Inclusion of experiments into tuition of chemistry is required and a topic of natural compounds enables combination of chemistry with biology and subjects of common life. This dissertation concerns experiments with natural compounds, their utilization within project education at educational and popularizing events which are held by Charles University in Prague. Researches of selected secondary textbooks and professional publications are parts of the thesis. A questionnaire survey is also included on which basis opinions of secondary teachers were evaluated. A collection of instruction in the experiments was prepared. The main part of the thesis is focused on detailed desription of experiments supplemented with pictures and information about selected natural compounds. A proposal to educational excursions focused on natural compounds and project tuition is also included. The whole thesis bring a new look into experiments with natural compounds in sense of searching individual compounds in blends, discovering composition of food processing products not only by chromatography.

Charles University, Faculty of Pharmacy in Hradec Králové Department: Department of Pharmaceutical Botany Candidate: Simona Víchová Supervisor: RNDr. Jaroslav Jenčo, Ph.D. Title of dissertation thesis: The use of separation techniques in phytochemical analysis The alkaloid extract obtained from stems with immature capsules from Papaver rhoeas L. was subjected to a phytochemical study. The summary extract was separated into individual fractions by Flash chromatography. After performing biological tests for inhibitory activities of acetylcholinesterase and butyrylcholinesterase, the fraction PPR-11 and PPR-12 was selected. The fraction showed the highest activity against butyrylcholinesterase (95.55 ± 0.96 and 97.03 ± 0.79% inhibition of butyrylcholinesterase at 50 /g / ml). The combined PPR 11-12 fractions were purified by preparative chromatography to individual subfractions, which were purified by preparative thin layer chromatography. A monocomponent crystalline substance of alkaloid origin was obtained from the subfraction named PPR 11-12Fr # 8-A. Based on instrumental analysis, the analyte was identified as an alkaloid of the aporphine type (+)-caaverine. The inhibitory activities against acetylcholinesterase and butyrylcholinesterase for (+)-caaverine, were determined and compared with...

Natural products are acknowledged sources of novel compounds for use in the treatment of diseases such as cancer, malaria, and human African trypanosomiasis. However, health burdens of such diseases still remain high, with drug resistance leading to failure of current medication. Therefore, there is a need for new treatments, and this project considers the potential of Nigerian ethno-medicinal plants and their products. Firstly, the aims were to isolate cytotoxic compounds through bio-guided evaluation and fractionation from 3 medicinal plants; Vitellaria paradoxa, Cyperus articulatus and Securidaca longepedunculata used traditionally in the treatment of cancer in North-East Nigeria. Extracts from S. longepedunculata were the most active when assessed in a panel of cancer cell lines, with IC50 values below 10 µg/ml, whilst fractions isolated from V. paradoxa and C. articulatus were moderately cytotoxic and able to overcome drug resistance mechanisms in drug resistant cell lines. In the second part of the thesis, novel cryptolepine analogues were semi-synthesized using environmentally friendly methods and evaluated for cytotoxic, anti-plasmodial and anti-trypanosomal activity. The compounds were found to be highly cytotoxic in cancer cell lines with the ability to overcome drug resistant mechanisms, with sub-µM IC50 values, and were also active against drug resistant strains of Plasmodium parasites in addition to Trypanosoma brucei, with IC50 values below 500 nM, and 300 pM respectively. / Schlumberger Faculty for the Future Foundation

Neste trabalho foram investigadas a atividade antialérgica de extratos, ou substâncias isoladas, obtidos de fontes naturais. Para isso foi utilizado o sistema biossensor baseado em mastócitos os quais liberam a enzima beta-hexosaminidase usada como marcador da degranulação. Para algumas substâncias naturais da classe dos flavonóides (quercetina-Qc e rutina-Rt) e ácidos polifenólicos (ácido dimetoxicinâmico-Dm e ácido cafeico-Cf), os ensaios biológicos foram conduzidos na presença de beta-ciclodextrina (beta-CD) a fim de estudar a eficiência do ensaio biológico e o efeito de complexação na atividade antialérgica. Inicialmente, foram investigadas, as propriedades espectroscópicas destes flavonóides e ácidos polifenólicos, na ausência, e presença de beta-CD. As mudanças nos espectros de absorção e fluorescência, em presença de beta-CD, mostraram que ocorre a associação dos fármacos com a beta-CD. Assim, as constantes de incorporação (Kc) foram determinadas pelo método de Higuchi e Connors e os resultados mostraram maior incorporação da Qc (Kc = 172 /M) na cavidade da beta-CD quando comparada a Rt (Kc = 139 /M). No caso dos polifenóis, Dm mostrou incorporação maior em relação ao Cf, com valores de Kc iguais a 718 e 278 /M, respectivamente. Os valores de Kc foram considerados apropriados para a aplicação de compostos de inclusão como agentes terapêuticos. Assim, os complexos de inclusão sólidos, foram preparados por uma adaptação do método da co-evaporação e caracterizados por Análise Termogravimétrica (TGA), Análise Térmica Diferencial (DTA), Calorimetria Diferencial de Varredura (DSC), espectroscopia na região do Infravermelho (FTIR) e Ressonância Magnética Nuclear de Prótons (1H-RMN). O parâmetro físico-químico para interação hidrofóbica (log P) foi determinado para os flavonóides e acidos polifenólicos e os resultados indicaram que a hidrofobicidade seguiu a seguinte ordem: Dm > Cf > Qc > Rt. Os complexos de inclusão foram mais eficazes para inibir a liberação da beta-hexosaminidase do que os fármacos na forma livre. A atividade anti-alérgica da Qc livre (IC50= 5,1 µM) mostrou um aumento de oito vêzes quando complexada com a beta-CD (IC50= 0,62 µM). Um aumento da atividade foi observado, também, para os complexos Rt/CD, Cf/CD e Dm/CD. Este efeito foi mais forte para os compostos com maior hidrofobicidade. A atividade antialérgica das substâncais naturais livres provenientes de várias classes de plantas tais como flavonóides, ácidos polifenólicos, terpenos, alcalóides e iridóides foi, também, investigada. Os flavonóides tais como quercetina (IC50= 5,1 µM), 7-metil quercetina (IC50= 6,2 µM), caempferol-3-glicosideo (IC50= 6,7 µM) and 4-O-(6-trans-p-coumaroil)--D-glicopyranosil okanina (IC50= 5,8 µM) mostraram a maior atividade antialérgica comparados ao fumarato de cetotifeno (IC50= 15,1 µM). Os extratos provenientes de diversas espécies de plantas tais como Bidens sulphurea, Bidens gardneri, Bidens graveolens, Mikania parodii Cabrera e Mikania pilosa Baker foram, também, investigados. Os resultados mostraram maior atividade para o extrato de Bidens obtido de acetato de etila. Este extrato é rico em derivados metilados de quercetina os quais exibiram forte atividade antialérgica quando utilizados no ensaio biológico como substância isolada. / Anti-allergic activity of extracts and isolated compounds obtained from natural sources was investigated using the mast-cell based biosensor system. Mast cells release beta-hexosaminidase enzyme which is used as a marker of degranulation. Flavonoids (quercetin-Qc and rutin-Rt) and polyphenolic acids (caffeic acid-Cf and dimethoxy cinnamic acid-Dm) were used as inclusion compounds with beta-cyclodextrin (beta-CD) in order to compare the efficiency of the biological assay and the anti-allergic activity of the drugs free or associated with beta-CD. Spectroscopic properties of the flavonoids and polyphenolic acids were monitored in the absence or presence of beta-CD. The absorbance and fluorescence spectra showed drug association with beta-CD; subsequently the stability constants (kc) of the drugs were obtained in accordance with the method of the Higuchi-Connors. The results showed higher association of Qc with beta-CD (Kc= 172 /M) compared to Rt (Kc= 139 /M). For the polyphenolic acids, Dm exhibited the higher association with beta-CD compared to Cf (718 and 278 /M respectively). The Kc values felt within the range considered adequate for the formation of inclusion complex, and they can be used to improve the bioavailability of the flavonoids and polyphenolic acids. The solid inclusion compounds were obtained by an adaptation of the co-evaporation method and characterized by Thermo Gravimetric Analysis (TG), Differential Thermal Analysis (DTA), Differential Scanning Calorimetry (DSC), Fourier Transform Infrared Spectroscopy (FTIR) and Proton Nuclear Magnetic Resonance Spectroscopy (1H NMR). Physico-chemical parameter for hydrophobic interaction (log P) was determined for the flavonoids and polyphenolic acids and the results indicated that the hydrophobicity followed the order: Dm > Cf > Qc > Rt. The inclusion complexes were more effective at inhibiting beta-hexosaminidase release than plain drugs. The anti-allergic activity of plain Qc (IC50= 5.05 M) showed eightfold improvement when included inside the beta-CD cavity (IC50= 0.62 M). Higher biological activity on the part of the complex was also observed for the complexes Rt/CD, Cf/CD and Dm/CD. This effect was stronger for the compounds with higher hydrophobicity. The anti-allergic activity of plain natural compounds from several classes of plants such as flavonoids, polyphenolic acids, terpenes, alkaloids and iridoids was investigated. Flavonoids such as quercetin (IC50= 5.1 µM), 7-methyl quercetin (IC50= 6.2 µM), kaempferol-3-glycoside (IC50= 6.7 µM) and 4-O-(6-trans-p-coumaroil)--D-glucopyranosyl okanin (IC50= 5.8 µM) showed the stronger anti-allergic activity compared with ketotifen fumarate, a reference drug (IC50= 15.1 µM). Extracts proceeding from different species of plants such as Bidens sulphurea, Bidens gardneri, Bidens graveolens, Mikania parodii Cabrera and Mikania pilosa Baker were also investigated. The results showed stronger anti-allergic activity for ethyl acetate extracts obtained from Bidens specie. This extracts are rich in methylated quercetin derivatives which showed strong anti-allergic activity when assayed as isolated substances

This diploma thesis is focused on the creation and usage of a computer game (adventure) for chemistry of natural compounds. The game was developed especially for students of the second grade of elementary and lower grades of grammar school. The aim of this adventure game is to motivate and activate during chemistry lessons. This adventure game is embedded to picturesque town Pelhřimov and its surroundings.

Submitted by PPG Odontologia (odontologia-pg@pucrs.br) on 2018-06-27T15:29:59Z No. of bitstreams: 1 JULIANE_DE_QUADROS_DE_BORTOLLI_DIS.pdf: 1560215 bytes, checksum: 631d814b124322abfc0f1aaf6c260aa3 (MD5) / Approved for entry into archive by Sheila Dias (sheila.dias@pucrs.br) on 2018-07-04T13:31:02Z (GMT) No. of bitstreams: 1 JULIANE_DE_QUADROS_DE_BORTOLLI_DIS.pdf: 1560215 bytes, checksum: 631d814b124322abfc0f1aaf6c260aa3 (MD5) / Made available in DSpace on 2018-07-04T13:41:52Z (GMT). No. of bitstreams: 1 JULIANE_DE_QUADROS_DE_BORTOLLI_DIS.pdf: 1560215 bytes, checksum: 631d814b124322abfc0f1aaf6c260aa3 (MD5) Previous issue date: 2018-03-27 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES / The oral mucosa is a frequent site for traumatic ulcers, which can be caused by mechanical or chemical agents. There is no a gold standard treatment for the management of these lesions, which can be painful and have a negative impact on quality of life. Although studies suggest the use of chamomile and curcumin in the treatment of ulcerated lesions of the oral mucosa, there is no a consensus as to its efficacy in the management of these lesions. The literature has shown that both phytotherapics modulate the levels of inflammatory cytokines such as TNF-? and IL-1?. Therefore, in the first article of this dissertation, an integrative literature review was conducted investigating the efficacy of topical interventions with chamomile and curcumin in the management of pain and in the healing of ulcerated lesions of the oral mucosa. Few controlled clinical trials have been found and they suggest a beneficial effect of chamomile and curcumin in the healing process and in the reduction of symptoms in patients with oral mucositis, recurrent aphthous ulceration and oral lichen planus. Studies in animal demonstrated a reduction in the inflammatory wound healing phase, increased deposition of collagen fibers and epithelization. The second article of this dissertation presents an experimental study, which was carried out to evaluate the effect of the 10% chamomile extract and 2% curcumin in the repair of traumatic ulcers on tongue of rats. Thirty-nine Wistar rats were divided into three groups: control, chamomile extract and curcumin. A 5-mm-diameter excisional wound was made in the center of ventral tongue. The substances were applied as a gel twice daily for five days. The animals were euthanized 7 days after the lesions were made. In the macroscopic evaluation, there was no significant difference among chamomile, curcumin and control groups regarding to area of residual ulcer (P= 0.20). Histological analysis also showed no difference among the groups regarding newly formed epithelium area (P=0.97) or intensity of inflammatory infiltrate (P=0.72). Considering the experimental model, the findings of the present study showed that 10% chamomile extract and 2% curcumin did not accelerate the repair of traumatic oral ulcers or reduced the intensity of the inflammatory infiltrate, contradicting previous findings in the literature. / A mucosa bucal ? um s?tio frequente para a ocorr?ncia de ?lceras traum?ticas, as quais podem ser causadas por agentes mec?nicos ou qu?micos. At? o momento, n?o existe um tratamento padr?o-ouro para o manejo dessas les?es, as quais podem ser dolorosas e ter impacto negativo na qualidade de vida dos pacientes. Apesar de estudos sugerirem a utiliza??o da camomila e da curcumina no tratamento de les?es ulceradas da mucosa bucal, n?o h? consenso sobre a sua efic?cia no manejo dessas les?es. A literatura tem demonstrado que ambos os fitoter?picos modulam os n?veis de citocinas pr?-inflamat?rias como TNF-? e IL-1?. No primeiro artigo desta disserta??o foi realizada uma revis?o integrativa da literatura investigando a efic?cia das interven??es t?picas com camomila e curcumina no manejo da dor e na cicatriza??o de les?es ulceradas da mucosa bucal. Poucos ensaios cl?nicos controlados foram encontrados e estes sugerem um efeito ben?fico da camomila e da curcumina no processo cicatricial e na redu??o da sintomatologia em pacientes com mucosite oral, ulcera??o aftosa recorrente e l?quen plano oral. Estudos em modelos animais investigando os efeitos desses fitoter?picos em ?lceras traum?ticas bucais demonstraram redu??o da fase inflamat?ria do processo de cicatriza??o, maior deposi??o de fibras col?genas e epiteliza??o. O segundo artigo desta disserta??o apresenta um estudo experimental, que foi realizado com o objetivo de avaliar o efeito do extrato de camomila 10% e curcumina 2% no reparo de ?lceras traum?ticas em l?ngua de ratos. Trinta e nove ratos Wistar foram distribu?dos em tr?s grupos: controle, extrato de camomila e curcumina. Uma ?lcera de 5 mm de di?metro foi confeccionada no ventre lingual de cada animal. As subst?ncias foram aplicadas na forma de gel, duas vezes ao dia, durante cinco dias. Os animais foram eutanasiados sete dias ap?s a confec??o das les?es. Na avalia??o macrosc?pica, n?o houve diferen?a entre os grupos camomila, curcumina e controle quanto ? ?rea de ?lcera remanescente (P=0.20). A an?lise histol?gica tamb?m n?o demonstrou diferen?a entre os grupos quanto ? ?rea de tecido epitelial neoformado (P=0.97) ou intensidade do infiltrado inflamat?rio (P=0.72). Considerando o modelo experimental empregado, os achados do presente estudo demonstraram que extrato de camomila 10% e a curcumina 2% n?o aceleraram o reparo de ?lceras mecanicamente induzidas na mucosa bucal nem reduziram a intensidade do infiltrado inflamat?rio, contrariando achados pr?vios na literatura.

Neste trabalho foram investigadas a atividade antialérgica de extratos, ou substâncias isoladas, obtidos de fontes naturais. Para isso foi utilizado o sistema biossensor baseado em mastócitos os quais liberam a enzima beta-hexosaminidase usada como marcador da degranulação. Para algumas substâncias naturais da classe dos flavonóides (quercetina-Qc e rutina-Rt) e ácidos polifenólicos (ácido dimetoxicinâmico-Dm e ácido cafeico-Cf), os ensaios biológicos foram conduzidos na presença de beta-ciclodextrina (beta-CD) a fim de estudar a eficiência do ensaio biológico e o efeito de complexação na atividade antialérgica. Inicialmente, foram investigadas, as propriedades espectroscópicas destes flavonóides e ácidos polifenólicos, na ausência, e presença de beta-CD. As mudanças nos espectros de absorção e fluorescência, em presença de beta-CD, mostraram que ocorre a associação dos fármacos com a beta-CD. Assim, as constantes de incorporação (Kc) foram determinadas pelo método de Higuchi e Connors e os resultados mostraram maior incorporação da Qc (Kc = 172 /M) na cavidade da beta-CD quando comparada a Rt (Kc = 139 /M). No caso dos polifenóis, Dm mostrou incorporação maior em relação ao Cf, com valores de Kc iguais a 718 e 278 /M, respectivamente. Os valores de Kc foram considerados apropriados para a aplicação de compostos de inclusão como agentes terapêuticos. Assim, os complexos de inclusão sólidos, foram preparados por uma adaptação do método da co-evaporação e caracterizados por Análise Termogravimétrica (TGA), Análise Térmica Diferencial (DTA), Calorimetria Diferencial de Varredura (DSC), espectroscopia na região do Infravermelho (FTIR) e Ressonância Magnética Nuclear de Prótons (1H-RMN). O parâmetro físico-químico para interação hidrofóbica (log P) foi determinado para os flavonóides e acidos polifenólicos e os resultados indicaram que a hidrofobicidade seguiu a seguinte ordem: Dm > Cf > Qc > Rt. Os complexos de inclusão foram mais eficazes para inibir a liberação da beta-hexosaminidase do que os fármacos na forma livre. A atividade anti-alérgica da Qc livre (IC50= 5,1 µM) mostrou um aumento de oito vêzes quando complexada com a beta-CD (IC50= 0,62 µM). Um aumento da atividade foi observado, também, para os complexos Rt/CD, Cf/CD e Dm/CD. Este efeito foi mais forte para os compostos com maior hidrofobicidade. A atividade antialérgica das substâncais naturais livres provenientes de várias classes de plantas tais como flavonóides, ácidos polifenólicos, terpenos, alcalóides e iridóides foi, também, investigada. Os flavonóides tais como quercetina (IC50= 5,1 µM), 7-metil quercetina (IC50= 6,2 µM), caempferol-3-glicosideo (IC50= 6,7 µM) and 4-O-(6-trans-p-coumaroil)--D-glicopyranosil okanina (IC50= 5,8 µM) mostraram a maior atividade antialérgica comparados ao fumarato de cetotifeno (IC50= 15,1 µM). Os extratos provenientes de diversas espécies de plantas tais como Bidens sulphurea, Bidens gardneri, Bidens graveolens, Mikania parodii Cabrera e Mikania pilosa Baker foram, também, investigados. Os resultados mostraram maior atividade para o extrato de Bidens obtido de acetato de etila. Este extrato é rico em derivados metilados de quercetina os quais exibiram forte atividade antialérgica quando utilizados no ensaio biológico como substância isolada. / Anti-allergic activity of extracts and isolated compounds obtained from natural sources was investigated using the mast-cell based biosensor system. Mast cells release beta-hexosaminidase enzyme which is used as a marker of degranulation. Flavonoids (quercetin-Qc and rutin-Rt) and polyphenolic acids (caffeic acid-Cf and dimethoxy cinnamic acid-Dm) were used as inclusion compounds with beta-cyclodextrin (beta-CD) in order to compare the efficiency of the biological assay and the anti-allergic activity of the drugs free or associated with beta-CD. Spectroscopic properties of the flavonoids and polyphenolic acids were monitored in the absence or presence of beta-CD. The absorbance and fluorescence spectra showed drug association with beta-CD; subsequently the stability constants (kc) of the drugs were obtained in accordance with the method of the Higuchi-Connors. The results showed higher association of Qc with beta-CD (Kc= 172 /M) compared to Rt (Kc= 139 /M). For the polyphenolic acids, Dm exhibited the higher association with beta-CD compared to Cf (718 and 278 /M respectively). The Kc values felt within the range considered adequate for the formation of inclusion complex, and they can be used to improve the bioavailability of the flavonoids and polyphenolic acids. The solid inclusion compounds were obtained by an adaptation of the co-evaporation method and characterized by Thermo Gravimetric Analysis (TG), Differential Thermal Analysis (DTA), Differential Scanning Calorimetry (DSC), Fourier Transform Infrared Spectroscopy (FTIR) and Proton Nuclear Magnetic Resonance Spectroscopy (1H NMR). Physico-chemical parameter for hydrophobic interaction (log P) was determined for the flavonoids and polyphenolic acids and the results indicated that the hydrophobicity followed the order: Dm > Cf > Qc > Rt. The inclusion complexes were more effective at inhibiting beta-hexosaminidase release than plain drugs. The anti-allergic activity of plain Qc (IC50= 5.05 M) showed eightfold improvement when included inside the beta-CD cavity (IC50= 0.62 M). Higher biological activity on the part of the complex was also observed for the complexes Rt/CD, Cf/CD and Dm/CD. This effect was stronger for the compounds with higher hydrophobicity. The anti-allergic activity of plain natural compounds from several classes of plants such as flavonoids, polyphenolic acids, terpenes, alkaloids and iridoids was investigated. Flavonoids such as quercetin (IC50= 5.1 µM), 7-methyl quercetin (IC50= 6.2 µM), kaempferol-3-glycoside (IC50= 6.7 µM) and 4-O-(6-trans-p-coumaroil)--D-glucopyranosyl okanin (IC50= 5.8 µM) showed the stronger anti-allergic activity compared with ketotifen fumarate, a reference drug (IC50= 15.1 µM). Extracts proceeding from different species of plants such as Bidens sulphurea, Bidens gardneri, Bidens graveolens, Mikania parodii Cabrera and Mikania pilosa Baker were also investigated. The results showed stronger anti-allergic activity for ethyl acetate extracts obtained from Bidens specie. This extracts are rich in methylated quercetin derivatives which showed strong anti-allergic activity when assayed as isolated substances

Tendo como base o escasso conhecimento dos efeitos causados por eucaliptos sobre a biota aquática e o intenso plantio em áreas de entorno de inúmeros lagos no Vale do rio Doce, o presente estudo avaliou a extração, identificação e os efeitos tóxicos dos compostos naturais presentes nas folhas de Eucalyptus grandis e E. urophylla das áreas de entorno das lagoas Palmeirinha e Ferruginha, respectivamente, através de destilação por arraste a vapor de água, cromatografia gasosa de alta resolução (CGC), análise por infravermelho e testes ecotoxicológicos com as águas de decomposição das folhas (laboratório), com os óleos essenciais, extratos hidroalcólicos e aquosos das folhas da serapilheira, 30 e 60 dias após contato com as lagoas. Nos testes de toxicidade foram utilizados organismos zooplanctônicos (Daphnia similis, Daphnia laevis e Ceriodaphnia silvestrii) e bentônicos (Chironomus xanthus). As folhas de E. grandis apresentaram maior rendimento de óleo essencial que as de E. urophylla, tendo sido identificado maior número de substâncias nas folhas de E. urophylla. No caso dos extratos o E. grandis apresentou maior rendimento dos extratos hexânicos, tanto na primeira como na segunda etapa de extração enquanto o E. urophylla apresentou maior rendimento de extrato etanólico. Verificou-se como principais compostos nos extratos de E. urophylla esteróides e triterpenos. Os resultados dos testes de toxicidade aguda realizados com a água de decomposição das duas espécies de eucaliptos mostraram efeito tóxico a Daphnia similis, D. laevis e C.silvestrii e Chironomus xanthus o qual, entretanto, diminuiu com o aumento do tempo de decomposição. Os óleos essenciais apresentaram efeito tóxico em todos os testes realizados com cladóceros (folhas da serapilheira, 30 e 60 dias), assim como os extratos hidroalcoólicos (menos polares) a Chironomus xanthus e aquosos (mais polares) à D. similis e D. laevis verificou-se, portanto, no presente estudo, que os compostos naturais presentes nas folhas de E. grandis e E. urophylla podem afetar a biota aquática, sendo importante o monitoramento de ambientes aquáticos circundados por monoculturas de Eucalyptus spp. / Based on the scarce knowledge of the effect caused by eucalyptus on aquatic biota and the intense plantation in the surroundings of innumerable lakes in the Valley of Rio Doce, the present study evaluated extraction, identification and toxic effect of natural compounds found in leaves of Eucalyptus grandis and E. urophylla nearby Palmeirinha and Ferruginha lagoons, respectively, through vapor dragging distillation, high resolution gas chromatography (HRGC), Infrared spectroscopy (IR) and ecotoxicological tests with leaves decomposition water (laboratory), essential oils, hydroalcoholic and aqueous extracts of litter leaves, and after 30 and 60 days in contact with the lagoons. For the toxicity tests, zooplanktonic (Daphnia similis, Daphnia laevis and Ceriodaphnia silvestrii) and benthic (Chironomus xanthus) organisms were used. The leaves of E. grandis showed higher outcome of essential oils compared to E. urophylla, being identified a higher number of substances in E. urophylla leaves. In the case of extracts, E. grandis showed higher outcome of hexanic extracts in the first and second steps of extractions, while E. urophylla presented higher outcome of ethanolic extracts. The main compounds found in E. urophylla extracts were steroids and triterpenes, and in E. grandis were saponins, steroids and triterpenes. The results of the acute ecotoxicological tests carried out with decomposition water of both eucalyptus species showed toxic effect to Daphnia similis, D. laevis, C. silvestrii and Chironomus xanthus, which, however, decreased with decomposition time. The essential oils, showed toxic effect in all tests performed with cladocerans (litter leaves, 30 and 60 days), as well as the hydroalcoholic extracts to Chironomus xanthus and aqueous to D. similis and D. laevis. Thus, it was verified, in the present study, that the natural compounds found in E. grandis and E urophylla leaves can affect the aquatic biota, being important the monitoring of aquatic environments surrounded by Eucalyptus monocultures.

No description available.

Submitted by Maike Costa (maiksebas@gmail.com) on 2017-09-12T12:14:46Z No. of bitstreams: 1 arquivototal.pdf: 6051062 bytes, checksum: 9d8a71da8da5797495aee64e3b141b54 (MD5) / Made available in DSpace on 2017-09-12T12:14:46Z (GMT). No. of bitstreams: 1 arquivototal.pdf: 6051062 bytes, checksum: 9d8a71da8da5797495aee64e3b141b54 (MD5) Previous issue date: 2016-10-31 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPq / Natural compounds, as coumarins and others oxygenated heterocycles, has been shown with a rich source of bioactive substances, however, due to difficulty of getting into large amounts of these substances isolated, many total synthesis or semi-synthesis methods has been developed. Among these many synthetic derivation strategies currently, the metal-catalyzed cross-coupling reactions have been highlighted in the literature, such as: Suzuki-Miyaura, Sonogashira, Heck, Negishi and Buchwald-Hartwig. In the present work, it is aimed the obtaining and preparation of natural heterocycles skeleton, and your derivations via cross-coupling palladium-catalyzed reactions; of which were obtained excellent results for the first three mentioned above, which was not repeated for the last two protocols, from the reactional conditions used. In all synthetics strategies realized, reactional conditions were diversify, such as temperature, reactional time, energy source, base, catalysts, among others; with the in order to observe the effects these changes and obtain the best sets of conditions. Besides the palladium-catalyzed reactions, some of cumarinic alkynes obtained by Sonogashira were submitted to the catalytic hydrogenation, to provide new alkanes with different spacers between the coumarinic ring and their phenyl groups. In general, the final compounds obtained showed from good to great yield values, reflecting on success in mostprotocols tested, where a total of 48 final molecules were obtained, of which 26 are novel compounds, all being characterized and proven according to their chemical structures. / Compostos naturais, como cumarinas e outros heterociclos oxigenados, tem se mostrado como uma rica fonte de substâncias bioativas, porém, devido à dificuldade da obtenção em grandes quantidades dessas substâncias isoladas, vários métodos de síntese total, ou semi-síntese têm sido desenvolvidos. Dentre as muitas estratégias de derivação sintética utilizadas atualmente, as reações de acoplamento cruzado catalisadas por metais têm tido destaque na literatura, como: Suzuki-Miyaura, Sonogashira, Heck, Negishi e Buchwald- Hartwig. No presente trabalho, objetivou-se a obtenção e preparação de esqueletos de heterociclos naturais, e suas derivações via reações de acoplamento cruzado catalisadas por paládio; das quais foram obtidos excelentes resultados para as três primeiras citadas anteriormente, o que não se repetiu para os dois últimos protocolos, a partir das condições reacionais utilizadas. Em todas as estratégias sintéticas realizadas, condições reacionais foram variadas, como temperatura, tempo recional, fonte de energia, base, catalisadores, entre outros; com o intuito de se observar os efeitos dessas mudanças e obter os melhores conjuntos de condições. Além das reações catalisadas por paládio, alguns dos alcinos cumarínicos obtidos por Sonogashira foram submetidos à hidrogenação catalítica, para fornecer novos alcanos com diferentes espaçadores entre o anel cumarínico e seus grupos fenílicos. De maneira geral, os compostos finais obtidos demonstraram de bons a ótimos valores de rendimento, refletindo no sucesso em boa parte dos protocolos testados, onde um total de 48 moléculas finais foram obtidas, das quais 26 são compostos inéditos, sendo todas caracterizadas e comprovadas de acordo com suas estruturas químicas.