was to isolate at least one pure alkaloid from the extract of Geissospermum vellosii Alemão bark. The whole process involved bark processing, to obtain summary and alkaloid extract and subsequent column chromatography. GV-4, one of the 16 obtained fractions, was separated into 5 subfractions. The GV-4bsubfraction was used to isolate pure alkaloids, processed by preparative thin layer chromatography and crystallization of pure compound. The structure of pure compound was determined by using NMR, GC-MS analysis and optical rotation. This compound was identified as anhydropereirine and was tested its inhibitory activity against human cholinesterases, AChE and BuChE. The alkaloids GV-1-a, GV-8-3-B, GV-9-c were isolated in the course of further work on the extract. Their inhibitory activity against GSK-3β was tested as well as their possibility to cross the blood-brain-barieer with...
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Screening of biological activity of various species of the genus Kalanchoe
Mai, Thanh Tam ; Šafratová, Marcela (advisor) ; Hošťálková, Anna (referee)
Mai T. T.: Screening of biological activity of various species of the genus Kalanchoe, Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmacognosy and Pharmaceutical botany, Hradec Králové 2023. The content of this diploma thesis was the screening of the biological activity of dried flowers, stems and roots of four species from plants of the genus Kalanchoe: Kalanchoe delagoensis Eckl. & Zeyh., Kalanchoe fedschenkoi Raym.-Hamet & H.Perrier, Kalanchoe blossfeldiana Poelln. and Kalanchoe manginii 'Wendy' Raym.-Hamet & H.Perrier. By boiling the dried parts of the plants with ethanol, the summary ethanolic extracts were obtained, which were subjected to control TLC to detect the presence of alkaloids using Dragendorff's reagent. The presence of alkaloids was confirmed in the species Kalanchoe blossfeldiana Poelln, Kalanchoe manginii 'Wendy' Raym.-Hamet & H.Perrier and Kalanchoe delagoensis Eckl. & Zeyh. Furthermore, they were subjected to evidence reactions to identify the substances contained on TLC. In comparison with the literature, the presence of flavonoids, steroids substances, coumarins, triterpenes and alkaloids was confirmed in most plant extracts. Plants extracts of Kalanchoe blossfeldiana Poelln (AL-756 - extract from flowers and stems) and...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity VII.
Strašková, Veronika ; Šafratová, Marcela (advisor) ; Hradiská Breiterová, Kateřina (referee)
Strašková, V.: Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity VII. Diploma thesis, Charles University, Pharmaceutical Faculty in Hradec Králové, Department of pharmacognosy and pharmaceutical botany, Hradec Králové 2023, 75 s. Key words: Geissospermum vellosii, bark, alkaloidal extracts, isolation of alkaloids, GC/MS analysis, biological activity, acetylcholinesterase, butyrylcholinesterase. The main goal of this diploma thesis was isolation of pure alkaloids from the stem bark of Geissospermum vellosii and test their biological activity. G. vellosii is a South American tree from the Apocynaceae family. It is used in traditional medicine for various pathological conditions (e.g., bacterial, inflammatory, and fungal diseases). Indole alkaloids isolated from the stem bark of this tree exhibit significant biological activities such as antineoplastic, antimalarial, and anticholinesterase activities. For processing, the GV-2, GV-7-D, and GV-4-F fractions were selected in this diploma thesis. These fractions were obtained in previous studies from the original alkaloid extract of the stem bark, which showed interesting inhibitory activity against AchE and BuChE (AChE: IC50 = 15,19±0,96 µg/ml, BuChE: IC50 = 0,37±0,049 µg/ml). Four alkaloids,...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity II.
Václavíková, Kateřina ; Šafratová, Marcela (advisor) ; Hradiská Breiterová, Kateřina (referee)
Václavíková, K., Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity II., Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmacognosy, Hradec Králové 2020. The genus Geissospermum growing in South Amerika is important for phytochemistry because it contains indole alkaloids. This southamerican tree is in traditional treatment used for therapy of different diseases such as cognitive disorders, malaria or therapy of cancer. This plant was chosen for next investigation because of screening study that has shown very interesting activity against cholinesterases (IC50 AChE = 10.51 ± 3.03 μg/ml a IC50 BuChE = 0.39 ± 0.057 μg/ml). The aim of this study was to get summary extract from the stem bark, its processing, isolation of at least one pure alkaloid and definition of its structure. Thanks to chromatographic methods the alkaloid extract was separated into 16 fractions, which were processed afterwards. The isolation of alkaloids was from the fraction GV-8, which was separated by flash chromatography and following purification of isolated alkaloids by thin layer chromatography. The only pure alkaloid was isolated form this fraction (vellosimine), in which was tested the inhibition activity against human...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity IV.
Emrichová, Eliška ; Šafratová, Marcela (advisor) ; Hradiská Breiterová, Kateřina (referee)
Eliška Emrichová: Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity IV. Diploma thesis 2020. Charles University, faculty of Pharmacy in Hradec Králové, Department of Pharmacognosy. Key words: Geissospermum vellosii, bark, alkaloidal extracts, isolation of alkaloids, GC/MS analysis, biological aktivity, acetylcholinesterase, butyrylcholinesterase. The aim of this study was to isolate at least one pure alkaloid from the extract of Geissospermum vellosii Alemão bark. The whole process involved bark processing, to obtain summary and alkaloid extract and subsequent column chromatography. GV-4, one of the 16 obtained fractions, was separated into 5 subfractions. The GV-4bsubfraction was used to isolate pure alkaloids, processed by preparative thin layer chromatography and crystallization of pure compound. The structure of pure compound was determined by using NMR, GC-MS analysis and optical rotation. This compound was identified as anhydropereirine and was tested its inhibitory activity against human cholinesterases, AChE and BuChE. The alkaloids GV-1-a, GV-8-3-B, GV-9-c were isolated in the course of further work on the extract. Their inhibitory activity against GSK-3β was tested as well as their possibility to cross the blood-brain-barieer with...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity VI.
Váňová, Lucie ; Šafratová, Marcela (advisor) ; Chlebek, Jakub (referee)
Lucie Váňová: Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity IV. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmacognosy and Pharmaceutical Botany, Hradec Králové 2022. Key words: bark, Geissospermum vellosii Allemão, alkaloids, preparative TLC, GC-MS, NMR, (+)-19,20-dehydrotubifolidine, aspidolimidine, geissoreticulatine, inhibition activity, AChE, BuChE, Alzheimer's disease The aim of this diploma thesis was the isolation of at least 3 alkaloids in pure form from the GV-5 fraction, which was extracted from the bark of the South American tree Geissospermum vellosii Allemão. By using preparative thin layer chromatography (TLC), 9 subfracions (GV-5-A až GV-5-I) were acquired from this fraction. Those that were of sufficient mass were subsequently subjected to further division. Three alkaloids in pure form were isolated through purification using preparative TLC: GV-5-B-3-A, GV-5-C-4-C, GV-5-C-2-B-1. Gained active substances from this plant were analyzed by gas chromatography- mass spektrometry (GC-MS) and nuclear magnetic resonance (NMR). By comparing the obtained alcaloid's spectra with available data and literature, those alkaloids were identified as: (+)-19,20-dehydrotubifolidine...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity VIII.
Pelnář, Tomáš ; Šafratová, Marcela (advisor) ; Siatka, Tomáš (referee)
ISOLATION OF ALKALOIDS OF THE SPECIES GEISSOSPERMUM VELLOSII ALLEMÃO AND STUDY THEIR BIOLOGICAL ACTIVITY VIII. PELNÁŘ T. 1 , JANOUŠEK J. 2 , HRADISKÁ BREITEROVÁ K. 1 , ŠAFRATOVÁ M. 1 1 Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Czech Republic 2 Biomedical Research Center, University Hospital in Hradec Králové, Czech Republic e-mail: pelnart@faf.cuni.cz The aim of this work was to determine the activity of indole alkaloids, including their separation and purification from the South American tree Geissopsermum vellossi, which is used in traditional medicine to treat various diseases. It shows possible use in the treatment of benign prostatic hyperplasia, tumor treatment, plasmodial diseases, and especially cognitive disorders. The isolated structures were subsequently tested for inhibition of human cholinesterases.1 These substances could be used to treat Alzheimer's disease, which has been increasing in recent years. We are not yet able to stop disease, just slow it down. The starting product was a summary alkaloid extract from crushed tree bark, which showed very interesting activity against AChE and BChE (IC50 = 15,19±0,96 µg/ml for AChE and IC50 = 0,37±0,049 µg/ml for BChE). The GV-4 fraction has been processed using...
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Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity V.
Vlková, Markéta ; Šafratová, Marcela (advisor) ; Cahlíková, Lucie (referee)
1 ABSTRACT Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy and Pharmaceutical Botany Candidate: Markéta Vlková Supervisor: PharmDr. Marcela Šafratová, Ph.D. Title of Diploma Thesis: Isolation of alkaloids of the species Geissospermum vellosii Allemão and study of their biological activity V. The study was supported by projects SVV 260 550 and PROGRES Q42 Key words: Geissospermum vellosii, isolation, indol alkaloids, Alzheimer's disease, AChE, BChE, cytotoxicity, Apocynaceae The Geissospermum vellosii, a tree traditionally growing in the Amazon rainforest is rich in indole alkaloids, which showed a potential effect in the treatment of cognitive degeneration such as Alzheimer's disease. In the previous study of ADINACO group, a diethylether alkaloidal extract from 43 kg of dried crushed stem bark was prepared and separated by column chromatography into 16 fractions (GV). In this study, we used flash chromatography to further separate the fraction GV-3 (1.37 g) into 11 subfractions (A-K). Based on control TLC, we focused on subfractions C and J, from which three alkaloids were isolated by preparative TLC. The NMR and GC/MS-EI techniques determined the structure and confirmed the purity of the obtained compounds. The compounds were identified as 19,20-dihydrovincanine,...
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