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Submitted by Sheila MONTEIRO (sheila.monteiro@ufma.br) on 2022-05-24T12:35:28Z No. of bitstreams: 1 MARCOS - MARINHO.pdf: 252515 bytes, checksum: 0a5900dff3591c7d825467ad40cd3a9e (MD5) Made available in DSpace on 2022-05-24T12:35:28Z (GMT). No. of bitstreams: 1 MARCOS - MARINHO.pdf: 252515 bytes, checksum: 0a5900dff3591c7d825467ad40cd3a9e (MD5) Previous issue date: 2021-07-16 FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DO MARANHÃO - FAPEMA COORDENAÇÃO DE APERFEIÇOAMENTO DE PESSOAL DE NÍVEL SUPERIOR - CAPES Brazilian red propolis is produced in the Northeast Region of the country by Apis mellifera L. bees and has Dalbergia ecastophyllum as its botanical source. The literature describes propolis antibacterial, antifungal, antitumor, antioxidant, anti-inflammatory, cytotoxic, and antiparasitic activities. The objective of the present study was carrying out a literature review on the chemical composition and leishmanicidal activity of Brazilian propolis by evaluating the leishmanicidal activity and characterizing the chemical composition and palynological profile of red propolis produced in the Brazilian state of Tocantins, a region that has not been mentioned in the literature as a place known for the production of this type of propolis. The first chapter shows a literature survey and discusses studies on evaluation of the chemical composition and leishmanicidal activity of Brazilian propolis found in the following databases: National Library of Medicine (National Institutes of Health, PubMed), Science Direct, Scopus, and Latin America and Caribbean Center on Health Sciences Information. The integrative reviewing method was applied. The search identified 28 articles published between 2004 and 2020 addressing red, green, and brown propolis. Chemical analyses of Brazilian propolis essential oils were carried out by using gas chromatography associated with mass spectrometry or flame ionization and identified the presence of monoterpenes, sesquiterpenes, and phenylpropanoids. Analysis of hydroethanolic extracts were carried out by using high-performance liquid chromatography with UV-Vis detection (HPLC/UV-Vis) and connected to mass spectrometer (HPLC/MS), which identified terpenes, phenolic acids, flavonoids, and benzophenones. Studies that assessed the leishmanicidal activity of Brazilian propolis in different species of Leishmaniawere more abundant between 2007 and 2020 and reported use of hydroethanolic extracts, essential oils, polymeric nanoparticles, and metal complexes in combination with propolis to inhibit promastigote and amastigote forms. The second chapter shows the palynological profile of propolis obtained by applying characterization performed by using HPLC/MS in both positive and negative modes. Botanical analysis identified 22 pollen types that belonged to 15 botanical families, among which Arecaceae, Asteraceae, Fabaceae, Myrtaceae, Melastomataceae, Rubiaceae, and Urticaceae were more frequent. Polliniferous and nectariferous species were identified. However, the palynological profile of Dalbergia ecastophyllum, a species related to production of red propolis in the Brazilian Northeast coast, was not obtained. Mass spectra obtained by using HPLC/MS showed a precursor ion fragmentation pattern compatible with compounds belonging to the classes of isoflavonoids, pterocarpanes, flavanones, chalcones, as well as isoflavones condensed with a chalcone (retusapurpurin). The third chapter shows the results of the evaluation of propolis extracts and fractions regarding leishmanicidal activity against the promastigote form of Leishmania amazonensis and cytotoxicity induced in RAW 264.7 macrophages measured by applying the cell viability method with (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). Total phenolic content and flavonoid concentration were measured by using UV-vis spectrophotometry, whereas chemical composition was obtained by HPLC/MS. The extracts inhibited promastigote forms, with IC50 ranging from 21.98 to 86.12 µg/mL. The chloroform fraction was the most effective (16.02 µg/mL). Evaluation of cytotoxicity against RAW 264.7 macrophages indicated that red propolis extract and chloroform fraction showed cell toxicity for concentrations equal to or higher than 100 µg/mL. The samples had high total phenolic content and flavonoid concentration for extracts and chloroform fraction, whereas HPLC/UV-Vis showed similar chemical profiles, with identification of the substances formononetin and biochanin A in all samples, which are considered chemical markers. The results allowed to conclude that red propolis produced in the Brazilian state of Tocantins has leishmanicidal potential, low cell toxicity, and high concentrations of phenolic compounds. This is the first study oriented toward characterizing red propolis produced in Brazilian Amazon and will contribute to the development of apiculture in Tocantins based on production and commercialization of this product. A própolis vermelha brasileira é produzida na região Nordeste por abelhas da espécie Apis mellifera L. e tem como fonte botânica a espécie Dalbergia ecastophyllum. Na literatura são descritas atividades antibacteriana, antifúngica, antitumoral, antioxidante, anti-inflamatória, citotóxica e antiparasitária. O presente trabalho teve como objetivo realizar uma revisão de literatura sobre a composição química e atividade leishmanicida da própolis brasileira, avaliar a atividade leishmanicida, caracterizar a composição química e os tipos polínicos da própolis vermelha produzida no estado do Tocantins, Brasil. Região não mencionada na literatura como produtora desse tipo de própolis. No primeiro capítulo foi realizado o levantamento da literatura investigando publicações sobre avaliação da composição química e atividade leishmanicida da própolis brasileira nas bases de dados National Library of Medicine - National Institutes of Health (PubMed), ScienceDirect, Scopus e Literatura Latino-Americana e do Caribe em Ciências da Saúde (LILACS) pelo método de revisão integrativa. A busca identificou 28 publicações entre os anos de 2004 a 2020 com própolis vermelha, verde e marrom. As análises químicas com óleos essenciais da própolis brasileira foram realizadas por ensaios de cromatografia gasosa acoplada a espectrômetro de massas e com ionização de chama (CG-EM, CG-FID), identificando a presença de monoterpenos, sesquiterpenos e fenilpropanoides. Para análise de extratos hidroetanólicos foram empregadas técnicas de cromatografia líquida de alta eficiência com detector de ultravioleta e acoplada a espectrômetro de massas (CLAE/UV-Vis e CLAE-EM/EM), que identificaram terpenos, ácidos fenólicos, flavonoides e benzofenonas. Estudos avaliando a atividade leishmanicida de própolis brasileira para diferentes espécies de Leishmania concentram-se entre os anos de 2007 a 2020, utilizando extratos hidroetanólicos, óleos essenciais, nanopartículas poliméricas e complexos metálicos associados à própolis para a inibição de formas promastigotas e amastigotas. O segundo capítulo apresenta a identificação polínica da própolis pelo método de acetólise de Erdtman e a caracterização química por CLAE- EM/EM nos modos positivo e negativo. A análise botânica identificou 22 tipos polínicos, pertencentes a 15 famílias botânicas, com maior frequência para as famílias Arecaceae, Asteraceae, Fabaceae, Myrtaceae, Melastomataceae, Rubiaceae e Urticaceae, identificando espécies poliniferas e nectaríferas, contudo, não foi identificado o tipo polínico de Dalbergia ecastophyllum, espécie associada à produção da própolis vermelha no litoral nordeste do Brasil. Os espectros de massas obtidos por CLAE-EM/EM apresentaram um padrão de fragmentação dos íons precursores compatível com compostos das classes dos isoflavonoides, pterocarpanos, flavonona, chalcona, além da isoflavona condensada com uma chalcona (retusapurpurina). No terceiro capítulo os extratos e frações da própolis foram avaliados quanto à atividade leishmanicida contra a forma promastigotas de Leishmania amazonensis e citotoxicidade frente a macrófagos RAW 264.7, utilizando o método de viabilidade celular com o reagente brometo de 3-(4,5-dimetil tiazol-2-il)-2,5-difenil tetrazólio (MTT), a concentração de fenóis totais e flavonoides foi obtida por espectrofotometria UV-Vis e a composição química por CLAE/UV- Vis. Os extratos inibiram as formas promastigotas, com CI50 variando de 21,98 a 86,12 µg/mL, enquanto a fração clorofórmica foi mais efetiva (16,02 µg/mL). A avaliação da citotoxicidade contra células Raw 264.7 demonstrou que o extrato de própolis vermelha e a fração clorofórmica apresentaram toxicidade celular em concentrações 100 µg/mL. As amostras demonstraram elevada concentração de fenóis totais e flavonoides para os extratos e fração clorofórmica, enquanto nas análises por CLAE/UV-Vis foi observado semelhança no perfil químico, com identificação dos compostos formononetina e biochanina A em todas as amostras, sendo considerados marcadores químicos. Os resultados permitem concluir que a própolis vermelha produzida no estado do Tocantins apresenta potencial leishmanicida, baixa toxicidade celular e elevadas concentrações de compostos fenólicos. Este é primeiro estudo com própolis vermelha produzida na região da Amazônia brasileira e contribuem para o desenvolvimento da apicultura do estado do Tocantins a partir da produção e comercialização de própolis vermelha.

Orientador: Yong Kun Park Tese (doutorado) - Universidade Estadual de Campinas, Faculdade de Engenharia de Alimentos Resumo: Própolis é uma substância resinosa elaborada por abelhas da espécie Apis mellifera e usada como revestimento da colméia. Para a produção da própolis as abelhas usam a matéria-prima coletada de diversas partes da planta como broto, botões florais, exsudatos resinosos e outras partes do tecido vegetal. A própolis é utilizada na medicina popular há 3000 anos a.C. principalmente por apresentar propriedades antimicrobiana, anti-inflamatória e cicatrizante (Marcucci, 1995; Khayyal et al., 1993). Nos últimos anos foi demonstrado que alguns tipos de própolis apresentam atividade antioxidante, hipotensiva, anestésica, anticâncer, anti-HIV e anticariogênica. As própolis brasileiras são classificadas em 13 grupos conforme sua composição físico-química, que é diretamente relacionada com a planta utilizada pelas abelhas para coleta das resinas e exsudatos. Nesse trabalho foi escolhida a própolis do grupo 13 por possuir altas atividades biológicas. Nessa tese foram avaliados a quantidade de compostos fenólicos totais e flavonóides totais presentes na própolis do grupo 13 de diferentes colméias e em diferentes épocas do ano, além de testar suas atividades biológicas. Além disso, foram realizados o isolamento e a identificação da formononetina (7-hidroxi-4¿metoxi-isoflavona), principal isoflavona encontrada na própolis do grupo 13, e foram testadas suas atividades biológicas. Demonstrou-se que a própolis vermelha de João Pessoa - PB apresenta grandes variações entre as colméias e em diferentes épocas do ano em relação à composição de compostos fenólicos totais e flavonóides totais. Mostrou-se também que as própolis com maiores quantidades de compostos fenólicos totais e flavonóides totais apresentaram melhores atividade antimicrobiana contra Staphylococcus aureus e atividade antiradical livre. Foi demonstrado um método de extração da formononetina de própolis do grupo 13, e mostrou-se que esse composto possui alta atividade antiradical e antimicrobiana contra Staphylococcus aureus Abstract: Propolis is a resinous substance produced by the honeybee Apis mellifera. Bees use propolis to seal holes and to protect the beehive. To produce propolis the honeybee uses resins of leaf buds and buds, resinous exudates and other parts of plant tissues. Propolis is used as a folk medicine since 3000 BC. Numerous biological properties have been found including antimicrobial, anti-inflammatory and cicatrizing (Marcucci, 1995, Khayyal et al., 1993). Recently, studies revealed that propolis also has antioxidant, hypotensive, anesthetic, anticancer, anti-HIV and anticariogenic activities. The Brazilian propolis is classified into 13 distinct groups according to their chemical composition, which is directly related to the plants used to collect resins and exudates. In this study, propolis of group 13 was chosen, as it shows high biological activity. In this thesis were analyzed the quantity of whole phenolic compounds and flavonoids content was analyzed in each sample of propolis group 13, collected in different beehives and in different seasons. Furthermore, it was tested the biological activities of each sample. In addition, formononetin (7-hydroxy-4¿methoxyisoflavone), the main isoflavonoid found in propolis group 13, was isolated and identified and its biological activity was analyzed. It was demonstrated that João Pessoa ¿ PB red propolis has great variations of phenolic compounds and flavonoids among honeybees and different seasons. It was showed that propolis with greater amount of phenolic compounds and flavonoids have better antimicrobial activity against Staphylococcus aureus and antiradical activity. It was demonstrated a method of formononetin extraction of red propolis group 13, and it was showed that this compound has high antimicrobial activity against Staphylococcus aureus and antiradical activity Doutorado Doutor em Ciência de Alimentos

El presente se realizó con el objetivo de evaluar la presencia y tipo de flavonoides y saponinas en extractos alcohólicos de hojas de Desmodium molliculum HBK “manayupa” con el propósito de contribuir a un mejor conocimiento de la composición química de esta planta. La especie fue colectada en el distrito de Baños del Inca de la Ciudad de Cajamarca, departamento de Cajamarca a 2776 msnm. La marcha fitoquímica confirmó la presencia de taninos, flavonoides, alcaloides y saponinas. El análisis cromatográfico del extracto alcohólico usando como patrones los isoflavonoides genisteína y daizeína y el flavonoide vitexina, reveló la probable presencia de estos flavonoides en el extracto alcohólico. El análisis espectroscópico UV permitió confirmar uno de los isoflavonoides como genisteína y otro probablemente 5-O-metil-genisteína. Adicionalmente el análisis cromatográfico usando como referencia extractos metanólicos de semillas desengrasadas de soya, mostró la presencia de trazas de soyasaponinas en el extracto alcohólico., The aim of this study was evaluate presence of flavonoids and saponins in alcoholic extracts of leaves of Desmodium molliculum HBK " manayupa " These metabolites was valuated with the aim of contributing to a better understanding of the chemical composition of this plant. The species was collected in the district of Baños del Inca City of Cajamarca, department of Cajamarca to 2776 meters. The phytochemical march revealed the presence of tannins, flavonoids, alkaloids and saponins in the alcoholic extract. Chromatographic analysis of the alcoholic extract using isoflavones genistein and daizein and vitexin flavonoid as reference standard revealed the probable presence of these isoflavonoids and the flavonoid in the alcohólic extract. UV spectroscopic analysis allowed us to confirm one of the isoflavone as genistein and 5-O-methylgenistein in addition chromatographic analysis using methanol extracts of defatted soybeans showed the probable presence of soyasaponins in the alcoholic extract.

Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmacology & Toxicology Student: Lucie Ungerová Supervisor: PharmDr. Jana Pourová, Ph.D. Title of diploma thesis: The pharmakokinetics of isoflavonoids The aim of this diploma thesis is to summarize currently available informations about the pharmacokinetics of the polyfenolic compounds from a large group of flavonoids, isoflavonoids. Isoflavonoids are coumpounds found in many plant families, but especially in some members of Fabaceae family. One of the main well-known sources are soy beans containing the most famous isoflavones - genistein and daidzein, their pharmakokinetics is the main theme of this diploma thesis. Since isoflavonoids are mainly contained in the diet, their oral administration is very relevant. Isoflanonoids in the human diet occurs predominantly in the form of glykosides and therefore, after ingestion, they have to be deglycosylated by β- glucosidase enzyme family to aglycones. After that they are able to pass through the intestine into the systemic circulation and they are available for action. This is already happening in the oral cavity and the absorption occurs in the small intestine. The intestinal bacterial microflora composition is also very important for pharmacokinetics, for example I can mention...

Aim: The aim of the work was isolation and identification of the phenolic compounds from the rhizomes of Iris hungarica. Materials and methods: To establish by chemical and spectral methods for the structures of phenolic compounds, which were isolated from the rhizomes of Iris hungarica Waldst. et Kit. (Iridaceae family). Compounds were obtained by column chromatography on silica gel and their structures were determined by UV, IR, MS, 1H-NMR spectra methods. Preliminary screening of antibacterial activity was determined. Results: From the ethanolic extract of the rhizomes of I. hungarica, which is widespread in Ukraine, for the first time two new for this species isoflavones, tectorigenin and tectoridin and xanthone mangiferin, together with known isoflavonoids daidzein, genistein, formononetin were isolated. The dry extract of the rhizomes of I. hungarica at a concentration of 1% has shown the highest inhibitory activity for Gram-positive bacteria and fungi. Resumen Objetivo: El objetivo del trabajo es el aislamiento y la identificación de los compuestos fenólicos de los rizomas de Iris hungarica. Materiales y métodos: Se utilizaron métodos químicos y espectrales para conocer las estructuras de compuestos fenólicos que se aislaron de los rizomas de Iris hungarica Waldst. et Kit. (Familia de Iridaceae). Los compuestos se obtuvieron mediante cromatografia en columna sobre gel de sílice y se determinaron sus estructuras mediante análisis de sus espectros por UV, IR, MS, 1H-RMN. Se determinó el cribado preliminar de la actividad antibacteriana. Resultados: Se aislaron por primera vez de los rizomas de Iris hungarica (común en Ucra-nia) dos isoflavonas, tectorigenina y tectoridina (nuevas para esta especie), el xan-tonoide mangiferina y los isoflavonoides daidzeina, genisteina y formononetina. El extracto seco de los rizomas de I. hungarica a una concentración de 1% ha mostrado la actividad inhibitoria más alta para bacterias y hongos Gram-positivos.

Since the anti-inflammatory, antidiabetic and hypolipidemic effects of soy isoflavones may be mediated by activation of peroxisome proliferator-activated receptors (PPAR), the present study investigated whether the methanolic fractions obtained from soybean seeds (E1) and soybean seed coats with hypocotyls (E2) could influence PPARα, PPARγ and PPARβ/δ transcriptional activity. The isoflavones from E1 and E2 were quantified by HPLC analysis. E1 and E2 were rich in isoflavones (daidzin, glycitin, genistin, malonyldaidzin, malonylglycitin, malonylgenistin, daidzein, glycitein, and genistein). Moreover, E1 and E2 showed no evidence of genetically modified material containing the gene CP4 EPSPS. To investigate PPAR transcriptional activity, human promonocytic U-937 cells were treated with E1 and E2 (200, 400, 800, and 1600 µg/mL), positive controls or vehicle. Data are reported as fold-activation of the luciferase reporter driven by the PPAR-responsive element. Dose-response analysis revealed that E1 and E2 induced the transcriptional activity of PPARα (P < 0.001), with activation comparable to that obtained with 0.1 mM bezafibrate (positive control) at 1600 µg/mL (4-fold) and 800 µg/mL (9-fold), respectively. In addition, dose-response analysis revealed that E1 and E2 activated PPARβ/δ (P < 0.05), and the activation at 800 µg/mL (4- and 9-fold, respectively) was comparable to that of 0.1 mM bezafibrate (positive control). However, no effect on PPARγ was observed. Activation of PPARα is consistent with the lipid-lowering activity of soy isoflavones in vivo, but further studies are needed to determine the physiological significance of PPARβ/δ activation.

A atividade antiviral de compostos flavonoídicos tem sido amplamente investigada nos últimos anos. Nesse contexto, a primeira etapa da presente tese teve por objetivo avaliar a atividade anti-herpética in vitro dos principais isoflavonóides de Glycine max (soja): genisteína, daidzeína, gliciteína e cumestrol. Dentre os isoflavonóides investigados, a genisteína e o cumestrol mostraram uma interessante atividade frente aos vírus HSV-1 (cepa KOS e 29R, sensível e resistente ao aciclovir, respectivamente) e HSV-2 (cepa 333), interferindo em diferentes etapas do ciclo de replicação dos vírus. Devido à reduzida hidrossolubilidade desses isoflavonóides, foi proposta a sua incorporação em nanoemulsões de uso tópico. As formulações foram otimizadas através de um experimento fatorial completo do tipo 23 . O efeito dos fatores tipo de óleo (óleo de rícino ou miristato de isopropila), co-tensoativo iônico (oleilamina ou ácido olêico) e fosfolipídeo (DSPC ou DOPC) sobre as propriedades das nanoemulsões e a retenção da genisteína na pele de orelha suína foi investigado. Nanoemulsões compostas de miristato de isopropila/ oleilamina/DOPC apresentaram um menor diâmetro de gotícula e uma maior retenção de genisteína na pele de orelha suína enquanto que a combinação miristato de isopropila/oleilamina/DSPC mostrou o menor índice de polidispersão. A viscosidade das formulações selecionadas foi ajustada através do uso de hidroxietilcelulose visando à obtenção de produtos de uso tópico, obtendo-se hidrogéis de comportamento pseudoplástico. Na sequência, um conjunto de resultados obtidos demonstrou que a composição das formulações (especialmente o fosfolipídeo DOPC e o agente espessante hidroxietil celulose) pode influenciar a liberação e a retenção dos isoflavonóides em mucosa esofágica suína. A integridade da mucosa também desempenha um papel no aumento da permeação/retenção do cumestrol, conforme ilustrado nas imagens de microscopia confocal, utilizando vermelho do Nilo como marcador fluorescente. De maneira geral, a incorporação dos isoflavonóides nas nanoemulsões aumenta a atividade anti-herpética desses compostos in vitro. O conjunto dos resultados demonstra que as formulações desenvolvidas são potenciais carreadores de uso tópico para genisteína e cumestrol no tratamento das infecções herpéticas. The antiviral activity of flavonoid compounds has been extensively investigated in recent years. In this context, the first step of this study was to evaluate the antiherpes activity in vitro of the main isoflavonoids of Glycine max (soybean): genistein, daidzein, glycitein and coumestrol. Among the investigated isoflavonoids, genistein and coumestrol showed interesting activity against HSV-1 (KOS and 29R strains, which are acyclovir-sensitive and acyclovir–resistant strains, respectively) and HSV-2 (333 strain), interfering at different stages of the virus replication cycle. Due to the low hydrosolubility of these isoflavonoids, their incorporation into topical nanoemulsions was proposed in this study. The formulations were optimized through a 23 full factorial design. The factors effect of oil type (castor oil or isopropyl myristate), ionic co-surfactant (oleylamine or oleic acid) and phospholipid type (DSPC or DOPC) on physicochemical properties and genistein retention into porcine ear skin was investigated. Nanoemulsions composed of isopropyl myristate/ DOPC/oleylamine showed the smaller particle size and higher genistein retention into skin, whereas the formulation composed of isopropyl myristate/DSPC/oleylamine exhibited the lower polydispersity index. The viscosity of selected formulations was adjusted with hydroxyethyl cellulose to obtain topical products, which showed nonNewtonian behavior. In sequence, a set of results showed that formulations composition (especially the phospholipid DOPC and the thickening agent hydroxyethyl cellulose) could influence the release and retention of isoflavonoids in porcine esophagus mucosa. The integrity of mucosa plays a role on the increase of coumestrol permeation/retention, according to confocal microscopy images, using Red Nile as fluorescent label. In general terms, the incorporation of isoflavonoids into nanoemulsions increases the antiherpes activity of these compounds in vitro. The overall results show that the formulations developed in this study are potential topical carriers for genistein and coumestrol in the treatment of herpes infections.

"La Isoorientina (ISO), una isoflavona presente en numerosas plantas empleadas por la medicina tradicional, posee probados efectos hipoglucemiantes pero sus mecanismos de acción son aún poco conocidos. Al analizar los mecanismos moleculares de ISO encontramos que estimula la captación de glucosa en adipocitos múridos y humanos, tanto sensibles como resistentes a insulina. ISO ejerce este efecto mediante la inducción de la fosforilación apropiada de las proteínas de la vía de señalización canónica de la insulina (PI3K) y estimula la transcripción de genes que codifican para esta vía de señalización. Asimismo, encontramos que ISO bloquea la adipogénesis múrida y humana mediante la inhibición de la expresión de los genes proadipogénicos PPARy, C/EBPa y KLF4 e induce la de los genes antiadipogénicos GATA2 y WNT10B, Nuestros resultados sugieren que ISO modula la expresión de estos genes por medio de la translocación al núcleo del factor de transcripción Nrf2. Por otra parte dado que WNT10B induce la osteogénesis de células troncales mesenquimales, analizamos el efecto de ISO sobre la actividad de la fosfatasa alcalina y la deposición extracelular de calcio en preadipocitos 3T3-F442A. Encontramos que ISO induce la expresión de ambos marcadores en preadipocitos múridos. En resumen, ISO induce la captación de glucosa por adipocitos activando las vía de señalización de insulina, bloquea la fromación de nuevos adipocitos e induce la expresión de marcadores osteogénicos en preadipocitos 3T3-F442A. Estos resultados sugieren que ISO tiene un alto potencial para el desarrollo de nuevos tratamientos para el síndrome metabólico." "Isoorientin, an isoflavonoid widely present in the plants, is commonly used in traditional medicine, and has shown hypoglycemic effects, but its mode of action in not well understood. In this study we found that ISO induced glucose uptake in both insulinsenstive and insulin resistant murine and human adipocytes by stimulating the proper phosphorylation of proteins of the insulin canonic signaling pathway (PI3K) and the transcription of the genes encoding its proteins, was also induced. In addition, ISO inhibited the murine and human adipogenesis by inhibiting the expression of proadipogenic genes PPARy, C/EBPa and KLF4 and by inducing the transcription of the antiadipogenic genes GATA2 and WNT10B. Our results suggest that ISO modulates gene expression by promoting the nuclear translocation of the transcription factor Nrf2. Given that it has been shown that WNT10B transcription factor induces osteogenesis in mesenchymal stem cells, we analyzed the effect of ISO on the activity of alkaline phosphatase and extracellular calcium deposition in 3T3-F442A preadipocytes and found that ISO increased the expression of both markers in murine preadipocytes. In summary, ISO iduces glucose uptake in adipocytes through activation of the insulin signaling pathways, the inhibition of adipogenesis and induction of osteogenic markers in 3T3-F442A preadipocytes. These properties confers ISO a therapeutic potential to develop new drugs for metabolic syndrome treatment."

Made available in DSpace on 2016-08-29T15:35:33Z (GMT). No. of bitstreams: 1 tese_6797_Eder Lana e Silva.pdf: 2095519 bytes, checksum: 1cfc6feafafa1891d9501f8ae993c817 (MD5) Previous issue date: 2013-08-29 Este trabalho descreve o estudo químico das folhas e dos galhos da espécie Dalbergia miscolobium visando à busca de inibidores das catepsinas K e V. A espécie de estudo é encontrada em regiões de Cerrado do Estado do Piauí ao Estado do Paraná, possuindo alguns relatos sobre as substâncias do tronco e uma isoflavona das folhas. Neste trabalho, os extratos hexânicos e acetato de etila das folhas e dos galhos de D. miscolobium foram submetidos a metodologias cromatográficas visando o isolamento dos constituintes químicos. Foram identificados quatro terpenos: α-amirina (1), β-amirina (2), lupeol (3) e fitol (4), três esteroides: campesterol (5), estigmasterol (6) e sitosterol (7) e isolados seis isoflavonoides: prunetina (8), di-O-metildaidzeina (9), 8-O-metilretusina (10), duartina (11), sativan (12) e salisoflavan (13). Todos os isoflavonoides foram ensaiados na concentração de 100 μM como inibidores das catepsinas K e V e para a primeira, a K, nenhuma substância mostrou-se efetiva, mas para a catepsina V, as isoflavanas 12 e 11 mostraram-se como potentes inibidoras, com valores de 88 e 89% respectivamente.

Submitted by Alisson Mota (alisson.davidbeckam@gmail.com) on 2015-07-16T19:33:56Z No. of bitstreams: 1 Disserta????o - Mauro Galucio Garcia.pdf: 8414985 bytes, checksum: 192bccb9ac6b0279be9e5ff578bb8132 (MD5) Approved for entry into archive by Divis??o de Documenta????o/BC Biblioteca Central (ddbc@ufam.edu.br) on 2015-07-17T18:21:58Z (GMT) No. of bitstreams: 1 Disserta????o - Mauro Galucio Garcia.pdf: 8414985 bytes, checksum: 192bccb9ac6b0279be9e5ff578bb8132 (MD5) Approved for entry into archive by Divis??o de Documenta????o/BC Biblioteca Central (ddbc@ufam.edu.br) on 2015-07-17T18:26:31Z (GMT) No. of bitstreams: 1 Disserta????o - Mauro Galucio Garcia.pdf: 8414985 bytes, checksum: 192bccb9ac6b0279be9e5ff578bb8132 (MD5) Made available in DSpace on 2015-07-17T18:26:31Z (GMT). No. of bitstreams: 1 Disserta????o - Mauro Galucio Garcia.pdf: 8414985 bytes, checksum: 192bccb9ac6b0279be9e5ff578bb8132 (MD5) Previous issue date: 2013-08-01 CNPq - Conselho Nacional de Desenvolvimento Cient??fico e Tecnol??gico During wood processing by timber industry around 70% of lumber becomes unusable (garbage), which usually is thrown away at inappropriate places, causing environmental troubles. In attempt to assuage this problem and trying harnessing the underused waste, some proposals have been emerged, like the use of these residues to produce handcrafts which reduces the waste of wood and adds a great value to a thing that is seen as a trash. Other proposal is the present study, which proposed the phytochemical study of three timber species of Fabaceae family: Dipteryx odorata (cumaru), Swartzia laevicarpa (saboarana) e Andira parviflora (sucupira-vermelha), contributing for the knowledge of the chemical constituents of the wood, and in search for secondary metabolites with biological activity or chemical relevance. The organic crude extracts were fractionated by chromatography column (CC). The fractionation of the dichloromethane extract from residues of S. laevicarpa, resulted in the isolation of 8-hydroxy-3,4,9,10-tetramethoxipterocarpan. The methanolic extract of D. odorata fractionated in CC led the isolation of four isoflavones: 8-O-metilretusin, cladrastrin, 7,3???-dihydroxy-8,4???dimethoxi-isoflavone and the 7,3???-dihydroxy-5,6,4???-trimethoxi-isoflavone, this last one is reported for the first time. The fractionation of the methanolic extract of the alburnum of A. parviflora in CC led the isolation of the isoflavone genistein, and in the methanolic extract of A. parviflora's core were isolated the 7,5???,6???-trihydroxy-4???-methoxi-isoflavan and biochanin A. The resulting mother liquor of biochanin A, was evaluated by HPLC-EFS-NMR, leading to the isolation and identification of substances 3,8-dihydroxy-9-methoxipterocarpan,8-dihydroxy-9-methoxipterocarpan, nissolin, medicarpin, biochanin A and the novel bipterocarpan medicarpin secundiflorol-I (OC 3 ??? C-3 '). In this work were identified by spectroscopic techniques flavonoids (isoflavone, isoflavan and pterocarpan) typical of the Fabaceae family. lixo, geralmente descartado em locais inadequados causando grandes problemas ambientais. Na tentativa de amenizar esses problemas e na busca de aproveitamento dos res??duos s??lidos t??m surgido propostas como a produ????o de pequenos objetos a qual ?? uma forma s??cio-econ??mica de agregar valor aos res??duos. Por meio de estudos fitoqu??micos dos res??duos, a presente proposta visou proporcionar o conhecimento qu??mico de madeiras das esp??cies de fam??lia Fabaceae Dipteryx odorata (cumaru), Swartzia laevicarpa (saboarana) e Andira parviflora (sucupira-vermelha). Os extratos org??nicos foram fracionados por cromatografia em coluna (CC). O fracionamento do extrato diclorometano dos res??duos de S. laevicarpa resultou no isolamento de 8-hidroxi-3,4,9,10-tetrametoxipterocarpano. O extrato metan??lico de D. odorata fracionado em CC forneceu 4 isoflavonas: 8-O-metilretusina, cladastrina, 7,3???-dihidroxi-8,4???dimetoxiisoflavona e a in??dita 7,3???-dihidroxi-5,6,4???-trimetoxiisoflavona. Os fracionamentos dos extratos metan??lico do alburno de A. parviflora em CC forneceu a isoflavona geniste??na e do cerne o isolamento de 7,5???,6???-trihidroxi-4???-metoxiisoflavana e biochanina A, ambas purificadas por recrsitaliza????o. A ??gua-m??e resultante desta ??ltima foi avaliada a t??cnica hifenada CLAE-EFS-RMN, levando ao isolamento e identifica????o das subst??ncias 3,8-dihidroxi-9-metoxipterocarpano, 8-dihidroxi-9-metoxipterocarpano, nissolina, medicarpina, biochanina A e o in??dito bipterocarpano medicarpina-secundiflorol I (C-3???O-C-3'). Nesse estudo identificou-se por t??cnicas especterosc??picas flavon??ides (isoflavona, isoflavana e pterocarpano) t??picos da fam??lia Fabaceae.

The aim of this investigation was to determine if the production of daidzein, genistein and coumestrol, compounds reported as antimicrobial principles in this species, is affected by the presence of the endophyte Phomopsis sp. in the young twigs of Erythrina crista-galli. HPLC profiles of the acetone extracts from cultivated plants and plants over-infected with Phomopsis sp. were obtained. Daidzein, coumestrol, genistein, biochanin A, and formononetin were identified in all the acetone extracts. Coumestrol and daidzein content (0.04 and 0.05 %) was higher in over infected plants than in control plants (0.01 and 0.02%). A major peak was observed in the HPLC/DAD profile of the acetone extract from over-infected plants. This was partially identified as a 3-glucosyl-rhamnosyl isorhamnetin derivative. Fil: Redko, Flavia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco (i); Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina Fil: Clavin, María L.. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco (i); Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina Fil: Giberti, Gustavo Carlos. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina Fil: Anke, Timm. Institut für Biotechnologie und Wirkstoff-Forschung; Alemania Fil: Martino, Virginia Susana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco (i); Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina

Plants of the genus Derris (Fabaceae)are known to contain flavonoids particularly isoflavonoids such as rotenoids. Derris ferruginea (Benth.), originate to Asia, is traditionally used as insecticide, fish poison and in the fight against ectoparasites. Phytochemical study of extracts from stems and leaves of Derris ferruginea were made to isolate and characterize 14 compounds mainly flavanones and isoflavonoids. Almost of them are prenylated. An extended biological evaluation was performed for crude extracts and some isolated compounds. Alternatives methods were developed to obtain two interesting compounds. Centrifugal partition chromatography has resulted in purification in larger amounts of cajaflavanone which possess intersting properties in terms of biological ( anti-inflammatory effect on microglia1 cells, inhibiting the formation of advanced glycation and products by a non-antioxidant mechanism, proangiogenic / effect ex vivo). The synthesis of a novel compound was undertaken and permitted to validate its structure. Finally, the major compound of the leaf was preliminary tested on a model to study its insecticidal activity: the DUM neurons of Periplaneta americana. This electrophysiological technique allows understanding the mechanism of action of this compound.; Les plantes du genre Derris (Fabaceae) sont connues pour contenir des flavonoïdes, en particulier des isoflavonoïdes dont des roténoïdes. Derris ferruginea (Benth.), liane originaire d'Asie, est utilisée traditionnellement comme insecticide, poison de pêche et dans la lutte contre les ectoparasites. L'étude phytochimique d'extraits de tiges et de feuilles de Derris ferruginea a permis d'isoler et de caractériser 14 composés essentiellement de type flavanones et isoflavonoïdes. Ces composés comportent pour la plupart des prénylations. Une évaluation biologique étendue à la fois des extraits et de certains composés a été réalisée. Pour deux composés, des méthodes d'obtention alternatives ont été utilisées. La chromatographie de partage centrifuge a permis d'obtenir en quantité plus importante la cajaflavanone qui s'avère posséder des propriétés intéressantes du point de vue biologique (effet anti-inflammatoire sur cellules microgliales, inhibiteur de la formation des produits terminaux de glycation par un mécanisme non-antioxydatif, effet proangiogénique ex vivo). La synthèse d'un composé original a été entreprise et a permis de valider sa structure. Enfin, le composé majoritaire des feuilles a fait l'objet d'une étude préliminaire sur un modèle d'étude de l'activité insecticide : les DUM neurones de Periplaneta americana. Cette technique électrophysiologique a permis d'appréhender le mécanisme d'action de ce composé.

Plants of the genus Derris (Fabaceae)are known to contain flavonoids particularly isoflavonoids such as rotenoids. Derris ferruginea (Benth.), originate to Asia, is traditionally used as insecticide, fish poison and in the fight against ectoparasites. Phytochemical study of extracts from stems and leaves of Derris ferruginea were made to isolate and characterize 14 compounds mainly flavanones and isoflavonoids. Almost of them are prenylated. An extended biological evaluation was performed for crude extracts and some isolated compounds. Alternatives methods were developed to obtain two interesting compounds. Centrifugal partition chromatography has resulted in purification in larger amounts of cajaflavanone which possess intersting properties in terms of biological ( anti-inflammatory effect on microglia1 cells, inhibiting the formation of advanced glycation and products by a non-antioxidant mechanism, proangiogenic / effect ex vivo). The synthesis of a novel compound was undertaken and permitted to validate its structure. Finally, the major compound of the leaf was preliminary tested on a model to study its insecticidal activity: the DUM neurons of Periplaneta americana. This electrophysiological technique allows understanding the mechanism of action of this compound.; Les plantes du genre Derris (Fabaceae) sont connues pour contenir des flavonoïdes, en particulier des isoflavonoïdes dont des roténoïdes. Derris ferruginea (Benth.), liane originaire d'Asie, est utilisée traditionnellement comme insecticide, poison de pêche et dans la lutte contre les ectoparasites. L'étude phytochimique d'extraits de tiges et de feuilles de Derris ferruginea a permis d'isoler et de caractériser 14 composés essentiellement de type flavanones et isoflavonoïdes. Ces composés comportent pour la plupart des prénylations. Une évaluation biologique étendue à la fois des extraits et de certains composés a été réalisée. Pour deux composés, des méthodes d'obtention alternatives ont été utilisées. La chromatographie de partage centrifuge a permis d'obtenir en quantité plus importante la cajaflavanone qui s'avère posséder des propriétés intéressantes du point de vue biologique (effet anti-inflammatoire sur cellules microgliales, inhibiteur de la formation des produits terminaux de glycation par un mécanisme non-antioxydatif, effet proangiogénique ex vivo). La synthèse d'un composé original a été entreprise et a permis de valider sa structure. Enfin, le composé majoritaire des feuilles a fait l'objet d'une étude préliminaire sur un modèle d'étude de l'activité insecticide : les DUM neurones de Periplaneta americana. Cette technique électrophysiologique a permis d'appréhender le mécanisme d'action de ce composé.

Tese (doutorado)—Universidade de Brasília, Instituto de Ciências Biológicas, Programa de Pós-Graduação em Biologia Animal, 2011. O controle biológico associado ao uso de cultivares resistentes ao ataque de insetos apresenta interesse e potencial para ser utilizado no manejo de pragas. Os objetivos do trabalho foram investigar os mecanismos envolvidos na resistência das cultivares de soja Dowling e IAC100 ao percevejo Euschistus heros, em comparação com a cultivar suscetível Silvânia; avaliar a atração do parasitóide de ovos, Telenomus podisi, e do percevejo a essas cultivares com diferentes tipos de injúrias (herbivoria, herbivoria+oviposição e oviposição); avaliar a resposta do parasitóide aos compostos induzidos pela herbivoria, assim como investigar a distribuição de ninfas e adultos do percevejo e os parasitóide de ovos de E. heros nas diferentes cultivares em condições de campo. No teste de oviposição do percevejo, com escolha entre as cultivares, não houve diferença significativa no número de posturas e ovos entre as cultivares, enquanto no teste sem chance de escolha, o número de ovos deixados na cultivar Silvânia foi maior do que nas demais. As cultivares resistentes afetaram o desenvolvimento do percevejo. As ninfas mantidas na cultivar Dowling não completaram seu ciclo biológico. Houve diferença nos pesos médios e na longevidade dos adultos do percevejo para as cultivares IAC100 e Silvânia. A fecundidade foi maior para fêmeas alimentadas na cultivar Silvânia, porém não houve diferença na viabilidade dos ovos. A sobrevivência do percevejo da fase ninfal até adulto diferiu significativamente entre os tratamentos. Houve maior produção dos isoflavonóides na cultivar Silvânia, sendo que apenas o composto genisteína, 48hr após a herbivoria, foi produzido em maior quantidade. Nos bioensaios com olfatômetro em “Y”, os parasitóides foram atraídos para as plantas injuriadas pela herbivoria e pela associação de herbivoria+oviposição quando comparadas com plantas não atacadas de soja nas cultivares resistentes, mas não mostrou preferência para cultivar Silvânia em nenhum dos tratamentos. Os voláteis da planta emitidos nas três cultivares após a oviposição não atraíram o parasitóide. Nos bioensaios com o olfatômetro de quatro escolhas, fêmeas de E. heros não mostraram preferência para os odores das plantas de soja atacadas ou não paras as três cultivares. Porém, com o olfatômetro em “Y”, o percevejo foi atraído para plantas não atacadas quando comparadas com o controle (somente ar). As análises de Curvas de Respostas Principais (PRC) mostraram que houve diferença entre os tratamentos ao longo do tempo no perfil químico dos voláteis entre os tratamentos para a cultivar Dowling. Os xix compostos que mais contribuíram para a diferença ente plantas de soja injuriadas comparadas com plantas não atacadas foram (E,E)-a-farneseno, salicilato de metila, (Z)-3-acetato de hexenila e (E)-2-octen-1-ol. O parasitóide foi atraído somente para o (E,E)-α-farneseno a 1x10-5M nos testes no olfatômetro em “Y”, feitos com cada um dos compostos, com exeção do (E)-2-octen-1-ol, e comparados ao controle (hexano). Porém, houve diferença no tempo de residência para o composto salicilato de metila nas concentrações 1x10-4 e 1x10-5M. Não houve diferença significativa na primeira escolha, nem no tempo que o parasitóide permaneceu nos braços do olfatômetro, tratamento e controle, quando as misturas: (1) (E,E)-α-farneseno+salicilato de metila+(Z)-3-acetato de hexenila; (2) (E,E)-α-farneseno+ salicilato de metila; (3) (E,E)-α-farneseno+(Z)-3- acetato de hexenila e (4) salicilato de metila+(Z)-3-acetato de hexenila foram testadas contra o controle (E,E)-α-farneseno a 1x10-5M. O parasitóide também não mostrou preferência pelas misturas testadas, com o hexano como controle. Entretanto, o tempo de residência no braço com a mistura 2, especificada acima, foi estatisticamente diferente. Telenomus podisi foi atraído para as plantas com herbivoria, permanecendo também a maior parte do tempo no braço do olfatômetro com o tratamento, nos bioensaios utilizando plantas atacadas e não atacadas pelo E. heros, após 96 hr, comparado com o (E,E)-α-farneseno a 1x10-5M. Não houve diferença entre as cultivares na distribuição do percevejo nas plantas do campo. A maior população foi observada no final do ciclo da soja, porém, o maior número de ovos naturais e parasitismo foram encontrados entre os estágios reprodutivos R1 e R5. Os parasitóides T. podisi, Trissolcus teretis, Tr. urichi e Tr. brochymenae emergiram dos ovos sentinela de E. heros, sendo T. podisi o mais freqüente e com maior ocorrência a partir do estágio reprodutivo R6. Os resultados sugerem que as cultivares IAC100 e Dowling possuem defesa direta (constitutiva) contra E. heros e que não houve indução da produção dos isoflavonóides na cultivar de soja resistente Dowling pela injúria de herbivoria. As plantas das cultivares resistentes danificadas pelo percevejo apresentaram defesa induzida indireta. Os compostos (E,E)-a-farneseno, salicilato de metila, (Z)-3-acetato de hexenila estão, provavelmente, envolvidos na atração do parasitóide T. podisi. O parasitóide T. podisi foi atraído pela cultivar de soja resistente Dowling em condições de campo. _________________________________________________________________________________ ABSTRACT The association of resistant varieties and biological control has great interest and potential to be used for pest management. The aims of this work were to evaluate the mechanisms involved in resistance of the soybean cultivars Dowling and IAC100 for the stinkbug Euschistus heros, in contrast with the suscetible Silvânia; the attraction of Telenomus podisi and the stinkbug to different types of damage (herbivory, herbivory+oviposition and oviposition) to these cultivars; the response of the parasitoid to compounds induced by herbivory damage and the distribution of nymphs and adults of the stinkbug and the egg parasitoid on different cultivars under field conditions. In choice tests, there was no difference in the number of clutches and the number of eggs between the cultivars, but the cultivar Silvânia received more eggs in the test without choice. The nymphs reared on cv Dowling did not complete their biological cycle. The mean weight and the longevity of adults on the different cultivars were different. Female fecundity on cultivar Silvânia was higher than on cultivar IAC100, however the egg fertility was not different. The survivorship of nymphs until adults differed significantly between treatments. Total amount of isoflavonoids compounds was higher in cultivar Silvânia, and only the compound genistein at 48 hr after damage, was produced in greater quantity in the herbivory treatment. In a Y-tube olfactometer, the parasitoids were attracted to herbivory and herbivory+oviposition damaged soybean plants when compared to undamaged soybean plants for the resistant cultivars, but did not show preference for the susceptible cultivar Silvânia in any of the damage treatments. The plant volatiles emitted by oviposition damaged plants in the three cultivars did not attract the egg parasitoid. In four-arm-olfactometer bioassays E. heros females did not show a preference for odors of damaged or undamaged soybean plants of the three cultivars studied. In a Y-tube olfactometer, the stink bug was attracted to undamaged soybean plants for all cultivars compared with air. The Principal Response Curves (PRC) analysis showed consistent variability over time in the chemical profile of volatiles between treatments for the cultivar Dowling. The compounds that most contributed to the divergence between damaged soybean plants compared to undamaged plants were (E,E)-a-farnesene, methyl salicylate, (Z)-3-hexenyl acetate and (E)-2-octen- 1-ol. Testing the compounds in a Y-tube olfactometer, the parasitoids were attracted only to (E,E)-α-farnesene at 1x10-5M, when both individual compounds and hexane xxi were contrasted. However, the residence time was different to methyl salicylate at concentrations of 1x10-4 e 1x10-5M. No difference was observed on the initial choice neither on the time that the parasitoid remained in the arms of the olfactometer, treatment and control, when the blends of volatiles: (1) (E,E)-α-farnesene+methyl salicylate+(Z)-3-hexenyl acetate; (2) (E,E)-α-farnesene+methyl salicylate; (3) (E,E)-α- farnesene+(Z)-3-hexenyl acetate and (4) methyl salicylate+(Z)-3-hexenyl acetate were tested against (E,E)-α-farnesene at 1x10-5M. Testing hexane as control, the parasitoid did not show preference to the blends tested, but the residence time in the arm supplied with the blend 2 was statistically different. In the bioassays with 96 hr herbivory damage caused by E. heros, and undamaged soybean plants against (E,E)-α-farnesene at 1x10-5M, T. podisi was attracted to herbivory damaged soybean plants, also remaining a long of time in the olfactometer arm supplied with the odor of herbivory damaged plants. There was no difference between cultivars in stink bug distribution in the field; the highest population was observed in the final stages of crop, however, more natural eggs and parasitism were found among the reproductive stages R1 and R5. The parasitoids T. podisi, Trissolcus teretis, Tr. urichi e Tr. brochymenae emerged from the sentinel eggs of E. heros, where T. podisi was the most common and occured more from the reproductive stage R6. These results suggest that the cv IAC100 and Dowling present direct defense (constitutive) against E. heros; that the herbivory damage did not induce isoflavonoids production on resistant soybean cultivar Dowling; the plants of the resistant cultivars damaged by the stinkbug have indirect induced defense; the compounds (E,E)-a-farnesene, methyl salicylate, (Z)-3-hexenyl acetate are probably involved in the attraction of the egg parasitoid T. podisi and that the parasitoid T. podisi is attracted by the cultivar Dowling in field conditions.

O cumestrol é um isoflavonóide presente em diferentes leguminosas como a alfafa, soja e trevo vermelho. Estudos demonstraram uma relevante atividade antioxidante e estrogênica deste composto. Neste contexto, o objetivo deste estudo foi desenvolver nanoemulsões contendo cumestrol visando a sua aplicação tópica. Na primeira fase, nanoemulsões foram obtidas por emulsificação espontânea. Tal procedimento conduziu à obtenção de nanoemulsões monodispersas, confirmado por microscopia eletrônica de transmissão. A viscosidade das formulações permaneceu similar, enquanto que o potencial zeta foi influenciado pela presença dos tensoativos. Após espessamento, as formulações demonstraram um comportamento não-Newtoniano pseudoplástico. Na segunda etapa, o teor de cumestrol nas formulações foi determinado por CLAE. O método foi específico, linear, preciso e exato para quantificação de cumestrol nas formulações desenvolvidas. Os perfis de liberação do cumestrol, através de membrana artificial, demonstraram uma liberação imediata para todas as formulações. Por fim, estudos de permeação/retenção do cumestrol através de pele de orelha suína foram realizados utilizando-se células de difusão de Franz. Os resultados obtidos demonstram um fluxo lento do cumestrol através da pele. O conjunto de resultados obtidos demonstra o efeito da composição sobre as propriedades das formulações e distribuição do cumestrol através das camadas da pele. Coumestrol is an isoflavonoid present in various legumes such as alfalfa, soybeans, and red clovers. Studies have shown significant estrogenic and antioxidant activities for this compound. With this in mind, the main purpose of this study was to develop nanoemulsion containing coumestrol for topic application. In the first phase, nanoemulsions were obtained by spontaneous emulsification. This procedure yielded monodisperse nanoemulsions, confirmed by transmission electron microscopy. The viscosity of the formulations remained similar, while the zeta potential was influenced by the surfactants. After thickening, the formulations showed a pseudplastic non-Newtonian behavior. In the second step, the coumestrol content in the formulations was determined by HPLC. The method was specific, linear, precise, and accurate for coumestrol quantification in the developed formulations. The coumestrol release profile through artificial membrane showed immediate release for all formulations. Finally, studies of coumestrol permeation/retention through porcine ear skin were performed using Franz diffusion cells. The results showed a slow flow of coumestrol through the skin. The overall results show the effect of the composition on the properties of the formulations and coumestrol distribution through the layers of the skin.

To describe and analyse the importance of food compounds with anticarcinogenic properties was the objective of this review. Minerals, as Selenium and Calcium, and compounds present in teas (catechins), citrics (terpenes), persimmon, milk, fish, grapes and wine (phenolics), soy beans and its products (isoflavonoids) have confirmed anticarcinogenic effects in vitro and in vivo, constituting promising functional foods to cancer prevention. Esta revisão teve como objetivo descrever e analisar a importância de compostos alimentares com propriedades anticarcinogênicas. Minerais, como o Selênio e o Cálcio, e compostos presentes em chás (catequinas), cítricos (terpenos), no caqui, no leite, em peixes, em uvas e vinhos (fenólicos), na soja e derivados (isoflavonóides) apresentam comprovados efeitos anticarcinogênicos in vitro e in vivo, constituindo promissores alimentos funcionais para a prevenção do câncer.

The authors would like gratitude to acting as a Head of the Laboratory of Biochemistry of Microorganisms and Nutrient Media of the State Institution “Institute of Microbiology and Immunology named after I.I. Mechnikov of the National Academy of Medical Sciences of Ukraine,” Cand. Med. Sci. T.P. Osolodchenko for the preliminary screening of antimicrobial activities and a Head of Department of the Ornamental plants, Senior Researcher of the National Botanical Garden n.a. M.M. Gryshko of NAS of Ukraine (Kyiv), Cand. Biol. Sci. Yu.V. Buidin for help in systematical classification of plants., Aim: The aim of the work was isolation and identification of the phenolic compounds from the rhizomes of Iris hungarica. Materials and methods: To establish by chemical and spectral methods for the structures of phenolic compounds, which were isolated from the rhizomes of Iris hungarica Waldst. et Kit. (Iridaceae family). Compounds were obtained by column chromatography on silica gel and their structures were determined by UV, IR, MS, 1H-NMR spectra methods. Preliminary screening of antibacterial activity was determined. Results: From the ethanolic extract of the rhizomes of I. hungarica, which is widespread in Ukraine, for the first time two new for this species isoflavones, teсtorigenin and tectoridin and xanthone mangiferin, together with known isoflavonoids daidzein, genistein, formononetin were isolated. The dry extract of the rhizomes of I. hungarica at a concentration of 1% has shown the highest inhibitory activity for Gram-positive bacteria and fungi., Objetivo: El objetivo del trabajo es el aislamiento y la identificación de los compuestos fenólicos de los rizomas de Iris hungarica. Materiales y métodos: Se utilizaron métodos químicos y espectrales para conocer las estructuras de compuestos fenólicos que se aislaron de los rizomas de Iris hungarica Waldst. et Kit. (Familia de Iridaceae). Los compuestos se obtuvieron mediante cromatografía en columna sobre gel de sílice y se determinaron sus estructuras mediante análisis de sus espectros por UV, IR, MS, 1H-RMN. Se determinó el cribado preliminar de la actividad antibacteriana. Resultados: Se aislaron por primera vez de los rizomas de Iris hungarica (común en Ucrania) dos isoflavonas, teсtorigenina y tectoridina (nuevas para esta especie), el xantonoide mangiferina y los isoflavonoides daidzeina, genisteina y formononetina. El extracto seco de los rizomas de I. hungarica a una concentración de 1% ha mostrado la actividad inhibitoria más alta para bacterias y hongos Gram-positivos.