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Preparation of Lupane and 18alfa-Oleanane Triterpenoids for Biological Testing
Kvasnica, Miroslav ; Šarek, Jan (advisor) ; Klinotová, Eva (referee) ; Drašar, Pavel (referee) ; Pouzar, Vladimir (referee)
T =t a a !r a a a t I a a a - - 5. CONCLUSION 5. CONCLUSION This work was focused on the synthesis of new triterpenoids - named highly oxidized derivatives of 18o-oleanane, their reductive products or products with heteroatoms, for example fluorine, nitrogen, suflur or phosphorus. Part of this thesis was focused on reactions of lupane and I 8cr-oleanane triterpenoids with Lawesson's reagent. l. Highly oxidized l8cr-oleanane derivatives were synthesised, in particular on A-ring. Commercially available reagents were used for these oxidations: MCPBA, SeOr or pero- xyacetic acid (as a persteril). A group of seco derivatives was prepared by reactions with in situ prepared RuOo. A great deal of this section has been already published in scienti- fic journal.2a 2. Agroup of 18ct-oleanane alcohols (e.g. L5,16a,16b, 19, 20,22) was prepared from some oxidized derivatives (e.g.2,3, 13, L8) by reactions with LiAlHo or NaBI{.. 3. Reactions of some ketones were carried out (e.g. 3) with fluorinating agent DAST for preparation of new fluorous derivatives (e.g. 24,25). The same ketones reacted with ethanedithiol to afford new dithiolanes (e.g. 26). Diketone 3 was'also used for synhesis of several nitrogen containing derivatives. Preparation of pyrazine 27 and quinoxaline 28 has been already published in scientific...
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Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III
Šafratová, Marcela ; Cahlíková, Lucie (advisor) ; Kokoška, Ladislav (referee) ; Drašar, Pavel (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Marcela Šafratová Supervisor: Doc. Ing. Lucie Cahlíková PhD. Title of Doctoral Thesis: Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III Key words: Narcissus poeticus cv. Pink Parasol, Amaryllidaceae, alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase, cytotoxicity Bulbs of Narcissus poeticus. cv. Pink Parasol were selected as a source of Amaryllidaceae alkaloids for study of their biological activity. Concentrated alkaloid extract has been prepared were prepared by standard extraction and fractionated in aluminium oxide column chromatography column using step gradient elution with petrol, chloroform and ethanol. Column chromatography, vacuum liquid column chromatography, preparative TLC and crystallizations resulted in the isolation of 15 alkaloids, 2 of them were identified as new structures. The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS, optical rotation) and by comparison with literature. Alkaloids isolated in sufficient amounts were tested on their inhibitory ability of human...
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Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III
Šafratová, Marcela ; Cahlíková, Lucie (advisor) ; Drašar, Pavel (referee) ; Kokoška, Ladislav (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Marcela Šafratová Supervisor: Doc. Ing. Lucie Cahlíková PhD. Title of Doctoral Thesis: Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III Key words: Narcissus poeticus cv. Pink Parasol, Amaryllidaceae, alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase, cytotoxicity Bulbs of Narcissus poeticus. cv. Pink Parasol were selected as a source of Amaryllidaceae alkaloids for study of their biological activity. Concentrated alkaloid extract has been prepared were prepared by standard extraction and fractionated in aluminium oxide column chromatography column using step gradient elution with petrol, chloroform and ethanol. Column chromatography, vacuum liquid column chromatography, preparative TLC and crystallizations resulted in the isolation of 15 alkaloids, 2 of them were identified as new structures. The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS, optical rotation) and by comparison with literature. Alkaloids isolated in sufficient amounts were tested on their inhibitory ability of human...
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Study of Chemical Constituents of Taxons from Order Laurales and Ranunculales with Potential Neuroprotective Activity
Hošťálková, Anna ; Opletal, Lubomír (advisor) ; Kokoška, Ladislav (referee) ; Drašar, Pavel (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Anna Hošťálková Supervisor: Prof. RNDr. Lubomír Opletal, CSc. Title of Doctoral Thesis: Study of chemical constituents of taxons from order Laurales and Ranunculales with potential neuroprotective activity. Key words: Berberis vulgaris, Peumus boldus, Hydrastis canadensis, isoquinoline alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase. Commercial goldenseal extrakt, boldo leaves and barberry root bark were selected as sources of isoquinoline alkaloids for study of their biological activity. Mixtures of summary tertiary alkaloids were prepared by standard extraction and subsequently fractionated in aluminium oxide chromatography column using the step gradient elution with petrol, chloroform and ethanol. Repeated column chromatographies, preparative TLC and crystallizations led to the isolation of 28 isoquinoline alkaloids, 6 of them were identificated as new structures (some of them were propably artifacts). The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS) and by comparison with literature. Isolated alkaloids in sufficient amount were tested on ability to inhibit human...
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Preparation of Lupane and 18alfa-Oleanane Triterpenoids for Biological Testing
Kvasnica, Miroslav ; Šarek, Jan (advisor) ; Klinotová, Eva (referee) ; Drašar, Pavel (referee) ; Pouzar, Vladimir (referee)
T =t a a !r a a a t I a a a - - 5. CONCLUSION 5. CONCLUSION This work was focused on the synthesis of new triterpenoids - named highly oxidized derivatives of 18o-oleanane, their reductive products or products with heteroatoms, for example fluorine, nitrogen, suflur or phosphorus. Part of this thesis was focused on reactions of lupane and I 8cr-oleanane triterpenoids with Lawesson's reagent. l. Highly oxidized l8cr-oleanane derivatives were synthesised, in particular on A-ring. Commercially available reagents were used for these oxidations: MCPBA, SeOr or pero- xyacetic acid (as a persteril). A group of seco derivatives was prepared by reactions with in situ prepared RuOo. A great deal of this section has been already published in scienti- fic journal.2a 2. Agroup of 18ct-oleanane alcohols (e.g. L5,16a,16b, 19, 20,22) was prepared from some oxidized derivatives (e.g.2,3, 13, L8) by reactions with LiAlHo or NaBI{.. 3. Reactions of some ketones were carried out (e.g. 3) with fluorinating agent DAST for preparation of new fluorous derivatives (e.g. 24,25). The same ketones reacted with ethanedithiol to afford new dithiolanes (e.g. 26). Diketone 3 was'also used for synhesis of several nitrogen containing derivatives. Preparation of pyrazine 27 and quinoxaline 28 has been already published in scientific...
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Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III
Šafratová, Marcela ; Cahlíková, Lucie (advisor) ; Kokoška, Ladislav (referee) ; Drašar, Pavel (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Marcela Šafratová Supervisor: Doc. Ing. Lucie Cahlíková PhD. Title of Doctoral Thesis: Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III Key words: Narcissus poeticus cv. Pink Parasol, Amaryllidaceae, alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase, cytotoxicity Bulbs of Narcissus poeticus. cv. Pink Parasol were selected as a source of Amaryllidaceae alkaloids for study of their biological activity. Concentrated alkaloid extract has been prepared were prepared by standard extraction and fractionated in aluminium oxide column chromatography column using step gradient elution with petrol, chloroform and ethanol. Column chromatography, vacuum liquid column chromatography, preparative TLC and crystallizations resulted in the isolation of 15 alkaloids, 2 of them were identified as new structures. The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS, optical rotation) and by comparison with literature. Alkaloids isolated in sufficient amounts were tested on their inhibitory ability of human...
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Study of Chemical Constituents of Taxons from Order Laurales and Ranunculales with Potential Neuroprotective Activity
Hošťálková, Anna ; Opletal, Lubomír (advisor) ; Kokoška, Ladislav (referee) ; Drašar, Pavel (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Anna Hošťálková Supervisor: Prof. RNDr. Lubomír Opletal, CSc. Title of Doctoral Thesis: Study of chemical constituents of taxons from order Laurales and Ranunculales with potential neuroprotective activity. Key words: Berberis vulgaris, Peumus boldus, Hydrastis canadensis, isoquinoline alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase. Commercial goldenseal extrakt, boldo leaves and barberry root bark were selected as sources of isoquinoline alkaloids for study of their biological activity. Mixtures of summary tertiary alkaloids were prepared by standard extraction and subsequently fractionated in aluminium oxide chromatography column using the step gradient elution with petrol, chloroform and ethanol. Repeated column chromatographies, preparative TLC and crystallizations led to the isolation of 28 isoquinoline alkaloids, 6 of them were identificated as new structures (some of them were propably artifacts). The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS) and by comparison with literature. Isolated alkaloids in sufficient amount were tested on ability to inhibit human...
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Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III
Šafratová, Marcela ; Cahlíková, Lucie (advisor) ; Drašar, Pavel (referee) ; Kokoška, Ladislav (referee)
Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany and Ecology Candidate: Mgr. Marcela Šafratová Supervisor: Doc. Ing. Lucie Cahlíková PhD. Title of Doctoral Thesis: Study of inhibition (toxicity) activity of alkaloids from selected plant species of Amaryllidaceae family on human enzyme systems (in vitro study) III Key words: Narcissus poeticus cv. Pink Parasol, Amaryllidaceae, alkaloids, acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase, cytotoxicity Bulbs of Narcissus poeticus. cv. Pink Parasol were selected as a source of Amaryllidaceae alkaloids for study of their biological activity. Concentrated alkaloid extract has been prepared were prepared by standard extraction and fractionated in aluminium oxide column chromatography column using step gradient elution with petrol, chloroform and ethanol. Column chromatography, vacuum liquid column chromatography, preparative TLC and crystallizations resulted in the isolation of 15 alkaloids, 2 of them were identified as new structures. The chemical structures of isolated compounds were determined on the basis of spectrometric techniques (NMR, MS, optical rotation) and by comparison with literature. Alkaloids isolated in sufficient amounts were tested on their inhibitory ability of human...
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