Síntese de derivados aminados do limoneno e desenvolvimento de nanopartículas estáveis para o tratamento de leishmaniose e câncer cervical

O limoneno é um terpeno presente no óleo essencial de plantas cítricas. É relatado na literatura como um composto com atividades farmacológicas interessantes tais como: atividades antimicrobiana, antifúngica, citotóxica e nociceptiva, e antileishmanial. A presente tese relata a funcionalização do limoneno utilizando Síntese Orgânica Clássica (em solução) através das reações de aminólise e tosilação. Obtiveram-se seis compostos que foram testados para avaliar uma possível atividade antileishmania. Dentre esses derivados, os compostos tosilados apresentaram maior citotoxicidade frente a formas promastigotas de L. amazonensis. Porém, os compostos LaSOM 08 e LaSOM 28 apresentaram atividade mais pronunciada em estudos desenvolvidos anteriormente, assim, foram os derivados escolhidos para o desenvolvimento das nanoestruturas. Nanopartículas contendo limoneno e dois derivados mais ativos, LaSOM 08 e LaSOM 28 foram desenvolvidas. Dentre os nanossistemas, nanocápsulas poliméricas e nanoemulsão foram os dois sistemas contemplados nesse estudo. Foi possível obter nanoestruturas com características monomodais, nanométricas, com diâmetro desejado para a finalidade proposta, além de serem estáveis no período de 30 dias. Nanocápsulas de núcleo lipídico foram incorporadas em hidrogéis e apresentaram-se estáveis nessas formulações. Com a nanocápsulas de núcleo lipídico contendo limoneno, ensaios in vitro em células de câncer cervical humano (SiHa) foram realizadas e demonstraram que o limoneno apresentou interessante atividade antitumoral potencializada quando esse terpeno estava contido na nanocápsulas poliméricas.Limonene is a terpene present in the essential oil of citrus plants. It is reported in the literature as a compound with interesting pharmacological activities such as: antimicrobial, antifungal, cytotoxic nociceptive and antileishmanial activities. This thesis, reports the functionalization of limonene using Classical Organic Synthesis (in solution) especially through aminolysis and tosylation reactions. Six compounds were obtained and tested for a possible activity Leishmania. Among these derivatives, compounds tosilados showed higher cytotoxicity against promastigotes of L. amazonensis. However, the compounds LaSOM 08 and LaSOM 28 showed activity more pronounced in studies conducted previously. Thus, the derivatives were selected for the development of nanostructures. Nanoparticles containing limonene and two most active derivatives (LaSOM 08 and LaSOM 28) were developed. Among the nanosystems, polymeric nanocapsules and nanoemulsion were the two systems included in this study. Was possible to obtain characteristics nanostructures with monomodal, nanometric, diameter desired and stable over 30 days. Core lipid nanocapsules were incorporated into hydrogels and were stable in these formulations. In vitro assays with human cervical cancer cells (SiHa) and ore lipid nanocápsulas containing limonene, demonstrated that terpene has interesting antitumor activity that was potentiated when the limonene polymer was contained in the nanocapsules

EFEITO DE EXTRATOS DE SECREÇÕES GLANDULARES DE ANFÍBIOS NA FERRUGEM ASIÁTICA (Phakopsora pachyrhizi) E BIOMETRIA DE PLANTAS DE SOJA

The objective of this study was to analyze the effects of glandular secretion extracts from Rhaebo guttatus and Rhinella marina on TMG 132 RR soybean cultivar against the fungi Phakopsora pachyrhizi. Thirty days after seeding, a spontaneously arise of the disease was noticed and, two days after the arise of the first pustules, plants were treated with glandular secretion extracts at the concentrations 0,1; 0,2; 0,3; 0,4 e 0,5 mg mL-1, acibenzolar-S-methyl (500 L ha) and distilled water. None of the treatments resulted in statistical differences at the photosynthetic rates of the plants for chlorophyll a, chlorophyll b and total chlorophyll content. Glandular secretion extracts of R. guttatus and R. marina were not effective to reduce disease severity. There wasn’t statistical difference among treatments for defoliation percentage. For the biometrical evaluations, glandular secretion extracts of R. guttatus resulted in statistical difference only for the variable plant height but not for the remaining variables. Glandular secretion extracts of R. marina resulted in statistical difference only for number of root nodules but was not significant for the remaining variables.E Extratos de secreções de anfíbios da família Bufonidae têm sido estudados pelo potencial de controle direto de fitopatógenos, bem como na ativação de mecanismos de defesa contra doenças em plantas. Assim, este estudo analisa os efeitos de extratos de secreções glandulares de Rhaebo guttatus e Rhinela marina contra o fungo Phakopsora pachyrhizi e na biometria de plantas de soja da cultivar TMG 132 RR. Aos 30 dias após semeadura, notou-se o surgimento espontâneo da doença e, dois dias após o surgimento das primeiras pústulas, as plantas foram tratadas com extratos de secreções glandulares nas concentrações de 0,1; 0,2; 0,3; 0,4 e 0,5 mg mL-1, acibenzolar-S-metil (500 L ha) e água destilada. Com relação ao número total de trifólios, teores de clorofila a, b e total não houve diferença estatística entre os tratamentos. Nas avaliações biométricas, o extrato de secreção glandular de R. guttatus proporcionou diferença estatística apenas na variável altura de plantas. Quando as plantas foram tratadas com extrato de secreção glandular de R. marina, houve diferença estatística no número de nódulos, porém, sem diferença estatística para as demais variáveis analisadas. Conclui-se que extratos de secreções glandulares de R. guttatus e R. marina não controlam ferrugem asiática da soja; porém concentrações de 0,1mg mL-1, 0,2 mg mL-1 e 0,3 mg mL-1 de extrato de secreção glandular de R. guttatus promovem maior altura de plantas e extrato de secreção glandular de R. marina, nas concentrações de 0,1mg mL-1, 0,2 mg mL-1 e 0,4 mg mL-1, afeta negativamente o número de nódulos. Palavras-chave: altura de plantas; glândulas parotóides; Rhaebo guttatus; Rhinella marina; oleaginosa.   Effect of extracts from amphibian glandular secretions on asian rust (Phakopsora pachyrhizi) and biometry of soybean plants   ABSTRACT: Extracts from secretions of amphibians of the Bufonidae family were studied for their potential for direct control of phytopathogens, as well as for the activation of mechanism of defense against plant diseases. Thus, this study assessed the effects of glandular secretion extracts from Rhaebo guttatus and Rhinella marina against the fungi Phakopsora pachyrhizi and biometric responses on TMG 132 RR soybean cultivar. Thirty days after seeding, a spontaneously arise of the disease was noticed and, two days after the arise of the first pustules, plants were treated with glandular secretion extracts at the concentrations 0,1; 0,2; 0,3; 0,4 e 0,5 mg mL-1, acibenzolar-S-methyl (500 L ha) and distilled water. None of the treatments resulted in statistical differences at the photosynthetic rates of the plants for chlorophyll a, chlorophyll b and total chlorophyll content. For the biometrical evaluations, glandular secretion extracts of R. guttatus resulted in statistical difference only for the variable plant height variable. Glandular secretion extracts from R. marina resulted in statistical difference only for number of root nodules but was not significant for the remaining variables. The results showed that glandular secretion extracts from R. guttatus and R. marina does not control Asian soybean rust; however glandular secretion extracts from R. guttatus at the concentrations 0,1mg mL-1, 0,2 mg mL-1 e 0,3 mg mL-1 promotes greater plant height. The glandular secretion extracts from R. marina at the 0,1mg mL-1, 0,2 mg mL-1 e 0,4 mg mL-1 negatively affects the number of plant nodules. Keywords: height of plants; paratoid gland; Rhaebo guttatus; Rhinella marina; oleaginous

Preparation and characterization of steam and CO2 activated carbon from Brazil nut shell

Activated carbon is a porous material with several industrial applications. In this research, brazil nut shell was used to produce activated carbon, a promising raw material based on its low cost and high quality. Also, nut processing generates an extensive amount of waste, requiring proper disposal. The carbon was produced at temperatures of 600, 700, and 800 °C and activated by physical method using steam or CO2. Yield was calculated, and the activated carbon was analyzed according to the following physical-chemical parameters: water content, volatile material, fixed carbon, ash, apparent density, and pH. Infrared spectroscopy and BET adsorption isotherms were also performed. The fixed carbon contents of the carbons produced at 700 and 800 °C remained above 84%. The pH values characterized them as basic. The surface areas of the carbon obtained at 800 °C were 397 ± 8 m2 g–1 and 325 ± 7 m2 g–1 in those which were activated by steam and CO2, respectively

New alternative for adsorption of 2,4-dichlorophenoxyacetic acid herbicide (2,4-D)

The adsorptive capacity of charcoal from the husk of the brazil nut fruit, called “ouriço” (the hard ball with nuts inside) for the herbicide dichlorophenoxyacetic acid (2,4-D) was evaluated. Activated carbons were produced from the brazil nut in a tubular oven at 800 °C and activated with CO2 or water steam. The specific surface area was determined by the Brunauer, Emmett and Teller (BET) method, demonstrating the mean density of micropores. Analysis of N2 adsorption/desorption isotherms was undertaken and the morphology of activated carbons was visualized by Scanning Microscopy (SEM). The activated carbons were successfully obtained and had a specific surface area of 395 m2.g-1 and 401 m2.g-1 after activation with either CO2 or water steam, respectively. The highest pore mean density occurred with a diameter of 1.17 nm for carbons activated in both atmospheres. The graph of the adsorption/desorption isotherms of N2 showed Type I isotherms, regardless of the activation atmosphere. The SEM analysis showed that, for both activation atmospheres, pore formation occurred in the shape of uniform honeycomb craters. Adsorption kinetics followed the pseudo-second order model, indicating chemisorption. Regardless of the activation atmosphere, the activated carbon from the brazil nut “ouriço”, was highly efficient for 2,4-D adsorption

Synthesis of Limonene ß-amino alcohol derivatives and in vitro biological evoluation

Nesse trabalho, foram sintetizados seletivamente, a partir do óxido do limoneno em oposição a diversas aminas primárias e secundárias, onze b-aminoálcoois derivados do limoneno através de aquecimento convencional e sob irradiação com microondas, fornecendo produtos com moderados a bons rendimentos. O limoneno e nove destes aminoálcoois foram testados contra ovos e larvas de carrapatos da espécie de Rhipicephalus (Boophilus) microplusn no intervalo de concentração de 0,150-10mg/mL. Os resultados revelaram que em doses entre 10 μl/ml - 2.5 μl/ml todos os compostos testados foram letais às larvas. Frente ao teste ovicida os compostos 2, 6, 8, 9 e 10 foram os mais ativos, impedindo a eclosão total ou quase total dos ovos na menor dose utilizada (0,150 μg/ml). Este é o primeiro relato da atividade carrapaticida de limoneno, óxido de limoneno e dos b- aminoálcoois do limoneno para a espécie de carrapato Rhipichephalus (Boophilus) microplus. O limoneno e sete β-aminoálcoois foram testatdos in vitro contra forma promastigota de Leishmania (Vianna) braziliensis. Os resultados dos testes mostraram que, dentre os sete β-aminoálcoois testados dois deles foram mais ativos que o padrão pentamidina (48,5 ± 28,7 μM) e cinco foram mais ativos que o limoneno 1. Destes, dois deles (compostos 7 e 9) apresentaram alta atividade frente a formas promastigotas do ciclo parasitário numa concentração de 0,156mg/mL. O Limoneno 1 nesse teste se mostrou inativo (876,2 ± 216 μM) demonstrando que este terpeno isolado não é um bom antiparasitário contra formas promastigotas de Leishmania (Vianna) braziliensis. Este é o primeiro relato de atividade contra leishmania para amino-álcoois derivados do limoneno.In this work, a series of seven limonene β-amino alcohols derivatives have been regioselectively synthesized from moderate to good yields. The eleven β-amino alcohols Limonene derivatives were synthesized through aminólisis of Limonene oxide, using several primary and secondary amines by both conventional heating and under microwave irradiation. Limonene, Limonene oxide and nine ß-amino alcohol derivatives were investigated for the effect on egg hatchability and mortality rates of newly hatched larvae of cattle tick Rhipicephalus (Boophilus) microplus. At the doses between 10 μl/ml to 2.5 μl/ml all compounds were highly lethal to the larvae and at lower concentrations some of them (2, 6, 8, 9 and 10) showed activity. The effect on hatchbility of the eggs was observed in all treatments. This is the first report of carrapicide activity for Limonene, Limonene oxide and nine ß-amino alcohol derivatives against cattle tick Rhipicephalus (Boophilus) microplus. The leishmanicidal activity was performed and according to the results two of these compounds were more powerful against in vitro cultures of Leishmania (Vianna) braziliensis promastigote form in a range of μM. The activities observed for 3b and 3f were about 100 folds more potent than the drug standard Pentamidine, while the limonene hasn’t shown any activity in the same test. This is the first report of antileishmanial activity of Limonene β-amino alcohol derivatives

El Telegrama del Rif: El Telegrama del Rif - Año XX Número 7257 - 1921 enero 15 (15/01/1921)

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EXTRACT OF Punica granatum L.: AN ALTERNATIVE TO BHT AS AN ANTIOXIDANT IN SEMISSOLID EMULSIFIED SYSTEMS

Pomegranate (Punica granatum L.) is a fruit which has important pharmacological activities and has been attracting attention due to its important antioxidant activity, a significant feature in relation to cosmetics. Formulations containing different concentrations of an ethanolic extract of pomegranate (0.1, 1.0 and 5.0%) (w/w) as an antioxidant agent showed that this is an interesting alternative for the use of natural products with biological activity. The stability and rheology of semissolid systems containing an extract of this plant were evaluated. Preliminary stability studies showed greater physico-chemical stability of the formulation, and thus it was used in an accelerated stability study, as well the quantification of total phenolic compounds and the determination of antioxidant activity. It was observed that different concentrations of the extract did not significantly influence the stability. Moreover, the formulation was found to have better stability when stored at room temperature than under heated or cooled conditions. Formulations containing 0.1 and 5.0% of extract showed more stable rheological behavior, due to the absence of a solid/liquid transition in the rheogram. Tests confirmed the high phenolic content and antioxidant activity, demonstrating the potential of this plant for use in cosmetology as an antioxidant