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Alkaloids of genus Narcissus: isolation, structural identification, biological activity
Šimková, Hana ; Cahlíková, Lucie (advisor) ; Opletal, Lubomír (referee)
Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany Author: Hana Šimková Supervisor: prof. Ing. Lucie Cahlíková, Ph.D. Title of diploma thesis: Alkaloids of genus Narcissus: isolation, structural identification, biological activity Key words: Narcissus, alkaloids, biological activity, Alzheimer's disease, cytotoxic activity The aim of the diploma thesis was an isolation of alkaloids with a focus on minor fractions. These fractions were obtained from the summary alkaloid extract of Narcissus pseudonarcissus cv. Carlton. The method of preparative TLC was used for the isolation of alkaloids. Three substances of alkaloid origin marked as Fj 3-4/kr, F 7/2-1, F 7/2-3 were isolated from the assigned fractions. These substances were identified as alkaloids of homolycorine type lycorenine, homolycorine and hippeastrine by using GC-MS, NMR and optical rotation. The results were also compared with data in the literature. These three alkaloids were tested for their inhibitory activity against AChE, BuChE, POP and GSK-3β. The inhibitory activity against AChE and BuChE was compared with the reference substances galanthamine (IC50 AChE = 1,71 ± 0,07 μM, IC50 BuChE = 42,3 ± 1,3 μM) and huperzine A (IC50 AChE = 0,033 ± 0,001 μM, IC50 BuChE> 1000 μM). The inhibitory...
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Alkaloid isolation from Vinca minor and their biological activity II.
Míšek, Vít ; Hošťálková, Anna (advisor) ; Chlebek, Jakub (referee)
Míšek, V.: Alkaloid isolation from Vinca minor and their biological activity II. Diploma thesis, Faculty of Pharmacy in Hradec Králové, Charles University, Department of Pharmacognosy and Pharmaceutical Botany, Hradec Králové, 2023 Supervisor: PharmDr. Anna Hošťálková, Ph.D. Key words: secondary metabolites, Apocynaceae, Vinca minor, cholinesterases, cytotoxicity, alkaloids, isolation, biological activity Alzheimer's disease (AD) is a neurodegenerative disease characterized by the progressive development of cognitive dysfunction, impact on normal daily functions and neuropsychiatric symptoms. There is a limited number of compounds for pharmacotherapy AD, moreover, AD cannot be treated causally. Therefore, research focused on the discovery of new active substances, including natural origin ones, could be one of the possible options for widening the pool of substances used in AD treatment. An extract was prepared by extracting the aerial parts of Vinca minor L. with ethanol and subsequent liquid-luquid extractin at different pH. Using column and preparative thin layer chromatography, this extract was further processed to isolate individual alkaloids. The structure of isolated alkaloids was determined by spectrometric methods (GC/MS and NMR). After comparing the obtained structures with the literature...
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Alkaloid isolation from Fontinalis antipyretica Hedw.
Malá, Marie ; Martin, Jan (advisor) ; Kašparová, Marie (referee)
Marie Malá, Isolation of alkaloids from Fontinalis antipyretica, thesis, Charles University in Prague, Faculty Of Pharmacy in Hradec Králové, 2012, 55 pages. The thesis Isolation of alkaloids from Fontinalis antipyretica, deals with quantification and isolation of substances of alkaloid character from above mentioned moss. The plant material collected in different localities in Czech Republic was extracted with methanol. The extract was subesquently used for isolation of alkaloids by HPLC method. The obtained amount of β-Carboline alkaloid was 2,4mg. The results of HPLC analysis (retention time, spectrum) of this sample were compared to harmalol standard and found the same. Finally the H NMR analysis proved, that the substance obtained by this experiment is not harmalol, but someother β-Carboline alkaloid.
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Alkaloid and flavonoid content in Fontinalis antipyretica Hedw.
Ptáčníková, Lucie ; Martin, Jan (advisor) ; Tůmová, Lenka (referee)
Lucie Ptáčníková, The volume of alkaloids and flavonoids in Fontinalis antipyretica, Thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, thesis tutor: PharmDr. Jan Martin, PhD., Hradec Králové, 2012, 55 pages. Thesis called "Content of alkaloids and flavonoids in Fontinalis anitpyretica" establishes alkaloids and flavonoids and identifies one substance of these alkaloids in the above-mentioned water moss. The main purpose of this thesis was to obtain samples of Fontinalis antipyretica from selected locations in the Czech Republic (Ledce, Rychnovek, Kunvald). Next purpose was to determine alkaloids and flavonoids of collected material, isolated one substance of alkaloid character and verify identity of selected alkaloid. The content of alkaloids and flavonoids was determined by using the high-performance liquid chromatography (HPLC). The results show that β - carboline alkaloid harmin was determined by consensus UV spectrum and retention time with standard. Consequently flavonoids called myricetin and hyperosid was determined. Identity of β - carboline alkaloid harmin was verified by using NMR analysis. Keywords: alkaloids - harmalol - harmin - Fontinalis antipyretica - flavonoids
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Alkaloids of genus Narcissus: isolation, structural identification, biological activity
Šimková, Hana ; Cahlíková, Lucie (advisor) ; Opletal, Lubomír (referee)
Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany Author: Hana Šimková Supervisor: prof. Ing. Lucie Cahlíková, Ph.D. Title of diploma thesis: Alkaloids of genus Narcissus: isolation, structural identification, biological activity Key words: Narcissus, alkaloids, biological activity, Alzheimer's disease, cytotoxic activity The aim of the diploma thesis was an isolation of alkaloids with a focus on minor fractions. These fractions were obtained from the summary alkaloid extract of Narcissus pseudonarcissus cv. Carlton. The method of preparative TLC was used for the isolation of alkaloids. Three substances of alkaloid origin marked as Fj 3-4/kr, F 7/2-1, F 7/2-3 were isolated from the assigned fractions. These substances were identified as alkaloids of homolycorine type lycorenine, homolycorine and hippeastrine by using GC-MS, NMR and optical rotation. The results were also compared with data in the literature. These three alkaloids were tested for their inhibitory activity against AChE, BuChE, POP and GSK-3β. The inhibitory activity against AChE and BuChE was compared with the reference substances galanthamine (IC50 AChE = 1,71 ± 0,07 μM, IC50 BuChE = 42,3 ± 1,3 μM) and huperzine A (IC50 AChE = 0,033 ± 0,001 μM, IC50 BuChE> 1000 μM). The inhibitory...
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Derivatives of Amaryllidaceae alkaloid vittatine as potential drugs
Teplanská, Michaela ; Hulcová, Daniela (advisor) ; Kučera, Tomáš (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmacognosy Candidate: Michaela Teplanská Supervisor: PharmDr. Daniela Hulcová, Ph.D. Title of diploma thesis: Derivatives of Amaryllidaceae alkaloid vittatine as potential drugs Haemanthamine type Amaryllidaceae alkaloids are characterized by interesting biological activity. This group also includes alkaloid vittatine with antitumor, antibacterial, antifungal and antimalarial effects. Although vittatine does not inhibit cholinesterases, its derivatives have shown promising activity against butyrylcholinesterase, which is one of the targets of potential drugs in the treatment of Alzheimer's disease. Another series of semisynthetic vittatine derivatives was prepared in order to examine their biological activity. Reactions with acyl chlorides gave 11 aromatic esters. Identification of the prepared substances was performed by ESI HRMS, NMR and optical rotation measurements. The derivatives were tested for inhibitory activity against human cholinesterases. The results show that the substances were not active against acetylcholinesterase, but almost all of them inhibited butyrylcholinesterase. The most active was 3-O-(6-chloro-2- fluoro-3-methylbenzoyl)vittatine with an IC50 value 0.29 ± 0.03 μM. According to the calculated value...
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Alkaloids from the wood of the species Liriodendron tulipifera L. and their activity against human cholinesterases
Hrušková, Magda ; Hošťálková, Anna (advisor) ; Chlebek, Jakub (referee)
Hrušková M.: Alkaloids from the wood of the species Liriodendron tulipifera L. and their activity against human cholinesterase. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2018. Key words: Liriodendron tulipifera, alkaloids, biological activity. The alkaloids from the wood of the species Liriodendron tulipifera L. were isolated and their inhibitory activity against acetylcholinesterase, butyrylcholinesterase and propyl oligopeptidase, which are enzymes involved in the pathophysiology of Alzheimer's disease (AD), was investigated. The search and testing of new substances, which are used in AD treatment, is very relevant, as this disease cannot be casually treated yet. An alkaloid extract of Liriodendron tulipifera L. wood was tested in a preliminary testing for inhibitory activity against human cholinesterase. Because of the promising results, it was chosen for an isolation and identification of possible effective alkaloids. The extract was carried out by column chromatography with a step gradient elution. A preparative TLC was used to isolate alkaloids. The identification of alkaloids was done by structural analyses (NMR and MS). Optically active substances were measured for their optical rotation. A modified...
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Preparation of lycorine derivatives and their biological activity
Lipovská, Kamila ; Cahlíková, Lucie (advisor) ; Kuneš, Jiří (referee)
Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany Candidate: Kamila Lipovská Supervisor: doc. Ing. Lucie Cahlíková, Ph.D. Title of Diploma thesis: Preparation of lycorine derivatives and their biological activity The plants of the Amaryllidaceae family are one of the most important sources of biologically active alkaloids. Lycorine, a phenanthridine alkaloid, isolated from various species of the Amaryllidaceae plant family, has attracted considerable attention due to its promising biological activities. Specifically, its anticancer properties have been evaluated in vitro and in vivo in various preclinical models of human cancers. Further biological effects manifested by lycorine are: antiviral, antibacterial, antifungal, antiplasmodial, anti-oxidant, anti-inflammatory and insect antifeedant effects, as well as ascorbic acid biosynthesis and RNA inhibitory activity. So far, lycorine was used for preparation of many derivatives by modification of different functional groups in its molecule, and screened for a various biological activities such as anticancer activity, inhibition of cholinesterases, antiplasmodial, antitrypanosomal, antiviral and anti-Trichomonas vaginalis activity. The present work deals with the preparation of lycorine derivatives and their...
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Alkaloids from the wood of the species Liriodendron tulipifera L. and their activity against human cholinesterases
Hrušková, Magda ; Hošťálková, Anna (advisor) ; Chlebek, Jakub (referee)
Hrušková M.: Alkaloids from the wood of the species Liriodendron tulipifera L. and their activity against human cholinesterase. Diploma thesis, Charles University, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany, Hradec Králové, 2018. Key words: Liriodendron tulipifera, alkaloids, biological activity. The alkaloids from the wood of the species Liriodendron tulipifera L. were isolated and their inhibitory activity against acetylcholinesterase, butyrylcholinesterase and propyl oligopeptidase, which are enzymes involved in the pathophysiology of Alzheimer's disease (AD), was investigated. The search and testing of new substances, which are used in AD treatment, is very relevant, as this disease cannot be casually treated yet. An alkaloid extract of Liriodendron tulipifera L. wood was tested in a preliminary testing for inhibitory activity against human cholinesterase. Because of the promising results, it was chosen for an isolation and identification of possible effective alkaloids. The extract was carried out by column chromatography with a step gradient elution. A preparative TLC was used to isolate alkaloids. The identification of alkaloids was done by structural analyses (NMR and MS). Optically active substances were measured for their optical rotation. A modified...
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Alkaloid and flavonoid content in Fontinalis antipyretica Hedw.
Ptáčníková, Lucie ; Martin, Jan (advisor) ; Tůmová, Lenka (referee)
Lucie Ptáčníková, The volume of alkaloids and flavonoids in Fontinalis antipyretica, Thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, thesis tutor: PharmDr. Jan Martin, PhD., Hradec Králové, 2012, 55 pages. Thesis called "Content of alkaloids and flavonoids in Fontinalis anitpyretica" establishes alkaloids and flavonoids and identifies one substance of these alkaloids in the above-mentioned water moss. The main purpose of this thesis was to obtain samples of Fontinalis antipyretica from selected locations in the Czech Republic (Ledce, Rychnovek, Kunvald). Next purpose was to determine alkaloids and flavonoids of collected material, isolated one substance of alkaloid character and verify identity of selected alkaloid. The content of alkaloids and flavonoids was determined by using the high-performance liquid chromatography (HPLC). The results show that β - carboline alkaloid harmin was determined by consensus UV spectrum and retention time with standard. Consequently flavonoids called myricetin and hyperosid was determined. Identity of β - carboline alkaloid harmin was verified by using NMR analysis. Keywords: alkaloids - harmalol - harmin - Fontinalis antipyretica - flavonoids
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