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Alkaloids of Dicranostigma franchetianum (Prain) Fedde and their selected biological activity
Wijaya, Viriyanata ; Opletal, Lubomír (advisor) ; Šmejkal, Karel (referee) ; Klouček, Pavel (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy and Pharmaceutical Botany Candidate: Viriyanata Wijaya, M.Sc. Supervisor: Prof. RNDr. Lubomír Opletal, CSc. Title of Doctoral Thesis: Alkaloids of Dicranostigma franchetianum (Prain) Fedde and their selected biological activity Dicranostigma franchetianum (Prain) Fedde (Papaveraceae) is one of the representatives of the small genus Dicranostigma Hook. f. & Thomson. D. franchetianum (Prain) Fedde has been selected for the phytochemical investigation according to the screening study. In the primary screening of the alkaloid extract for cholinesterases inhibition, the inhibitory value was high (hAChE/hBChE, IC50 g/ml; 1.67 0.11 and 3.85 0.31) and together at least 15 alkaloids were found in the extract. The primary ethanol extract was prepared from 11.8 kg of dry herb (Garden of Medicinal Plants, Faculty of Pharmacy in Hradec Kralove). Using common chromatographic methods, 21 isoquinoline alkaloids of various structural types were isolated. All compounds have been identified using various spectrometric techniques (GC-MS, HPLC- MS, and 1D- and 2D-NMR, optical rotatory. The alkaloids obtained in sufficient amounts were determined for human acetylcholinesterase (hAChE), human butyrylcholinesterase (hBChE), and...
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Amaryllidaceae alkaloids of montanine type and their derivatives as potential drugs.
Maafi, Negar ; Cahlíková, Lucie (advisor) ; Šmejkal, Karel (referee) ; Havlík, Jaroslav (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy and Pharmaceutical Botany Candidate: Negar Maafi Supervisor: Prof. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Amaryllidaceae alkaloids of montanine type and their derivatives as potential drugs. Based on the knowledge of the biological activity of montanine-type alkaloids of Amaryllidaceae, these alkaloids were selected for the preparation of their semisynthetic derivatives to study the relationship between structure and the activity. Derivatives of montanine-type alkaloids were prepared using haemanthamine and montanine as starting substances. The montanine-type alkaloid 3-O- methylpancracine was prepared using intramolecular rearrangement of haemanthamine. Previously isolated montanine from bulbs of Hippeastrum x hybridum cv. Ferrari was used in synthesize of derivatives. In total, more than 80 aliphatic and aromatic derivatives of montanine and 3-O- methylpancracine have been prepared. All compounds were identified using 1D- and 2D-NMR, MS, HRMS, and so forth. The prepared derivatives were screened for a wide range of biological activities (inhibitory potential against hAChE/hBuChE, antimycobacterial, antibacterial and antifungal activity, cytotoxicity, and others). In the hAChE/hBuChE study, the...
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Organosulfur compounds of garlic (Allium sativum).
ŠMEJKAL, Karel
This bachelor thesis is focused on organosulfur compounds of garlic (Allium sativum). The theoretical part describes the genus Allium, organosulfur compounds of garlic, their precursors as well as their formation pathways. The experimental part was focused on the optimalization of an HPLC/PDA method for the isolation of the selected group of organosulfur compounds, i.e. ajothiolanes. This part also describes the preparation of four different samples that were used for HPLC/PDA analysis. The suitability of these samples for isolation of ajothiolanes was analyzed by using HPLC/MS.
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Phytochemical study of individual plant species of Bergenia genus
Hendrychová, Helena ; Tůmová, Lenka (advisor) ; Nagy, Milan (referee) ; Šmejkal, Karel (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy Candidate: Mgr. Helena Hendrychová Supervisor: doc. PharmDr. Lenka Tůmová, CSc. Title of Doctoral Thesis: Phytochemical study of individual plant species of Bergenia genus Bergenia, native to central Asia, is promising source of medicinal compounds mainly in the system of Chinese and Indian traditional medicine. These species have been used for centuries in therapy of various diseases. They are valued for their ability to dissolve kidney or bladder stones. Bergenia plants are used for therapy of pulmonary diseases and cold. They have demonstrated antioxidant, antibacterial, antiviral, immunostimulant, anti-inflammatory, anticancer, antidiabetic, antitussive, hepatoprotective and diuretic effects. The main aim of this thesis was to determine the content of secondary metabolites (arbutin, total polyphenols, bergenin and anthocyanins) in three taxons of Bergenia genus - Bergenia crassifolia (L.) Fritsch, Bergenia ciliata (Haw.) Sternb. a Bergenia x ornata Stein., to compare their biological activities and to identify the most appropriate kind of Bergenia plants with the greatest potential for use in therapy. Plant hybrid B. x ornata was evaluated on the content of phenolic compounds and biological activity...
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Biological activity of alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae)
Hulcová, Daniela ; Cahlíková, Lucie (advisor) ; Valterová, Irena (referee) ; Šmejkal, Karel (referee)
5. Abstract Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Daniela Hulcová Supervisor: Doc. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Biological activity of alkaloids Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae) Keywords: Narcissus pseudonarcissus L. cv. Dutch Master, Amaryllidaceae, alkaloids, AChE, BuChE, POP, GSK-3β, biological activity. Bulbs of Narcissus pseudonarcissus L. cv. the Dutch Master of the Amaryllidaceae family, along with other species of the genus Narcissus, was subjected to a bio-guided study. This study evaluated summary alkaloid extracts using spectrophotometric Ellmans method and GC-MS analysis as a possible source of biologically active Amaryllidaceae alkaloids. Narcissus pseudonarcissus L. cv. Dutch Master was selected as a suitable source for isolation of alkaloids. The fresh bulbs of this daffodil were extracted with ethanol and the crude extract was separated into individual fractions by column chromatography using alumina and silica gel as a stationary phase. Subsequently a stepwise elution was performed, where the mobile phase was a mixture of different ratios of petrol - chloroform and chloroform - ethanol. Some fractions had to be repeatedly partitioned by column...
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NMR Spectroscopy in Structure Elucidation of Isolated Alkaloids
Maříková, Jana ; Kuneš, Jiří (advisor) ; Šmejkal, Karel (referee) ; Šaman, David (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of Organic and Bioorganic Chemistry Candidate: Mgr. Jana Maříková Supervisor: doc. PharmDr. Jiří Kuneš, CSc. Title of Doctoral Thesis: NMR Spectroscopy in Structure Elucidation of Isolated Alkaloids This doctoral thesis deals with the structure elucidation of secondary metabolites isolated from two different plant families - Amaryllidaceae and Apocynaceae. Isolation of analyzed compounds from these plants was performed by colleagues from the Department of Pharmaceutical Botany. Nuclear magnetic resonance (NMR) spectroscopy was the crucial method for the structure determination of isolated alkaloids. Processed data acquired from one-dimensional NMR experiments, as well as multidimensional and dynamic NMR methods, led to the identification of various alkaloid structures. Furthermore, in certain specific cases of the analysis, chiral solvents were employed to determine enantiomeric purity. Other analytical experiments commonly used in the field of natural product identification were carried out. The outcome of this work is the elucidation of 30 alkaloid structures not described in the literature or insufficiently characterized. Several new structural types have been identified, as well as structures representing isolation...
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Alkaloids of genus Hippeastrum (Amaryllidaceae): isolation, identification, biological activity
Al Shammari, Latifah Ajaj M ; Cahlíková, Lucie (advisor) ; Nagy, Milan (referee) ; Šmejkal, Karel (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany Candidate: MSc. Latifah Al Shammari Supervisor: Prof. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Alkaloids of the genus Hippeastrum (Amaryllidaceae): isolation, identification, biological activity. Hippeastrum x hybridum cv. Ferrari was chosen based on results of previous screening studies for detailed phytochemical study for the purpose of isolation of the widest range of AAs. From 25 kg of fresh bulbs was obtained 29,46 g of purified alkaloidal extract, which was processed using column chromatography. Finally, 18 pure alkaloids were isolated including one new homolycorine-type alkaloid (9-O-demethyllycorenine). All compounds were identified by spectrometric techniques (GC-MS, ESI-MS, NMR, optical rotation) and by comparison with literature data. All alkaloids, isolated in sufficient amount, were tested for their biological activities associated with Alzheimer's disease (inhibition of hAChE, hBuChE, and POP), and cytotoxic activity. The inhibitory activity against human cholinesterases was determined in vitro by a modified Ellmanʼs spectrophotometric method. In the hAChE/hBuChE assay, except for 1,2- O,O'-diacetyl-dihydrolycorine which demonstrated a mild hBuChE inhibition potency...
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NMR Spectroscopy in Structure Elucidation of Isolated Alkaloids
Maříková, Jana ; Kuneš, Jiří (advisor) ; Šmejkal, Karel (referee) ; Šaman, David (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of Organic and Bioorganic Chemistry Candidate: Mgr. Jana Maříková Supervisor: doc. PharmDr. Jiří Kuneš, CSc. Title of Doctoral Thesis: NMR Spectroscopy in Structure Elucidation of Isolated Alkaloids This doctoral thesis deals with the structure elucidation of secondary metabolites isolated from two different plant families - Amaryllidaceae and Apocynaceae. Isolation of analyzed compounds from these plants was performed by colleagues from the Department of Pharmaceutical Botany. Nuclear magnetic resonance (NMR) spectroscopy was the crucial method for the structure determination of isolated alkaloids. Processed data acquired from one-dimensional NMR experiments, as well as multidimensional and dynamic NMR methods, led to the identification of various alkaloid structures. Furthermore, in certain specific cases of the analysis, chiral solvents were employed to determine enantiomeric purity. Other analytical experiments commonly used in the field of natural product identification were carried out. The outcome of this work is the elucidation of 30 alkaloid structures not described in the literature or insufficiently characterized. Several new structural types have been identified, as well as structures representing isolation...
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Biological activity of alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae)
Hulcová, Daniela ; Cahlíková, Lucie (advisor) ; Valterová, Irena (referee) ; Šmejkal, Karel (referee)
5. Abstract Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Daniela Hulcová Supervisor: Doc. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Biological activity of alkaloids Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae) Keywords: Narcissus pseudonarcissus L. cv. Dutch Master, Amaryllidaceae, alkaloids, AChE, BuChE, POP, GSK-3β, biological activity. Bulbs of Narcissus pseudonarcissus L. cv. the Dutch Master of the Amaryllidaceae family, along with other species of the genus Narcissus, was subjected to a bio-guided study. This study evaluated summary alkaloid extracts using spectrophotometric Ellmans method and GC-MS analysis as a possible source of biologically active Amaryllidaceae alkaloids. Narcissus pseudonarcissus L. cv. Dutch Master was selected as a suitable source for isolation of alkaloids. The fresh bulbs of this daffodil were extracted with ethanol and the crude extract was separated into individual fractions by column chromatography using alumina and silica gel as a stationary phase. Subsequently a stepwise elution was performed, where the mobile phase was a mixture of different ratios of petrol - chloroform and chloroform - ethanol. Some fractions had to be repeatedly partitioned by column...
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Biological activity of alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae)
Hulcová, Daniela ; Cahlíková, Lucie (advisor) ; Valterová, Irena (referee) ; Šmejkal, Karel (referee)
5. Abstract Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Daniela Hulcová Supervisor: Doc. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Biological activity of alkaloids Narcissus pseudonarcissus L. cv. Dutch Master (Amaryllidaceae) Keywords: Narcissus pseudonarcissus L. cv. Dutch Master, Amaryllidaceae, alkaloids, AChE, BuChE, POP, GSK-3β, biological activity. Bulbs of Narcissus pseudonarcissus L. cv. the Dutch Master of the Amaryllidaceae family, along with other species of the genus Narcissus, was subjected to a bio-guided study. This study evaluated summary alkaloid extracts using spectrophotometric Ellmans method and GC-MS analysis as a possible source of biologically active Amaryllidaceae alkaloids. Narcissus pseudonarcissus L. cv. Dutch Master was selected as a suitable source for isolation of alkaloids. The fresh bulbs of this daffodil were extracted with ethanol and the crude extract was separated into individual fractions by column chromatography using alumina and silica gel as a stationary phase. Subsequently a stepwise elution was performed, where the mobile phase was a mixture of different ratios of petrol - chloroform and chloroform - ethanol. Some fractions had to be repeatedly partitioned by column...
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