ABSTRACT Propolis, is a bee product collected from exudates and flower buds of several plants, has strong aroma and several biological applications. This study aimed at evaluating the chemical composition and in vitro antioxidant, antibacterial and cytotoxic properties of volatile oil from Brazilian brown propolis. It was extracted by hydrodistillation and analyzed by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. Volatile oil from brown propolis exhibited strong antibacterial activity against H. pylori (MIC 3.25 µg/ml), Mycobacterium tuberculosis (MIC 50 µg/ml) and M. avium (MIC 62.5 µg/ml). It was evaluated in vitro for antioxidant activity by DPPH (IC50 25.0 µg/ml) and ABTS (IC50 30.1 µg/ml) methods. Its cytotoxic property was evaluated in normal (human fibroblasts, GM07429A) and tumor (MCF-7-human breast adenocarcinoma; HeLa-human cervical adenocarcinoma and M059J-human glioblastoma) cell lines. IC50 values were 81.32 µg/ml for GM07429A and 85.00, 129.40 and 84.12 µg/ml for MCF-7, HeLa and M059J cells, respectively. Three major dereplicated components of volatile oil from brown propolis were acetophenone (15.2%), nerolidol (13.3%), and spathulenol (11.6%). Our results contribute to a better understanding of the chemical and biological properties of Brazilian brown propolis and provide evidence for its potential medicinal use.

ABSTRACT Besides their value as therapeutic resources, medicinal plants may also be used as sources of active ingredients against phytopathogens. Fungi can grow and cause spoilage in food, thus, resusting in decrease in its quality and quantity. This research aimed at evaluating the effect of essential oil from Murraya paniculata (ML-EO) leaves on mycelial growth of Sclerotinia sclerotiorum, a fungus that poses high risk to several cultures, mainly soybean. Essential oil from M. paniculata (Rutaceae) leaves was obtained by hydrodistillation which was carried out by a Clevenger-type apparatus while its chemical composition was analyzed by GC-FID and GC-MS. β-Caryophyllene (23.8%), α-zingiberene (21.0%) and β-cubebene (10.2%) were the main constituents found in ML-EO leaves. In vitro antifungal activity showed that ML-EO, at a 300 µL dose, inhibited 91.2% of mycelial growth of Sclerotinia sclerotiorum . This is the first report of the antifungal activity of ML-EO against S. sclerotiorum and results suggest that the essential oil under evaluation has good potential to control this phytopathogenic fungus.

RESUMO: A Campomanesia adamantium é uma espécie frutífera nativa do Cerrado que se destaca pela utilização na alimentação, na medicina e como pasto apícola. A composição química dos óleos essenciais obtidos de plantas de uma mesma espécie pode sofrer variação de seus constituintes por influência de vários fatores incluindo o método de extração do óleo essencial, fatores ambientais, genéticos e ontogenéticos. Neste sentido, o presente trabalho tem como objetivo identificar a influencia do tempo de hidrodestilação sobre o teor e a composição química do óleo essencial das folhas de C. adamantium . Os tratamentos constituíram-se de cinco tempos de extração (1, 2, 3, 4 e 5 horas) utilizando aparelho Clevenger com cinco repetições, sendo o delineamento inteiramente casualizado. Foi observado que após duas horas de hidrodestilação o teor de óleo essencial permanece constante. Em relação aos constituintes químicos do óleo essencial ocorreu variação das proporções dos compostos em todos os tempos de hidrodestilação testados, os compostos sesquiterpenos oxigenados espatulenol e óxido cariofileno foram majoritários nos cinco tempos de hidrodestilação.

ABSTRACT: Campomanesia adamantium is a native fruit species of the Cerrado and is used in food and medicines and as bee pasture. The chemical composition of essential oils obtained from plants of the same species have varying constituent proportions due to the influence of extractive factors, environmental, genetic and ontogenetic. This study aimed to identify the influence of hydrodistillation time on the content and chemical composition of essential oil extracted from the leaves of C. adamantium . Treatments consisted of five extraction times (1, 2, 3, 4, and 5h) using Clevenger with five replications in a completely randomized design. It was observed that after two hours of hydrodistillation, the essential oil content remains constant. Regarding the chemical constituents of essential oil, variation of the proportions of the compounds tested occurred at all hydrodistillation times. The compounds spathulenol oxygenated sesquiterpenes and caryophyllene oxide were the majority in the five hydrodistillation times.

RESUMO: Existem fatores que podem afetar o conteúdo de óleo essencial das plantas, sendo o horário de coleta um deles. Assim, observa-se que o teor e a composição química de óleo essencial podem variar em certas plantas de acordo com horário de coleta. O objetivo deste trabalho foi avaliar o efeito do horário de coleta sobre o conteúdo e a composição química do óleo essencial das folhas de goiabeira ( Psidium guajava ). Folhas de Psidium guajava foram coletadas em diferentes horários do dia para determinar teor e composição química de seu óleo essencial. O óleo essencial não apresentou variação qualitativa da composição química em relação ao horário de coleta das folhas de Psidium guajava , mas alterou a concentração das substâncias, entre elas o α-humuleno e o trans-cariofileno. Os constituintes principais do óleo essencial das folhas de Psidium guajava são o limoneno (2,2-4,4%), trans-cariofileno (18,1-17,1%), α-humuleno (26,3-20,4%), aromadendreno (7,6-12,2%), α-selineno (7,3-11,3%), óxido de cariofileno (3,7-3,3%) epóxido de humuleno II (4,1-1,9%) e o selin-11-en-4α-ol (7,2-11,1%). No entanto, a maior produção de óleo essencial, foi obtida com as folhas coletadas às 19h, apresentando conteúdo de 0,38% (b.s.) e a mais baixa produção às 07h, apresentando conteúdo de 0,24% (b.s.). Através da análise química, identificou-se que compostos sesquiterpênicos apresentaram uma maior concentração (62,0%) e os monoterpenos e monoterpenoides foram os que apresentaram menor concentração (2,2 e 1,1%, respectivamente). As classes que sofreram maiores mudanças em relação ao horário de coleta foram os monoterpenos (2,2-4,4%) e os sesquiterpenos e os sesquiterpenoides (63,8-61,7% e 15,9-13,2%, respectivamente).

ABSTRACT: The essential oil plants contents can be affected by several factors. For example, in certain plants, collection time has been observed to affect the content and chemical composition of the essential oil obtained from the plant. The objective of this study was to evaluate the effect of collection time on the content and chemical composition of the essential oil from guava ( Psidium guajava L.) leaves. Leaves were collected at different times of the day and the content and chemical composition of their essential oil was determined. Collection time did not qualitatively affect the chemical composition of the essential oil. However, concentration of certain substances in the oil, such as α-humulene and trans-caryophyllene, did significantly vary at different collection times. The main constituents of the essential oil of Psidium guajava are limonene (2.2-4.4%), trans-caryophyllene (18.1-17.1%), α-humulene (26.3-20.4%), aromadendrene (7.6-12.2%), α-selinene (7.3-11.3%), caryophyllene oxide (3.7-3.3%), humulene epoxide II (4.1-1.9%), and selin-11-en-4α-ol (7.2-11.1%). Leaves collected at 7:00 AM had higher essential oil production, with a content of 0.38% (d.b.), whereas leaves collected at 7:00 PM had lower essential oil production, 0.24% (d.b.). Chemical analysis showed that sesquiterpene compounds represented the highest concentration (62.0%), and monoterpenoids and monoterpenes represented the lowest concentrations (1.1 and 2.2%, respectively). Chemical classes that underwent major changes with respect to collection time were monoterpenes, sesquiterpenes, and sesquiterpenoids (2.2-4.4%, 63.8-61.7%, and 15.9-13.2%, respectively).

ABSTRACT The total glycoalkaloids fraction obtained from the unripe fruit of Solanum crinitum was chromatographed on sephadex LH-20 column to yield the solasonine, a glycoalkaloid which structure was identified by IR and NMR spectral data analysis. The allelopathic effect of the extract and solasonine on the seeds germination and lettuce seedlings development was detected. The tests were conduced with four replications of five concentration (0, 100, 200, 400, 800 ppm) using 25 seeds. Although both show high allelopathic activity. The solasonine was more effetive. LH20 LH 20 LH-2 analysis detected 0, 0 (0 100 200 400 80 ppm 2 activity effetive LH2 LH- ( 10 40 8 1 4

RESUMO Afração contendo os alcalóides glicosilados totais dos frutos verdes de Solanum crinitum foi cromatografado em coluna de Sephadex e forneceu a solasonina, um alcalóide glicosilado cuja estrutura foi definida através da análise de dados espectrométricos no IV e de RMN de 1H e 13C. Os testes realizados com quatro repetições de cinco concentrações (0, 100, 200, 400 e 800 ppm) usando 25 sementes de alface (Lactuca sativa) permitiram verificar elevada atividade do extrato dos alcalóides glicosilados totais e da solasonina sobre a germinação e o desenvolvimento dessas plântulas, sendo a solasonina mais ativa. H 13C C 0, 0 (0 100 200 40 80 ppm 2 Lactuca sativa plântulas ativa ( 10 20 4 8 1

ABSTRACT Cromatographic fracionation of leaves extracts from Simira glaziovii (Rubiaceae) afforded methyl hexadecanoate, hexadecanoic, octadecanoic and eicosanoic acids, inositol, sitosterol, two triterpenes acetyl derivatives, butirospermol acetate and eufol acetate beside the saponin, 3b-O-b-D-glucopyranosylsitosterol. From the woods were isolated a carbohydrate mixture beside the harmane alkaloid. The identification of the compounds were stablished by IR, 1H and 13C NMR and GC-MS analysis beside comparison with the literature data. Rubiaceae (Rubiaceae hexadecanoate hexadecanoic acids inositol sitosterol derivatives saponin 3bObDglucopyranosylsitosterol. 3bObDglucopyranosylsitosterol bObDglucopyranosylsitosterol 3b O b D glucopyranosylsitosterol. glucopyranosylsitosterol 3b-O-b-D-glucopyranosylsitosterol alkaloid IR H C GCMS GC MS data

RESUMO O fracionamento cromatográfico dos extratos obtidos com solventes orgânicos das folhas de Simira glaziovii permitiu o isolamento do sitosterol, dois triterpenos acetilados, acetato de butirospermol e acetato de eufol, hexadecanoato de metila, os ácidos hexadecanóico, octadecanóico e eicosanóico, inositol e a saponina 3b-O-b-D-glicopiranosilsitosterol. Do extrato metanólico da madeira isolaram-se mistura de carboidratos e o alcalóide harmana. As substâncias foram identificadas através de análise dos dados espectrométricos de IV, RMN de 1H e 13C (PND e DEPT) e CG-EM, incluindo comparação com dados da literatura. sitosterol acetilados eufol metila hexadecanóico eicosanóico 3bObDglicopiranosilsitosterol. 3bObDglicopiranosilsitosterol bObDglicopiranosilsitosterol 3b b D glicopiranosilsitosterol. glicopiranosilsitosterol 3b-O-b-D-glicopiranosilsitosterol isolaramse isolaram se harmana IV H C PND DEPT CGEM, CGEM CG EM, EM CG-EM literatura