Os produtos naturais têm se destacado ao longo dos anos como princípios ativos eficazes e muitos deles são utilizados até hoje no tratamento de certas doenças. Considerando as informações advindas da medicina popular, o vasto potencial terapêutico de alcalóides e a quimiotaxonomia dos vegetais, a família Amaryllidaceae se candidata a celeiro de novas moléculas bioativas. Verifica-se que os compostos alcaloídicos isolados a partir desta família apresentam atividades biológicas bem reportadas, tais como, antitumoral, antiviral, antimalárica, antiinflamatória e anticolinesterásica. Assim, o objetivo deste trabalho foi o isolamento de alcalóides a partir de Hippeastrum morelianum Lem. e Hippeastrum santacatarina (Traub) Dutilh, além da investigação das atividades antioxidante, anticolinesterásica e antimicrobiana dos produtos isolados, bem como dos extratos obtidos. O material de ambos vegetais foi separado em bulbos, raízes e folhas e submetido à extração ácido-base, clássica para alcalóides.Com auxílio de métodos cromatográficos a partir de H. morelianum foram isolados doze produtos, com destaque para o alcalóide candimina (110 mg) sendo este trabalho a fonte pioneira dos dados espectroscópicos completos deste alcalóide, bem como das primeiras avaliações farmacológicas do mesmo. A partir de H. santacatarina foram isolados três produtos, com destaque para a licorina (100 mg). Todos os extratos avaliados, de ambos vegetais, mostraram potenciais efeitos antioxidante (10 mg/ml) e anticolinesterásico (0,1 mg/ml), porém não antimicrobiano. Quanto aos produtos isolados destaca-se a atividade antioxidante da licorina, verificada pelo método da inativação do radical 2,2-difenil-1-picrilidrazila (DPPH), com IC50: 112,4 μg/ml. Entretanto, no screening de atividade anticolinesterásica todos os isolados de H. morelianum, exceto o produto A12, apresentaram resultado positivo com 5 μg de amostra. Para H. santacatarina, a licorina, assim como os isolados B2 e B3, demonstraram atividade anticolinesterásica, também com 5 μg de amostra. Finalmente, não foi detectada atividade antimicrobiana para licorina e candimina, alcalóides majoritários em suas plantas de origem, até 0,5 mg/ml. / Natural products have been employed over the years as active compounds, and many of them are currently used in the treatment of certain diseases. Considering the information stemming from the popular medicine, the vast therapeutic potential of alkaloids and quimiotaxonomy of plants, the family Amaryllidaceae is known as the source of new bioactive molecules. The alkaloids isolated from this family have many biological activities, such as antitumor, antiviral, antiplasmodial, antiinflammatory and analgesic. Considering the potential pharmacological activity, the aim of this work was to isolate alkaloids from Hippeastrum morelianum Lem. and Hippeastrum santacatarina (Traub) Dutilh. In addition, we investigated the antioxidant, antimicrobial and anticolinesterasic activities of the isolated products and of the extracts. The material of both plants was separated into bulbs, roots and leaves (the last one only from H. morelianum), and it was extracted through the acid-basic method, classical to alkaloids. By chromatographic methods, twelve products were isolated from H. morelianum, with emphasis for the candimine alkaloid (110 mg). Importantly, this is the first report on the complete spectroscopic data and the former evaluations of this alkaloid. Sequentially, tree products were obtained from H. santacatarina, with emphasis on the licorine alkaloid (100 mg). All extracts evaluated, in both plants, demonstrated antioxidant (10 mg/ml) and anticolinesterasic (0,1 mg/ml) potentials, although not antimicrobial. Taking in account the isolated products, it is of interest the antioxidant activity of licorine, revealed by the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, with IC50: 112,4 μg/ml. On the other hand, all isolates of H. morelianum showed anticolinesterasic activity, except the product A12, at 5 μg. For H. santacatarina, licorine, as well as isolates B2 and B2 showed anticolinesterasic activity, too at 5 μg. Finally, it was not detected antimicrobial activity for the alkaloids licorine and candimine at 0,5 mg/ml or less.

A família Amaryllidaceae é reconhecida como fonte de compostos bioativos, sendo o isolamento e elucidação estrutural de seus alcaloides, aliado às avaliações farmacológicas, um tema importante. Estudos mostram que o mecanismo de ação da citotoxicidade desses alcaloides é seletivo e depende da linhagem celular. Trichomonas vaginalis é um protozoário parasita que causa a tricomonose, a doença sexualmente transmissível de origem não viral mais comum no mundo. Além de ser considerado um importante organismo patogênico, suas características bioquímicas peculiares, como a ausência de mitocôndrias, torna o tricomonas um adequado modelo para estudos de vias metabólicas de morte celular. A atividade anti-T. vaginalis dos alcaloides de Amaryllidaceae licorina e candimina, assim como o potencial citotóxico de diaminas sintéticas, foram investigados. Estudos de semi-síntese com a licorina também foram desenvolvidos. Nossos resultados mostraram que a licorina e candimina induzem importantes alterações na ultraestrutura dos parasitos e nenhum marcador morfológico clássico de apoptose, como corpos apoptóticos, foi observado. Além disso, nem a fragmentação do DNA genômico nem a exposição de resíduos de fosfatidilserina foram detectadas. Por outro lado, ambos os alcaloides atrasaram o ciclo celular do parasito e inibiram a atividade das enzimas NTPDase e ecto-5`- nucleotidase, importantes na manutenção da relação parasito/hospedeiro. O alcaloide pró-apoptótico licorina e a candimina induziram morte celular no parasito amitocondriado T. vaginalis por um mecanismo de ação que não cumpre as características morfológicas de apoptose. Entretanto, similaridades com a morte celular denominada paraptose foram observadas: intensa vacuolização citoplasmática periférica aliada à integridade nuclear. Considerando que a citotoxicidade dos alcaloides pode ser considerada moderada (250 μM), derivados de poliaminas foram escolhidos para desenvolver estudos de semi-síntese com a licorina e aperfeiçoar a atividade do alcalóide. Poliaminas são moléculas catiônicas de estruturas simples, essenciais para a diferenciação celular e regulação do ciclo celular. Neste trabalho demonstrou-se a síntese e avaliação da atividade anti-T. vaginalis de uma série de derivados de diaminas, dos quais N-hexadecil-1,4-butanodiamina apresentou CIM igual a 2,5 μg/ml, duas vezes mais ativo em comparação ao metronidazol, utilizado como composto de referência. A hibridização molecular da licorina com as diaminas foi prejudicada pela instabilidade da licorina mesilada, intermediário chave para prosseguir a rota sintética. No entanto, seis derivados inéditos da licorina, todos ésteres, aromáticos ou alifáticos, foram sintetizados. / Amaryllidaceae family has proven to be plentiful sources for therapeutic agents. Hence, the isolation, biology and chemistry of the Amaryllidaceae alkaloids make an important subject. Investigations on cytotoxic mechanisms of these alkaloids indicate a promising selective cell-type-dependent cytotoxicity. Trichomonas vaginalis is a parasite that causes trichomonosis, the number one non-viral sexually-transmitted disease in the world. However, whilst T. vaginalis is a prime pathogenic target, its lack of mitochondria makes it a suitable biochemical model to study cell death-related mechanisms. Anti-T. vaginalis activity of lycorine and candimine alkaloids were investigated, as well as the cytotoxic potential of diamine analogs. Finally, studies on lycorine semi-synthesis were developed. Our results showed that, after lycorine and candimine treatment, no hallmark suggestive of apoptosis were observed, such as apoptotic bodies, but instead several important ultrastructural alterations, assessed by electronic microscopy. Additionally, DNA fragmentation and membrane phosphatidylserine exposure were not detected. Analysis showed that lycorine and candimine arrested T. vaginalis cell cycle and inhibited the NTPDase and ecto-5`- nucleotidase activities, important enzymes on parasite/host relationship. The proapoptotic alkaloid, lycorine, and the lactone alkaloid, candimine, caused cell death in the amitochondriate T. vaginalis by a mechanism of action that fails to completely fulfill the criteria for apoptosis. However, some similarities were observed to paraptotic cell death, like intense cytoplasmic periferic vacuolization and nuclear integrity. Since the cytotoxic potential of the alkaloids was moderated (250 μM), the polyamines analogs were chosen to investigate the anti-T. vaginalis activity and to develop semi-synthesis studies with lycorine in order to improve the alkaloid cytotoxicity. Polyamines are simple structured aliphatic amines essential for cell proliferation and differentiation and it has been shown that interfering with their function or biosynthesis the cellular growth can be blocked. Our results showed the synthesis of a series of diamine derivatives, and N-hexadecil-1,4-butanediamine was found to be the most active compound in vitro against T. vaginalis with MIC of 2.5 μg/mL, twice more active in comparison to the reference drug metronidazole. The molecular hybridization of lycorine with diamines was impaired by the unsuccessful synthesis of the lycorine mesilate, a key intermediary on the synthetic route. However, six new lycorine ester derivatives were synthesized.

A família Amaryllidaceae é reconhecida como fonte de compostos bioativos, sendo o isolamento e elucidação estrutural de seus alcaloides, aliado às avaliações farmacológicas, um tema importante. Estudos mostram que o mecanismo de ação da citotoxicidade desses alcaloides é seletivo e depende da linhagem celular. Trichomonas vaginalis é um protozoário parasita que causa a tricomonose, a doença sexualmente transmissível de origem não viral mais comum no mundo. Além de ser considerado um importante organismo patogênico, suas características bioquímicas peculiares, como a ausência de mitocôndrias, torna o tricomonas um adequado modelo para estudos de vias metabólicas de morte celular. A atividade anti-T. vaginalis dos alcaloides de Amaryllidaceae licorina e candimina, assim como o potencial citotóxico de diaminas sintéticas, foram investigados. Estudos de semi-síntese com a licorina também foram desenvolvidos. Nossos resultados mostraram que a licorina e candimina induzem importantes alterações na ultraestrutura dos parasitos e nenhum marcador morfológico clássico de apoptose, como corpos apoptóticos, foi observado. Além disso, nem a fragmentação do DNA genômico nem a exposição de resíduos de fosfatidilserina foram detectadas. Por outro lado, ambos os alcaloides atrasaram o ciclo celular do parasito e inibiram a atividade das enzimas NTPDase e ecto-5`- nucleotidase, importantes na manutenção da relação parasito/hospedeiro. O alcaloide pró-apoptótico licorina e a candimina induziram morte celular no parasito amitocondriado T. vaginalis por um mecanismo de ação que não cumpre as características morfológicas de apoptose. Entretanto, similaridades com a morte celular denominada paraptose foram observadas: intensa vacuolização citoplasmática periférica aliada à integridade nuclear. Considerando que a citotoxicidade dos alcaloides pode ser considerada moderada (250 μM), derivados de poliaminas foram escolhidos para desenvolver estudos de semi-síntese com a licorina e aperfeiçoar a atividade do alcalóide. Poliaminas são moléculas catiônicas de estruturas simples, essenciais para a diferenciação celular e regulação do ciclo celular. Neste trabalho demonstrou-se a síntese e avaliação da atividade anti-T. vaginalis de uma série de derivados de diaminas, dos quais N-hexadecil-1,4-butanodiamina apresentou CIM igual a 2,5 μg/ml, duas vezes mais ativo em comparação ao metronidazol, utilizado como composto de referência. A hibridização molecular da licorina com as diaminas foi prejudicada pela instabilidade da licorina mesilada, intermediário chave para prosseguir a rota sintética. No entanto, seis derivados inéditos da licorina, todos ésteres, aromáticos ou alifáticos, foram sintetizados. / Amaryllidaceae family has proven to be plentiful sources for therapeutic agents. Hence, the isolation, biology and chemistry of the Amaryllidaceae alkaloids make an important subject. Investigations on cytotoxic mechanisms of these alkaloids indicate a promising selective cell-type-dependent cytotoxicity. Trichomonas vaginalis is a parasite that causes trichomonosis, the number one non-viral sexually-transmitted disease in the world. However, whilst T. vaginalis is a prime pathogenic target, its lack of mitochondria makes it a suitable biochemical model to study cell death-related mechanisms. Anti-T. vaginalis activity of lycorine and candimine alkaloids were investigated, as well as the cytotoxic potential of diamine analogs. Finally, studies on lycorine semi-synthesis were developed. Our results showed that, after lycorine and candimine treatment, no hallmark suggestive of apoptosis were observed, such as apoptotic bodies, but instead several important ultrastructural alterations, assessed by electronic microscopy. Additionally, DNA fragmentation and membrane phosphatidylserine exposure were not detected. Analysis showed that lycorine and candimine arrested T. vaginalis cell cycle and inhibited the NTPDase and ecto-5`- nucleotidase activities, important enzymes on parasite/host relationship. The proapoptotic alkaloid, lycorine, and the lactone alkaloid, candimine, caused cell death in the amitochondriate T. vaginalis by a mechanism of action that fails to completely fulfill the criteria for apoptosis. However, some similarities were observed to paraptotic cell death, like intense cytoplasmic periferic vacuolization and nuclear integrity. Since the cytotoxic potential of the alkaloids was moderated (250 μM), the polyamines analogs were chosen to investigate the anti-T. vaginalis activity and to develop semi-synthesis studies with lycorine in order to improve the alkaloid cytotoxicity. Polyamines are simple structured aliphatic amines essential for cell proliferation and differentiation and it has been shown that interfering with their function or biosynthesis the cellular growth can be blocked. Our results showed the synthesis of a series of diamine derivatives, and N-hexadecil-1,4-butanediamine was found to be the most active compound in vitro against T. vaginalis with MIC of 2.5 μg/mL, twice more active in comparison to the reference drug metronidazole. The molecular hybridization of lycorine with diamines was impaired by the unsuccessful synthesis of the lycorine mesilate, a key intermediary on the synthetic route. However, six new lycorine ester derivatives were synthesized.

Os produtos naturais têm se destacado ao longo dos anos como princípios ativos eficazes e muitos deles são utilizados até hoje no tratamento de certas doenças. Considerando as informações advindas da medicina popular, o vasto potencial terapêutico de alcalóides e a quimiotaxonomia dos vegetais, a família Amaryllidaceae se candidata a celeiro de novas moléculas bioativas. Verifica-se que os compostos alcaloídicos isolados a partir desta família apresentam atividades biológicas bem reportadas, tais como, antitumoral, antiviral, antimalárica, antiinflamatória e anticolinesterásica. Assim, o objetivo deste trabalho foi o isolamento de alcalóides a partir de Hippeastrum morelianum Lem. e Hippeastrum santacatarina (Traub) Dutilh, além da investigação das atividades antioxidante, anticolinesterásica e antimicrobiana dos produtos isolados, bem como dos extratos obtidos. O material de ambos vegetais foi separado em bulbos, raízes e folhas e submetido à extração ácido-base, clássica para alcalóides.Com auxílio de métodos cromatográficos a partir de H. morelianum foram isolados doze produtos, com destaque para o alcalóide candimina (110 mg) sendo este trabalho a fonte pioneira dos dados espectroscópicos completos deste alcalóide, bem como das primeiras avaliações farmacológicas do mesmo. A partir de H. santacatarina foram isolados três produtos, com destaque para a licorina (100 mg). Todos os extratos avaliados, de ambos vegetais, mostraram potenciais efeitos antioxidante (10 mg/ml) e anticolinesterásico (0,1 mg/ml), porém não antimicrobiano. Quanto aos produtos isolados destaca-se a atividade antioxidante da licorina, verificada pelo método da inativação do radical 2,2-difenil-1-picrilidrazila (DPPH), com IC50: 112,4 μg/ml. Entretanto, no screening de atividade anticolinesterásica todos os isolados de H. morelianum, exceto o produto A12, apresentaram resultado positivo com 5 μg de amostra. Para H. santacatarina, a licorina, assim como os isolados B2 e B3, demonstraram atividade anticolinesterásica, também com 5 μg de amostra. Finalmente, não foi detectada atividade antimicrobiana para licorina e candimina, alcalóides majoritários em suas plantas de origem, até 0,5 mg/ml. / Natural products have been employed over the years as active compounds, and many of them are currently used in the treatment of certain diseases. Considering the information stemming from the popular medicine, the vast therapeutic potential of alkaloids and quimiotaxonomy of plants, the family Amaryllidaceae is known as the source of new bioactive molecules. The alkaloids isolated from this family have many biological activities, such as antitumor, antiviral, antiplasmodial, antiinflammatory and analgesic. Considering the potential pharmacological activity, the aim of this work was to isolate alkaloids from Hippeastrum morelianum Lem. and Hippeastrum santacatarina (Traub) Dutilh. In addition, we investigated the antioxidant, antimicrobial and anticolinesterasic activities of the isolated products and of the extracts. The material of both plants was separated into bulbs, roots and leaves (the last one only from H. morelianum), and it was extracted through the acid-basic method, classical to alkaloids. By chromatographic methods, twelve products were isolated from H. morelianum, with emphasis for the candimine alkaloid (110 mg). Importantly, this is the first report on the complete spectroscopic data and the former evaluations of this alkaloid. Sequentially, tree products were obtained from H. santacatarina, with emphasis on the licorine alkaloid (100 mg). All extracts evaluated, in both plants, demonstrated antioxidant (10 mg/ml) and anticolinesterasic (0,1 mg/ml) potentials, although not antimicrobial. Taking in account the isolated products, it is of interest the antioxidant activity of licorine, revealed by the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, with IC50: 112,4 μg/ml. On the other hand, all isolates of H. morelianum showed anticolinesterasic activity, except the product A12, at 5 μg. For H. santacatarina, licorine, as well as isolates B2 and B2 showed anticolinesterasic activity, too at 5 μg. Finally, it was not detected antimicrobial activity for the alkaloids licorine and candimine at 0,5 mg/ml or less.

Orientador: Fernando Antonio Santos Coelho / Tese (doutorado) - Universidade Estadual de Campinas, Instituto de Química / Made available in DSpace on 2018-08-26T02:39:26Z (GMT). No. of bitstreams: 1 Ullah_Hamid_D.pdf: 4284540 bytes, checksum: 3371acfc6c696bf069405b0e69378616 (MD5) Previous issue date: 2014 / Resumo: Esse trabalho de doutorado visou explorar o potencial sintetico da reacao de Morita-Baylis- Hillman (MBH) na preparacao de intermediarios sinteticos, que possam ser utilizados na sintese total de produtos naturais. Na primeira parte deste trabalho, realizamos estudos para a sintese total do alcaloide (})-Plicamina e de outros alcaloides, isolados de plantas da familia das Amaryllidaceae, estruturalmente semelhantes. Desenvolvemos uma nova abordagem sintetica para esse trabalho, que culminou com o estabelecimento de uma nova metodologia para a preparacao de ¿À-hidroxi-¿¿-amino esteres. A ozonolise, oximacao e subsequente reducao do aduto de Morita-Baylis-Hillman sililado, proveniente do bromopiperonal, forneceu um ¿À-hidroxi-¿¿-aminoester, com estereoquimica relativa anti, e elevada diastereosseletividade. Esse foi transformado em um intermediario avancado (¿À-hidroxi-¿¿-aminoester N-alquilado) para a sintese do alcaloide, ja que possui todos os grupos funcionais necessarios para atingir o alvo final. Na segunda parte desse trabalho, avaliamos o escopo da nova metodologia de sintese de ¿À-hidroxi-¿¿-aminoesteres. Essa metodologia, simples e direta, permitiu a preparacao de diferentes ¿À-hidroxi-¿¿-aminoesteres, com elevada diastereosseletividade em 4 etapas e bons rendimento globais. Esse e o primeiro exemplo de sintese ¿À-hidroxi-¿¿-aminoesteres, a partir de adutos de Morita-Baylis- Hillman (MBH) / Abstract: This work of doctorate explored the synthetic potential of Morita-Baylis-Hillman (MBH) reaction in the preparation of synthetic intermediates that could be utilized in the synthesis of natural products. In the first part of this work we performed studies towards the total synthesis of (±)-Plicamin and the other structurally related alkaloids, isolated from the plants of the Amaryllidaceae family. We developed a new synthetic approach, which culminated with the establishment of the new methodology for the preparation of â-hydroxy-á-amino esters. The ozonolysis, oxymation and subsequent reduction of the silylated Morita-Baylis-Hillman adduct, obtained from bromopiperonal, furnished a â-hydroxy-á-aminoester, with a relative stereochemistry anti, in high diastereoselectivity. This was transformed further to an intermediate (N-alkylated â-hydroxy-á-aminoester), which has almost all the necessary functional groups to allow the synthesis of the target alkaloid. In the second part of this work we evaluated the scope of the new methodology of the synthesis of â-hydroxy-á-aminoester. This simple and direct methodology allowed us the preparation of different â-hydroxy-á-aminoesters, with high diastereoselectivities, in four steps with good global yield. Additionally, this work demonstrates a first example the synthesis of â-hydroxy-á-aminoesters from the Morita-Baylis- Hillman (MBH) adducts / Doutorado / Quimica Organica / Doutor em Ciências

Charles University, Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Botany Candidate: Mgr. Eliška Kohelová Supervisor: prof. Ing. Lucie Cahlíková, Ph.D. Title of Doctoral Thesis: Alkaloids of Zephyranthes citrina (Amaryllidaceae): isolation, structure identification, biological activity. Key words: Amaryllidaceae alkaloids, Zephyranthes, Alzheimer's disease, AChE, BuChE, POP, oncological diseases Zephyranthes citrina Baker was chosen, based on result of previous screening study and literatury research, for detailed phytochemical work for the purpose of isolation of the widest range of AAs. From 35 kg of fresh bulbs was obtained 151 g of purified alkaloidal extract, which was processed using column chromatography to almost 700 fractions. These fractions were connected into 27 subfractions, which were processed by liquid-liquid extraction, flash chromatography, preparative TLC and crystallization. Finally, 27 pure alkaloids were isolated. All compounds were identified by MS (EI, ESI), HRMS, 1D- and 2D-NMR, CD, optical rotation and by comparison with literature data. Seven compounds were identified as new undescribed alkaloids (6α-ethoxyhippeastidine, 10-deoxy-6α-ethoxyhippeastidine, narcieliine, zephyjanine, zephycitrine I, 7-ethoxy-10-methoxy-1-methyllycorenane-9-ol a zephycitrin...

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...

Nováková D.: Biological activity of secondary plants metabolites I. Alkaloids of Narcissus jonquilla L. Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové 2015, pp. 70. The aim of the diploma thesis was a preparation of alkaloid extracts to identification of alkaloid patterns and measure cholinesterase inhibitory activity. This activity is useful for treating Alzheimer's disease. Alkaloid extracts of seven Narcissus jonquilla L. (Amaryllidaceae) varieties (Sundial, Sundisc, Sweetness, Waterperry, Simplex, Twinkling Yellow, Yazz) were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Twenty-three alkaloids were determined by GC/MS, and ten of them identified from their mass spectra and retention times. All samples exhibited content of galanthamine, most samples contained lycorine and tazettine. Promising HuAChE inhibition activity was demonstrated by Narcissus jonquilla L. cv. Waterperry with IC50 values of 6.53 ± 0.88 μg/mL. The strongest inhibitory activity against HuBuChE was detected in extract from Narcissus jonquilla L. cv. Sundisc with IC50 value of 5.09 ± 0.64 μg/mL. Keywords: Alzheimer's disease, Amaryllidaceae, Narcissus,...

Panchartková, M.: Biological aktivity of secondary plants metabolites III. Alkaloids of Narcissus tazetta L., Diploma thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology, Hradec Králové, 2015, 67s. Plants from the Amaryllidaceae family contain alkaloids that have multiple biological effects. There is described antiviral, antitumor, antibacterial, antimalarial and anti-fungal effect. Activity against human cholinesterases is important too. The aim of this thesis was to prepare seven alkaloid extracts of individual cultivars of the plants Narcissus and then to realize their GC/MS analysis. Thanks to this analysis, several different structural types of alkaloids from the Amaryllidaceae family were identified. The most frequently identified alkaloids were homolycorine, lycorine, tazettine and galanthamine type. This was followed by the measuring of biological activity against human acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE). The highest inhibitory activity IC50 identified the alkaloidal extract of the Narcissus jonquilla cv. New baby with the values in relation to HuAChE 13,78 ± 1,48 and in relation to HuBuChE 96,12 ± 9,55. The main reason was probably the highest content of galanthamine of all cultivars,...

Author: Petra Nekolná Title: Alkaloids of family Amaryllidaceae: genus Lycoris Diploma thesis Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Department of Pharmaceutical Botany and Ecology 2015, 79 p. The aim of this diploma thesis was to summarize the findings about alkaloids which were isolated from Lycoris plants of Amaryllidaceae family. It contains a botanical characteristics of species of genus Lycoris which were studied phytochemically, a file of alkaloids which were isolated from these plants and findings about the biological activity of these compounds. Within the genus Lycoris 11 species were studied phytochemically and 118 alkaloids were isolated from these plants. Alkaloids which were isolated from Lycoris plants are divided in several structural groups. The lycorine-, homolycorine-, crinine-, galanthamine- and pancratistatine-type alkaloids occur the most numerously. Anticancer, acetylcholinesterase-inhibitory and antimalarial activity of the alkaloids were described. The biological activity of alkaloids is connected with their structure. The most significant anticancer activity was observed in alkaloids from lycorine-, crinine- and pancratistatine-type. Acetylcholinesterase-inhibitory activity was pronounced the most in galanthamine-type alkaloids. The most...